42
Context
Alkaptonuria
Alkaptonuria (Homogentisic acid oxidase deficiency) is an autosomal recessive disease caused by a mutation in the HGD gene which codes for homogentisate 1,2-dioxygenase. A mutation in this enzyme results in accumulation of homogentisic acid in urine. Symptoms, which present in adulthood, include arthritis, black or brown urine, and urolithiasis. Treatment includes a low-protein diet with vitamin C.
Disease
PW000180
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87
Tyrosine Metabolism
The tyrosine metabolism pathway describes the many ways in which tyrosine is catabolized or transformed to generate a wide variety of biologically important molecules. In particular, tyrosine can be metabolized to produce hormones such as thyroxine and triiodothyronine or it can be metabolized to produce neurotransmitters such as L-DOPA, dopamine, adrenaline, or noradrenaline. Tyrosine can also serve as a precursor of the pigment melanin and for the formation of Coenzyme Q10. Additionally, tyrosine can be catabolized all the way down into fumarate and acetoacetate. This particular pathway for tyrosine degradation starts with an alpha-ketoglutarate-dependent transamination reaction of tyrosine, which is mediated through the enzyme known as tyrosine transaminase. This process generates p-hydroxyphenylpyruvate. This aromatic acid is then acted upon by p-hydroxylphenylpyruvate-dioxygenase which generates the compound known as homogentisic acid or homogentisate (2,5-dihydroxyphenyl-1-acetate). In order to split the aromatic ring of homogentisate, a unique dioxygenase enzyme known as homogentisic acid 1,2-dioxygenase is required. Through this enzyme, maleylacetoacetate is created from the homogentisic acid precursor. The accumulation of excess homogentisic acid and its oxide (named alkapton) in the urine of afflicted individuals can lead to a condition known as alkaptonuria. This genetic condition, also known as an inborn error of metabolism or IEM, occurs if there are mutations in the homogentisic acid 1,2-dioxygenase gene. After the breakdown of homogentisate is achieved, maleylacetoacetate is then attacked by the enzyme known as maleylacetoacetate-cis-trans-isomerase, which generates fumarylacetate. This isomerase catalyzes the rotation of the carboxyl group created from the hydroxyl group via oxidation. This cis-trans-isomerase uses glutathione as a coenzyme or cofactor. The resulting product, fumarylacetoacetate, is then split into acetoactate and fumarate via the enzyme known as fumarylacetoacetate-hydrolase through the addition of a water molecule. Through this set of reactions fumarate and acetoacetate (3-ketobutyroate) are liberated. Acetoacetate is a ketone body, which is activated with succinyl-CoA, and thereafter it can be converted into acetyl-CoA, which in turn can be oxidized by the citric acid cycle (also known as the TCA cycle) or used for fatty acid synthesis. Other aspects of tyrosine metabolism include the generation of catecholamines. In this process, the enzyme known as tyrosine hydroxylase (or AAAH or TYH) catalyzes the conversion of tyrosine to L-DOPA. The L-DOPA can then be converted via the enzyme DOPA decarboxylase (DDC) to dopamine. Dopamine can then be converted to 3-methoxytyramine via the action of catechol-O-methyltransferase (COMT). Dopamine can also be converted to norepinephrine (noradrenaline) through the action of the enzyme known as dopamine beta hydroxylase (DBH). Norepinephrine can then be converted to epinephrine (adrenaline) through the action of phenyethanolamine N-methyltransferase (PNMT). Catecholamines such as L-DOPA, dopamine and methoxytyramine are produced mainly by the chromaffin cells of the adrenal medulla and by neuronal cells found in the brain. For example, dopamine, which acts as a neurotransmitter, is mostly produced in neuronal cell bodies in the ventral tegmental area and the substantia nigra while epinephrine is produced in neurons in the human brain that express PMNT. Catecholamines typically have a half-life of a few minutes in the blood. They are typically degraded via catechol-O-methyltransferases (COMT) or by deamination via monoamine oxidases (MAO). Another important aspect of tyrosine metabolism includes the production of melanin. Melanin is produced through a mechanism known as melanogenesis, a process that involves the oxidation of tyrosine followed by the polymerization of these oxidation by-products. Melanin pigments are produced in a specialized group of cells known as melanocytes. There are three types of melanin: pheomelanin, eumelanin, and neuromelanin of which eumelanin is the most common. Melanogenesis, especially in the skin, is initiated through the exposure to UV light. Melanin is the primary pigment that determines skin color. Melanin is also found in hair and the pigmented tissue underlying the iris. The first step in the synthesis for both eumelanins and pheomelanins is the conversion of tyrosine to dopaquinone by the enzyme known as tyrosinase. The resulting dopaquinone can combine with cysteine to produce cysteinyldopa, which then polymerizes to form pheomelanin. Dopaquinone can also form lecuodopachrome, which then can be converted to dopachrome (a cyclization product) and this eventually becomes eumelanin. Tyrosine plays a critical role in the synthesis of thyroid hormones. Thyroid hormones are produced and released by the thyroid gland and include triiodothyronine (T3) and thyroxine (T4). These two hormones are responsible for regulating metabolism. Thyroxine was discovered and isolated by Edward Calvin Kendall in 1915. Thyroid hormones are produced by the follicular cells of the thyroid gland through the action of thyroperoxidase, which iodinates reactive tyrosine residues on thyroglobulin. Proteolysis of the thyroglobulin in cellular lysosomes releases the small molecule thyroid hormones. In mammals, tyrosine can be formed from dietary phenylalanine by the enzyme phenylalanine hydroxylase, found in large amounts in the liver. Phenylalanine is considered an essential amino acid, while tyrosine (which can be endogenously synthesized) is not. In plants and most microbes, tyrosine is produced via prephenate, an intermediate that is produced as part of the shikimate pathway.
Metabolic
1
163
72
SubPathway
258
103
Compound
2
787
399
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1304
103
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2
28
Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.
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Pathway
29
Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.
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Yang YS, Wang CC, Chen BH, Hou YH, Hung KS, Mao YC: Tyrosine sulfation as a protein post-translational modification. Molecules. 2015 Jan 28;20(2):2138-64. doi: 10.3390/molecules20022138.
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Pathway
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6577005
Lee RW, Huttner WB: Tyrosine-O-sulfated proteins of PC12 pheochromocytoma cells and their sulfation by a tyrosylprotein sulfotransferase. J Biol Chem. 1983 Sep 25;258(18):11326-34.
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Westmuckett AD, Thacker KM, Moore KL: Tyrosine sulfation of native mouse Psgl-1 is required for optimal leukocyte rolling on P-selectin in vivo. PLoS One. 2011;6(5):e20406. doi: 10.1371/journal.pone.0020406. Epub 2011 May 25.
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Ruzzene M, Donella-Deana A, Marin O, Perich JW, Ruzza P, Borin G, Calderan A, Pinna LA: Specificity of T-cell protein tyrosine phosphatase toward phosphorylated synthetic peptides. Eur J Biochem. 1993 Jan 15;211(1-2):289-95. doi: 10.1111/j.1432-1033.1993.tb19897.x.
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Honova E, Miller SA, Ehrenkranz RA, Woo A: Tyrosine transaminase: development of daily rhythm in liver of neonatal rat. Science. 1968 Nov 29;162(3857):999-1001. doi: 10.1126/science.162.3857.999.
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Bartesaghi S, Valez V, Trujillo M, Peluffo G, Romero N, Zhang H, Kalyanaraman B, Radi R: Mechanistic studies of peroxynitrite-mediated tyrosine nitration in membranes using the hydrophobic probe N-t-BOC-L-tyrosine tert-butyl ester. Biochemistry. 2006 Jun 6;45(22):6813-25. doi: 10.1021/bi060363x.
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Goldstein S, Czapski G, Lind J, Merenyi G: Tyrosine nitration by simultaneous generation of (.)NO and O-(2) under physiological conditions. How the radicals do the job. J Biol Chem. 2000 Feb 4;275(5):3031-6. doi: 10.1074/jbc.275.5.3031.
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Radi R: Protein tyrosine nitration: biochemical mechanisms and structural basis of functional effects. Acc Chem Res. 2013 Feb 19;46(2):550-9. doi: 10.1021/ar300234c. Epub 2012 Nov 16.
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Sherry DM, Kanan Y, Hamilton R, Hoffhines A, Arbogast KL, Fliesler SJ, Naash MI, Moore KL, Al-Ubaidi MR: Differential developmental deficits in retinal function in the absence of either protein tyrosine sulfotransferase-1 or -2. PLoS One. 2012;7(6):e39702. doi: 10.1371/journal.pone.0039702. Epub 2012 Jun 22.
87
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Cell
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Astrocyte
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Homo sapiens
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Escherichia coli
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Arabidopsis thaliana
3702
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Pseudomonas aeruginosa
287
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Mus musculus
10090
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Bos taurus
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Rattus norvegicus
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Caenorhabditis elegans
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Solanum lycopersicum
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Bathymodiolus platifrons
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Plant-Type Vacuole
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PW_BS000024
65
11
1
PW_BS000065
308
10
1
1
PW_BS000024
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
436
25
5
PW_BS000115
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
487
18
10
1
PW_BS000115
790
6
11
1
PW_BS000524
834
6
1
1
1
PW_BS000549
102
12
3
1
PW_BS000102
156
12
24
1
PW_BS000156
179
12
21
1
PW_BS000179
369
12
60
1
PW_BS000028
21
5
1
1
4
PW_BS000021
35
5
19
1
4
PW_BS000035
47
19
1
4
PW_BS000047
58
1
14
1
1
PW_BS000058
66
18
5
1
8
PW_BS000066
74
1
3
PW_BS000074
51
8
1
PW_BS000051
39
7
1
1
3
PW_BS000039
59
27
1
1
PW_BS000059
91
8
5
1
1
PW_BS000091
56
26
1
1
PW_BS000056
104
14
3
1
PW_BS000104
199
14
18
1
PW_BS000024
288
14
4
1
PW_BS000024
335
27
12
1
PW_BS000028
184
1
2
1
PW_BS000024
372
10
2
PW_BS000028
422
27
5
1
PW_BS000115
375
27
17
1
PW_BS000053
491
27
10
1
PW_BS000115
508
27
6
1
PW_BS000115
891
14
2
1
PW_BS000552
168
32
1
PW_BS000168
98
11
2
PW_BS000098
109
32
3
PW_BS000109
189
32
18
PW_BS000024
317
32
23
PW_BS000024
48
1
1
3
PW_BS000048
30
17
1
1
PW_BS000030
195
13
18
PW_BS000024
309
39
1
1
PW_BS000024
338
17
12
1
PW_BS000028
351
15
12
PW_BS000028
361
39
12
1
PW_BS000028
386
39
5
1
PW_BS000100
397
39
6
1
PW_BS000113
401
39
17
1
PW_BS000113
413
17
5
1
PW_BS000115
435
15
5
PW_BS000115
449
17
17
1
PW_BS000115
470
15
17
PW_BS000115
499
15
10
PW_BS000115
517
15
6
PW_BS000115
41
8
1
1
PW_BS000041
45
10
1
4
PW_BS000045
63
6
1
PW_BS000063
87
24
5
1
1
PW_BS000087
342
6
12
PW_BS000028
340
24
5
12
1
PW_BS000028
381
7
1
1
PW_BS000088
326
8
12
PW_BS000028
416
8
5
PW_BS000115
452
8
17
PW_BS000115
488
8
10
PW_BS000115
505
8
6
PW_BS000115
358
39
12
PW_BS000028
186
12
2
1
PW_BS000024
141
1
7
19
1
PW_BS000141
219
31
4
PW_BS000024
312
5
23
1
PW_BS000024
310
31
2
PW_BS000024
304
1
2
PW_BS000024
882
31
202
PW_BS000552
883
1
202
1
PW_BS000552
167
31
1
PW_BS000167
788
24
11
1
3
PW_BS000524
599
8
56
PW_BS000501
789
24
1
1
3
PW_BS000524
865
24
18
1
3
PW_BS000552
77
25
1
1
1
PW_BS000077
1213
57
1
1
PW_BS000588
866
24
55
1
3
PW_BS000552
1060
3
1
1
3
PW_BS000578
912
24
1
3
PW_BS000558
787
24
10
1
3
PW_BS000524
1070
24
14
1
3
PW_BS000578
1143
1
14
1
5
PW_BS000583
394
5
1
PW_BS000176
847
1
1
PW_BS000549
393
1
5
1
PW_BS000173
103
L-Tyrosine
HMDB0000158
Tyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the body's sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the body's natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinson's, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinson's. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa. (http://www.dcnutrition.com).
60-18-4
C00082
6057
17895
TYR
5833
DB00135
N[C@@H](CC1=CC=C(O)C=C1)C(O)=O
C9H11NO3
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1
OUYCCCASQSFEME-QMMMGPOBSA-N
(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid
181.1885
181.073893223
-1.37
3
L-tyrosine
0
0
FDB000446
(-)-a-amino-p-hydroxyhydrocinnamate;(-)-a-amino-p-hydroxyhydrocinnamic acid;(-)-alpha-amino-p-hydroxyhydrocinnamate;(-)-alpha-amino-p-hydroxyhydrocinnamic acid;(s)-(-)-tyrosine;(s)-2-amino-3-(p-hydroxyphenyl)propionate;(s)-2-amino-3-(p-hydroxyphenyl)propionic acid;(s)-3-(p-hydroxyphenyl)alanine;(s)-tyrosine;(s)-a-amino-4-hydroxybenzenepropanoate;(s)-a-amino-4-hydroxybenzenepropanoic acid;(s)-a-amino-4-hydroxy-benzenepropanoate;(s)-a-amino-4-hydroxy-benzenepropanoic acid;(s)-alpha-amino-4-hydroxybenzenepropanoate;(s)-alpha-amino-4-hydroxybenzenepropanoic acid;(s)-alpha-amino-4-hydroxy-benzenepropanoate;(s)-alpha-amino-4-hydroxy-benzenepropanoic acid;2-amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoate;2-amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoic acid;3-(4-hydroxyphenyl)-l-alanine;4-hydroxy-l-phenylalanine;Benzenepropanoate;Benzenepropanoic acid;L-tyrosine;L-p-tyrosine;Tyr;Tyrosine;P-tyrosine;(2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;L-tyrosin;Y;(-)-α-amino-p-hydroxyhydrocinnamate;(-)-α-amino-p-hydroxyhydrocinnamic acid;(2s)-2-amino-3-(4-hydroxyphenyl)propanoate;(s)-α-amino-4-hydroxybenzenepropanoate;(s)-α-amino-4-hydroxybenzenepropanoic acid
PW_C000103
Tyr
396
19
686
20
1284
8
1979
2
4707
23
5665
107
5666
108
5886
105
8342
225
12348
151
42412
318
42413
315
77051
224
77754
341
78469
111
79046
128
79102
132
79236
253
82189
377
82473
378
117773
402
117774
403
121001
122
121589
124
122652
441
122653
442
122655
410
123566
135
124147
118
125226
476
125227
477
125229
444
127552
388
134
Oxoglutaric acid
HMDB0000208
Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207).
328-50-7
C00026
51
30915
2-KETOGLUTARATE
50
DB02926
OC(=O)CCC(=O)C(O)=O
C5H6O5
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
KPGXRSRHYNQIFN-UHFFFAOYSA-N
2-oxopentanedioic acid
146.0981
146.021523302
-0.44
2
oxoglutarate
0
-2
FDB003361
2-ketoglutarate;2-ketoglutaric acid;2-oxo-1,5-pentanedioate;2-oxo-1,5-pentanedioic acid;2-oxoglutarate;2-oxoglutaric acid;2-oxopentanedioate;2-oxopentanedioic acid;Oxoglutarate;Alpha-ketoglutaric acid;Oxoglutaric acid;A-ketoglutarate;A-ketoglutaric acid;Alpha-ketoglutarate;α-ketoglutarate;α-ketoglutaric acid
PW_C000134
AKG
15
2
42
3
141
4
146
8
499
18
673
31
1108
42
1263
5
1447
50
1455
26
1467
54
5375
103
5414
117
5438
118
5564
132
6008
147
6036
155
6069
157
6092
161
6482
178
6530
85
7471
222
7515
224
7519
151
8209
225
8374
220
11863
198
12681
289
77054
253
77135
133
77481
111
77523
112
77746
129
77967
345
77970
346
77976
327
77984
347
78425
334
80018
368
80694
135
113162
94
119972
406
120022
124
120084
407
120174
122
120552
414
120814
418
120989
408
121146
423
121152
424
121160
425
122757
120
122831
119
123186
450
123399
454
123554
374
123718
458
123724
459
123732
460
125357
479
125400
299
125455
481
125533
297
125800
489
125929
482
126900
501
126940
388
126993
206
127066
205
127255
506
127388
502
558
4-Hydroxyphenylpyruvic acid
HMDB0000707
4-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid that is involved in the tyrosine catabolism pathway. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase [EC 1.1.1.222] and is formed during tyrosine metabolism. The conversion from tyrosine to 4-HPPA is catalyzed by tyrosine aminotransferase. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction that converts 4-hydroxyphenylpyruvic acid to homogentisic acid. A deficiency in the catalytic activity of HPD is known to lead to tyrosinemia type III, an autosomal recessive disorder characterized by elevated levels of blood tyrosine and massive excretion of tyrosine derivatives into urine. It has been shown that hawkinsinuria, an autosomal dominant disorder characterized by the excretion of 'hawkinsin,' may also be a result of HPD deficiency (PMID: 11073718). There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common.
156-39-8
C01179
979
15999
P-HYDROXY-PHENYLPYRUVATE
954
DB07718
OC(=O)C(=O)CC1=CC=C(O)C=C1
C9H8O4
InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
KKADPXVIOXHVKN-UHFFFAOYSA-N
3-(4-hydroxyphenyl)-2-oxopropanoic acid
180.1574
180.042258744
-2.08
2
4-hydroxyphenylpyruvic acid
0
-1
FDB022193
(p-hydroxyphenyl)pyruvate;(p-hydroxyphenyl)pyruvic acid;(p-hydroxyphenyl)-pyruvate;(p-hydroxyphenyl)-pyruvic acid;3-(4-hydroxyphenyl)-2-oxo-propanoate;3-(4-hydroxyphenyl)-2-oxo-propanoic acid;3-(4-hydroxyphenyl)-2-oxopropionate;3-(4-hydroxyphenyl)-2-oxopropionic acid;3-(4-hydroxyphenyl)pyruvate;3-(4-hydroxyphenyl)pyruvic acid;3-(p-hydroxyphenyl)-2-oxopropionate;3-(p-hydroxyphenyl)-2-oxopropionic acid;3-(p-hydroxyphenyl)pyruvate;3-(p-hydroxyphenyl)pyruvic acid;4-hydroxy-a-oxobenzenepropanoate;4-hydroxy-a-oxobenzenepropanoic acid;4-hydroxy-alpha-oxobenzenepropanoate;4-hydroxy-alpha-oxobenzenepropanoic acid;4-hydroxyphenylpyruvate;4hppa;Hppa;Hydroxyphenylpyruvate;Hydroxyphenylpyruvic acid;Testacid;P-hydroxyphenylpyruvic;3-(4-hydroxy-phenyl)pyruvic acid;3-(p-hydroxyphenyl)-2-oxopropanoic acid;4-hydroxy alpha-oxobenzenepropanoic acid;4-hydroxyphenylpyruvic acid;P-hydroxyphenylpyruvic acid;(4-hydroxyphenyl)pyruvate;3-(4-hydroxy-phenyl)pyruvate;3-(p-hydroxyphenyl)-2-oxopropanoate;4-hydroxy a-oxobenzenepropanoate;4-hydroxy a-oxobenzenepropanoic acid;4-hydroxy alpha-oxobenzenepropanoate;4-hydroxy α-oxobenzenepropanoate;4-hydroxy α-oxobenzenepropanoic acid;P-hydroxyphenylpyruvate
PW_C000558
4HPPA
1287
8
1992
2
8343
225
12349
151
77039
224
77055
253
78471
111
79103
132
121004
122
121590
124
123569
135
124148
118
127553
388
95
L-Glutamic acid
HMDB0000148
Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid).
56-86-0
C00025
33032
16015
GLT
30572
DB00142
N[C@@H](CCC(O)=O)C(O)=O
C5H9NO4
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
WHUUTDBJXJRKMK-VKHMYHEASA-N
(2S)-2-aminopentanedioic acid
147.1293
147.053157781
-0.26
3
L-glutamic acid
0
-1
FDB012535
(2s)-2-aminopentanedioate;(2s)-2-aminopentanedioic acid;(s)-(+)-glutamate;(s)-(+)-glutamic acid;(s)-2-aminopentanedioate;(s)-2-aminopentanedioic acid;(s)-glutamate;(s)-glutamic acid;1-amino-propane-1,3-dicarboxylate;1-amino-propane-1,3-dicarboxylic acid;1-aminopropane-1,3-dicarboxylate;1-aminopropane-1,3-dicarboxylic acid;2-aminoglutarate;2-aminoglutaric acid;2-aminopentanedioate;2-aminopentanedioic acid;Aciglut;Aminoglutarate;Aminoglutaric acid;E;Glt;Glu;Glusate;Glut;Glutacid;Glutamicol;Glutamidex;Glutaminate;Glutaminic acid;Glutaminol;Glutaton;L-(+)-glutamate;L-(+)-glutamic acid;L-glu;L-glutamate;L-glutaminate;L-glutaminic acid;L-a-aminoglutarate;L-a-aminoglutaric acid;L-alpha-aminoglutarate;L-alpha-aminoglutaric acid;A-aminoglutarate;A-aminoglutaric acid;A-glutamate;A-glutamic acid;Alpha-aminoglutarate;Alpha-aminoglutaric acid;Alpha-glutamate;Alpha-glutamic acid;Acide glutamique;Acido glutamico;Acidum glutamicum;Glutamate;Glutamic acid;L-glutaminsaeure
PW_C000095
Glu
16
2
44
3
65
8
119
1
138
4
164
14
969
9
1105
42
1448
50
1456
26
1462
54
5323
111
5344
113
5415
117
5439
118
5565
132
5631
107
5632
108
5859
105
6006
147
6071
157
6191
94
6531
85
6838
187
6844
188
7092
72
7093
71
7165
205
7182
207
7514
224
7518
151
8208
225
8373
220
11792
198
11855
161
12004
222
12621
31
12683
289
12697
290
42348
315
42349
318
42845
320
77020
253
77332
133
77525
112
77971
346
77977
327
77981
347
78291
345
80649
135
120023
124
120040
122
120086
407
120347
406
120692
126
120816
418
121147
423
121153
424
121157
425
122833
119
122997
120
123299
443
123401
454
123719
458
123725
459
123729
460
125401
299
125418
297
125457
481
125667
479
125769
301
125802
489
126941
388
126995
206
127162
501
127257
506
140738
84
140739
597
1148
Pyridoxal 5'-phosphate
HMDB0001491
This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). -- Pubchem; Pyridoxal-phosphate (PLP, pyridoxal-5'-phosphate) is a cofactor of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. -- Wikipedia.
54-47-7
C00018
1051
18405
PYRIDOXAL_PHOSPHATE
1022
DB00114
CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O
C8H10NO6P
InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
NGVDGCNFYWLIFO-UHFFFAOYSA-N
[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
247.1419
247.024573569
-1.64
3
pyridoxal phosphate
0
-2
FDB021820
Apolon b6;Biosechs;Codecarboxylase;Coenzyme b6;Hairoxal;Hexermin-p;Hi-pyridoxin;Hiadelon;Himitan;Pal-p;Plp;Phosphopyridoxal;Phosphopyridoxal coenzyme;Pidopidon;Piodel;Pydoxal;Pyridoxal 5'-phosphate;Pyridoxal 5-phosphate;Pyridoxal p;Pyridoxal phosphate;Pyridoxal-p;Pyridoxyl phosphate;Pyromijin;Sechvitan;Vitahexin-p;Vitazechs;3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate;Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphoric acid ester;Pyridoxal 5'-(dihydrogen phosphate);Pyridoxal-5'-phosphate;Pyridoxal 5'-phosphoric acid;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid;Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphate ester;Pyridoxal 5'-(dihydrogen phosphoric acid);Pyridoxal 5-phosphoric acid;Pyridoxal phosphoric acid;Pyridoxal-5'-phosphoric acid
PW_C001148
Pyr-5'P
18
2
32
4
45
3
51
8
122
1
401
19
696
20
1110
42
1450
50
1458
26
2120
10
2150
49
5325
111
5416
117
5421
103
5441
118
5455
120
5567
132
5581
133
6533
85
7018
160
7167
205
7216
212
7222
213
11858
161
12175
151
12623
31
12628
18
12684
289
12689
290
77017
253
77037
225
77041
293
77052
224
77526
112
77764
341
77973
346
77979
327
78292
345
78855
332
78862
331
80696
135
98630
7
119912
122
120024
124
120029
406
120087
407
120817
418
121149
423
121155
424
122069
123
122076
383
122834
119
123402
454
123721
458
123727
459
124620
447
124627
398
125302
297
125402
299
125407
479
125458
481
125803
489
126224
298
126231
495
126942
388
126947
501
126996
206
127258
506
127786
513
127793
390
123
L-Aspartic acid
HMDB0000191
Aspartic acid (Asp, D), also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong (Wikipedia). Aspartic acid is a nonessential amino acid that is made from glutamic acid by enzymes using vitamin B6. The amino acid has important roles in the urea cycle and DNA metabolism. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, with the amino acid phenylalanine, is a part of a new natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners, and is probably safe in normal doses to all except phenylketonurics. The jury is still out on the long-term effects it has on many brain neurohormones. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Many claims have been made for the special value of administering aspartic acid in the form of potassium and magnesium salts. Since aspartic acid is relatively nontoxic, studies are now in progress to elucidate its pharmacological and therapeutic roles (http://www.dcnutrition.com/AminoAcids).
56-84-8
C00049
44367445
17053
L-ASPARTATE
5745
DB00128
N[C@@H](CC(O)=O)C(O)=O
C4H7NO4
InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1
CKLJMWTZIZZHCS-REOHCLBHSA-N
(2S)-2-aminobutanedioic acid
133.1027
133.037507717
0.03
3
L-aspartic acid
0
-1
FDB012567
Asp;(+)-aspartate;(+)-aspartic acid;(2s)-aspartate;(2s)-aspartic acid;(l)-aspartate;(l)-aspartic acid;(r)-2-aminosuccinate;(s)-(+)-aspartate;(s)-(+)-aspartic acid;(s)-2-aminosuccinate;(s)-2-aminosuccinic acid;(s)-aminobutanedioate;(s)-aminobutanedioic acid;(s)-aspartate;(s)-aspartic acid;(s)-amino-butanedioate;(s)-amino-butanedioic acid;2-amino-3-methylsuccinate;2-amino-3-methylsuccinic acid;2-aminosuccinate;2-aminosuccinic acid;Aminosuccinate;Asparagate;Asparagic acid;Asparaginate;Asparaginic acid;Asparatate;Aspartate;H-asp-oh;L-(+)-aspartate;L-(+)-aspartic acid;L-aminosuccinate;L-aminosuccinic acid;L-asparagate;L-asparagic acid;L-asparaginate;L-asparaginic acid;L-aspartate;Alpha-aminosuccinate;Alpha-aminosuccinic acid;(s)-2-aminobutanedioic acid;Aspartic acid;D;L-asparaginsaeure;(s)-2-aminobutanedioate
PW_C000123
Asp
48
8
93
9
1101
3
1103
4
1104
42
1994
2
5663
107
5664
108
6851
188
7570
160
8185
225
11802
198
12686
290
12704
291
42363
318
42364
315
77323
111
77510
132
77532
113
78288
133
78289
345
79307
112
80699
135
119878
232
119881
117
120037
122
120421
124
120809
406
120813
418
123057
118
123394
120
123398
454
125415
297
125795
479
125799
489
126955
205
127250
501
127254
506
127555
388
148
Oxalacetic acid
HMDB0000223
Oxaloacetic acid, also known as oxosuccinic acid or oxalacetic acid, is a four-carbon dicarboxylic acid appearing as an intermediate of the citric acid cycle. In vivo, oxaloacetate (the ionized form of oxaloacetic acid) is formed by the oxidation of L-malate, catalyzed by malate dehydrogenase, and reacts with Acetyl-CoA to form citrate, catalyzed by citrate synthase.(wikipedia) A class of ketodicarboxylic acids derived from oxalic acid. Oxaloacetic acid is an intermediate in the citric acid cycle and is converted to aspartic acidD by a transamination reaction.
328-42-7
C00036
970
30744
OXALACETIC_ACID
945
OC(=O)CC(=O)C(O)=O
C4H4O5
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
KHPXUQMNIQBQEV-UHFFFAOYSA-N
2-oxobutanedioic acid
132.0716
132.005873238
-0.36
2
oxalacetate
0
-2
FDB001479
2-ketosuccinate;2-ketosuccinic acid;2-oxobutanedioate;2-oxobutanedioic acid;2-oxosuccinate;2-oxosuccinic acid;Ketosuccinate;Ketosuccinic acid;Oaa;Oxalacetate;Oxaloacetate;Oxaloacetic acid;Oxaloethanoate;Oxaloethanoic acid;Oxosuccinate;Oxosuccinic acid;A-ketosuccinate;A-ketosuccinic acid;Alpha-ketosuccinate;Alpha-ketosuccinic acid;3-carboxy-3-oxopropanoic acid;Keto-succinic acid;Oxalacetic acid;Oxobutanedioic acid;3-carboxy-3-oxopropanoate;Keto-succinate;Oxobutanedioate
PW_C000148
Oaa
25
4
96
9
111
5
1099
3
1109
42
1113
2
1688
8
5371
103
5448
120
5574
133
6033
155
6088
161
6478
178
7468
222
7513
224
7517
151
8372
220
8378
225
11744
117
11891
160
12707
291
12717
292
43792
322
77508
132
77533
113
77538
334
77958
112
78009
111
78290
345
80015
368
80700
135
119964
406
120048
408
120062
126
120180
122
120419
124
120815
418
121207
407
122799
374
122813
443
123055
118
123400
454
123777
119
125354
479
125426
482
125439
301
125537
297
125801
489
125807
299
126897
501
126965
502
126977
207
127070
205
127256
506
127261
388
1065
Oxygen
HMDB0001377
Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).
7782-44-7
C00007
977
15379
CPD-6641
952
O=O
O2
InChI=1S/O2/c1-2
MYMOFIZGZYHOMD-UHFFFAOYSA-N
dioxygen
31.9988
31.989829244
0
singlet oxygen
0
0
FDB022589
Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948
PW_C001065
O2
95
9
110
5
245
16
500
18
505
8
549
14
625
28
638
3
649
10
674
31
688
20
754
15
763
4
769
33
836
2
1375
49
2016
24
2531
22
2803
29
4260
42
4747
13
5467
123
5480
125
5493
126
5508
127
5809
108
5973
147
6129
159
7006
188
7032
163
7050
160
7319
213
7533
210
7560
212
8395
151
11816
216
11864
198
11883
215
11894
211
12057
225
12063
164
12247
286
12279
226
12325
249
12706
291
12716
292
13004
298
13016
300
13026
301
13038
302
13260
223
42276
17
42657
315
76910
293
77044
294
77214
134
77350
111
77363
130
77377
331
77395
332
77497
113
77512
115
77537
334
77626
336
77723
337
77736
112
77747
129
77756
341
77805
114
77812
133
78070
329
78151
132
78381
345
78805
343
79111
360
120047
408
120383
122
120426
405
120542
407
120553
414
120594
409
120601
406
120883
415
121045
124
121104
383
121605
434
121656
429
122117
382
122573
418
122689
384
122798
374
122822
443
123027
135
123060
376
123128
447
123139
136
123163
448
123176
119
123187
450
123219
137
123226
120
123459
451
123609
118
123669
398
124163
469
124214
464
124669
399
125145
454
125275
121
125425
482
125706
478
125731
483
125737
297
125740
479
125884
481
126100
299
126272
484
126522
495
126721
489
126825
480
126964
502
126986
207
127198
209
127214
208
127219
205
127222
501
127305
504
127345
206
127557
388
127574
515
127835
389
128081
395
128095
390
128312
506
128432
391
84
Homogentisic acid
HMDB0000130
Homogentisic acid, also known as melanic acid, is an intermediate in the breakdown or catabolism of tyrosine and phenylalanine. It is generated from the compound p-hydroxyphenylpyruvate through the enzyme p-hydroxyphenylpyruvate dehydrogenase. The resulting homogentisic acid is then broken down into 4-maleylacetoacetate via the enzyme homogentisate 1,2-dioxygenase. Homogentisic acid is also found in other organisms. For instance, it can found in Arbutus unedo (strawberry-tree) honey, in the bacterial plant pathogen Xanthomonas campestris as well as in the yeast Yarrowia lipolytica where it is associated with the production of brown pigments. Homogentisic acid can be oxidatively dimerized to form hipposudoric acid, one of the main constituents of the 'blood sweat' of hippopotamuses. When present in sufficiently high levels, homogentisic acid can function as an osteotoxin and a renal toxin. An osteotoxin is a substance that causes damage to bones and/or joints. A renal toxin causes damage to the kidneys. Chronically high levels of homogentisic acid are associated with alkaptonuria (OMIM: 203500), an inborn error of metabolism. Alkaptonuria is a rare inherited genetic disorder in which the body cannot process the amino acids phenylalanine and tyrosine. It is caused by a mutation in the enzyme homogentisate 1,2-dioxygenase (EC 1.13.11.5), which leads to an accumulation of homogentisic acid in the blood and tissues. Homogentisic acid and its oxidized form benzoquinone acetic acid are excreted in the urine, giving it an unusually dark color. The accumulating homogentisic acid (and benzoquinone acetic acid) causes damage to cartilage (ochronosis, leading to osteoarthritis) and heart valves as well as precipitating as kidney stones and stones in other organs. More specifically, homogentisic acid can be converted to benzoquinone acetic acid (BQA), and the resulting BQA can be readily converted to polymers that resemble the dark skin pigment melanin. These polymers are deposited in the collagen, a connective tissue protein, of particular tissues such as cartilage. This process is called ochronosis (as the tissue looks ochre); ochronotic tissue is stiffened and unusually brittle, impairing its normal function and causing damage. Homogentisic acid is the primary precursor of melanin synthesis in Vibrio cholerae.
451-13-8
C00544
780
44747
759
DB08327
OC(=O)CC1=C(O)C=CC(O)=C1
C8H8O4
InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
IGMNYECMUMZDDF-UHFFFAOYSA-N
2-(2,5-dihydroxyphenyl)acetic acid
168.1467
168.042258744
-1.32
3
homogentisic acid
0
-1
FDB021899
(2,5-dihydroxyphenyl)-acetate;(2,5-dihydroxyphenyl)-acetic acid;2,5-dihydroxy-a-toluate;2,5-dihydroxy-a-toluic acid;2,5-dihydroxy-alpha-toluate;2,5-dihydroxy-alpha-toluic acid;2,5-dihydroxy-benzeneacetate;2,5-dihydroxy-benzeneacetic acid;2,5-dihydroxyphenylacetate;2,5-dihydroxyphenylacetic acid;Alcapton;Homogentisate;Homogentisate acid;Homogentisinate;Homogentisinic acid;Melanic acid;2-(3,6-dihydroxyphenyl)acetic acid;2-(3,6-dihydroxyphenyl)acetate
PW_C000084
HMGNCA
1295
8
1996
2
9059
151
78478
111
79104
132
121012
122
121592
124
123577
135
124150
118
127558
388
1316
Carbon dioxide
HMDB0001967
Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.
124-38-9
C00011
280
16526
274
O=C=O
CO2
InChI=1S/CO2/c2-1-3
CURLTUGMZLYLDI-UHFFFAOYSA-N
methanedione
44.0095
43.989829244
0.63
0
carbon dioxide
0
0
DBMET00423
FDB014084
Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744
PW_C001316
CO2
50
8
121
1
204
4
480
13
503
18
640
3
677
31
695
20
806
5
1133
43
1638
49
1745
2
2551
17
3144
70
5283
103
5320
111
5750
108
5771
101
5968
100
6026
155
6078
161
6471
178
6637
107
6922
190
7017
160
7035
163
7061
188
7163
205
7308
198
7333
213
7461
222
7530
210
8215
225
8223
151
9158
249
11849
277
11908
170
12464
226
12688
290
42626
315
43523
318
76994
293
77122
133
77170
132
77470
333
77739
112
77750
129
77763
341
78077
134
78405
356
78427
334
78941
331
79227
130
80008
368
80675
119
80717
135
94836
384
113291
391
115549
121
119954
406
120089
122
120155
407
120364
412
120556
414
120833
419
120922
124
120991
408
121284
125
121505
383
122744
120
123011
446
123190
450
123418
455
123489
118
123556
374
123855
136
124063
398
125344
479
125460
297
125516
481
125824
490
125870
299
125931
482
126280
480
126887
501
127052
206
127277
507
127331
388
127390
502
140798
185
8133
Fe3+
HMDB0012943
Fe3+, also known as ferric ion or fe(iii), belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Fe3+ exists in all living organisms, ranging from bacteria to humans. 2,3-Dihydroxybenzoylserine and fe3+ can be biosynthesized from ferric enterobactin through its interaction with the enzyme enterochelin esterase. Outside of the human body, fe3+ can be found in a number of food items such as bamboo shoots, catjang pea, chickpea, and orange bell pepper. This makes fe3+ a potential biomarker for the consumption of these food products. The major activity of supplemental iron is in the prevention and treatment of iron deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic and cognition-enhancing activities.
20074-52-6
C14819
29936
29034
CPD-10134
27815
[Fe+3]
Fe
InChI=1S/Fe/q+3
VTLYFUHAOXGGBS-UHFFFAOYSA-N
iron(3+) ion
55.845
55.934942133
0
iron(3+) ion
3
3
C14819
Fe(iii);Ferric ion;Iron(3+);Fe (iii) ion;Fe(3+);Ferric iron;Iron, ion (fe(3+))
PW_C008133
Fe3+
1230
3
1296
8
1420
49
1997
2
7042
163
11841
160
12675
151
77431
111
77450
331
78599
112
78721
132
120949
407
121013
122
121127
383
121593
124
123515
119
123578
135
123696
398
124151
118
125890
481
127351
206
127559
388
140718
18
1376
Maleylacetoacetic acid
HMDB0002052
4-Maleylacetoacetate is an intermediate in the metabolism of tyrosine. Homogentisate 1,2-dioxygenase is the enzyme, which catalyzes the conversion of homogentisate to 4-maleylacetoacetate. Homogentisate 1,2-dioxygenase or HGD is involved in the catabolism of aromatic rings, more specifically in the break down of the amino acids tyrosine and phenylalanine.
5698-52-2
C01036
5280393
47904
4-MALEYL-ACETOACETATE
4444078
OC(=O)CC(=O)CC(=O)\C=C/C(O)=O
C8H8O6
InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1-
GACSIVHAIFQKTC-UPHRSURJSA-N
(2Z)-4,6-dioxooct-2-enedioic acid
200.1455
200.032087988
-2.08
2
maleylacetoacetic acid
0
-2
FDB022817
4-maleylacetoacetate;4-maleylacetoacetic acid;Maleylacetoacetate
PW_C001376
MalaceA
1298
8
1999
2
9061
151
78480
111
79105
132
121015
122
121595
124
123580
135
124153
118
127561
388
981
4-Fumarylacetoacetic acid
HMDB0001268
Fumarylacetoacetate is an intermediate in the metabolism of tyrosine. Fumarylacetoacetate hydrolase (FAH) is an enzyme which catalyzes the hydrolysis of 4-fumarylacetoacetate into fumarate and acetoacetate. FAH is the last enzyme in the tyrosine catabolism pathway. FAH deficiency is associated with Type 1 hereditary tyrosinemia.
28613-33-4
C01061
5280398
30907
4-FUMARYL-ACETOACETATE
4444081
OC(=O)CC(=O)CC(=O)\C=C\C(O)=O
C8H8O6
InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1+
GACSIVHAIFQKTC-OWOJBTEDSA-N
(2E)-4,6-dioxooct-2-enedioic acid
200.1455
200.032087988
-2.08
2
4-fumarylacetoacetic acid
0
-2
FDB022522
(e)-4,6-dioxo-2-octenedioate;(e)-4,6-dioxo-2-octenedioic acid;4-fumaryl-acetoacetate;4-fumarylacetoacetate;Fumarylacetoacetate;Fumarylacetoacetone
PW_C000981
Fumaryl
1300
8
2001
2
9063
151
78482
111
79106
132
121017
122
121596
124
123582
135
124154
118
127562
388
1420
Water
HMDB0002111
Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).
7732-18-5
C00001
962
15377
937
O
H2O
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
18.0153
18.010564686
1
water
0
0
FDB013390
Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;Wasser
PW_C001420
H2O
55
8
94
9
109
5
139
4
151
3
162
14
481
13
526
15
624
28
652
10
691
20
770
33
823
18
838
2
1094
31
1377
49
1465
54
1590
43
2018
24
2532
22
2678
60
2727
46
2778
17
2805
29
3143
70
3164
72
3634
61
4598
36
4727
37
4941
93
5030
27
5156
7
5195
97
5214
100
5227
94
5236
103
5297
105
5319
111
5343
113
5355
112
5402
110
5470
123
5483
125
5492
126
5507
127
5534
130
5537
114
5541
129
5591
135
5608
118
5622
108
5691
6
5759
140
5778
101
5841
143
5853
146
5877
107
5890
95
5910
147
5940
151
6032
155
6059
157
6087
161
6123
163
6133
159
6215
1
6218
166
6477
178
6507
180
6600
152
6713
117
6840
188
6888
160
7162
205
7181
207
7193
206
7211
211
7228
213
7238
214
7243
215
7295
198
7350
216
7388
210
7401
212
7467
222
7492
224
7500
190
7588
170
8201
225
8237
226
8414
162
9265
26
11850
277
11922
164
12011
281
12213
285
12250
286
12264
287
12327
249
12520
227
12632
65
12693
290
12705
291
12715
292
13007
298
13019
300
13025
301
13037
302
13261
223
13327
294
15340
308
42327
315
42695
318
43691
322
76914
293
77019
253
77102
132
77131
133
77215
134
77378
331
77397
332
77471
333
77516
115
77536
334
77628
336
77722
337
77759
341
77816
343
77982
347
78071
329
78235
352
78242
353
78270
356
79113
360
80014
368
80039
370
80591
228
80656
119
93830
383
94794
384
110557
390
110639
391
115844
398
119879
232
119915
122
119963
406
120008
407
120046
408
120113
124
120365
412
120430
405
120438
409
120606
415
120794
414
121158
425
121240
429
121351
121
121381
419
121607
434
122118
382
122384
436
122753
120
122797
374
122804
443
123012
446
123064
376
123072
137
123131
447
123142
136
123162
448
123231
451
123384
450
123730
460
123810
464
123940
455
124165
469
124670
399
124938
471
124945
472
125305
297
125353
479
125386
481
125424
482
125480
299
125682
483
125707
478
125745
487
126054
490
126238
495
126273
484
126764
480
126896
501
126963
502
127017
388
127177
208
127199
209
127227
504
127506
507
127576
515
127836
389
128082
395
128176
513
140674
790
140675
834
140755
185
42
Acetoacetic acid
HMDB0000060
Acetoacetic acid (AcAc) is a weak organic acid that can be produced in the human liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis). It is then partially converted into acetone by decarboxylation and excreted either in urine or through respiration. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first two weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies are utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life (PMID: 3884391). The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected.
541-50-4
C00164
96
15344
3-KETOBUTYRATE
94
DB01762
CC(=O)CC(O)=O
C4H6O3
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
WDJHALXBUFZDSR-UHFFFAOYSA-N
3-oxobutanoic acid
102.0886
102.031694058
0.37
1
acetoacetic acid
0
-1
FDB021801
3-ketobutyrate;3-ketobutyric acid;3-oxo-butanoate;3-oxo-butanoic acid;3-oxobutyrate;3-oxobutyric acid;Acetoacetate;Diacetate;Diacetic acid;3-oxobutanoic acid;Beta-ketobutyric acid;3-oxobutanoate;B-ketobutyrate;B-ketobutyric acid;Beta-ketobutyrate;β-ketobutyrate;β-ketobutyric acid
PW_C000042
LIN
597
4
1053
3
1302
8
2003
2
6929
160
7360
163
9066
151
15242
222
77694
133
77835
132
78227
112
78483
111
120511
406
120767
407
121019
122
121598
124
123117
120
123363
119
123584
135
124156
118
126609
299
127564
388
88
Fumaric acid
HMDB0000134
Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia).
110-17-8
C00122
21883788
18012
FUM
10197150
DB04299
OC(=O)\C=C\C(O)=O
C4H4O4
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
VZCYOOQTPOCHFL-OWOJBTEDSA-N
(2E)-but-2-enedioic acid
116.0722
116.010958616
-0.68
2
fumaric acid
0
-2
FDB003291
(2e)-but-2-enedioate;(2e)-but-2-enedioic acid;(e)-2-butenedioate;(e)-2-butenedioic acid;2-(e)-butenedioate;2-(e)-butenedioic acid;Allomaleate;Allomaleic acid;Boletate;Boletic acid;Fc 33;Fumarate;Fumaric acid;Lichenate;Lichenic acid;Sodium fumarate;Trans-1,2-ethylenedicarboxylate;Trans-1,2-ethylenedicarboxylic acid;Trans-2-butenedioate;Trans-2-butenedioic acid;Trans-butenedioate;Trans-butenedioic acid;(2e)-2-butenedioic acid;E297;Fumarsaeure;Trans-but-2-enedioic acid;(2e)-2-butenedioate;Trans-but-2-enedioate
PW_C000088
Fumarat
102
8
254
17
2004
2
5053
4
5388
102
6047
156
6107
162
6458
107
6459
108
6492
179
6763
117
6837
166
7480
223
9065
151
11804
198
12713
290
42400
322
42496
318
42497
315
77148
134
77466
111
79107
132
80027
369
117808
133
119989
384
120043
122
121599
124
122661
406
122772
121
122794
135
124157
118
125236
120
125369
480
125421
297
126793
479
126911
391
126960
205
127565
388
128391
501
353
Calcium
HMDB0000464
Calcium is essential for the normal growth and maintenance of bones and teeth, and calcium requirements must be met throughout life. Requirements are greatest during periods of growth, such as childhood, during pregnancy and when breast-feeding. Long-term calcium deficiency can lead to osteoporosis, in which the bone deteriorates and there is an increased risk of fractures. Adults need between 1,000 and 1,300 mg of calcium in their daily diet. Calcium is essential for living organisms, particularly in cell physiology, and is the most common metal in many animals. Physiologically, it exists as an ion in the body. Calcium combines with phosphorus to form calcium phosphate in the bones and teeth. It is essential for the normal functioning of nerves and muscles and plays a role in blood coagulation (as factor IV) and in many enzymatic processes. Calcium is an important component of a healthy diet. A deficit can affect bone and tooth formation, while overretention can cause kidney stones. Vitamin D is needed to absorb calcium. Dairy products, such as milk and cheese, are a well-known source of calcium. However, some individuals are allergic to dairy products and even more people, particularly those of non-European descent, are lactose-intolerant, leaving them unable to consume dairy products. Fortunately, many other good sources of calcium exist. These include: seaweeds such as kelp, wakame and hijiki; nuts and seeds (like almonds and sesame); beans; amaranth; collard greens; okra; rutabaga; broccoli; kale; and fortified products such as orange juice and soy milk. Calcium has also been found to assist in the production of lymphatic fluids.
14127-61-8
C00076
271
29108
CA%2b2
266
DB01373
[Ca++]
Ca
InChI=1S/Ca/q+2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N
calcium(2+) ion
40.078
39.962591155
0
calcium(2+) ion
2
2
FDB003513
Ca;Calcium element;Ca(2+);Ca2+;Calcium ion;Calcium, doubly charged positive ion
PW_C000353
Ca2+
276
16
303
8
553
14
601
2
941
15
993
21
997
35
1046
3
1163
46
1164
47
1478
49
1491
42
1552
43
2116
58
2138
17
2796
18
2937
9
3159
71
3160
72
3942
29
4186
66
4782
10
4822
28
5340
111
5780
101
7179
205
7232
211
7258
160
7281
190
11774
213
11837
198
11842
210
12198
164
12215
285
15288
151
15350
308
69336
1
77389
331
77600
115
78154
132
78266
356
78526
345
78724
130
78908
114
80413
74
80589
228
81826
51
120220
122
120465
405
121049
124
121300
418
121377
419
121850
383
121923
125
122370
409
122895
135
123099
376
123613
118
123870
454
123936
455
124403
398
124476
136
124924
137
125571
297
125711
478
125981
489
126009
299
126050
490
126533
495
127203
209
127434
506
127460
388
127502
507
128105
390
140676
790
140677
834
140695
50
423
Magnesium
HMDB0000547
Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.
22537-22-0
C00305
888
18420
13-HYDROXY-MAGNESIUM-PROTOPORP
865
DB01378
[Mg++]
Mg
InChI=1S/Mg/q+2
JLVVSXFLKOJNIY-UHFFFAOYSA-N
magnesium(2+) ion
24.305
23.985041898
0
magnesium(2+) ion
2
2
FDB003518
Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+
PW_C000423
Mg2+
86
8
227
4
268
16
476
2
727
26
811
5
819
18
883
22
936
39
983
3
992
21
1167
46
1483
49
1529
43
1764
14
2124
10
2411
59
2942
23
3126
29
3373
7
4540
31
4774
91
4869
54
4974
56
5253
104
5329
111
5356
112
5376
103
5906
147
5934
151
6038
155
6094
161
6250
166
6484
178
6594
164
6881
160
6979
199
7170
205
7194
206
7227
213
7233
211
7250
214
7310
216
7313
198
7473
222
11763
132
11843
210
12312
225
12324
249
12513
288
12581
226
12729
290
15275
285
15337
308
77137
133
77236
329
77937
336
78393
334
78417
335
78489
115
78522
331
78536
356
78574
130
80020
368
80045
184
80048
372
80623
118
80654
135
80865
15
80965
253
81841
51
93832
383
94900
27
108596
223
110559
390
115687
398
119974
406
120070
122
120247
382
120702
407
120981
408
121181
124
121265
429
121319
419
121924
125
122086
405
122408
422
122759
120
122921
399
123307
119
123546
374
123835
464
123889
455
124477
136
124637
376
124978
375
125447
297
125598
484
125669
479
125777
481
125921
482
125947
299
125973
495
126000
490
126243
478
126553
491
126753
300
127125
389
127164
501
127380
502
127407
388
127451
507
127804
209
128125
508
128347
395
140773
891
210
Tyramine
HMDB0000306
Tyramine is a monoamine compound derived from the amino acid tyrosine. Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals.
51-67-2
C00483
5610
15760
CPD-7650
5408
NCCC1=CC=C(O)C=C1
C8H11NO
InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
DZGWFCGJZKJUFP-UHFFFAOYSA-N
4-(2-aminoethyl)phenol
137.179
137.084063979
-1.38
2
tyramine
0
1
FDB000433
2-(4'-hydroxyphenyl)ethylamine;2-(4-hydroxyphenyl)ethylamine;2-(p-hydroxyphenyl)ethylamine;4- (2-aminoethyl)-phenol;4-(2-aminoethyl)-phenol;4-(2-aminoethyl)-phenol(thyramin);4-(2-aminoethyl)phenol;4-hydroxy-benzeneethanamine;4-hydroxy-b-phenylethylamine;4-hydroxy-beta-phenylethylamine;4-hydroxyphenethylamine;4-hydroxyphenylethylamine;P-hydroxy-b-phenethylamine;P-hydroxy-b-phenylethylamine;P-hydroxy-beta-phenethylamine;P-hydroxy-beta-phenylethylamine;P-hydroxyphenethylamine;P-hydroxyphenylethylamine;P-tyramine;P-beta-aminoethylphenol;Systogene;Tenosin-wirkstoff;Tocosine;Tyramin;Tyramine base;Tyrosamine;Uteramine;A-(4-hydroxyphenyl)-b-aminoethane;Alpha-(4-hydroxyphenyl)-beta-aminoethane;Alpha.-(4-hydroxyphenyl)-beta-aminoethane;B-(4-hydroxyphenyl)ethylamine;Beta-(4-hydroxyphenyl)ethylamine;P-(2-aminoethyl)-phenol;P-(2-aminoethyl)phenol;4-hydroxy-β-phenylethylamine;β-(4-hydroxyphenyl)ethylamine
PW_C000210
Tyramin
2008
2
77040
293
79108
132
121601
124
124159
118
127567
388
2411
Homovanillin
HMDB0005175
3 -Methoxy-4-hydroxyphenylacetaldehyde is an intermediary aldehyde of dopamine metabolism, metabolized by the class I human liver alcohol dehydrogenases (ADHs). ADH catalyzes both ethanol and acetaldehyde, and the dopamine intermediates compete for the same site of ADH, a basis for the ethanol-induced in vivo alterations of dopamine metabolism. (PMID 2432930).
5703-24-2
C05581
151276
28111
133331
COC1=C(O)C=CC(CC=O)=C1
C9H10O3
InChI=1S/C9H10O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,5-6,11H,4H2,1H3
GOQGGGANVKPMNH-UHFFFAOYSA-N
2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
166.1739
166.062994186
-1.76
1
homovanillin
0
0
FDB023632
(4-hydroxy-3-methoxyphenyl)acetaldehyde;2-(4-hydroxy-3-methoxyphenyl) ethanal;4-hydroxy-3-methoxy-benzeneacetaldehyde;4-hydroxy-3-methoxybenzeneacetaldehyde;Hmpal;3-methoxy-4-hydroxyphenylacetaldehyde;Homovanillin
PW_C002411
Homovan
2010
2
79109
132
121603
124
124161
118
127569
388
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H28N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-N
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
743.405
743.075452041
-2.22
8
1-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
0
-3
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
140709
168
13
p-Hydroxyphenylacetic acid
HMDB0000020
p-Hydroxyphenylacetic acid is an oxidative deaminated metabolite of p-tyramine. Also a metabolite of tyrosine via enteric bacteria. The bacterial origin of this compound was confirmed by the finding that this compound in urine decreased significantly after the use of the antibiotic neomycin.
156-38-7
C00642
127
18101
4-HYDROXYPHENYLACETATE
124
OC(=O)CC1=CC=C(O)C=C1
C8H8O3
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
XQXPVVBIMDBYFF-UHFFFAOYSA-N
2-(4-hydroxyphenyl)acetic acid
152.1473
152.047344122
-1.33
2
4-hydroxyphenylacetic acid
0
-1
FDB010534
(4-hydroxy-phenyl)-essigsaeure;(4-hydroxy-phenyl)-acetate;(4-hydroxy-phenyl)-acetic acid;(4-hydroxyphenyl)acetate;(4-hydroxyphenyl)acetic acid;(p-hydroxyphenyl)acetate;(p-hydroxyphenyl)acetic acid;(p-hydroxyphenyl)-acetate;(p-hydroxyphenyl)-acetic acid;4-hydroxy-benzeneacetate;4-hydroxy-benzeneacetic acid;4-hydroxybenzeneacetate;4-hydroxybenzeneacetic acid;4-hydroxyphenylacetate;4-hydroxyphenylacetic acid;4-hydroxyphenyl-acetic acid;Parahydroxy phenylacetate;Parahydroxy phenylacetic acid;Parahydroxyphenylacetate;P-hydroxyphenylacetate;P-hydroxyphenylacetic acid;4-carboxymethylphenol
PW_C000013
p-Hpaa
2014
2
79110
132
121604
124
124162
118
127571
388
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
ACFIXJIJDZMPPO-NNYOXOHSSA-N
{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
745.4209
745.091102105
-2.14
9
nadph
0
-4
FDB021909
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
140706
168
52
Dopamine
HMDB0000073
Dopamine is a member of the catecholamine family of neurotransmitters in the brain and is a precursor to epinephrine (adrenaline) and norepinephrine (noradrenaline). Dopamine is synthesized in the body (mainly by nervous tissue and adrenal glands) first by the hydration of the amino acid tyrosine to DOPA by tyrosine hydroxylase and then by the decarboxylation of DOPA by aromatic-L-amino-acid decarboxylase. Dopamine is a major transmitter in the extrapyramidal system of the brain, and important in regulating movement. A family of receptors (dopamine receptors) mediates its action, which plays a major role in reward-motivated behaviour. Dopamine has many other functions outside the brain. In blood vessels, dopamine inhibits norepinephrine release and acts as a vasodilator (at normal concentrations); in the kidneys, it increases sodium excretion and urine output; in the pancreas, it reduces insulin production; in the digestive system, it reduces gastrointestinal motility and protects intestinal mucosa; and in the immune system, it reduces the activity of lymphocytes. Parkinson's disease, a degenerative condition causing tremor and motor impairment, is caused by a loss of dopamine-secreting neurons in an area of the midbrain called the substantia nigra. There is evidence that schizophrenia involves altered levels of dopamine activity, and most antipsychotic drugs used to treat this are dopamine antagonists, which reduce dopamine activity. Attention deficit hyperactivity disorder, bipolar disorder, and addiction are also characterized by defects in dopamine production or metabolism. It has been suggested that animals derived their dopamine-synthesizing machinery from bacteria via horizontal gene transfer that may have occurred relatively late in evolutionary time. This is perhaps a result of the symbiotic incorporation of bacteria into eukaryotic cells that gave rise to mitochondria. Dopamine is elevated in the urine of people who consume bananas. When present in sufficiently high levels, dopamine can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of dopamine are associated with neuroblastoma, Costello syndrome, leukemia, phaeochromocytoma, aromatic L-amino acid decarboxylase deficiency, and Menkes disease (MNK). High levels of dopamine can lead to hyperactivity, insomnia, agitation and anxiety, depression, delusions, excessive salivation, nausea, and digestive problems.
51-61-6
C03758
681
18243
DOPAMINE
661
DB00988
NCCC1=CC(O)=C(O)C=C1
C8H11NO2
InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2
VYFYYTLLBUKUHU-UHFFFAOYSA-N
4-(2-aminoethyl)benzene-1,2-diol
153.1784
153.078978601
-1.31
3
dopamine
0
1
FDB012163
2-(3,4-dihydroxyphenyl)ethylamine;3,4-dihydroxyphenethylamine;3,4-dihydroxyphenylethylamine;3-hydroxytyramine;4-(2-aminoethyl)-1,2-benzenediol;4-(2-aminoethyl)-pyrocatechol;4-(2-aminoethyl)catechol;4-(2-aminoethyl)pyrocatechol;Deoxyepinephrine;Dopamin;Dopamine;Dopaminum;Dopastat;Dophamine;Dynatra;Hydroxytyramin;Hydroxytyramine;Intropin;Oxytyramine;Revivan;A-(3,4-dihydroxyphenyl)-b-aminoethane;Alpha-(3,4-dihydroxyphenyl)-beta-aminoethane;4-(2-aminoethyl)benzene-1,2-diol;Dopamina
PW_C000052
LDP
400
19
694
20
2017
24
2080
2
3187
74
3188
71
4161
15
77043
293
77762
341
79112
360
79138
132
80050
98
80051
184
121606
434
121637
124
124164
469
124195
118
127575
515
127611
388
514
Copper
HMDB0000657
Copper is an essential nutrient to all higher plants and animals. Physiologically, it exists as an ion in the body. In animals, it is found primarily in the bloodstream, as a cofactor in various enzymes, and in copper-based pigments. In the body, copper shifts between the cuprous (Cu1+) and cupric (Cu2+) forms, though the majority of the body's copper is in the Cu2+ form. The ability of copper to easily accept and donate electrons explains its important role in oxidation-reduction (redox) reactions and in scavenging free radicals. Copper is a critical functional component of a number of essential enzymes known as cuproenzymes. For instance, the copper-dependent enzyme, cytochrome c oxidase, plays a critical role in cellular energy production. By catalyzing the reduction of molecular oxygen (O2) to water (H2O), cytochrome c oxidase generates an electrical gradient used by the mitochondria to create the vital energy-storing molecule, ATP. Another cuproenzyme, lysyl oxidase, is required for the cross-linking of collagen and elastin, which are essential for the formation of strong and flexible connective tissue. Another cuproeznyme, Monoamine oxidase (MAO), plays a role in the metabolism of the neurotransmitters norepinephrine, epinephrine, and dopamine. MAO also functions in the degradation of the neurotransmitter serotonin, which is the basis for the use of MAO inhibitors as antidepressants. One of the most important cuproenzymes is Superoxide dismutase (SOD). SOD functions as an antioxidant by catalyzing the conversion of superoxide radicals (free radicals or ROS) to hydrogen peroxide, which can subsequently be reduced to water by other antioxidant enzymes. Two forms of SOD contain copper: 1) copper/zinc SOD is found within most cells of the body, including red blood cells, and 2) extracellular SOD is a copper-containing enzyme found at high levels in the lungs and low levels in blood plasma. In sufficient amounts, copper can be poisonous or even fatal to organisms. Copper is normally bound to cuproenzymes (such as SOD, MOA) and is thus only toxic when unsequestered and unmediated. It is believed that zinc and copper compete for absorption in the digestive tract so that a diet that is excessive in one of these minerals may result in a deficiency in the other. An imbalance of zinc and copper status might be involved in human hypertension.
15158-11-9
C00070
27099
29036
CUCL2
25221
[Cu++]
Cu
InChI=1S/Cu/q+2
JPVYNHNXODAKFH-UHFFFAOYSA-N
copper(2+) ion
63.546
62.929601079
0
copper(2+) ion
2
2
FDB003582
Copper;Cu;Copper (ii) ion;Copper(ii) cation;Copper, ion (cu2+);Cu(ii);Cu2+;Cu(2+);Cupric ion
PW_C000514
Cu
408
19
552
14
702
20
756
15
761
8
771
33
2011
2
2019
24
6587
109
7009
189
42791
317
77049
294
77599
115
77770
341
77807
114
77811
111
77817
343
78153
132
79114
360
79246
293
120464
405
120596
409
120599
122
120607
415
121048
124
121608
434
123098
376
123221
137
123224
135
123232
451
123612
118
124166
469
125710
478
125733
483
125738
297
125746
487
127202
209
127216
208
127220
205
127228
504
127577
515
127588
388
31
Ascorbic acid
HMDB0000044
Ascorbic acid is found naturally in citrus fruits and many vegetables and is an essential nutrient in human diets. It is necessary to maintain connective tissue and bone. The biologically active form of ascorbic acid is vitamin C. Vitamin C is a water soluble vitamin. Primates (including humans) and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid and must obtain it in their food. Vitamin C functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant. [PubChem] Ascorbic acid is an electron donor for enzymes involved in collagen hydroxylation, biosynthesis of carnitine and norepinephrine, tyrosine metabolism, and amidation of peptide hormones. Ascrobic acid (vitamin C) deficiency causes scurvy. The amount of vitamin C necessary to prevent scurvy may not be adequate to maintain optimal health. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. In this setting, several mechanisms could account for a link between vitamin C and heart disease. One is the relation between LDL oxidation and vitamins C and E. Vitamin C in vitro can recycle vitamin E, which can donate electrons to prevent LDL oxidation in vitro. As the lipid-phase vitamin E is oxidized, it can be regenerated by aqueous vitamin C. Other possibilities are that vitamin C could decrease cholesterol by mechanisms not well characterized, or could improve vasodilatation and vascular reactivity, perhaps by decreasing the interactions of nitric oxide with oxidants. (PMID: 10799361).
50-81-7
C00072
54670067
29073
ASCORBATE
10189562
DB00126
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
C6H8O6
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N
(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
176.1241
176.032087988
0.14
4
vitamin C
0
-1
FDB001224
(+)-sodium l-ascorbate;(+)-ascorbate;(+)-ascorbic acid;3-keto-l-gulofuranolactone;3-oxo-l-gulofuranolactone;Adenex;Allercorb;Antiscorbic vitamin;Antiscorbutic vitamin;Arco-cee;Ascoltin;Ascor-b.i.d.;Ascorb;Ascorbajen;Ascorbate;Ascorbic acid;Ascorbicab;Ascorbicap;Ascorbicin;Ascorbin;Ascorbutina;Ascorin;Ascorteal;Ascorvit;C-level;C-long;C-quin;C-span;C-vimin;Cantan;Cantaxin;Catavin c;Ce lent;Ce-mi-lin;Ce-vi-sol;Cebicure;Cebid;Cebion;Cebione;Cecon;Cee-caps td;Cee-vite;Cegiolan;Ceglion;Ceklin;Celaskon;Celin;Cell c;Cemagyl;Cemill;Cenetone;Cenolate;Cereon;Cergona;Cescorbat;Cetamid;Cetane;Cetane-caps tc;Cetane-caps td;Cetebe;Cetemican;Cevalin;Cevatine;Cevex;Cevi-bid;Cevimin;Cevital;Cevitamate;Cevitamic acid;Cevitamin;Cevitan;Cevitex;Cewin;Chewcee;Ciamin;Cipca;Citriscorb;Citrovit;Colascor;Concemin;Davitamon c;Dora-c-500;Duoscorb;Ferrous ascorbate;Hicee;Hybrin;Ido-c;Juvamine;Kangbingfeng;Kyselina askorbova;L(+)-ascorbate;L(+)-ascorbic acid;L-(+)-ascorbate;L-(+)-ascorbic acid;L-3-ketothreohexuronic acid lactone;L-ascorbate;L-ascorbic acid;L-lyxoascorbate;L-lyxoascorbic acid;L-threo-ascorbic acid;L-xyloascorbate;L-xyloascorbic acid;Laroscorbine;Lemascorb;Liqui-cee;Meri-c;Natrascorb;Natrascorb injectable;Planavit c;Proscorbin;Redoxon;Ribena;Ronotec 100;Rontex 100;Roscorbic;Rovimix c;Scorbacid;Scorbu c;Scorbu-c;Secorbate;Sodascorbate;Suncoat vc 40;Testascorbic;Vasc;Vicelat;Vicin;Vicomin c;Viforcit;Viscorin;Viscorin 100m;Vitace;Vitacee;Vitacimin;Vitacin;Vitamin c;Vitamisin;Vitascorbol;Xitix;Gamma-lactone l-threo-hex-2-enonate;Gamma-lactone l-threo-hex-2-enonic acid;Acide ascorbique;Acido ascorbico;Acidum ascorbicum;Acidum ascorbinicum;Ascorbinsaeure;E 300;E-300;E300
PW_C000031
VitC
679
31
698
20
1267
5
2021
14
6252
107
12146
151
12297
225
13402
222
42506
318
77752
129
77766
341
78429
334
79116
115
115855
336
120558
414
120993
408
121610
405
123192
450
123558
374
124168
376
125933
482
127392
502
127579
209
142
Norepinephrine
HMDB0000216
Precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic.
51-41-2
C00547
439260
18357
NOREPINEPHRINE
388394
DB00368
NC[C@H](O)C1=CC(O)=C(O)C=C1
C8H11NO3
InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
SFLSHLFXELFNJZ-QMMMGPOBSA-N
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
169.1778
169.073893223
4
norepinephrine
0
1
FDB000895
(-)-(r)-norepinephrine;(-)-arterenol;(-)-noradrenaline;(-)-norepinephrine;(-)-alpha-(aminomethyl)protocatechuyl alcohol;(r)-(-)-norepinephrine;(r)-4-(2-amino-1-hydroxyethyl)-1,2-benzenediol;(r)-noradrenaline;(r)-norepinephrine;4-(2-amino-1-hydroxyethyl)-1,2-benzenediol;4-[(1r)-2-amino-1-hydroxyethyl]-1,2-benzenediol;Adrenor;Aktamin;Arterenol;L-2-amino-1-(3,4-dihydroxyphenyl)ethanol;L-3,4-dihydroxyphenylethanolamine;L-arterenol;L-noradrenaline;L-norepinephrine;L-alpha-(aminomethyl)-3,4-dihydroxybenzyl alcohol;Levarterenol;Levoarterenol;Levonor;Levonoradrenaline;Levonorepinephrine;Levophed;Nor-epirenan;Noradrenalin;Noradrenaline;Norartrinal;Norepirenamine;Sympathin e;Norepinefrina;Norepinephrine;Norepinephrinum
PW_C000142
Norpp
406
19
699
20
999
14
1081
37
1165
48
1166
15
3179
74
3180
71
77767
341
79117
115
121611
405
124169
376
127580
209
977
Dehydroascorbic acid
HMDB0001264
Dehydroascorbic acid is the oxidized form of vitamin C. Reduced Vitamin C concentrations in the brain exceed those in blood by 10 fold. Dehydroascorbic acid readily enters the brain and is retained in the brain tissue in the form of ascorbic acid (ascorbic acid is not able to cross the blood-brain barrier). Therefore, transport of dehydroascorbic acid by the Glucose Transporter 1 (GLUT1, Glucose transporters are integral membrane glycoproteins involved in transporting glucose into most cells. GLUT1 is a major glucose transporter in the mammalian blood-brain barrier. It is present at high levels in primate erythrocytes and brain endothelial cells.) is a mechanism by which the brain acquires vitamin C. (OMIM 138140).
490-83-5
C00425
210328
17242
L-DEHYDRO-ASCORBATE
182283
[H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO
C6H6O6
InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1
SBJKKFFYIZUCET-DUZGATOHSA-N
(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
174.1082
174.016437924
0.04
2
(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione
0
-1
FDB021459
1-dehydroascorbate;1-dehydroascorbic acid;Dhaa;Dehydro-l-ascorbate;Dehydro-l-ascorbic acid;Dehydroascorbate;L-dehydroascorbate;L-dehydroascorbic acid;L-threo-2,3-hexodiulosonic acid gamma-lactone;L-threo-hexo-2,3-diulosono-1,4-lactone;Oxidized ascorbate;Oxidized ascorbic acid;Oxidized vitamin c
PW_C000977
DHAA
700
20
2022
14
12298
225
13404
222
77768
341
79118
115
121612
405
124170
376
127581
209
8525
Pyrroloquinoline quinone
HMDB0013636
Enzymes containing PQQ are called quinoproteins. PQQ and quinoproteins play a role in the redox metabolism and structural integrity of cells and tissues [PMID:2558842]. It was reported that aminoadipate semialdehyde dehydrogenase (AASDH) might also use PQQ as a cofactor, suggesting a possibility that PQQ is a vitamin in mammals. [PMID:12712191].
72909-34-3
C00113
1024
18315
PQQ
997
DB03205
OC(=O)C1=CC2=C(N1)C1=C(N=C(C=C1C(O)=O)C(O)=O)C(=O)C2=O
C14H6N2O8
InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)
MMXZSJMASHPLLR-UHFFFAOYSA-N
4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
330.206
330.012415178
-3.53
4
pyrroloquinoline quinone
0
-3
C00113
Methoxatin;Pqq;Pyrrolo-quinoline quinone;Pyrroloquinoline-quinone;2,4,6-tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone;2,7,9-tricarboxy-1h-pyrrolo(2,3-f)quinoline-4,5-dione;4,5-dihydro-4,5-dioxo-1h-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid;4,5-dioxo-4,5-dihydro-1h-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate;Coenzyme pqq;4,5-dihydro-4,5-dioxo-1h-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylate;4,5-dioxo-4,5-dihydro-1h-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
PW_C008525
Pqq
407
19
701
20
2023
14
77769
341
79119
115
121613
405
124171
376
127582
209
117
L-Dopa
HMDB0000181
L-Dopa is the naturally occurring form of dihydroxyphenylalanine and the immediate precursor of dopamine. Unlike dopamine itself, L-Dopa can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. In particular, it is metabolized to dopamine by aromatic L-amino acid decarboxylase. Pyridoxal phosphate (vitamin B6) is a required cofactor for this decarboxylation, and may be administered along with levodopa, usually as pyridoxine. L-Dopa is used for the treatment of Parkinsonian disorders and Dopa-Responsive Dystonia and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. Peripheral tissue conversion may be the mechanism of the adverse effects of levodopa. It is standard clinical practice to co-administer a peripheral DOPA decarboxylase inhibitor - carbidopa or benserazide - and often a catechol-O-methyl transferase (COMT) inhibitor, to prevent synthesis of dopamine in peripheral tissue.
59-92-7
C00355
6047
15765
L-DOPA
5824
DB01235
N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O
C9H11NO4
InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
WTDRDQBEARUVNC-LURJTMIESA-N
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
197.1879
197.068807845
4
levodopa
0
0
FDB000567
(-)-3-(3,4-dihydroxyphenyl)-l-alanine;(-)-dopa;(2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoate;(2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid;3,4-dihydroxy-l-phenylalanine;3,4-dihydroxyphenyl-l-alanine;3,4-dihydroxyphenylalanine;3-(3,4-dihydroxyphenyl)-l-alanine;3-hydroxy-l-tyrosine;Bendopa;Cidandopa;Dihydroxy-l-phenylalanine;Dihydroxyphenylalanine;Dopaflex;Dopaidan;Dopal;Dopalina;Dopar;Doparkine;Doparl;Dopasol;Dopaston;Dopastone;Dopastral;Dopicar;Doprin;Eldopal;Eldopar;Eldopatec;Eurodopa;Helfo-dopa;Insulamina;L-(-)-dopa;L-3-(3,4-dihydroxyphenyl)-alanine;L-4-5-dihydroxyphenylalanine;L-dihydroxyphenylalanine;L-dopa;L-b-(3,4-dihydroxyphenyl)-a-alanine;L-beta-(3,4-dihydroxyphenyl)-alpha-alanine;Laradopa;Larodopa;Ledopa;Levedopa;Levodopa;Levopa;Maipedopa;Parda;Pardopa;Prodopa;Syndopa;Veldopa;Weldopa;B-(3,4-dihydroxyphenyl)-l-alanine;B-(3,4-dihydroxyphenyl)-a-l-alanine;B-(3,4-dihydroxyphenyl)alanine;Beta-(3,4-dihydroxyphenyl)-l-alanine;Beta-(3,4-dihydroxyphenyl)-alpha-l-alanine;Beta-(3,4-dihydroxyphenyl)alanine;L-beta-(3,4-dihydroxyphenyl)alanine;Levodopum;β-(3,4-dihydroxyphenyl)-l-alanine;β-(3,4-dihydroxyphenyl)alanine;L-b-(3,4-dihydroxyphenyl)alanine;L-β-(3,4-dihydroxyphenyl)alanine
PW_C000117
L-Dopa
397
19
689
20
2025
2
77042
293
77757
341
79120
132
121615
124
124173
118
127584
388
19
Tetrahydrobiopterin
HMDB0000027
Tetrahydrobiopterin or BH4 is a cofactor in the synthesis of nitric oxide. In fact it is used by all three human nitric-oxide synthases (NOS) eNOS, nNOS, and iNOS as well as the enzyme glyceryl-ether monooxygenase. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase. Specifically, tetrahydrobiopterin is a cofactor for tryptophan 5-hydroxylase 1, tyrosine 3-monooxygenase, and phenylalanine hydroxylase all of which are essential for the formation of the neurotransmitters dopamine, noradrenaline and adrenaline. Tetrahydrobiopterin has been proposed to be involved in promotion of neurotransmitter release in the brain and the regulation of human melanogenesis. A defect in BH4 production and/or a defect in the enzyme dihydropteridine reductase (DHPR) causes phenylketonuria type IV, as well as dopa-responsive dystonias. BH4 is also implicated in Parkinson's disease, Alzheimer's disease and depression. Tetrahydrobiopterin is present in probably every cell or tissue of higher animals. On the other hand, most bacteria, fungi and plants do not synthesize tetrahydrobiopterin. -- Wikipedia.
17528-72-2
C00272
1125
15372
TETRA-H-BIOPTERIN
1093
DB00360
[H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O
C9H15N5O3
InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1
FNKQXYHWGSIFBK-RPDRRWSUSA-N
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one
241.2471
241.117489371
-2.04
6
tetrahydrobiopterin
0
0
FDB021880
(1r,2s)-(2-amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)-1,2-propandiol;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1h)-5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1h)-pteridinone;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1h)-pteridinone;5,6,7,8-erythro-tetrahydrobiopterin;5,6,7,8-tetra-h-biopterin;5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1h)-pteridinone;5,6,7,8-tetrahydrobiopterin;L-erythro-2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3h)-pteridinon;Tetra-h-biopterin;Tetra-hydro-biopterin;Tetrahydrobiopterin;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1h)-pteridinone;Bh4
PW_C000019
BH4
1957
2
4085
8
4800
14
4803
14
4962
31
11901
211
77520
115
78663
132
120434
405
121616
124
123068
376
124174
118
126493
299
127585
388
1541
4a-Hydroxytetrahydrobiopterin
HMDB0002281
Tetrahydrobiopterin (BH4) is essential to catalyze the conversion of phenylalanine to tyrosine by phenylalanine hydroxylase. During this physiological reaction, the oxidation of BH4 creates 4a-hydroxytetrahydropterin intermediates and hydrogen peroxide is formed. The hydrogen peroxide and the hydroxytetrahydropterin can both derive from alternate routes of breakdown of a common precursor, the corresponding 4a-hydroperoxytetrahydropterin. (PMID 8323303).
70110-58-6
C15522
129803
15374
114908
[H][C@@]1(CNC2=NC(N)=NC(=O)[C@]2(O)N1)[C@@H](O)[C@H](C)O
C9H15N5O4
InChI=1S/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17)/t3-,4+,5-,9-/m0/s1
KJKIEFUPAPPGBC-XXKOCQOQSA-N
(4aS,6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4a-hydroxy-4,4a,5,6,7,8-hexahydropteridin-4-one
257.25
257.112403983
-1.73
6
(4aS,6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4a-hydroxy-5,6,7,8-tetrahydropteridin-4-one
0
0
FDB022944
(6r)-6-(l-erythro-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin;2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-5,6,7,8-tetrahydropteridin-4(4ah)-one;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxy-4(4ah)-pteridinone;2-amino-6-[(1r,2s)-1,2-dihydroxypropyl]-4a-hydroxy-1,5,6,7-tetrahydropteridin-4-one;4a-hydroxy-5,6,7,8-tetrahydrobiopterin;4a-hydroxytetrahydrobiopterin;4alpha-hydroxytetrahydrobiopterin;4a-hydroxy-5,6,4,8-tetrahydrobiopterin
PW_C001541
4aHtHbp
1285
8
2026
2
78470
111
79082
132
121002
122
121617
124
123567
135
124175
118
127586
388
952
Dopaquinone
HMDB0001229
Dopaquinone, also known as o-dopaquinone or L-dopaquinone, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha-amino acids which have the L-configuration of the alpha-carbon atom. Dopaquinone is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-Dopaquinone is a metabolite of L-DOPA and a precursor of melanin. Melanin is synthesized from tyrosine by hydroxylation to dihydroxyphenylalanine (DOPA) and subsequent oxidation to dopaquinone. Both reactions are catalyzed by the enzyme tyrosinase, which is the rate-limiting step. Dopaquinone has an ortho-quinone ring, which is known to be neurotoxic and highly reactive with many other compounds (PMID: 413870). Dopaquinone typically combines with cysteine to form pheomelanin (a pigment-polymer). Alternatively, dopaquinone can be converted to leucodopachrome and eventually to eumelanin (also a pigment-polymer). Dopaquinone can be found in skin and feces. Within the cell, dopaquinone is primarily located in the cytoplasm. Dopaquinone is involved in several metabolic disorders, some of which include transient tyrosinemia, hawkinsinuria, tyrosinemia type I, and alkaptonuria. Chronically high levels of dopaquinone are associated with Parkinson's disease (PD). Many Parkinson's patients are treated with L-DOPA. However, long-term treatment with L-DOPA may actually worsen symptoms or result in neurotic and psychotic symptoms. These may be due to dopachrome and dopaquinone accumulating in the brain of L-DOPA treated patients (PMID: 19131041, PMID: 12373519).
4430-97-1 25520-73-4
C00822
439316
16852
DOPAQUINONE
388447
N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O
C9H9NO4
InChI=1S/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)/t6-/m0/s1
AHMIDUVKSGCHAU-LURJTMIESA-N
(2S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
195.1721
195.053157781
-2.09
2
dopaquinone
0
0
FDB022501
o-Dopaquinone;L-Dopaquinone;(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoate;(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
PW_C000952
Dopqone
2028
2
79121
132
121618
124
124176
118
127587
388
2044
Leucodopachrome
HMDB0004067
Leucodopachrome is an indolic intermediate in the melanogenesis pathway, the non-enzymatic product of dopaquinone through cyclization in a reaction whose operation is determined by a pH greater than 4 (melanin synthesis in human pigment cell lysates is maximal at pH 6.8). Leucodopachrome participates in redox exchange with dopaquinone to give the eumelanin precursor dopachrome plus DOPA. Dopaquinone (the quinone intermediate resulting from tyrosinase-mediated oxidation of tyrosine, monophenol dihydroxyphenylalanine:oxygen oxidoreductase, EC 1.14.18.1) could be a toxic metabolite in melanin biosynthesis (PMID: 6807981, 1445949, 413870, 11461115, 11171088, 12755639).
18766-67-1
C05604
161255
60872
141655
OC(=O)[C@@H]1CC2=CC(O)=C(O)C=C2N1
C9H9NO4
InChI=1S/C9H9NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10-12H,1H2,(H,13,14)/t6-/m0/s1
JDWYRSDDJVCWPB-LURJTMIESA-N
(2S)-5,6-dihydroxy-2,3-dihydro-1H-indole-2-carboxylic acid
195.1721
195.053157781
-1.23
4
cyclodopa
0
-1
FDB023297
2,3-dihydro-5,6-dihydroxyindole-2-carboxylate;2-carboxy-2,3-dihydro-5,6-dihydroxyindole;Cyclodopa;(s)-2-carboxy-5,6-dihydroxyindoline;(s)-5,6-dihydroxyindoline-2-carboxylic acid;Cyclo-dopa;L-2-carboxy-2,3-dihydro-5,6-dihydroxyindole;Leukodopachrome;(2s)-5,6-dihydroxy-2,3-dihydro-1h-indole-2-carboxylate;(s)-5,6-dihydroxyindoline-2-carboxylate
PW_C002044
Leucpch
1105
L-Dopachrome
HMDB0001430
Dopachrome is a cyclization product of L-DOPA and is an intermediate in the biosynthesis of melanin. Dopaquinone has an ortho-quinone ring, which is known to be neurotoxic and highly reactive with many other compounds (PMID: 413870). Dopachrome spontaneously gives rise to 5,6-dihydroxyindole (DHI) or it can be enzymatically metabolized by dopachrome tautomerase to give 5,6-dihydroxyindole-2-carboxylic acid (DHICA). DHI and its oxidation products are also toxic to cells. Many Parkinson's patients are treated with L-DOPA. However, long-term treatment with L-DOPA may actually worsen symptoms or may result in neurotic and psychotic symptoms. These may be due to dopachrome and dopaquinone accumulating in the brain of L-DOPA treated patients (PMID: 19131041, PMID: 12373519).
89762-39-0
C01693
5459802
15772
4573572
OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1
C9H7NO4
InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10H,1H2,(H,13,14)/t6-/m0/s1
VJNCICVKUHKIIV-LURJTMIESA-N
(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid
193.158
193.037507709
-1.28
2
L-dopachrome
0
-1
FDB022618
2-l-carboxy-2,3-dihydroindole-5,6-quinone;L-Dopachrome
PW_C001105
L-Dopac
2029
2
79123
132
121620
124
124178
118
127590
388
2040
5,6-Dihydroxyindole
HMDB0004058
5,6-Dihydroxyindole, also known as DHI or dopamine lutine, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 5,6-Dihydroxyindole is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). In humans, 5,6-dihydroxyindole is involved in the tyrosine metabolism pathway and the disulfiram action pathway. 5,6-Dihydroxyindole is also involved in several metabolic disorders, some of which include tyrosinemia, transient, OF the newborn pathway, monoamine oxidase-a deficiency (mao-a), the tyrosinemia type I pathway, and the alkaptonuria pathway. 5,6-Dihydroxyindole is a substrate for Tyrosinase.
3131-52-0
C05578
114683
27404
56-DIHYDROXYINDOLE-2-CARBOXYLATE
102690
OC1=C(O)C=C2C=CNC2=C1
C8H7NO2
InChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H
SGNZYJXNUURYCH-UHFFFAOYSA-N
1H-indole-5,6-diol
149.1467
149.047678473
-1.41
3
5,6-dihydroxyindole
0
0
FDB023293
Aminochrome;Dhi;Dopaminochrome;Dopamine lutine
PW_C002040
56-DHD
2030
2
79124
132
121621
124
124179
118
127591
388
2926
Indole-5,6-quinone
HMDB0006779
Indole-5,6-quinone, also known as IQ, belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole-5,6-quinone is soluble (in water) and a strong basic compound (based on its pKa). In humans, indole-5,6-quinone is involved in the tyrosine metabolism pathway and the disulfiram action pathway. Indole-5,6-quinone is also involved in several metabolic disorders, some of which include the alkaptonuria pathway, the hawkinsinuria pathway, dopamine beta-hydroxylase deficiency, and monoamine oxidase-a deficiency (mao-a). Indole-5,6-quinone is involved in the tyrosine metabolism pathway. More specifically, indole-5,6-quinone is an intermediate in the production of melanin. Indole-5,6-quinone is produced from 5,6-dihydroxyindole by tyrosinase [EC:1.14.18.1].
C05579
440728
27406
389600
O=C1C=C2NC=CC2=CC1=O
C8H5NO2
InChI=1S/C8H5NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9H
IGGVVGHJSQSLFO-UHFFFAOYSA-N
5,6-dihydro-1H-indole-5,6-dione
147.1308
147.032028409
-1.15
1
indole-5,6-quinone
0
0
FDB024077
1h-indole-5,6-dione;Indole-5,6 quinone;Iq;Indolequinone
PW_C002926
ind56q
2031
2
79125
132
121622
124
124180
118
127592
388
2045
Melanin
HMDB0004068
Dermal melanin is produced by melanocytes, which are found in the stratum basale of the epidermis. Although human beings generally possess a similar concentration of melanocytes in their skin, the melanocytes in some individuals and races more frequently or less frequently express the melanin-producing genes, thereby conferring a greater or lesser concentration of skin melanin. Some individual animals and humans have no or very little melanin in their bodies, which is a condition known as albinism. Higher eumelanin levels also can be a disadvantage, however, beyond a higher disposition toward vitamin D deficiency. Dark skin is a complicating factor in the laser removal of port-wine stains. Effective in treating fair skin, lasers generally are less successful in removing port-wine stains in Asians and people of African descent. Higher concentrations of melanin in darker-skinned individuals simply diffuse and absorb the laser radiation, inhibiting light absorption by the targeted tissue. Melanin similarly can complicate laser treatment of other dermatological conditions in people with darker skin. Under the microscope melanin is brown, non-refractile and finely granular with individual granules having a diameter of less than 800 nanometers. This differentiates melanin from common blood breakdown pigments which are larger, chunky and refractile and range in color from green to yellow or red-brown. In heavily pigmented lesions, dense aggregates of melanin can obscure histologic detail. A dilute solution of potassium permanganate is an effective melanin bleach. Pigments causing darkness in skin, hair, feathers, etc. They are irregular polymeric structures and are divided into three groups: allomelanins in the plant kingdom and eumelanins and phaeomelanins in the animal kingdom. Because melanin is an aggregate of smaller component molecules, there are a number of different types of melanin with differing proportions and bonding patterns of these component molecules. Both pheomelanin and eumelanin are found in human skin and hair, but eumelanin is the most abundant melanin in humans, as well as the form most likely to be deficient in albinism. Freckles and moles are formed where there is a localized concentration of melanin in the skin. They are highly associated with pale skin. Melanin is a biopolymer and a neuropeptide. In the early 1970s, John McGinness, Peter Corry, and Peter Proctor reported that melanin is a high-conductivity organic semiconductor (Science, vol 183, 853-855 (1974)). Studies revealed that melanin acted as a voltage-controlled solid-state threshold switch. Further, it emitting a flash of light electroluminescence when it switched.
8049-97-6
C05606
6325610
MELANIN
4884931
CC1=C2NC=C3C2=C(C2=CNC4=C(C)C(=O)C(=O)C3=C24)C(=O)C1=O
C18H10N2O4
InChI=1S/C18H10N2O4/c1-5-13-9-7(3-19-13)12-10-8(11(9)17(23)15(5)21)4-20-14(10)6(2)16(22)18(12)24/h3-4,19-20H,1-2H3
XUMBMVFBXHLACL-UHFFFAOYSA-N
6,14-dimethyl-4,12-diazapentacyclo[8.6.1.1²,⁵.0¹³,¹⁷.0⁹,¹⁸]octadeca-1(17),2,5,9(18),10,13-hexaene-7,8,15,16-tetrone
318.283
318.064056818
-3.01
2
melanin
0
0
FDB023298
PW_C002045
Melanin
2032
2
79126
132
121623
124
124181
118
127593
388
968
5,6-Dihydroxyindole-2-carboxylic acid
HMDB0001253
5,6-Dihydroxyindole-2-carboxylic acid, also known as 5,6-dhica or DHI2C, belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. 5,6-Dihydroxyindole-2-carboxylic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, 5,6-dihydroxyindole-2-carboxylic acid is primarily located in the cytoplasm. In humans, 5,6-dihydroxyindole-2-carboxylic acid is involved in the disulfiram action pathway and the tyrosine metabolism pathway. 5,6-Dihydroxyindole-2-carboxylic acid is also involved in several metabolic disorders, some of which include dopamine beta-hydroxylase deficiency, the tyrosinemia type I pathway, the alkaptonuria pathway, and monoamine oxidase-a deficiency (mao-a). 5,6-Dihydroxyindole-2-carboxylic acid is an intermediate in the metabolism of Tyrosine. It is a substrate for Dopachrome tautomerase.
4790-08-3
C04185
119405
2003
56-DIHYDROXYINDOLE-2-CARBOXYLATE
106648
OC(=O)C1=CC2=C(N1)C=C(O)C(O)=C2
C9H7NO4
InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)
YFTGOBNOJKXZJC-UHFFFAOYSA-N
5,6-dihydroxy-1H-indole-2-carboxylic acid
193.1562
193.037507717
-1.92
4
dhica
0
-1
FDB022514
5,6-dhica;5,6-dihydroxy-1h-indole-2-carboxylate;5,6-dihydroxy-1h-indole-2-carboxylic acid;5,6-dihydroxy-2-indolecarboxylate;5,6-dihydroxy-2-indolecarboxylic acid;5,6-dihydroxy-2-indolylcarboxylate;5,6-dihydroxy-2-indolylcarboxylic acid;5,6-dihydroxyindole-2-carboxylate;Dhi2c;Dhica
PW_C000968
DHD-2CA
2034
2
79127
132
121624
124
124182
118
127594
388
9795
Zinc
HMDB0015532
Zinc is an essential element, necessary for sustaining all life. It is a trace element in the diet, forming an essential part of many enzymes, and playing an important role in protein synthesis and in cell division. Physiologically, it exists as an ion in the body. It is estimated that 3000 of the hundreds of thousands of proteins in the human body contain zinc prosthetic groups. In addition, there are over a dozen cell types in the human body that secrete zinc ions, and the roles of these secreted zinc signals in medicine and health are now being actively studied. Intriguingly, brain cells in the mammalian forebrain are one type of cell that secretes zinc, along with its other neuronal messenger substances. Cells in the salivary gland, prostate, immune system, and intestine are other types that secrete zinc. Obtaining a sufficient zinc intake during pregnancy and in young children is a problem, especially among those who cannot afford a good and varied diet. Zinc deficiency is associated with anemia, short stature, hypogonadism, impaired wound healing, and geophagia. Brain development is stunted by zinc deficiency in utero and in youth. Zinc is an activator of certain enzymes, such as carbonic anhydrase. Carbonic anhydrase is important in the transport of carbon dioxide in vertebrate blood. Even though zinc is an essential requirement for a healthy body, too much zinc can be harmful. Excessive absorption of zinc can also suppress copper and iron absorption. The free zinc ion in solution is highly toxic to plants, invertebrates, and even vertebrate fish. The Free Ion Activity Model (FIAM) is well-established in the literature and shows that just micromolar amounts of the free ion kill some organisms.
7440-66-6
23994
27363
22430
DB01593
[Zn++]
Zn
InChI=1S/Zn/q+2
PTFCDOFLOPIGGS-UHFFFAOYSA-N
zinc(2+) ion
65.409
63.929146578
0
zinc(2+) ion
2
2
30zn;Cinc;Zincum;Zink;Zn;Zn(ii);Zn2+
PW_C009795
Zinc
57
8
1711
2
1904
3
2137
17
2154
49
3610
29
4083
7
4469
18
4543
14
4999
31
6689
107
6690
101
6699
108
7020
160
11758
115
12229
151
12633
65
42397
315
42399
318
77030
253
78023
132
78328
112
78811
111
120119
124
120898
122
122308
407
122852
118
123469
135
124860
119
125486
299
126474
481
127023
388
127317
205
128043
206
654
Normetanephrine
HMDB0000819
Normetanephrine, also known as normetadrenaline, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Normetanephrine exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Normetanephrine has been found in human brain and endocrine gland tissues, and has also been primarily detected in feces, urine, blood, and cerebrospinal fluid. Within the cell, normetanephrine is primarily located in the cytoplasm. In humans, normetanephrine is involved in the tyrosine metabolism pathway and the disulfiram action pathway. Normetanephrine is also involved in several metabolic disorders, some of which include the tyrosinemia type I pathway, tyrosinemia, transient, OF the newborn pathway, dopamine beta-hydroxylase deficiency, and the alkaptonuria pathway. Normetanephrine is a methylated metabolite of norepinephrine that is excreted in the urine and found in certain tissues. It is a marker for tumors.
97-31-4
C05589
1237
144308
1200
COC1=CC(=CC=C1O)C(O)CN
C9H13NO3
InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3
YNYAYWLBAHXHLL-UHFFFAOYSA-N
4-(2-amino-1-hydroxyethyl)-2-methoxyphenol
183.2044
183.089543287
-1.34
3
(+/-)-normetanephrine
0
1
FDB022265
(+/-)-normetanephrine;(+/-)-alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol;3-methoxy-noradrenaline;3-o-methyl-noradrenaline;4-(2-amino-1-hydroxyethyl)-2-methoxyphenol;Dl-n-normetanephrine;Dl-normetanephrine;L-normetanephrine;N111;Normetadrenaline;O-methylnoradrenaline;Alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol;M-o-methylnorepinephrine
PW_C000654
Normeta
2036
2
79133
132
121631
124
124189
118
127605
388
921
S-Adenosylmethionine
HMDB0001185
S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.
485-80-3
C00019
24762165
15414
S-ADENOSYLMETHIONINE
31983
DB00118
C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
C15H23N6O5S
InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1
MEFKEPWMEQBLKI-AIRLBKTGSA-O
[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
399.445
399.145063566
-2.56
5
SAMe
1
1
FDB022473
(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine;2-s-adenosyl-l-methionine;5'-deoxyadenosine-5'-l-methionine disulfate ditosylate;Active methionine;Ademetionine;Adenosylmethionine;Adomet;Donamet;L-s-adenosylmethionine;S-(5'-adenosyl)-l-methionine;S-(5'-deoxyadenosin-5'-yl)-l-methionine;S-adenosyl methionine;S-adenosyl-l-methionine disulfate tosylate;S-adenosyl-l-methionine;S-adenosyl-methionine;S-adenosylmethionine;5'-deoxyadenosine-5'-l-methionine disulphate ditosylate;S-adenosyl-l-methionine disulphate tosylate;(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt;[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl][(3s)-3-amino-3-carboxypropyl](methyl)sulfonium;Acylcarnitine;Sam;Same
PW_C000921
SAMe
519
8
633
30
704
20
1220
3
1880
27
2066
2
4681
10
5023
50
5604
135
7136
163
7540
210
7544
213
7632
160
8266
151
9235
195
11874
198
12031
222
12358
225
15293
249
15345
18
15363
309
76897
293
76899
164
76984
224
77488
111
77731
338
77772
341
78099
132
78303
351
78335
346
79155
112
79961
361
80861
22
94830
382
94833
386
113286
389
113288
397
115543
399
115546
401
120393
122
120537
413
120939
407
121052
124
122282
435
123171
449
123505
119
123616
118
124836
470
125859
297
125879
481
126304
299
126447
499
127321
205
127340
206
127595
388
128017
517
749
S-Adenosylhomocysteine
HMDB0000939
S-Adenosyl-L-homocysteine (SAH) is formed by the demethylation of S-adenosyl-L-methionine. S-Adenosylhomocysteine (AdoHcy or SAH) is also the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of SAH. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, SAH is the product of all methylation reactions that involve S-adenosylmethionine (SAM) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these SAM-mediated processes by SAH is a proven mechanism for metabolic alteration. Because the conversion of SAH to homocysteine is reversible, with the equilibrium favoring the formation of SAH, increases in plasma homocysteine are accompanied by an elevation of SAH in most cases. Disturbances in the transmethylation pathway indicated by abnormal SAH, SAM, or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression, and Parkinson's disease (PMID: 18065573, 17892439). Therefore, when present in sufficiently high levels, S-adenosylhomocysteine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of S-adenosylhomocysteine are associated with S-adenosylhomocysteine (SAH) hydrolase deficiency and adenosine deaminase deficiency. S-Adenosylhomocysteine forms when there are elevated levels of homocysteine and adenosine. S-Adenosyl-L-homocysteine is a potent inhibitor of S-adenosyl-L-methionine-dependent methylation reactions. It is toxic to immature lymphocytes and can lead to immunosuppression (PMID: 221926).
979-92-0
C00021
25246222
16680
ADENOSYL-HOMO-CYS
388301
N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O
C14H20N6O5S
InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
ZJUKTBDSGOFHSH-WFMPWKQPSA-N
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid
384.411
384.12158847
-1.97
5
S-adenosyl-L-homocysteine
0
0
DBMET00514
FDB022327
(s)-5'-(s)-(3-amino-3-carboxypropyl)-5'-thioadenosine;2-s-adenosyl-l-homocysteine;5'-deoxy-s-adenosyl-l-homocysteine;5'-s-(3-amino-3-carboxypropyl)-5'-thio-l-adenosine;Adenosyl-l-homocysteine;Adenosyl-homo-cys;Adenosylhomo-cys;Adenosylhomocysteine;Adohcy;Formycinylhomocysteine;L-5'-s-(3-amino-3-carboxypropyl)-5'-thior-adenosine;L-s-adenosyl-homocysteine;L-s-adenosylhomocysteine;S-(5'-adenosyl)-l-homocysteine;S-(5'-deoxyadenosin-5'-yl)-l-homocysteine;S-(5'-deoxyadenosine-5')-l-homocysteine;S-adenosyl-l-homocysteine;S-adenosyl-homocysteine;Sah;(2s)-2-amino-4-({[(2s,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid;S-[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl]-l-homocysteine;S-adenosylhomocysteine
PW_C000749
SAH
520
8
575
18
635
30
705
20
1221
3
1882
27
2067
2
4683
10
5025
50
5607
136
7137
163
7542
210
7546
213
7634
160
8268
151
9237
195
11875
198
12359
225
15294
249
15364
309
77489
111
77611
130
77733
338
77773
341
78098
132
78305
351
78337
346
79156
112
79962
361
80863
22
94831
382
94834
386
113287
389
113289
397
115544
399
115547
401
120394
122
120486
125
120539
413
120940
407
121053
124
122284
435
123037
135
123173
449
123506
119
123617
118
124838
470
125880
481
126303
299
126449
499
127341
206
127596
388
128019
517
48
Epinephrine
HMDB0000068
Epinephrine is a catecholamine, a sympathomimetic monoamine derived from the amino acids phenylalanine and tyrosine. It is the active sympathomimetic hormone secreted from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics. Epinephrine also constricts arterioles in the skin and gut while dilating arterioles in leg muscles. It elevates the blood sugar level by increasing hydrolysis of glycogen to glucose in the liver, and at the same time begins the breakdown of lipids in adipocytes. Epinephrine has a suppressive effect on the immune system.
51-43-4
C00788
5816
28918
L-EPINEPHRINE
5611
DB00668
CNC[C@H](O)C1=CC(O)=C(O)C=C1
C9H13NO3
InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
UCTWMZQNUQWSLP-VIFPVBQESA-N
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
183.2044
183.089543287
-0.99
4
epinephrine
0
1
FDB021889
(-)-(r)-epinephrine;(-)-3,4-dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol;(-)-3,4-dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol;(-)-3,4-dihydroxy-a-[(methylamino)methyl]-benzyl alcohol;(-)-3,4-dihydroxy-alpha-[(methylamino)methyl]-benzyl alcohol;(-)-adrenaline;(-)-epinephrine;(r)-4-[1-hydroxy-2-(methylamino)ethyl]-1,2-benzenediol;(r)-adrenaline;(r)-epinephrine;4-[(1r)-1-hydroxy-2-(methylamino)ethyl]-1,2-benzenediol;Adnephrine;Adrenal;Adrenalin;Adrenaline;Adrenine;Adrin;Ana-kit;Bosmin;Bronkaid mist;Chelafrin;Epifrin;Epiglaufrin;Epinefrina;Epinephran;Epinephrine;Epipen;Epirenan;Eppy;Exadrin;Glauposine;Hemisine;Hemostasin;Hemostatin;Hypernephrin;Isoptoepinal;L-1-(3,4-dihydroxyphenyl)-2-methylaminoethanol;L-adrenaline;L-epinephrine;L-epirenamine;L-methylaminoethanolcatechol;Levoepinephrine;Levorenen;Levorenin;Levorenine;Levoreninum;Lyodrin;Methylarterenol;Mucidrina;Nephridine;Nieraline;Paranephrin;Primatene mist;R-(-)-epinephrine;Renaglandin;Renaleptine;Renalina;Renoform;Renostypticin;Renostyptin;Scurenaline;Simplene;Styptirenal;Supracapsulin;Supranephrane;Suprarenaline;Suprarenin;Surrenine;Sus-phrine;Takamina;Vasoconstrictine;Vasotonin;(-)-3,4-dihydroxy-alpha-((methylamino)methyl)benzyl alcohol;(r)-(-)-adrenaline;(r)-(-)-adnephrine;(r)-(-)-epinephrine;(r)-(-)-epirenamine;Epinephrin;Epinephrinum;Epipen jr;Primatene;(-)-3,4-dihydroxy-a-((methylamino)methyl)benzyl alcohol;(-)-3,4-dihydroxy-α-((methylamino)methyl)benzyl alcohol
PW_C000048
Eppy
706
20
749
14
1087
15
1088
41
1169
45
2068
2
4339
1
4635
63
4636
87
5084
65
77774
341
77776
342
77777
340
79129
132
82807
51
82838
381
121626
124
124184
118
127597
388
2683
3,4-Dihydroxymandelaldehyde
HMDB0006242
3,4-Dihydroxymandelaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of both norepinephrine and epinephrine. 3,4- dihydroxymandelaldehyde generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. There is an increasing body of evidence suggesting that these compounds are neurotoxic, and it has been recently hypothesized that neurodegenerative disorders may be associated with increased levels of this biogenic aldehyde. It is possible to speculate that reduced detoxification of 3,4- dihydroxymandelaldehyde from impaired or deficient aldehyde dehydrogenase function may be a contributing factor in the suggested neurotoxicity of these compounds. Aldehyde dehydrogenases are a group of NAD(P)+ -dependent enzymes that catalyze the oxidation of aldehydes, such as those derived from catecholamines, to their corresponding carboxylic acids. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. Several pharmaceutical agents and environmental toxins are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813, 14697885, 11164826).
13023-73-9
C05577
151725
27852
133725
OC(C=O)C1=CC(O)=C(O)C=C1
C8H8O4
InChI=1S/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H
YUGMCLJIWGEKCK-UHFFFAOYSA-N
2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde
168.1467
168.042258744
-1.19
3
dhmal
0
0
FDB023855
3,4-dihydroxyphenylglycolaldehyde;3,4-dihydroxyphenylglycolic aldehyde;A,3,4-trihydroxy-benzeneacetaldehyde;Alpha,3,4-trihydroxy-benzeneacetaldehyde;3,4-dihydroxymandelic aldehyde;Alpha,3,4-trihydroxybenzeneacetaldehyde;Alpha,3,4-trihydroxyphenylacetaldehyde;Dhmal;Dhpgald;Dopegal;A,3,4-trihydroxybenzeneacetaldehyde;α,3,4-trihydroxybenzeneacetaldehyde;A,3,4-trihydroxyphenylacetaldehyde;α,3,4-trihydroxyphenylacetaldehyde
PW_C002683
34DIHY
2070
2
79131
132
121628
124
124186
118
127599
388
35
Ammonia
HMDB0000051
Ammonia is a colourless alkaline gas and is one of the most abundant nitrogen-containing compounds in the atmosphere. It is an irritant with a characteristic pungent odor that is widely used in industry. Inasmuch as ammonia is highly soluble in water and, upon inhalation, is deposited in the upper airways, occupational exposures to ammonia have commonly been associated with sinusitis, upper airway irritation, and eye irritation. Acute exposures to high levels of ammonia have also been associated with diseases of the lower airways and interstitial lung. Small amounts of ammonia are naturally formed in nearly all tissues and organs of the vertebrate organism. Ammonia is both a neurotoxin and a metabotoxin. In fact, it is the most common endogenous neurotoxin. A neurotoxin is a compound that causes damage to neural tissue and neural cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Ammonia is recognized to be central in the pathogenesis of a brain condition known as hepatic encephalopathy, which arises from various liver diseases and leads to a build up ammonia in the blood (hyperammonemia). More than 40% of people with cirrhosis develop hepatic encephalopathy. Part of the neurotoxicity of ammonia arises from the fact that it easily crosses the blood-brain barrier and is absorbed and metabolized by the astrocytes, a population of cells in the brain that constitutes 30% of the cerebral cortex. Astrocytes use ammonia when synthesizing glutamine from glutamate. The increased levels of glutamine lead to an increase in osmotic pressure in the astrocytes, which become swollen. There is increased activity of the inhibitory gamma-aminobutyric acid (GABA) system, and the energy supply to other brain cells is decreased. This can be thought of as an example of brain edema. The source of the ammonia leading to hepatic encephalopathy is not entirely clear. The gut produces ammonia, which is metabolized in the liver, and almost all organ systems are involved in ammonia metabolism. Colonic bacteria produce ammonia by splitting urea and other amino acids, however this does not fully explain hyperammonemia and hepatic encephalopathy. The alternative explanation is that hyperammonemia is the result of the intestinal breakdown of amino acids, especially glutamine. The intestines have significant glutaminase activity, predominantly located in the enterocytes. On the other hand, intestinal tissues only have a little glutamine synthetase activity, making it a major glutamine-consuming organ. In addition to the intestine, the kidney is an important source of blood ammonia in patients with liver disease. Ammonia is also taken up by the muscle and brain in hepatic coma, and there is confirmation that ammonia is metabolized in muscle. Excessive formation of ammonia in the brains of Alzheimer's disease patients has also been demonstrated, and it has been shown that some Alzheimer's disease patients exhibit elevated blood ammonia concentrations. Ammonia is the most important natural modulator of lysosomal protein processing. Indeed, there is strong evidence for the involvement of aberrant lysosomal processing of beta-amyloid precursor protein (beta-APP) in the formation of amyloid deposits. Inflammatory processes and activation of microglia are widely believed to be implicated in the pathology of Alzheimer's disease. Ammonia is able to affect the characteristic functions of microglia, such as endocytosis, and cytokine production. Based on these facts, an ammonia-based hypothesis for Alzheimer's disease has been suggested (PMID: 17006913, 16167195, 15377862, 15369278). Chronically high levels of ammonia in the blood are associated with nearly twenty different inborn errors of metabolism including: 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, 3-methyl-crotonylglycinuria, argininemia, argininosuccinic aciduria, beta-ketothiolase deficiency, biotinidase deficiency, carbamoyl phosphate synthetase deficiency, carnitine-acylcarnitine translocase deficiency, citrullinemia type I, hyperinsulinism-hyperammonemia syndrome, hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, isovaleric aciduria, lysinuric protein intolerance, malonic aciduria, methylmalonic aciduria, methylmalonic aciduria due to cobalamin-related disorders, propionic acidemia, pyruvate carboxylase deficiency, and short chain acyl CoA dehydrogenase deficiency (SCAD deficiency). Many of these inborn errors of metabolism are associated with urea cycle disorders or impairment of amino acid metabolism. High levels of ammonia in the blood (hyperammonemia) lead to the activation of NMDA receptors in the brain. This results in the depletion of brain ATP, which in turn leads to the release of glutamate. Ammonia also leads to the impairment of mitochondrial function and calcium homeostasis, thereby decreasing ATP synthesis. Excess ammonia also increases the formation of nitric oxide (NO), which in turn reduces the activity of glutamine synthetase, and thereby decreases the elimination of ammonia in the brain (PMID: 12020609). As a neurotoxin, ammonia predominantly affects astrocytes. Disturbed mitochondrial function and oxidative stress, factors implicated in the induction of the mitochondrial permeability transition, appear to be involved in the mechanism of ammonia neurotoxicity. Ammonia can also affect the glutamatergic and GABAergic neuronal systems, the two prevailing neuronal systems of the cortical structures. All of these effects can lead to irreversible brain damage, coma, and/or death. Infants with urea cycle disorders and hyperammonemia initially exhibit vomiting and increasing lethargy. If untreated, seizures, hypotonia (poor muscle tone, floppiness), respiratory distress (respiratory alkalosis), and coma can occur. Adults with urea cycle disorders and hyperammonemia will exhibit episodes of disorientation, confusion, slurred speech, unusual and extreme combativeness or agitation, stroke-like symptoms, lethargy, and delirium. Ammonia also has toxic effects when an individual is exposed to ammonia solutions. Acute exposure to high levels of ammonia in air may be irritating to skin, eyes, throat, and lungs and cause coughing and burns. Lung damage and death may occur after exposure to very high concentrations of ammonia. Swallowing concentrated solutions of ammonia can cause burns in the mouth, throat, and stomach. Splashing ammonia into eyes can cause burns and even blindness.
7664-41-7
C00014
222
16134
AMMONIA
217
N
H3N
InChI=1S/H3N/h1H3
QGZKDVFQNNGYKY-UHFFFAOYSA-N
ammonia
17.0305
17.026549101
1
ammonia
0
1
FDB003908
Ammonia anhydrous;Ammonia inhalant;Ammonia solution strong [usan];Ammonia water;Ammoniak;Liquid ammonia;Am-fol;Ammonia;Ammonia (conc 20% or greater);Ammonia gas;Ammonia solution;Ammonia solution strong (nf);Ammonia water (jp15);Ammoniac [french];Ammoniaca [italian];Ammoniacum gummi;Ammoniak [german];Ammoniak kconzentrierter;Ammoniakgas;Ammonium ion;Amoniak [polish];Anhydrous ammonia;Aromatic ammonia vaporole;Azane;Nh(3);Nh3;Nitro-sil;Primaeres amin;Sekundaeres amin;Spirit of hartshorn;Tertiaeres amin;[nh3];Ammoniac;Amoniaco;R-717;Ammonia solution strong
PW_C000035
NH3
97
9
112
5
133
8
142
4
438
2
479
13
550
14
1468
54
2533
22
2572
3
5338
111
6016
147
7022
160
7177
205
11786
198
11848
277
11885
215
12708
291
12718
292
76966
225
77046
294
77329
133
77343
132
77469
333
77499
113
77539
334
77597
115
77985
347
77993
112
78072
329
79244
293
80650
135
80657
119
116203
109
119921
122
120049
408
120053
126
120136
407
120343
406
120363
412
120462
405
121046
124
121161
425
122119
382
122800
374
122805
443
122993
120
123010
446
123096
376
123610
118
123733
460
124671
399
125311
297
125427
482
125431
301
125502
481
125663
479
125708
478
126102
299
126274
484
126966
502
126970
207
127039
206
127158
501
127200
209
127600
388
127837
389
1783
Hydrogen peroxide
HMDB0003125
Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. It is a weak acid. It has strong oxidizing properties and is therefore a powerful bleaching agent that is mostly used for bleaching paper, but has also found use as a disinfectant and as an oxidizer. Hydrogen peroxide in the form of carbamide peroxide is widely used for tooth whitening (bleaching), both in professionally- and in self-administered products. Hydrogen peroxide (H2O2) is a well-documented component of living cells. It plays important roles in host defense and oxidative biosynthetic reactions. In addition there is growing evidence that at low levels, H2O2 also functions as a signaling agent, particularly in higher organisms. H2O2 has increasingly been viewed as an important cellular signaling agent in its own right, capable of modulating both contractile and growth-promoting pathways with more far-reaching effects. Due to the accumulation of hydrogen peroxide in the skin of patients with the depigmentation disorder vitiligo, the human epidermis cannot have the normal capacity for autocrine synthesis, transport and degradation of acetylcholine as well as the muscarinic (m1-m5) and nicotinic signal transduction in keratinocytes and melanocytes. Accumulating evidence suggests that hydrogen peroxide (H(2)O(2)) plays an important role in cancer development. Experimental data have shown that cancer cells produce high amounts of H(2)O(2). An increase in the cellular levels of H(2)O(2) has been linked to several key alterations in cancer, including DNA alterations, cell proliferation, apoptosis resistance, metastasis, angiogenesis and hypoxia-inducible factor 1 (HIF-1) activation. (PMID: 17150302, 17335854, 16677071, 16607324, 16514169).
7722-84-1
C00027
784
16240
HYDROGEN-PEROXIDE
763
OO
H2O2
InChI=1S/H2O2/c1-2/h1-2H
MHAJPDPJQMAIIY-UHFFFAOYSA-N
peroxol
34.0147
34.005479308
2
hydrogen peroxide
0
0
FDB014562
Adeka super el;Albone;Albone 35;Albone ds;Anti-keim 50;Asepticper;Baquashock;Cix;Clarigel gold;Crestal whitestrips;Crystacide;Dentasept;Deslime lp;Hioxyl;Hipox;Hybrite;Hydrogen dioxide;Hydrogen peroxide;Inhibine;Lase peroxide;Lensan a;Magic bleaching;Metrokur;Mirasept;Nite white excel 2;Odosat d;Opalescence xtra;Oxigenal;Oxydol;Oxyfull;Oxysept;Oxysept i;Pegasyl;Perhydrol;Perone;Peroxaan;Peroxclean;Quasar brite;Select bleach;Superoxol;T-stuff;Whiteness hp;Whitespeed;Xtra white;[oh(oh)];Dihydrogen dioxide;H2o2;Hooh
PW_C001783
H2O2
98
9
113
5
188
8
551
14
627
28
755
15
1243
3
1691
2
1749
51
2534
22
3818
10
4749
13
4752
31
5495
126
5502
123
5510
127
5810
108
6005
147
7038
163
8396
151
11817
216
11886
215
12461
226
12709
291
12719
292
13028
301
13035
298
13040
302
13405
222
42658
315
77022
225
77047
294
77079
293
77500
113
77540
334
77598
115
77720
332
77725
337
77806
114
77810
111
77819
326
78073
329
78152
132
78598
112
120050
408
120102
122
120463
405
120595
409
120609
416
120954
407
121047
124
122120
382
122801
374
122814
443
122839
135
123097
376
123157
447
123165
448
123220
137
123234
452
123520
119
123611
118
124672
399
125428
482
125469
297
125709
478
125732
483
125748
488
125895
481
126103
299
126275
484
126967
502
126978
207
127006
205
127201
209
127215
208
127230
505
127356
206
127601
388
127838
389
964
FAD
HMDB0001248
FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).
146-14-5
C00016
643975
16238
FAD
559059
DB03147
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2
C27H33N9O15P2
InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
VWWQXMAJTJZDQX-UYBVJOGSSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
785.5497
785.157134455
-2.27
9
flavine-adenine dinucleotide
0
-3
FDB022511
1h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;Adeflavin
PW_C000964
FAD
99
9
114
5
186
8
192
3
216
4
253
17
628
28
825
18
840
2
1188
14
1489
42
1612
29
1622
49
2133
58
2536
22
3723
26
4602
36
4688
31
4741
13
4758
10
4881
6
5268
103
5285
102
5335
111
5496
126
5511
127
5613
118
6030
155
6054
156
6082
161
6116
162
6390
1
6475
178
6499
179
6666
107
7039
163
7175
205
7321
213
7465
222
7487
223
9076
224
11818
216
11887
215
11899
211
12296
225
12328
249
12443
151
12519
227
12595
226
12710
291
12720
292
13029
301
13041
302
43623
318
77080
293
77126
133
77152
134
77501
113
77507
112
77518
115
77541
334
77615
132
77726
337
78054
329
78375
345
78930
331
79222
336
79272
358
80012
368
80034
369
80714
119
119958
406
119999
384
120051
408
120107
407
120432
405
120453
122
120490
124
121278
429
121298
418
121417
382
121489
383
122748
120
122776
121
122802
374
122823
443
123066
376
123087
135
123166
448
123849
464
123868
454
123976
399
124047
398
125348
479
125378
480
125429
482
125474
481
125697
297
125979
489
126107
299
126277
484
126891
501
126920
391
126968
502
126987
207
127011
206
127310
209
127432
506
127602
388
127840
389
140790
185
140799
186
108
Methylamine
HMDB0000164
Methylamine occurs endogenously from amine catabolism and its tissue levels increase in some pathological conditions, including diabetes. Interestingly, methylamine and ammonia levels are reciprocally controlled by a semicarbazide-sensitive amine oxidase activity that deaminates methylamine to formaldehyde with the production of ammonia and hydrogen peroxide. Methylamine also targets the voltage-operated neuronal potassium channels, probably inducing release of neurotransmitter(s). Semicarbazide-sensitive amine oxidase (SSAO) catalyzes the deamination of primary amines. Such deamination has been shown capable of regulating glucose transport in adipose cells. It has been independently discovered that the primary structure of vascular adhesion protein-1 (VAP-1) is identical to SSAO. Increased serum SSAO activities have been found in patients with diabetic mellitus, vascular disorders, and Alzheimer's disease. The SSAO-catalyzed deamination of endogenous substrates like methylamine led to production of toxic formaldehyde. Chronic elevated methylamine increases the excretion of malondialdehyde and microalbuminuria. Amine oxidase substrates such as methylamine have been shown to stimulate glucose uptake by increasing the recruitment of the glucose transporter GLUT4 from vesicles within the cell to the cell surface. Inhibition of this effect by the presence of semicarbazide and catalase led to the suggestion that the process is mediated by the hydrogen peroxide produced in the oxidation of these amines (PMID: 16049393, 12686132, 17406961).
74-89-5
C00218
6329
16830
CPD-4521
6089
DB01828
CN
CH5N
InChI=1S/CH5N/c1-2/h2H2,1H3
BAVYZALUXZFZLV-UHFFFAOYSA-N
methanamine
31.0571
31.042199165
1.07
1
methylamine
0
1
FDB003958
Aminomethane;Anhydrous methylamine;Carbinamine;Imizin;Mma;Mercurialin;Methanamine;Methyl group;Methyl of gamma-n-methylasparagine;Methylamine;Methylamine anhydrous;Methylamine aqueous solution;Methylamine solution;Methylamine solutions;Methylaminen;Metilamine;Metyloamina;Monomethylamine;N-methylamine;Nma;Nme
PW_C000108
Methyla
2071
2
79132
132
121630
124
124188
118
127604
388
2043
Metanephrine
HMDB0004063
Metanephrine is a metabolite of epinephrine created by action of catechol O-methyltransferase on epinephrine. Technically it is a product of epinephrine O-methylation. It is a commonly occurring, pharmacologically and physiologically inactive metabolite of epinephrine. The measurement of plasma free metanephrines is considered to be the best tool in the diagnosis of pheochromocytoma, a rare kind of adrenal medullary neoplasm. In adrenal chromaffin cells, leakage of norepinephrine and epinephrine from storage granules leads to substantial intracellular production of the O-methylated metabolite metanephrine. In fact, the adrenals constitute the single largest source out of any organ system including the liver for circulating metanephrine. In humans, about 93 percent of circulating metanephrine is derived from catecholamines metabolized within adrenal chromaffin cells. (PMID 15317907).
5001-33-2
C05588
21100
144365
19844
CNCC(O)C1=CC(OC)=C(O)C=C1
C10H15NO3
InChI=1S/C10H15NO3/c1-11-6-9(13)7-3-4-8(12)10(5-7)14-2/h3-5,9,11-13H,6H2,1-2H3
JWJCTZKFYGDABJ-UHFFFAOYSA-N
4-[1-hydroxy-2-(methylamino)ethyl]-2-methoxyphenol
197.231
197.105193351
-1.18
3
(+/-)-metanephrine
0
1
FDB023296
(+/-)-metanephrine;3-methoxy-adrenaline;3-methoxyadrenaline;3-o-methyl-adrenaline;3-o-methylepinephrine;4-hydroxy-3-methoxy-n-methylphenethanolamine;Dl-3-o-methyladrenaline;Dl-metanephrine;Metadrenaline;M-o-methyladrenaline
PW_C002043
Meta-np
2072
2
79135
132
121633
124
124191
118
127607
388
2041
3-Methoxy-4-hydroxyphenylglycolaldehyde
HMDB0004061
3-Methoxy-4-hydroxyphenylglycolaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of metanephrine. Metanephrine is an O-methylated metabolite formed by catechol-O-methyltransferase (COMT) from epinephrine. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. The inhibitory effects of methoxy phenolic derivatives on epinephrine-induced platelet aggregation may possibly be attributed to their free radical scavenging properties. There is substantial evidence to conclude that an internal rapid autoregulation of epinephrine-induced platelet aggregation, caused by its metabolic degradation products, takes place in vivo. (PMID: 11958479, 9706478).
17592-23-3
C05583
440729
389601
COC1=C(O)C=CC(=C1)C(O)C=O
C9H10O4
InChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3
VISAJVAPYPFKCL-UHFFFAOYSA-N
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
182.1733
182.057908808
-1.55
2
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
0
0
FDB023294
4-hydroxy-3-methoxy mandelaldehyde;4-hydroxy-3-methoxymandelaldehyde;4-hydroxy-3-methoxyphenylglycolaldehyde;A,4-dihydroxy-3-methoxy-benzeneacetaldehyde
PW_C002041
4H3M
2073
2
79134
132
121632
124
124190
118
127606
388
721
NAD
HMDB0000902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H27N7O14P2
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-N
1-[(2R,3R,4S,5R)-5-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy)(hydroxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium
663.4251
663.109121631
-2.52
8
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium
0
-1
FDB022309
3-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nad
PW_C000721
NAD
140
4
150
3
353
8
651
10
1114
2
1134
43
1273
5
1466
54
2229
49
2779
17
2835
29
3107
9
4807
18
4813
18
4819
28
4902
6
4960
31
5167
95
5238
103
5334
111
5360
112
5469
123
5482
125
5590
135
5610
118
5696
100
5738
108
5827
141
5912
147
5942
151
6024
155
6072
157
6076
161
6385
1
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
7459
222
8241
226
8359
225
9085
224
11819
216
12322
249
13006
298
13018
300
13256
223
42404
322
42619
315
77104
132
77120
133
77209
134
77370
331
77650
336
77667
334
77702
332
77709
130
77915
113
77983
347
78406
356
80006
368
80690
119
93825
124
110552
388
112750
166
112853
94
119929
122
119952
406
120171
407
120834
419
120984
408
121159
425
121242
126
121259
429
121817
383
122614
384
122742
120
123130
447
123141
136
123419
455
123549
374
123731
460
123812
443
123829
464
124370
398
125187
121
125319
297
125342
479
125530
481
125806
299
125825
490
125924
482
126515
495
126765
480
126885
501
127278
507
127383
502
128089
390
128360
391
128428
395
140757
185
1240
3,4-Dihydroxymandelic acid
HMDB0001866
3,4-Dihydroxymandelic acid is is a minor metabolite of norepinephrine in humans (PMID 12649306). Patients with neuroblastoma experience elevated levels of 3,4-Dihydroxymandelic acid and other Catecholamines metabolites, and their presence in urine is a good indicator for diagnosis and follow-up (PMID 8193481).
775-01-9
C05580
85782
27637
77371
OC(C(O)=O)C1=CC=C(O)C(O)=C1
C8H8O5
InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)
RGHMISIYKIHAJW-UHFFFAOYSA-N
2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid
184.1461
184.037173366
-1.24
4
dihydroxymandelic acid
0
-1
FDB022719
3,4 dihydroxymandelate;3,4 dihydroxymandelic acid;3,4-dihydroxymandelate;3,4-dihydroxyphenylglycolate;3,4-dihydroxyphenylglycolic acid;Dihydroxymandelate;Dihydroxymandelic acid;(3,4-dihydroxyphenyl)(hydroxy)acetic acid;Doma;(3,4-dihydroxyphenyl)(hydroxy)acetate;2-(3,4-dihydroxyphenyl)-2-hydroxyacetate;3,4-dihydroxymandelic acid
PW_C001240
34-DHMA
2074
2
79136
132
121634
124
124192
118
127608
388
1144
NADH
HMDB0001487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
665.441
665.124771695
-2.35
8
NADH
0
-2
FDB022649
1,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotide
PW_C001144
NADH
143
4
153
3
490
8
648
10
1115
2
1275
5
1469
54
2230
49
2781
17
2836
29
3109
9
4806
18
4812
18
4821
28
4904
6
4959
31
5169
95
5240
103
5332
111
5358
112
5466
123
5479
125
5593
135
5698
100
5737
108
5829
141
5915
147
5945
151
6027
155
6079
161
6387
1
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
7462
222
8244
226
8360
225
9086
224
11809
198
11821
216
12320
249
13003
298
13015
300
13255
223
42403
322
42618
315
77107
132
77123
133
77208
134
77371
331
77651
336
77668
334
77700
332
77707
130
77917
113
77986
347
80009
368
80691
119
93822
124
110549
388
112854
94
115838
118
119955
406
120172
407
120378
122
120986
408
121162
425
121244
126
121693
429
121818
383
122616
384
122745
120
123127
447
123138
136
123551
374
123734
460
123814
443
124242
464
124371
398
125189
121
125345
479
125531
481
125762
297
125808
299
125926
482
126516
495
126767
480
126888
501
127385
502
128090
390
128362
391
128429
395
140759
185
40034
Hydrogen Ion
HMDB0059597
Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])
C00080
1038
15378
1010
[H+]
H
InChI=1S/p+1
GPRLSGONYQIRFK-UHFFFAOYSA-N
hydron
1.0079
1.007825032
0
hydron
1
0
H+;H(+);Hydrogen cation;Hydron;Proton
PW_C040034
H+
215
4
670
8
753
15
788
31
848
3
1116
2
1463
26
1464
54
2231
49
2780
17
4250
22
4254
42
4547
10
4576
18
4694
70
5241
103
5327
111
5353
112
5626
108
5639
107
5699
100
5720
105
5742
117
5963
147
6037
155
6070
157
6093
161
6130
159
6232
166
6483
178
6601
152
6692
101
6843
188
6910
187
7100
163
7168
205
7191
206
7453
219
7454
220
7472
222
7525
213
7532
210
7558
212
7572
160
7590
170
8195
225
8218
151
8243
226
8413
162
8420
224
9139
195
9155
249
11915
164
12015
281
12181
285
12246
286
12266
287
12521
227
13257
223
13325
294
15330
308
42329
315
42354
318
42401
322
42405
312
42454
320
76912
293
77136
133
77210
134
77372
331
77804
114
77955
132
77990
327
77991
347
78379
345
79929
130
80019
368
80387
310
80388
304
80722
119
93823
124
94823
383
110550
388
112855
94
113280
390
115537
398
115539
118
115856
336
116205
109
119973
406
120193
407
120549
122
120593
409
121170
424
121171
425
122569
418
122615
384
122687
125
122758
120
123183
135
123218
137
123742
459
123743
460
125141
454
125188
121
125273
136
125359
479
125550
481
125730
483
125736
297
125809
299
126517
495
126717
489
126766
480
126823
300
126902
501
127213
208
128308
506
128361
391
128430
395
140692
882
140693
883
140699
167
140707
168
140715
14
140742
788
140743
597
140760
185
197
Vanillylmandelic acid
HMDB0000291
Vanillylmandelic acid is one of the products of the catabolism of catecholamines (epinephrine, norepinephrine and dopamine). High levels of vanillylmandelic acid can indicate an adrenal gland tumor (pheochromocytoma) or another type of tumor that produces catecholamines. (WebMD).
55-10-7
C05584
736172
1127735
643307
COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O
C9H10O5
InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m0/s1
CGQCWMIAEPEHNQ-QMMMGPOBSA-N
(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
198.1727
198.05282343
-1.58
3
(S)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
0
-1
FDB021931
(4-hydroxy-3-methoxyphenyl)glycolate;(4-hydroxy-3-methoxyphenyl)glycolic acid;3-methoxy-4-hydroxy-mandelic acid;3-methoxy-4-hydroxymandelate;3-methoxy-4-hydroxymandelic acid;3-methoxy-4-hydroxyphenylhydroxyacetate;3-methoxy-4-hydroxyphenylhydroxyacetic acid;4'-hydroxy-3'-methoxymandelate;4'-hydroxy-3'-methoxymandelic acid;4-hydroxy 3-methoxymandelic acid;4-hydroxy-3-methoxy-dl-mandelate;4-hydroxy-3-methoxy-dl-mandelic acid;4-hydroxy-3-methoxy-mandelate;4-hydroxy-3-methoxy-mandelic acid;4-hydroxy-3-methoxymandelate;4-hydroxy-3-methoxymandelic acid;Dl-3-methoxy-4-hydroxymandelate;Dl-3-methoxy-4-hydroxymandelic acid;Dl-4-hydroxy-3-methoxymandelate;Dl-4-hydroxy-3-methoxymandelic acid;Dl-vanillomandelate;Dl-vanillomandelic acid;Dl-vanillylmandelate;Dl-vanillylmandelic acid;Hmma;Hydroxymethoxymandelic acid;Lopac-h-0131;Vma;Vainillylmandelic acid;Vanillinmandelate;Vanillinmandelic acid;Vanillomandelate;Vanillomandelic acid;Vanillyl-mandelic acid;Vanillylmandelate;Vanillylmandellic acid;Vanillymandelic acid;Vanilmandelate;Vanilmandelic acid;Vanilylmandelic acid;Vanyl-mandelic acid;Vanylmandelic acid
PW_C000197
VMA
2075
2
79148
132
121649
124
124207
118
127623
388
222
3,4-Dihydroxyphenylglycol
HMDB0000318
3,4-Dihydroxyphenylglycol (DOPEG) is a normal norepinephrine metabolite present in CSF, plasma and urine in humans (PMID 6875564). In healthy individuals there is a tendency for free DOPEG to increase and for conjugated DOPEG to decrease with age; plasmatic DOPEG levels are significantly lower in depressed patients as compared to healthy controls (PMID 6671452).
3343-19-9
C05576
91528
1387
82648
OCC(O)C1=CC(O)=C(O)C=C1
C8H10O4
InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2
MTVWFVDWRVYDOR-UHFFFAOYSA-N
4-(1,2-dihydroxyethyl)benzene-1,2-diol
170.1626
170.057908808
-1.01
4
3,4-dihydroxyphenylglycol
0
0
FDB020084
(3,4-dihydroxyphenyl)ethylene glycol;1-(3,4-dihydroxyphenyl)-1,2-ethanediol;3,4-dihydroxyphenethyl glycol;3,4-dihydroxyphenylethyl glycol;3,4-dihydroxyphenylethyleneglycol;4-(1,2-dihydroxyethyl)-1,2-benzenediol;Dhpg;Dl-3,4-dihydroxyphenylglycol;Dopeg;2-hydroxy-2-(3,4-dihydroxy)phenylethanol;3,4-dihydroxyphenylglycol;Beta,3,4-trihydroxy phenethyl alcohol;Dihydroxyphenylethylene glycol;B,3,4-trihydroxy phenethyl alcohol;β,3,4-trihydroxy phenethyl alcohol
PW_C000222
DHPG
2076
2
79137
132
121635
124
124193
118
127609
388
9794
Iron
HMDB0015531
Iron is a metallic element found in certain minerals, in nearly all soils, and in mineral waters. Iron is required for life. It exists in all living species, ranging from bacteria to humans. It can be found primarily in blood and it is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. In humans, iron is involved in several metabolic pathways, some of which include the rofecoxib pathway, magnesium salicylate action pathway, etodolac pathway, and diclofenac pathway. Iron is also involved in several metabolic disorders, some of which include adenine phosphoribosyltransferase deficiency (APRT), porphyria variegata (PV), adenylosuccinate lyase deficiency, and AICA-ribosiduria. The major activity of supplemental iron is in the prevention and treatment of iron-deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic, and cognition-enhancing activities. Iron can be found in a number of food items such as chinese water chestnut, hyssop, daikon radish, and peppermint, which makes it a potential biomarker for the consumption of these food products.
7439-89-6
C00023
23925
18248
22368
DB01592
[Fe++]
Fe
InChI=1S/Fe/q+2
CWYNVVGOOAEACU-UHFFFAOYSA-N
lambda2-iron(2+) ion
55.845
55.934942133
0
lambda2-iron(2+) ion
2
2
C00023
26fe;Eisen;Fe;Fer;Ferrum;Hierro
PW_C009794
Iron
1138
8
1266
5
1533
2
1635
49
3119
29
4341
18
7330
213
12056
225
77683
130
77928
336
78261
132
78409
111
78428
334
78938
331
120838
122
120992
408
121256
429
121371
124
121502
383
121727
125
123423
135
123557
374
123826
464
123930
118
124060
398
124278
136
125829
297
125932
482
126044
299
127282
205
127391
502
127496
388
3007
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
HMDB0006915
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is an intermediate in tyrosine metabolism. It is reversibly converted from 4-hydroxyphenylpyruvate via phenylpyruvate tautomerase. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is typically a terminal product of tyrosine metabolism.
C05350
636708
27683
552441
OC(=O)C(\O)=C\C1=CC=C(O)C=C1
C9H8O4
InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-
GQYBCIHRWMPOOF-YVMONPNESA-N
(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid
180.1574
180.042258744
-2.35
3
4,α-dihydroxycinnamic acid
0
-1
FDB024152
2-hydroxy-3-(4-hydroxyphenyl)propenoate;2-hydroxy-3-(4-hydroxyphenyl)propenoic acid;4-hydroxy-enol-phenylpyruvate;4,alpha-dihydroxycinnamic acid;2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate;4,a-dihydroxycinnamate;4,a-dihydroxycinnamic acid;4,alpha-dihydroxycinnamate;4,α-dihydroxycinnamate;4,α-dihydroxycinnamic acid
PW_C003007
4AD
2006
2
79143
132
121644
124
124202
118
127618
388
7226
Topaquinone
HMDB0011639
Topaquinone (TPQ), is the quinone of 2,4,5-trihydroxyphenylalanine. TPQ is the cofactor in most copper-containing amine oxidases. It is produced by post-translational modification of a strictly conserved active-site tyrosine residue with the participation of the copper ion at the active site. Once formed, TPQ acts as a switch between the heterolytic transformation of amine substrates to aldehydes, via a pyridoxal phosphate-like Schiff base complex, and one electron chemistry involving reduction of molecular oxygen (PMID: 12686122).
64192-68-3
123871
36076
TOPAQUINONE
110408
N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O
C9H9NO5
InChI=1S/C9H9NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11H,1,10H2,(H,14,15)/t5-/m0/s1
YWRFBISQAMHSIX-YFKPBYRVSA-N
(2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
211.1715
211.048072403
-2.06
3
(2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid
0
-1
(s)-a-amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoate;(s)-a-amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acid;(s)-alpha-amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoate;(s)-alpha-amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acid;2,4,5-trihydroxyphenylalanine quinone;6-hydroxydopa quinone;6-hydroxydopaquinone;O-topaquinone;Tpq;Topa quinone;Topaquinone;A-amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoate;A-amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acid;Alpha-amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoate;Alpha-amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acid
PW_C007226
TopQne
554
14
4473
2
77048
294
77601
115
78155
132
79245
293
120466
405
121050
124
123100
376
123614
118
125712
478
127204
209
127620
388
1081
Guaiacol
HMDB0001398
Guaiacol is a phenolic compound with a methoxy group and is the monomethyl ether of catechol. Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes. It therefore serves as a reducing co-substrate for COX reactions. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is a yellowish aromatic oil that is now commonly derived from guaiacum or wood creosote. It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation, and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation. Guaiacol is also used in the preparation of synthetic vanillin. Guaiacol is also present in wood smoke, as a product of pyrolysis of lignin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma. (PMID 4344880, 16152729).
90-05-1
C01502
460
28591
CPD-400
447
COC1=C(O)C=CC=C1
C7H8O2
InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
LHGVFZTZFXWLCP-UHFFFAOYSA-N
2-methoxyphenol
124.139
124.052429498
-0.27
1
guaiacol
0
0
FDB011885
1-hydroxy-2-methoxybenzene;2-hydroxyanisole;2-methoxy-phenol;2-methoxyphenol;Anastil;Catechol monomethyl ether;Creodon;Guaiacol;Guaiacol (liquid) extra pure;Guaiastil;Guaicol;Guaicolina;Guajakol;Guajol;Guasol;Guiacol;Methoxyphenol;Methylcatachol;Methylcatechol;O-guaiacol;O-hydroxyanisole;O-methoxy-phenol;O-methoxyphenol;O-methyl catechol;Pyrocatechol monomethyl ether;Pyroguaiac acid
PW_C001081
Guajol
4500
2
79145
132
121646
124
124204
118
127621
388
764
Pyrocatechol
HMDB0000957
Pyrocatechol, often known as catechol or benzene-1,2-diol, is a benzenediol, with formula C6H4(OH)2. It was first prepared in 1839 by H. Reinsch by distilling catechin (the juice of Mimosa catechu). This colourless compound occurs naturally, but about 20000 tons are manufactured each year, mainly as precursors to pesticides, flavors, and fragrances. Its sulfonic acid is often present in the urine of many mammals. Small amounts of catechol occur naturally in fruits and vegetables, along with the enzyme polyphenol oxidase. Upon mixing the enzyme with the substrate and exposure to oxygen (as when a potato or apple is cut), the colorless catechol oxidizes to reddish-brown benzoquinone derivatives. The enzyme is inactivated by adding an acid, such as lemon juice, or by refrigeration. Excluding oxygen also prevents the browning reaction. Catechol melts at 28 oC and boils at 250 oC. It is employed in medicine as an expectorant. The dimethyl ether or veratrol is also used in medicine. Many other pyrocatechin derivatives have been suggested for therapeutic application.
120-80-9
C00090
289
18135
CATECHOL
13837760
DB02232
OC1=CC=CC=C1O
C6H6O2
InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
YCIMNLLNPGFGHC-UHFFFAOYSA-N
benzene-1,2-diol
110.1106
110.036779436
-0.17
2
catechol
0
0
FDB001512
1,2-dihydroxybenzene;2-hydroxyphenol;Catechol;Durafur developer c;Fouramine pch;Fourrine 68;O-benzenediol;O-dihydroxybenzene;O-dioxybenzene;O-hydroquinone;O-hydroxyphenol;O-phenylenediol;Oxyphenate;Oxyphenic acid;Pelagol grey c;Phthalhydroquinone;Phthalic alcohol;Pyrocatechin;Pyrocatechine;Pyrocatechol
PW_C000764
Catecho
2932
29
3834
14
4501
2
68497
60
79146
132
121647
124
124205
118
127622
388
1147
Vanylglycol
HMDB0001490
Vanylglycol (MHPG) is a O-methylated metabolite of normetanephrine. MHPG is formed by catechol-O-methyltransferase (COMT) from norepinephrine. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. MHPG is found normally in urine, in plasma and cerebrospinal fluid. Alcohol consumption increases the level of HMPG in urine and CSF. Alcohol dehydrogenase has been shown to act on norepinephrine and produce HMPG. (PMID: 11958479, 9706478, 7735466, 2455302).
534-82-7
C05594
10805
846276
10348
COC1=CC(=CC=C1O)C(O)CO
C9H12O4
InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3
FBWPWWWZWKPJFL-UHFFFAOYSA-N
1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol
184.1892
184.073558872
-1.31
3
methoxyhydroxyphenylglycol
0
0
FDB022651
1-(4-hydroxy-3-methoxyphenyl)-1,2-ethanediol;3-methoxy-4-hydroxyphenethylene glycol;3-methoxy-4-hydroxyphenyl glycol;4-hydroxy-3-methoxy-b-phenylglycol;4-hydroxy-3-methoxy-beta-phenylglycol;4-hydroxy-3-methoxyphenyl glycol;Hmpg;Hydroxymethoxyphenylglycol;Mhpg;Mopeg;Methoxyhydroxyphenylglycol;Vanylglycol
PW_C001147
Vanygly
2079
2
79149
132
121650
124
124208
118
127624
388
15
3-Methoxytyramine
HMDB0000022
The O-methylated derivative of dopamine. Dopamine is methylated by catechol-O-methyltransferase (COMT) to make 3-Methoxytyramine. This compound can be broken down to homovanillic acid by monoamine oxidase and aldehyde dehydrogenase. Elevated concentrations of this compound are indicated for a variety of brain and carcinoid tumors as well as certain mental disorders.
554-52-9
C05587
1669
742324
1606
COC1=C(O)C=CC(CCN)=C1
C9H13NO2
InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
DIVQKHQLANKJQO-UHFFFAOYSA-N
4-(2-aminoethyl)-2-methoxyphenol
167.205
167.094628665
-1.49
2
methoxytyramine
0
1
FDB021876
3-methoxy-4-hydroxyphenylethyl amine;3-methoxytyramine;3-o-methyldopamine;4-(2-amino-ethyl)-2-methoxy-phenol;4-(2-aminoethyl)-2-methoxy-phenol;4-(2-aminoethyl)-2-methoxyphenol;5-(2-aminoethyl)guaiacol
PW_C000015
3-Motyr
2081
2
79140
132
121639
124
124197
118
127613
388
1969
3,4-Dihydroxyphenylacetaldehyde
HMDB0003791
3,4-Dihydroxyphenylacetaldehyde (DOPAL) is a metabolite of the monoamine oxidase-catalyzed oxidative deamination of dopamine. Aldehydes are highly reactive molecules formed during the biotransformation of numerous endogenous and exogenous compounds, including biogenic amines. DOPAL generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. There is an increasing body of evidence suggesting that these compounds are neurotoxic, and it has been recently hypothesized that neurodegenerative disorders may be associated with increased levels of this biogenic aldehyde. It is possible to speculate that reduced detoxification of 3,4- dihydroxymandelaldehyde from impaired or deficient aldehyde dehydrogenase function may be a contributing factor in the suggested neurotoxicity of these compounds. Aldehyde dehydrogenases are a group of NAD(P)+ -dependent enzymes that catalyze the oxidation of aldehydes, such as those derived from catecholamines, to their corresponding carboxylic acids. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. Several pharmaceutical agents and environmental toxins (i.e.: 4-hydroxy-2-nonenal) are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813, 14697885, 11164826, 16956664.
5707-55-1
C04043
119219
27978
106504
OC1=C(O)C=C(CC=O)C=C1
C8H8O3
InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2
IADQVXRMSNIUEL-UHFFFAOYSA-N
2-(3,4-dihydroxyphenyl)acetaldehyde
152.1473
152.047344122
-1.24
2
dopal
0
0
FDB023227
3,4-dihydroxy-benzeneacetaldehyde;Protocatechuatealdehyde;2-(3,4-dihydroxyphenyl)ethanal;Dopal
PW_C001969
3,4-HPA
2082
2
77045
294
79139
132
79251
293
121638
124
124196
118
127612
388
1029
3,4-Dihydroxybenzeneacetic acid
HMDB0001336
3,4-dihydroxyphenylacetic acid (DOPAC) is a phenolic acid. DOPAC is a neuronal metabolite of dopamine (DA). DA undergoes monoamine oxidase-catalyzed oxidative deamination to 3,4-dihydroxyphenylacetaldehyde (DOPAL), which is metabolized primarily to DOPAC via aldehyde dehydrogenase (ALDH2). The biotransformation of DOPAL is critical as previous studies have demonstrated this DA-derived aldehyde to be a reactive electrophile and toxic to dopaminergic cells. Known inhibitors of mitochondrial ALDH2, such as 4-hydroxy-2-nonenal (4HNE) inhibit ALDH2-mediated oxidation of the endogenous neurotoxin DOPAL. 4HNE is one of the resulting products of oxidative stress, thus linking oxidative stress to the uncontrolled production of an endogenous neurotoxin relevant to Parkinson's disease. In early onset Parkinson disease there is markedly reduced activities of both monoamine oxidase (MAO) A and B. The amount of DOPAC, which is produced during dopamine oxidation by MAO, is greatly reduced as a result of increased parkin overexpression. Administration of methamphetamine to animals causes loss of DA terminals in the brain, and significant decreases in Dopamine and dihydroxyphenylacetic acid (DOPAC) in the striata. Renal dopamine produced in the residual tubular units may be enhanced during a sodium challenge, thus behaving appropriately as a compensatory natriuretic hormone; however the renal dopaminergic system in patients afflicted with renal parenchymal disorders should address parameters other than free urinary dopamine, namely the urinary excretion of L-DOPA and metabolites. DOPAC is one of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements. DOPAC exhibits a considerable antiproliferative effect in LNCaP prostate cancer and HCT116 colon cancer cells. The antiproliferative activity of DOPAC may be due to its catechol structure. A similar association of the catechol moiety in the B-ring with antiproliferative activity was demonstrated for flavanones. (PMID: 16956664, 16455660, 8561959, 11369822, 10443478, 16365058).
102-32-9
C01161
547
41941
CPD-782
532
DB01702
OC(=O)CC1=CC(O)=C(O)C=C1
C8H8O4
InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
CFFZDZCDUFSOFZ-UHFFFAOYSA-N
2-(3,4-dihydroxyphenyl)acetic acid
168.1467
168.042258744
-1.37
3
3,4 dihydroxyphenylacetic acid
0
-1
FDB000316
(3,4-dihydroxyphenyl)acetate;(3,4-dihydroxyphenyl)acetic acid;(3,4-dihydroxyphenyl)-acetic acid;2-(3,4-dihydroxyphenyl)acetic acid;3,4-dhpop;3,4-dihydroxy-benzeneacetic acid;3,4-dihydroxy-phenylacetic acid;3,4-dihydroxybenzeneacetate;3,4-dihydroxybenzeneacetic acid;3,4-dihydroxyphenyl acetate;3,4-dihydroxyphenyl acetic acid;3,4-dihydroxyphenylacetate;3,4-dihydroxyphenylacetic acid;Dhy;Dopac;Dihydroxyphenylacetate;Dihydroxyphenylacetic acid;Dopacetate;Dopacetic acid;Haa;Homogentisic acid;Homoprotocatechuate;Homoprotocatechuic acid
PW_C001029
34DHBzA
2083
2
79141
132
121640
124
124198
118
127614
388
544
Fe2+
HMDB0000692
Iron is a chemical element with the symbol Fe and atomic number 26. Iron makes up 5% of the Earth's crust and is second in abundance to aluminium among the metals and fourth in abundance among the elements. Physiologically, it. exists as an ion in the body. Iron (as Fe2+, ferrous ion) is a necessary trace element used by all known living organisms. Iron-containing enzymes, usually containing heme prosthetic groups, participate in catalysis of oxidation reactions in biology, and in transport of a number of soluble gases. Iron is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Inorganic iron involved in redox reactions is also found in the iron-sulfur clusters of many enzymes, such as nitrogenase (involved in the synthesis of ammonia from nitrogen and hydrogen) and hydrogenase. A class of non-heme iron proteins is responsible for a wide range of functions such as ribonucleotide reductase (reduces ribose to deoxyribose; DNA biosynthesis) and purple acid phosphatase (hydrolysis of phosphate esters). When the body is fighting a bacterial infection, the body sequesters iron inside of cells (mostly stored in the storage molecule ferritin) so that it cannot be used by bacteria. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. Humans experience iron toxicity above 20 milligrams of iron for every kilogram of weight, and 60 milligrams per kilogram is a lethal dose. Over-consumption of iron, often the result of children eating large quantities of ferrous sulfate tablets intended for adult consumption, is the most common toxicological cause of death in children under six. The DRI lists the Tolerable Upper Intake Level (UL) for adults as 45 mg/day. For children under fourteen years old the UL is 40 mg/day. Iron is a metal extracted from iron ore, and is almost never found in the free elemental state.
15438-31-0
C14818
27284
29033
Ferric-Hydroxamate-Complexes
25394
DB01592
[Fe++]
Fe
InChI=1S/Fe/q+2
CWYNVVGOOAEACU-UHFFFAOYSA-N
lambda2-iron(2+) ion
55.845
55.934942133
0
lambda2-iron(2+) ion
2
2
FDB016251
Armco iron;Carbonyl iron;Fe;Ferrovac e;Hematite;Infed;Loha;Limonite;Magnetite;Malleable iron;Metopirone;Metyrapone;Pzho;Pzh2m;Remko;Suy-b 2;Taconite;Venofer;Wrought iron;Fe (ii) ion;Fe(ii);Fe2+;Fe(2+);Ferrous ion;Iron ion(2+)
PW_C000544
Fe2+
398
19
641
3
678
31
692
20
709
8
1777
2
7041
163
7052
160
12060
225
12143
151
77179
132
77740
112
77751
129
77760
341
77782
111
120544
407
120557
414
120570
122
121765
124
123178
119
123191
450
123204
135
124316
118
126143
299
126185
481
127650
388
140710
49
140716
18
74
Homovanillic acid
HMDB0000118
Homovanillic acid is a dopamine metabolite occurring in human biofluids. A high proportion of patients with neuroblastoma excrete increased amounts of it in their urine. Homovanillic acid is a major catecholamine metabolite. It is used as a reagent to detect oxidative enzymes.(Wikipedia).
306-08-1
C05582
1738
545959
1675
COC1=CC(CC(O)=O)=CC=C1O
C9H10O4
InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
QRMZSPFSDQBLIX-UHFFFAOYSA-N
2-(4-hydroxy-3-methoxyphenyl)acetic acid
182.1733
182.057908808
-1.83
2
homovanillic acid
0
-1
FDB001783
(4-hydroxy-3-methoxyphenyl)acetate;(4-hydroxy-3-methoxyphenyl)acetic acid;3-methoxy-4-hydroxy-phenylacetic acid;3-methoxy-4-hydroxyphenylacetate;3-methoxy-4-hydroxyphenylacetic acid;4-hydroxy-3-methoxybenzeneacetate;4-hydroxy-3-methoxybenzeneacetic acid;4-hydroxy-3-methoxyphenylacetic acid;4-hydroxy 3-methoxyphenylacetic acid;Homovanilate;Homovanilic acid;Homovanillate;Homovanillinic acid;Vanilacetate;Vanilacetic acid;Hva;Vanillacetic acid;Vanillacetate
PW_C000074
HVA
2089
2
79142
132
121642
124
124200
118
127616
388
271
Tyrosine aminotransferase
P17735
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
HMDBP00277
TAT
16q22.1
X52518
1
2.6.1.5
1281
8
1993
2
141069
184
277
Aspartate aminotransferase, cytoplasmic
P17174
Plays a key role in amino acid metabolism (By similarity).
HMDBP00283
GOT1
10q24.1-q25.1
BC000498
1
2.6.1.1; 2.6.1.3
712
8
1995
2
141826
26
143143
1
786
4-hydroxyphenylpyruvate dioxygenase
P32754
Key enzyme in the degradation of tyrosine.
HMDBP00841
HPD
12q24-qter
CH471054
1
1.13.11.27
1297
8
1998
2
762
Maleylacetoacetate isomerase
O43708
Bifunctional enzyme showing minimal glutathione-conjugating activity with ethacrynic acid and 7-chloro-4-nitrobenz-2-oxa-1,3-diazole and maleylacetoacetate isomerase activity. Has also low glutathione peroxidase activity with T-butyl and cumene hydroperoxides. Is able to catalyze the glutathione dependent oxygenation of dichloroacetic acid to glyoxylic acid.
HMDBP00817
GSTZ1
14q24.3
AF053543
1
5.2.1.2; 2.5.1.18
1301
8
2002
2
677
Fumarylacetoacetase
P16930
HMDBP00713
FAH
15q25.1
M55150
1
3.7.1.2
1303
8
2005
2
272
Aromatic-L-amino-acid decarboxylase
P20711
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
HMDBP00278
DDC
7p12.2
M84588
1
4.1.1.28
402
19
697
20
2009
2
135586
599
139396
87
139448
48
139695
789
140549
33
140550
865
141305
77
143183
39
143363
26
143968
60
286
Aldehyde dehydrogenase, dimeric NADP-preferring
P30838
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
HMDBP00292
ALDH3A1
17p11.2
M77477
1
1.2.1.5
1317
8
2015
2
3402
7
3619
29
5002
31
142964
789
143384
26
84
Tyrosinase
P14679
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
HMDBP00087
TYR
11q14-q21
AF237809
1
1.14.18.1
1185
33
2020
24
2027
2
136163
415
144092
1213
247
Dopamine beta-hydroxylase
P09172
Conversion of dopamine to noradrenaline.
HMDBP00253
DBH
9q34
X13255
1
1.14.17.1
409
19
703
20
2024
14
139400
84
139402
476
139403
378
139696
789
141271
866
142624
2
142625
48
142894
39
142897
1060
143366
26
203
L-dopachrome tautomerase
P40126
Involved in regulating eumelanin and phaeomelanin levels.
HMDBP00209
DCT
13q32
BC028311
1
5.3.3.12
2035
2
136162
33
144093
1213
398
Phenylethanolamine N-methyltransferase
P11086
Converts noradrenaline to adrenaline.
HMDBP00406
PNMT
17q
BC037246
1
2.1.1.28
707
20
2069
2
139401
87
143368
26
164
Amine oxidase [flavin-containing] A
P21397
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
HMDBP00169
MAOA
Xp11.3
X60809
1
1.4.3.4
1315
8
2013
2
2537
22
3724
26
4742
13
142652
789
142654
912
142655
787
142963
1070
143184
39
143383
1143
729
Alcohol dehydrogenase 1A
P07327
HMDBP00784
ADH1A
4q23
BT019812
1
1.1.1.1
2077
2
3413
8
3611
29
5000
31
143572
26
787
Homogentisate 1,2-dioxygenase
Q93099
HMDBP00842
HGD
3q13.33
AK313563
1
1.13.11.5
1299
8
2000
2
97
Macrophage migration inhibitory factor
P14174
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
HMDBP00100
MIF
22q11.23
CR456520
1
5.3.2.1; 5.3.3.12
2007
2
382
Amiloride-sensitive amine oxidase [copper-containing]
P19801
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
HMDBP00390
ABP1
7q36.1
BC014093
1
1.4.3.22
1319
8
2012
2
144119
3
266
Catechol O-methyltransferase
P21964
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
HMDBP00272
COMT
22q11.21
BC011935
1
2.1.1.6
4502
2
4684
10
137072
394
137074
8
141114
847
142651
789
143360
26
1061
3-hydroxyanthranilate 3,4-dioxygenase
P46952
Catalyzes the oxidative ring opening of 3-hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate.
HMDBP01128
HAAO
2p21
BC029510
1
1.13.11.6
2084
2
135603
393
137073
8
357
Tyrosine aminotransferase
1
PW_P000357
378
271
2
163
1148
1
203
Aspartate aminotransferase, cytoplasmic
1
PW_P000203
221
277
2
92
1148
1
361
4-hydroxyphenylpyruvate dioxygenase
1
PW_P000361
383
786
2
165
8133
2
363
Maleylacetoacetate isomerase
1
PW_P000363
385
762
2
364
Fumarylacetoacetase
1
PW_P000364
386
677
2
167
353
1
168
423
1
96
Aromatic-L-amino-acid decarboxylase
1
PW_P000096
111
272
49
1148
1
371
Aldehyde dehydrogenase, dimeric NADP-preferring
1
PW_P000371
393
286
1
327
Tyrosinase
1
PW_P000327
348
84
1
147
514
2
98
Dopamine beta-hydroxylase
1
PW_P000098
113
247
50
8525
1
51
514
2
529
L-dopachrome tautomerase
1
PW_P000529
561
203
1
260
9795
2
2033
2
201
Phenylethanolamine N-methyltransferase
1
PW_P000201
219
398
1
370
Amine oxidase [flavin-containing] A
1
PW_P000370
392
164
1
171
964
1
544
Alcohol dehydrogenase 1A
1
PW_P000544
576
729
2
265
9795
4
362
Homogentisate 1,2-dioxygenase
1
PW_P000362
384
787
1
166
9794
1
528
Macrophage migration inhibitory factor
1
PW_P000528
560
97
2
372
Amiloride-sensitive amine oxidase [copper-containing]
1
PW_P000372
394
382
2
172
514
2
173
353
4
438
7226
1
1075
Catechol O-methyltransferase
1
PW_P001075
1235
266
1
439
423
1
546
3,4-Dihydroxyphenylacetaldehyde
1
PW_P000546
586
1061
2
333
544
1
80
false
PW_R000080
Both
311
103
1
Compound
false
312
134
1
Compound
true
313
558
1
Compound
false
314
95
1
Compound
true
440
357
2.6.1.5
1118
false
PW_R001118
Right
4317
134
1
Compound
false
4318
123
1
Compound
true
4319
148
1
Compound
true
4320
95
1
Compound
false
812
203
320
false
PW_R000320
Right
1342
558
1
Compound
false
1343
1065
1
Compound
true
1344
84
1
Compound
false
1345
1316
1
Compound
true
444
361
1.13.11.27
386
false
PW_R000386
Right
1589
1376
1
Compound
false
1590
981
1
Compound
false
446
363
263
false
PW_R000263
Right
1121
981
1
Compound
false
1122
1420
1
Compound
true
1123
42
1
Compound
false
1124
88
1
Compound
false
447
364
3.7.1.2
1120
false
PW_R001120
Right
4325
103
1
Compound
false
4326
210
1
Compound
false
4327
1316
1
Compound
true
815
96
4.1.1.28
1123
false
PW_R001123
Right
4338
2411
1
Compound
false
4339
143
1
Compound
true
4340
1420
1
Compound
true
4341
13
1
Compound
false
4342
146
1
Compound
true
818
371
1.2.1.5
1124
false
PW_R001124
Right
4343
210
1
Compound
false
4344
1065
1
Compound
true
4345
52
1
Compound
false
4346
1420
1
Compound
true
819
327
1.14.18.1
634
false
PW_R000634
Right
2625
52
1
Compound
false
4347
31
1
Compound
true
4348
1065
1
Compound
true
2626
142
1
Compound
false
4349
977
1
Compound
true
4350
1420
1
Compound
true
118
98
1.14.17.1
633
false
PW_R000633
Right
2623
117
1
Compound
false
4351
19
1
Compound
true
4352
1065
1
Compound
true
2624
52
1
Compound
false
4353
1541
1
Compound
true
117
96
4.1.1.28
543
false
PW_R000543
Right
2269
117
2
Compound
false
2270
1065
1
Compound
true
2271
952
2
Compound
false
2272
1420
2
Compound
true
822
327
1.14.18.1
1126
PW_R001126
Right
4356
952
1
Compound
false
4357
2044
1
Compound
false
1127
PW_R001127
Right
4358
2044
1
Compound
false
4359
1105
1
Compound
false
1128
false
PW_R001128
Right
4360
1105
1
Compound
false
4361
1065
1
Compound
true
4362
2040
1
Compound
false
4363
1420
1
Compound
true
823
327
1.14.18.1
1129
false
PW_R001129
Right
4364
2040
1
Compound
false
4365
1065
1
Compound
true
4366
2926
1
Compound
false
4367
1420
1
Compound
true
824
327
1.14.18.1
1130
PW_R001130
Right
4368
2926
1
Compound
false
4369
2045
1
Compound
false
1131
false
PW_R001131
Right
4370
1105
1
Compound
false
4371
968
1
Compound
false
825
529
5.3.3.12
1132
false
PW_R001132
Right
4372
968
2
Compound
false
4373
1065
1
Compound
true
4374
2045
1
Compound
false
4375
1420
1
Compound
true
826
327
1.14.18.1
466
false
PW_R000466
Right
1935
921
1
Compound
true
1936
142
1
Compound
false
1937
749
1
Compound
true
1938
48
1
Compound
false
218
201
2.1.1.28
153
false
PW_R000153
Right
677
142
1
Compound
false
678
1420
1
Compound
true
679
1065
1
Compound
true
680
2683
1
Compound
false
681
35
1
Compound
true
682
1783
1
Compound
true
847
370
1.4.3.4
155
false
PW_R000155
Right
689
48
1
Compound
false
690
1420
1
Compound
true
691
1065
1
Compound
true
692
2683
1
Compound
false
693
108
1
Compound
true
694
1783
1
Compound
true
848
370
1.4.3.4
1156
false
PW_R001156
Right
4437
654
1
Compound
false
4438
1420
1
Compound
true
4439
1065
1
Compound
true
4440
2041
1
Compound
false
4441
35
1
Compound
true
4442
1783
1
Compound
true
850
370
1.4.3.4
1157
false
PW_R001157
Right
4443
2043
1
Compound
false
4444
1420
1
Compound
true
4445
1065
1
Compound
true
4446
2041
1
Compound
false
4447
35
1
Compound
true
4448
1783
1
Compound
true
851
370
1.4.3.4
123
false
PW_R000123
Right
508
2683
1
Compound
false
509
721
1
Compound
true
510
1420
1
Compound
true
511
1240
1
Compound
false
512
1144
1
Compound
true
513
40034
1
Compound
true
852
371
1.2.1.5
1161
false
PW_R001161
Right
4460
2683
1
Compound
false
4461
721
1
Compound
true
4462
1144
1
Compound
true
4463
222
1
Compound
false
856
544
1.1.1.1
310
false
PW_R000310
Right
1306
84
1
Compound
false
1307
1065
1
Compound
true
1308
1376
1
Compound
false
445
362
1.13.11.5
392
false
PW_R000392
Right
1612
558
1
Compound
false
1613
3007
1
Compound
false
814
528
1121
false
PW_R001121
Right
4328
210
1
Compound
false
4329
1420
1
Compound
true
4330
1065
1
Compound
true
4331
2411
1
Compound
false
4332
1783
1
Compound
true
7992
35
1
Compound
true
816
372
1.4.3.22
1122
false
PW_R001122
Right
4333
210
1
Compound
false
4334
1420
1
Compound
true
4335
1065
1
Compound
true
4336
2411
1
Compound
false
4337
1783
1
Compound
true
7993
35
1
Compound
true
817
370
1.4.3.4
2250
false
PW_R002250
Right
8012
210
1
Compound
false
8013
1065
1
Compound
true
8014
117
1
Compound
false
8015
1420
1
Compound
true
2115
327
1.14.18.1
2251
false
PW_R002251
Right
8016
142
1
Compound
false
8017
1081
1
Compound
true
8018
654
1
Compound
false
8019
764
1
Compound
true
2116
1075
2.1.1.6
1159
false
PW_R001159
Right
4451
2041
1
Compound
false
4452
143
1
Compound
true
4453
1420
1
Compound
true
4454
197
1
Compound
false
4455
146
1
Compound
true
854
371
1.2.1.5
2252
false
PW_R002252
Right
8020
48
1
Compound
false
8021
1081
1
Compound
true
8022
2043
1
Compound
false
8023
764
1
Compound
true
2117
1075
2.1.1.6
1162
false
PW_R001162
Right
4464
222
1
Compound
false
8024
1081
1
Compound
true
4465
1147
1
Compound
false
8025
764
1
Compound
true
857
1075
2.1.1.6
1158
false
PW_R001158
Right
4449
1240
1
Compound
false
8026
1081
1
Compound
true
4450
197
1
Compound
false
8027
764
1
Compound
true
853
1075
2.1.1.6
1163
false
PW_R001163
Right
4466
52
1
Compound
false
8028
1081
1
Compound
true
4467
15
1
Compound
false
8029
764
1
Compound
true
858
1075
2.1.1.6
150
false
PW_R000150
Right
659
52
1
Compound
false
660
1420
1
Compound
true
661
1065
1
Compound
true
662
1969
1
Compound
false
663
35
1
Compound
true
664
1783
1
Compound
true
859
370
1.4.3.4
158
false
PW_R000158
Right
707
15
1
Compound
false
708
1420
1
Compound
true
709
1065
1
Compound
true
710
2411
1
Compound
false
711
1783
1
Compound
true
712
35
1
Compound
true
860
370
1.4.3.4
122
false
PW_R000122
Right
502
1969
1
Compound
false
503
721
1
Compound
true
504
1420
1
Compound
true
505
1029
1
Compound
false
506
1144
1
Compound
true
507
40034
1
Compound
true
861
546
1.13.11.6
199
false
PW_R000199
Right
878
1029
1
Compound
false
8030
1081
1
Compound
true
880
74
1
Compound
false
8031
764
1
Compound
true
863
1075
2.1.1.6
124
false
PW_R000124
Right
514
2411
1
Compound
false
515
721
1
Compound
true
516
1420
1
Compound
true
517
74
1
Compound
false
518
1144
1
Compound
true
519
40034
1
Compound
true
866
371
1.2.1.5
3583
103
2
81
false
1400
1575
10
regular
200
190
3616
134
2
81
false
1645
2015
10
regular
200
190
3617
558
2
81
false
805
2050
10
regular
200
190
3618
95
2
81
false
1065
2015
10
regular
200
190
3619
1148
2
9
false
1280
1882
10
regular
100
35
3620
123
2
81
false
1500
2210
10
regular
200
190
3621
148
2
81
false
1200
2215
10
regular
200
190
3622
1148
2
9
false
1415
2060
10
regular
100
35
3623
1065
2
65
false
975
2245
10
regular
78
78
3624
84
2
81
false
805
2480
10
regular
200
190
3625
1316
2
52
false
980
2400
10
regular
78
78
3626
8133
2
9
false
860
2320
19
regular
100
25
3636
1376
2
81
false
805
2880
10
regular
200
190
3638
981
2
81
false
1275
2875
10
regular
200
190
3639
1420
2
49
false
1475
2790
10
regular
78
78
3640
42
2
81
false
1690
2670
10
regular
200
190
3641
88
2
81
false
1850
2875
10
regular
200
190
3642
353
2
9
false
1610
2907
20
regular
100
25
3643
423
2
9
false
1610
2927
19
regular
100
25
3645
210
2
81
false
2160
1573
10
regular
200
190
3646
1316
2
52
false
1941
1489
10
regular
78
78
3647
1148
2
9
false
1745
1610
10
regular
100
35
3650
2411
2
81
false
2157
2083
10
regular
200
190
3658
143
2
61
false
2117
2308
10
regular
50
30
3659
1420
2
49
false
2342
2288
10
regular
78
78
3660
13
2
81
false
2157
2563
10
regular
200
190
3661
146
2
62
false
2112
2508
10
regular
50
30
3662
1065
33
65
false
2395
1143
10
regular
78
78
3663
52
33
81
false
2815
933
10
regular
200
190
3664
1420
33
49
false
2705
1143
10
regular
78
78
3665
514
33
9
false
2540
1228
19
regular
100
25
3666
31
14
81
false
2660
210
10
regular
200
190
3667
1065
14
65
false
2971
371
10
regular
78
78
3668
142
14
81
false
3365
210
10
regular
200
190
3669
977
14
81
false
3145
22
10
regular
200
190
3670
1420
14
49
false
3195
367
10
regular
78
78
3671
8525
14
9
false
3080
250
10
regular
100
35
3672
514
14
9
false
3085
340
10
regular
100
25
3673
117
2
81
false
2823
1643
10
regular
200
190
3674
19
2
81
false
3033
1403
10
regular
200
190
3675
1065
2
65
true
2439
1294
10
regular
78
78
3676
1541
2
81
false
3030
1133
10
regular
200
190
3677
1148
2
9
false
2868
1320
19
regular
100
35
3691
1065
33
65
false
2848
2003
10
regular
78
78
3692
952
2
81
false
3473
1948
10
regular
200
190
3693
1420
33
49
false
3253
1893
10
regular
78
78
3694
514
1213
9
false
3068
1998
10
regular
100
25
3695
2044
81
false
3473
2178
10
regular
200
190
3696
1105
2
81
false
3473
2413
10
regular
200
190
3701
1065
2
65
false
3368
2298
10
regular
78
78
3702
2040
2
81
false
2938
2418
10
regular
200
190
3703
1420
2
49
false
3058
2218
10
regular
78
78
3704
514
2
9
false
3243
2213
10
regular
100
25
3705
1065
1213
65
false
3158
2128
10
regular
78
78
3706
2926
2
81
false
2613
2338
10
regular
200
190
3707
1420
2
49
false
2748
2223
10
regular
78
78
3708
514
1213
9
false
2888
2123
10
regular
100
25
3709
2045
2
81
false
2613
2818
10
regular
200
190
3710
968
1213
81
false
3253
2813
10
regular
200
200
3711
9795
1213
9
false
3308
2690
19
regular
100
25
3715
1065
1213
65
false
3168
2778
10
regular
78
78
3716
1420
1213
49
false
2923
2773
10
regular
78
78
3717
514
1213
9
false
3045
2868
19
regular
100
25
3754
654
2
81
false
4130
540
10
regular
200
190
3756
921
2
81
false
3630
895
10
regular
200
190
3757
749
2
81
false
4175
745
10
regular
200
190
3758
48
2
81
false
4025
1015
10
regular
200
190
3765
1420
2
49
false
3525
965
10
regular
78
78
3766
1065
2
65
false
3330
960
10
regular
78
78
3767
2683
2
81
false
3365
1515
10
regular
200
190
3768
35
2
63
false
3340
1160
10
regular
78
78
3769
1783
2
56
false
3510
1160
10
regular
78
78
3770
964
2
9
false
3415
1055
19
regular
100
25
3771
1420
2
49
false
4050
1385
10
regular
78
78
3772
1065
2
65
false
4120
1285
10
regular
78
78
3773
108
2
81
false
3655
1385
10
regular
200
190
3774
1783
2
56
false
3760
1165
10
regular
78
78
3775
964
2
9
false
3882
1280
10
regular
100
25
3776
2043
2
81
false
4755
1010
10
regular
200
190
3784
1420
2
49
false
4375
505
10
regular
78
78
3785
1065
2
65
false
4310
405
10
regular
78
78
3786
2041
2
81
false
4755
535
10
regular
200
200
3787
35
2
63
false
4615
505
10
regular
78
78
3788
1783
2
56
false
4685
395
10
regular
78
78
3789
964
2
9
false
4480
585
10
regular
100
25
3790
1420
2
49
false
4900
920
10
regular
78
78
3791
1065
2
65
false
4730
925
10
regular
78
78
3792
35
2
63
false
4710
740
10
regular
78
78
3793
1783
2
56
false
4930
740
10
regular
78
78
3794
964
2
9
false
4805
830
19
regular
100
25
3795
721
2
59
false
3865
1675
10
regular
50
30
3796
1420
2
49
false
3865
1470
10
regular
78
78
3797
1240
2
81
false
4370
1515
10
regular
200
190
3798
1144
2
60
false
4170
1670
10
regular
50
30
3799
40034
2
55
false
4155
1470
10
regular
78
78
3800
197
2
81
false
5070
1515
10
regular
200
190
3811
721
2
59
false
3670
1860
10
regular
50
30
3812
1144
2
60
false
3955
1880
10
regular
50
30
3813
222
2
81
false
4030
1870
10
regular
200
190
3814
9795
2
9
false
3800
1915
10
regular
100
25
9212
1065
2
65
false
981
2678
10
regular
78
78
9213
9794
2
9
false
855
2752
19
regular
100
25
9214
3007
2
81
false
250
2045
10
regular
200
200
9250
1420
2
49
false
2457
1683
10
regular
78
78
9251
1065
2
65
false
2568
1744
10
regular
78
78
9252
1783
2
56
false
2457
2144
10
regular
78
78
9253
35
2
63
false
2560
2004
10
regular
78
78
9254
514
2
9
false
2387
1883
19
regular
100
25
9255
353
2
9
false
2442
1958
19
regular
100
25
9256
7226
2
9
false
2512
1883
10
regular
100
25
9257
1420
2
49
false
1967
1708
10
regular
78
78
9258
1065
2
65
false
1858
1779
10
regular
78
78
9259
1783
2
56
false
1967
2109
10
regular
78
78
9260
35
2
63
false
1875
2009
10
regular
78
78
9261
964
2
9
false
1957
1893
19
regular
100
25
9308
1065
33
65
false
2446
1341
10
regular
78
78
9309
1420
33
49
false
2678
1338
10
regular
78
78
9310
514
33
9
false
2561
1420
10
regular
100
25
9311
1081
2
81
false
3660
380
10
regular
200
190
9312
764
2
81
false
3925
375
10
regular
200
190
9313
423
2
9
false
3852
590
10
regular
100
25
9314
143
2
61
false
5040
1000
10
regular
50
30
9315
1420
2
49
false
5227
980
10
regular
78
78
9316
146
2
62
false
5050
1225
10
regular
50
30
9317
1081
2
81
false
4240
1165
10
regular
200
190
9318
764
2
81
false
4550
1165
10
regular
200
190
9319
423
2
9
false
4452
1055
10
regular
100
25
9322
1081
2
81
false
4235
1730
10
regular
200
190
9323
1147
2
81
false
4680
1870
10
regular
200
190
9324
764
2
81
false
4475
1720
10
regular
200
190
9325
423
2
9
false
4395
1920
10
regular
100
25
9326
1081
2
81
false
4570
1360
10
regular
200
190
9327
764
2
81
false
4850
1355
10
regular
200
190
9328
423
2
9
false
4767
1565
10
regular
100
25
2686717
1081
8
81
false
2070
608
10
regular
200
190
2686718
15
8
81
false
1625
805
10
regular
200
190
2686719
764
8
81
false
1760
605
10
regular
200
190
2686720
423
8
9
false
1980
855
10
regular
100
25
2686721
1420
22
49
false
2191
1302
10
regular
78
78
2686722
1065
22
65
false
2106
1235
10
regular
78
78
2686723
1969
22
81
false
1625
1103
10
regular
200
200
2686724
35
22
63
false
1866
1238
10
regular
78
78
2686725
1783
22
56
false
1806
1311
10
regular
78
78
2686726
964
22
9
false
1980
1152
10
regular
100
25
2686727
1420
22
49
false
1461
744
10
regular
78
78
2686728
1065
22
65
false
1541
772
10
regular
78
78
2686729
2411
22
81
false
940
807
10
regular
200
190
2686730
1783
22
56
false
1236
740
10
regular
78
78
2686731
35
22
63
false
1151
778
10
regular
78
78
2686732
964
22
9
false
1345
856
10
regular
100
25
2686733
721
8
59
false
1540
1245
10
regular
50
30
2686734
1420
8
49
false
1476
1275
10
regular
78
78
2686735
1029
8
81
false
955
1099
10
regular
200
200
2686736
1144
8
60
false
1180
1249
10
regular
50
30
2686737
40034
8
55
false
1226
1279
10
regular
78
78
2686738
544
8
9
false
1350
1146
10
regular
100
25
2686739
1081
8
81
false
750
1279
10
regular
200
190
2686740
74
8
81
false
250
955
10
regular
200
190
2686741
764
8
81
false
460
1271
10
regular
200
190
2686742
423
8
9
false
655
1146
10
regular
100
25
2686743
721
8
59
false
825
819
10
regular
50
30
2686744
1420
8
49
false
776
724
10
regular
78
78
2686745
1144
8
60
false
525
822
10
regular
50
30
2686746
40034
8
55
false
546
727
10
regular
78
78
1342
271
2
6
false
1255
1892
8
subunit
regular
160
80
1343
277
2
6
false
1380
2070
8
subunit
regular
160
80
1344
786
2
6
false
825
2320
8
subunit
regular
160
80
1348
762
2
6
false
1065
2932
8
subunit
regular
160
80
1349
677
2
6
false
1570
2932
8
subunit
regular
160
80
1351
272
2
2
false
1720
1635
8
subunit
regular
150
70
1354
286
2
6
false
2177
2388
8
subunit
regular
160
80
1355
84
33
2
false
2515
1243
8
subunit
regular
150
70
1356
247
14
8
false
3055
265
8
subunit
regular
140
85
1357
272
2
2
false
2843
1340
8
subunit
regular
150
70
1362
84
1213
2
false
3043
2008
8
subunit
regular
150
70
1364
84
2
2
false
3218
2223
8
subunit
regular
150
70
1365
84
1213
2
false
2858
2133
8
subunit
regular
150
70
1366
203
1213
2
false
3278
2695
8
subunit
regular
150
70
1368
84
1213
2
false
3020
2878
8
subunit
regular
150
70
1390
398
2
2
false
3820
805
8
subunit
regular
150
70
1392
164
2
2
false
3390
1070
8
subunit
regular
150
70
1393
164
2
2
false
3857
1290
8
subunit
regular
150
70
1396
164
2
2
false
4455
600
8
subunit
regular
150
70
1397
164
2
2
false
4780
840
8
subunit
regular
150
70
1398
286
2
6
false
3955
1570
8
subunit
regular
160
80
1402
729
2
2
false
3775
1930
8
subunit
regular
150
70
5100
787
2
2
false
830
2762
8
subunit
regular
150
70
5101
97
2
16
false
540
2102
8
subunit
regular
170
90
5103
382
2
2
false
2422
1898
8
subunit
regular
150
70
5104
164
2
2
false
1932
1903
8
subunit
regular
150
70
5142
84
33
2
false
2531
1435
8
subunit
regular
150
70
5143
266
2
2
false
3827
600
8
subunit
regular
150
70
5144
286
2
6
false
5090
1085
8
subunit
regular
160
80
5145
266
2
2
false
4422
1070
8
subunit
regular
150
70
5149
266
2
2
false
4365
1930
8
subunit
regular
150
70
5150
266
2
2
false
4747
1575
8
subunit
regular
150
70
951844
266
8
2
false
1955
865
8
subunit
regular
150
70
951845
164
22
2
false
1955
1167
8
subunit
regular
150
70
951846
164
22
2
false
1320
866
8
subunit
regular
150
70
951847
1061
8
6
false
1320
1161
8
subunit
regular
160
80
951848
266
8
2
false
630
1161
8
subunit
regular
150
70
951849
286
8
2
false
625
866
8
subunit
regular
150
70
1249
357
85
2
1335
1342
651
3619
5344
Cofactor
1250
203
85
2
1336
1343
652
3622
5349
Cofactor
1251
361
85
2
1337
1344
653
3626
5354
Cofactor
1255
363
85
2
1341
1348
1256
364
85
2
1342
1349
657
3642
5373
Cofactor
658
3643
5374
Cofactor
1258
96
85
2
1344
1351
659
3647
5380
Cofactor
1261
371
85
2
1347
1354
1262
327
85
33
1348
1355
663
3665
5403
Cofactor
1263
98
85
14
1349
1356
664
3671
5410
Cofactor
665
3672
5411
Cofactor
1264
96
85
2
1350
1357
666
3677
5417
Cofactor
1269
327
85
1213
1355
1362
671
3694
5440
Cofactor
1271
327
85
2
1357
1364
673
3704
5454
Cofactor
1272
327
85
1213
1358
1365
674
3708
5459
Cofactor
1273
529
85
1213
1359
1366
675
3711
5464
Cofactor
1275
327
85
1213
1361
1368
677
3717
5474
Cofactor
1297
201
85
2
1383
1390
1299
370
85
2
1385
1392
686
3770
5550
Cofactor
1300
370
85
2
1386
1393
687
3775
5557
Cofactor
1303
370
85
2
1389
1396
690
3789
5574
Cofactor
1304
370
85
2
1390
1397
691
3794
5581
Cofactor
1305
371
85
2
1391
1398
1309
544
85
2
1395
1402
693
3814
5609
Cofactor
4207
362
85
2
5073
5100
1804
9213
14516
Cofactor
4208
528
85
2
5074
5101
4210
372
85
2
5076
5103
1807
9254
14582
Cofactor
1808
9255
14583
Cofactor
1809
9256
14584
Cofactor
4211
370
85
2
5077
5104
1810
9261
14591
Cofactor
4229
327
85
33
5115
5142
1812
9310
14677
Cofactor
4230
1075
85
2
5116
5143
1813
9313
14682
Cofactor
4231
371
85
2
5117
5144
4232
1075
85
2
5118
5145
1814
9319
14692
Cofactor
4236
1075
85
2
5122
5149
1815
9325
14703
Cofactor
4237
1075
85
2
5123
5150
1816
9328
14708
Cofactor
805877
1075
85
8
947621
951844
36934
2686720
3673874
Cofactor
805878
370
85
22
947622
951845
36935
2686726
3673881
Cofactor
805879
370
85
22
947623
951846
36936
2686732
3673888
Cofactor
805880
546
85
8
947624
951847
36937
2686738
3673895
Cofactor
805881
1075
85
8
947625
951848
36938
2686742
3673900
Cofactor
805882
371
85
8
947626
951849
5335
M1400 1670 C1353 1670 1353 1671 1295 1670
5
false
18
true
M 1827.4823210481895 681.7351519276274 L 1840 690 L 1840.8987289131883 675.026947995128
false
false
false
5340
M1500 1765 C1499 1826 1504 1930 1415 1932
5
false
18
false
false
5341
M1745 2015 C1745 1991 1744 1952 1744 1928 C1696 1930 1469 1929 1415 1932
5
false
18
false
false
5342
M905 2050 C904 2002 904 1956 905 1932 C946 1931 1186 1932 1255 1932
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5343
M1165 2015 C1165 1985 1203 1933 1245 1932
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
false
false
5344
M1515 1522.5 L1515 1572.5 L1565 1522.5 z
10
true
18
5345
M1645 2110 C1615 2110 1570 2110 1540 2110
5
false
18
5346
M1600 2210 C1601 2170 1599 2112 1540 2110
5
false
18
5347
M1300 2215 C1300 2171 1330 2110 1380 2110
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5348
M1265 2110 C1295 2110 1350 2110 1380 2110
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5349
M1330 1530 L1330 1580 L1380 1530 z
10
true
18
5350
M905 2240 C904 2267 905 2293 905 2320
5
false
18
5351
M975 2284 C939 2288 905 2294 905 2320
5
false
18
5352
M905 2480 C905 2459 908 2433 905 2400
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5353
M980 2439 C942 2439 904 2433 905 2400
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5354
M945 1785 L945 1835 L995 1785 z
10
true
18
5367
M1005 2975 C1045 2974 1024 2973 1065 2972
5
false
18
5368
M1275 2970 C1259 2971 1242 2972 1225 2972
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5369
M1475 2970 C1504 2969 1532 2972 1570 2972
5
false
18
5370
M1514 2868 C1512 2913 1530 2972 1570 2972
5
false
18
5371
M1790 2860 C1791 2908 1780 2973 1730 2972
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5372
M1850 2970 C1791 2970 1783 2973 1730 2972
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5373
M240 2372.5 L240 2422.5 L290 2372.5 z
10
true
18
5374
M240 2372.5 L240 2422.5 L290 2372.5 z
10
true
18
5377
M1600 1670 C1630 1670 1690 1670 1720 1670
5
false
18
5378
M2160 1668 C2130 1668 1900 1670 1870 1670
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5379
M1980 1567 C1981 1612 1959 1670 1870 1670
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5380
M-200 650 L-200 700 L-150 650 z
10
true
18
5394
M2257 2273 C2257 2303 2257 2358 2257 2388
5
false
18
5395
M2167 2323 C2228 2328 2257 2358 2257 2388
5
false
18
5396
M2342 2327 C2295 2326 2257 2354 2257 2388
5
false
18
5397
M2257 2563 C2257 2533 2257 2498 2257 2468
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
false
false
5398
M2162 2523 C2198 2524 2257 2498 2257 2468
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
false
false
5399
M2260 1573 C2261 1472 2323 1282 2515 1278
5
false
18
5400
M2434 1221 C2435 1251 2477 1278 2515 1278
5
false
18
5401
M2915 1123 C2915 1161 2833 1275 2665 1278
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5402
M2744 1221 C2745 1262 2706 1279 2665 1278
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5403
M1965 1163 L1965 1213 L2015 1163 z
10
true
18
5404
M2915 933 C2910 582 2893 306 3055 305
5
false
18
5405
M2860 305 C2923 302 3035 306 3055 305
5
false
18
5406
M3010 371 C3009 326 3020 305 3055 305
5
false
18
5407
M3365 305 C3309 305 3247 306 3195 305
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5408
M3245 212 C3243 272 3242 303 3195 305
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5409
M3234 367 C3233 327 3226 306 3185 305
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5410
M-200 650 L-200 700 L-150 650 z
10
true
18
5411
M-200 650 L-200 700 L-150 650 z
10
true
18
5412
M2923 1643 C2923 1613 2918 1440 2918 1410
5
false
18
5413
M3033 1498 C2986 1498 2921 1482 2918 1410
5
false
18
5414
M2439 1333 C2385 1324 2918 1440 2918 1410
5
true
18
5415
M2915 1123 C2916 1219 2916 1187 2918 1340
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5416
M3030 1228 C2968 1228 2916 1279 2918 1340
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5417
M-200 650 L-200 700 L-150 650 z
10
true
18
5436
M2923 1833 C2916 1982 2994 2030 3043 2043
5
false
18
5437
M2926 2042 C2963 2042 3000 2041 3043 2043
5
false
18
5438
M3473 2043 C3386 2043 3274 2040 3193 2043
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5439
M3292 1971 C3293 2019 3246 2045 3193 2043
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5440
M2328 1698 L2328 1748 L2378 1698 z
10
true
18
5441
M3573 2138 C3573 2168 2599 1621 2623 1638
5
true
18
5442
M3573 2178 C3574 2148 3573 2164 3573 2138
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5443
M3673 2273 C3703 2273 2789 1701 2813 1718
5
true
18
5444
M3573 2413 C3573 2347 3572 2447 3573 2368
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5450
M3473 2508 C3451 2508 3483 2508 3454 2507 C3455 2448 3454 2356 3454 2256 C3426 2256 3394 2256 3368 2258
5
false
18
5451
M3407 2298 C3409 2272 3402 2256 3368 2258
5
false
18
5452
M3138 2513 C3153 2513 3175 2513 3185 2513 C3186 2453 3183 2314 3183 2259 C3196 2259 3202 2259 3218 2258
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5453
M3136 2257 C3169 2257 3174 2258 3218 2258
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5454
M2963 2033 L2963 2083 L3013 2033 z
10
true
18
5455
M3038 2418 C3036 2353 3039 2195 3037 2167 C3020 2166 3022 2166 3008 2168
5
false
18
5456
M3158 2167 C3139 2167 3036 2167 3008 2168
5
false
18
5457
M2713 2338 C2712 2286 2713 2202 2713 2170 C2788 2171 2810 2168 2858 2168
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5458
M2787 2223 C2784 2190 2828 2168 2858 2168
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5459
M2348 2043 L2348 2093 L2398 2043 z
10
true
18
5460
M2613 2433 C2583 2433 2084 1986 2108 2003
5
true
18
5461
M2713 2813 C2713 2760 2714 2576 2713 2523
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5462
M3473 2508 C3424 2507 3392 2506.5 3353 2507 C3353 2607 3353 2653 3353 2695
5
false
18
5463
M3353 2813 C3353 2783 3353 2795 3353 2765
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5464
M-200 650 L-200 700 L-150 650 z
10
true
18
5470
M3253 2913 C3223 2913 3208 2911 3170 2913
5
false
18
5471
M3207 2856 C3207 2884 3200 2912 3170 2913
5
false
18
5472
M2813 2913 C2843 2913 2974 2913 3020 2913
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5473
M2962 2851 C2960 2897 2976 2911 3020 2913
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5474
M2380.5 2568 L2380.5 2618 L2430.5 2568 z
10
true
18
5533
M3730 895 C3731 864 3752 838 3820 840
5
false
18
5534
M3465 400 C3465 648 3623 836 3820 840
5
false
18
5535
M4175 840 C4145 840 4000 840 3970 840
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5536
M4125 1015 C4123 876 4099 841 3970 840
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5544
M3465 400 C3466 487 3461 974 3465 1070
5
false
18
5545
M3525 1004 C3483 1004 3465 1041 3465 1070
5
false
18
5546
M3408 999 C3438 999 3466 1017 3465 1070
5
false
18
5547
M3465 1515 C3464 1444 3466 1198 3465 1140
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5548
M3418 1199 C3450 1200 3471 1169 3465 1140
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5549
M3510 1199 C3480 1199 3467 1177 3465 1140
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5550
M2690 850 L2690 900 L2740 850 z
10
true
18
5551
M4007 1325 C4125 1317 4112 1231 4125 1205
5
false
18
5552
M4089 1385 C4092 1350 4037 1325 4007 1325
5
false
18
5553
M4120 1324 C4090 1324 4037 1325 4007 1325
5
false
18
5554
M3465 1515 C3465 1448 3466 1393 3466 1323 C3579 1323 3802 1324 3857 1325
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5555
M3755 1385 C3756 1353 3798 1325 3857 1325
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5556
M3799 1243 C3802 1300 3817 1325 3857 1325
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
5557
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5583
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18
5606
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5607
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true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
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18
14513
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18
14514
M981 2717 C950 2718 907 2736 905 2762
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18
14515
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14516
M-200 650 L-200 700 L-150 650 z
10
true
18
14517
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18
14518
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5
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14576
M2360 1668 C2434 1669 2497 1829 2497 1898
5
false
18
14577
M2496 1761 C2496 1791 2497 1868 2497 1898
5
false
18
14578
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5
false
18
14579
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false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14580
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14581
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14582
M-200 650 L-200 700 L-150 650 z
10
true
18
14583
M-200 650 L-200 700 L-150 650 z
10
true
18
14584
M-200 650 L-200 700 L-150 650 z
10
true
18
14585
M2160 1668 C2059 1694 2007 1881 2007 1903
5
false
18
14586
M2006 1786 C2004 1811 2007 1873 2007 1903
5
false
18
14587
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5
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18
14588
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14589
M2006 2109 C2006 2079 2007 2003 2007 1973
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14590
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14591
M-200 650 L-200 700 L-150 650 z
10
true
18
14673
M2360 1668 C2393 1667 2424 1668 2454 1668 C2454 1612 2456 1569 2456 1469 C2476 1470 2499 1469 2531 1470
5
false
18
14674
M2485 1419 C2486 1460 2500 1471 2531 1470
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false
18
14675
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false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14676
M2717 1416 C2718 1459 2711 1470 2681 1470
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14677
M-200 650 L-200 700 L-150 650 z
10
true
18
14678
M3465 400 C3471 591 3662 626 3827 635
5
false
18
14679
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false
18
14680
M4130 635 C4100 635 4007 635 3977 635
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false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14681
M4025 565 C4024 615 4007 635 3977 635
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14682
M-200 650 L-200 700 L-150 650 z
10
true
18
14683
M4955 635 C5101 636 5109 636 5170 636 C5170 736 5170 994 5170 1085
5
false
18
14684
M5090 1015 C5137 1016 5170 1055 5170 1085
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false
18
14685
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5
false
18
14686
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false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14687
M5100 1240 C5161 1237 5170 1195 5170 1165
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14688
M4225 1110 C4255 1110 4392 1105 4422 1105
5
false
18
14689
M4340 1165 C4337 1146 4372 1106 4422 1105
5
false
18
14690
M4755 1105 C4725 1105 4602 1105 4572 1105
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14691
M4650 1165 C4649 1134 4602 1105 4572 1105
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14692
M-200 650 L-200 700 L-150 650 z
10
true
18
14699
M4230 1965 C4260 1965 4335 1965 4365 1965
5
false
18
14700
M4335 1920 C4336 1941 4343 1966 4365 1965
5
false
18
14701
M4680 1965 C4650 1965 4545 1965 4515 1965
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14702
M4575 1910 C4575 1958 4545 1965 4515 1965
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14703
M-200 650 L-200 700 L-150 650 z
10
true
18
14704
M4570 1610 C4600 1610 4717 1610 4747 1610
5
false
18
14705
M4670 1550 C4671 1605 4717 1610 4747 1610
5
false
18
14706
M5070 1610 C5040 1610 4927 1610 4897 1610
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14707
M4950 1545 C4951 1601 4927 1610 4897 1610
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14708
M-200 650 L-200 700 L-150 650 z
10
true
18
14719
M1500 1575 C1501 1497 1500 1547 1500 1465
5
false
18
true
M 1867.8578129391765 707.7771192298151 L 1860 695 L 1852.8635966293857 708.1936252384204
false
3673870
M2815 1028 C2785 1028 2235 1030 2205 1030 C2205 990 2205 931 2205 899 C2176 898 2192 898 2105 900
5
false
18
3673871
M2170 798 C2171 856 2135 900 2105 900
5
false
18
3673872
M1825 900 C1855 900 1925 900 1955 900
5
false
18
true
M 1689.9468550441647 136.26155629629605 L 1675 135 L 1681.380887721186 148.57513432307834
false
3673873
M1860 795 C1861 858 1925 900 1955 900
5
false
18
true
M 1689.9468550441647 136.26155629629605 L 1675 135 L 1681.380887721186 148.57513432307834
false
3673874
M2050 690.5 L2050 740.5 L2100 690.5 z
10
true
18
3673875
M2815 1028 C2785 1028 2235 1030 2205 1030 C2204 1063 2203 1159 2203 1202 C2153 1203 2156 1203 2105 1202
5
false
18
3673876
M2230 1302 C2230 1272 2197 1200 2105 1202
5
false
18
3673877
M2145 1235 C2145 1216 2135 1202 2105 1202
5
false
18
3673878
M1825 1203 C1855 1203 1925 1202 1955 1202
5
false
18
true
M 1473.9468550441647 13.26155629629604 L 1459 12 L 1465.380887721186 25.575134323078345
false
3673879
M1905 1238 C1904 1219 1925 1202 1955 1202
5
false
18
true
M 1473.9468550441647 13.26155629629604 L 1459 12 L 1465.380887721186 25.575134323078345
false
3673880
M1845 1311 C1846 1256 1862 1203 1955 1202
5
false
18
true
M 1473.9468550441647 13.26155629629604 L 1459 12 L 1465.380887721186 25.575134323078345
false
3673881
M2050 647 L2050 697 L2100 647 z
10
true
18
3673882
M1625 900 C1595 900 1500 901 1470 901
5
false
18
3673883
M1500 822 C1498 900 1500 901 1470 901
5
false
18
3673884
M1580 850 C1580 918 1500 901 1470 901
5
false
18
3673885
M1140 902 C1170 902 1290 901 1320 901
5
false
18
true
M 950.9468550441649 96.26155629629604 L 936 95 L 942.3808877211858 108.57513432307834
false
3673886
M1275 818 C1277 889 1290 901 1320 901
5
false
18
true
M 950.9468550441649 96.26155629629604 L 936 95 L 942.3808877211858 108.57513432307834
false
3673887
M1190 856 C1190 911 1290 901 1320 901
5
false
18
true
M 950.9468550441649 96.26155629629604 L 936 95 L 942.3808877211858 108.57513432307834
false
3673888
M805 661.5 L805 711.5 L855 661.5 z
10
true
18
3673889
M1625 1203 C1595 1203 1510 1201 1480 1201
5
false
18
3673890
M1565 1245 C1567 1194 1510 1201 1480 1201
5
false
18
3673891
M1515 1275 C1516 1218 1510 1201 1480 1201
5
false
18
3673892
M1155 1199 C1185 1199 1290 1201 1320 1201
5
false
18
true
M 831.9468550441649 221.26155629629605 L 817 220 L 823.3808877211858 233.57513432307834
false
3673893
M1205 1249 C1204 1198 1290 1201 1320 1201
5
false
18
true
M 831.9468550441649 221.26155629629605 L 817 220 L 823.3808877211858 233.57513432307834
false
3673894
M1265 1279 C1264 1213 1290 1201 1320 1201
5
false
18
true
M 831.9468550441649 221.26155629629605 L 817 220 L 823.3808877211858 233.57513432307834
false
3673895
M800 876.5 L800 926.5 L850 876.5 z
10
true
18
3673896
M955 1199 C925 1199 810 1196 780 1196
5
false
18
3673897
M850 1279 C849 1219 805 1196 780 1196
5
false
18
3673898
M450 1050 C480 1050 494 1048 524 1048 C524 1081 524 1174 524 1196 C549 1196 592 1196 630 1196
5
false
18
true
M 505.94685504416486 228.26155629629605 L 491 227 L 497.38088772118584 240.57513432307834
false
3673899
M560 1271 C559 1220 600 1196 630 1196
5
false
18
true
M 505.94685504416486 228.26155629629605 L 491 227 L 497.38088772118584 240.57513432307834
false
3673900
M350 896.5 L350 946.5 L400 896.5 z
10
true
18
3673901
M940 902 C910 902 805 901 775 901
5
false
18
3673902
M850 849 C851 885 792 901 775 901
5
false
18
3673903
M815 802 C817 867 797 901 775 901
5
false
18
3673904
M450 1050 C480 1050 495 1050 525 1050 C525 1016 525 921 525 900 C546 900 598 901 625 901
5
false
18
true
M 275.94685504416486 141.26155629629605 L 261 140 L 267.38088772118584 153.57513432307834
false
3673905
M550 852 C548 904 595 901 625 901
5
false
18
true
M 275.94685504416486 141.26155629629605 L 261 140 L 267.38088772118584 153.57513432307834
false
3673906
M585 805 C588 885 595 901 625 901
5
false
18
true
M 275.94685504416486 141.26155629629605 L 261 140 L 267.38088772118584 153.57513432307834
false
1128
85
80
2
4041
3583
5340
Left
4042
3616
5341
Left
4043
3617
5342
Right
4044
3618
5343
Right
1071
811
1249
1129
85
1118
2
4045
3616
5345
Left
4046
3620
5346
Left
4047
3621
5347
Right
4048
3618
5348
Right
1072
812
1250
1130
85
320
2
4049
3617
5350
Left
4050
3623
5351
Left
4051
3624
5352
Right
4052
3625
5353
Right
1073
813
1251
1134
85
386
2
4062
3636
5367
Left
4063
3638
5368
Right
1077
446
1255
1135
85
263
2
4064
3638
5369
Left
4065
3639
5370
Left
4066
3640
5371
Right
4067
3641
5372
Right
1078
447
1256
1137
85
1120
2
4070
3583
5377
Left
4071
3645
5378
Right
4072
3646
5379
Right
1080
815
1258
1140
85
1123
2
4083
3650
5394
Left
4084
3658
5395
Left
4085
3659
5396
Left
4086
3660
5397
Right
4087
3661
5398
Right
1083
818
1261
1141
85
1124
33
4088
3645
5399
Left
4089
3662
5400
Left
4090
3663
5401
Right
4091
3664
5402
Right
1084
819
1262
1142
85
634
14
4092
3663
5404
Left
4093
3666
5405
Left
4094
3667
5406
Left
4095
3668
5407
Right
4096
3669
5408
Right
4097
3670
5409
Right
1085
118
1263
1143
85
633
2
4098
3673
5412
Left
4099
3674
5413
Left
4100
3675
5414
Left
4101
3663
5415
Right
4102
3676
5416
Right
1086
117
1264
1148
85
543
1213
4117
3673
5436
Left
4118
3691
5437
Left
4119
3692
5438
Right
4120
3693
5439
Right
1091
822
1269
1149
85
1126
4121
3692
5441
Left
4122
3695
5442
Right
1150
85
1127
2
4123
3695
5443
Left
4124
3696
5444
Right
1152
85
1128
2
4129
3696
5450
Left
4130
3701
5451
Left
4131
3702
5452
Right
4132
3703
5453
Right
1093
823
1271
1153
85
1129
2
4133
3702
5455
Left
4134
3705
5456
Left
4135
3706
5457
Right
4136
3707
5458
Right
1094
824
1272
1154
85
1130
2
4137
3706
5460
Left
4138
3709
5461
Right
1155
85
1131
2
4139
3696
5462
Left
4140
3710
5463
Right
1095
825
1273
1157
85
1132
1213
4145
3710
5470
Left
4146
3715
5471
Left
4147
3709
5472
Right
4148
3716
5473
Right
1097
826
1275
1179
85
466
2
4199
3756
5533
Left
4200
3668
5534
Left
4201
3757
5535
Right
4202
3758
5536
Right
1119
218
1297
1181
85
153
2
4209
3668
5544
Left
4210
3765
5545
Left
4211
3766
5546
Left
4212
3767
5547
Right
4213
3768
5548
Right
4214
3769
5549
Right
1121
847
1299
1182
85
155
2
4215
3758
5551
Left
4216
3771
5552
Left
4217
3772
5553
Left
4218
3767
5554
Right
4219
3773
5555
Right
4220
3774
5556
Right
1122
848
1300
1185
85
1156
2
4229
3754
5568
Left
4230
3784
5569
Left
4231
3785
5570
Left
4232
3786
5571
Right
4233
3787
5572
Right
4234
3788
5573
Right
1125
850
1303
1186
85
1157
2
4235
3776
5575
Left
4236
3790
5576
Left
4237
3791
5577
Left
4238
3786
5578
Right
4239
3792
5579
Right
4240
3793
5580
Right
1126
851
1304
1187
85
123
2
4241
3767
5582
Left
4242
3795
5583
Left
4243
3796
5584
Left
4244
3797
5585
Right
4245
3798
5586
Right
4246
3799
5587
Right
1127
852
1305
1192
85
1161
2
4263
3767
5605
Left
4264
3811
5606
Left
4265
3812
5607
Right
4266
3813
5608
Right
1132
856
1309
2821
85
310
2
8794
3624
14513
Left
8795
9212
14514
Left
8796
3636
14515
Right
2819
445
4207
2822
85
392
2
8797
3617
14517
Left
8798
9214
14518
Right
2820
814
4208
2824
85
1121
2
8805
3645
14576
Left
8806
9250
14577
Left
8807
9251
14578
Left
8808
3650
14579
Right
8809
9252
14580
Right
8810
9253
14581
Right
2822
816
4210
2825
85
1122
2
8811
3645
14585
Left
8812
9257
14586
Left
8813
9258
14587
Left
8814
3650
14588
Right
8815
9259
14589
Right
8816
9260
14590
Right
2823
817
4211
2833
85
2250
33
8839
3645
14673
Left
8840
9308
14674
Left
8841
3673
14675
Right
8842
9309
14676
Right
2838
2115
4229
2834
85
2251
2
8843
3668
14678
Left
8844
9311
14679
Left
8845
3754
14680
Right
8846
9312
14681
Right
2839
2116
4230
2835
85
1159
2
8847
3786
14683
Left
8848
9314
14684
Left
8849
9315
14685
Left
8850
3800
14686
Right
8851
9316
14687
Right
2840
854
4231
2836
85
2252
2
8852
3758
14688
Left
8853
9317
14689
Left
8854
3776
14690
Right
8855
9318
14691
Right
2841
2117
4232
2837
85
1162
2
8856
3813
14699
Left
8857
9322
14700
Left
8858
9323
14701
Right
8859
9324
14702
Right
2842
857
4236
2838
85
1158
2
8860
3797
14704
Left
8861
9326
14705
Left
8862
3800
14706
Right
8863
9327
14707
Right
2843
853
4237
799982
85
1163
8
3232512
3663
3673870
Left
3232513
2686717
3673871
Left
3232514
2686718
3673872
Right
3232515
2686719
3673873
Right
755492
858
805877
799983
85
150
22
3232516
3663
3673875
Left
3232517
2686721
3673876
Left
3232518
2686722
3673877
Left
3232519
2686723
3673878
Right
3232520
2686724
3673879
Right
3232521
2686725
3673880
Right
755493
859
805878
799984
85
158
22
3232522
2686718
3673882
Left
3232523
2686727
3673883
Left
3232524
2686728
3673884
Left
3232525
2686729
3673885
Right
3232526
2686730
3673886
Right
3232527
2686731
3673887
Right
755494
860
805879
799985
85
122
8
3232528
2686723
3673889
Left
3232529
2686733
3673890
Left
3232530
2686734
3673891
Left
3232531
2686735
3673892
Right
3232532
2686736
3673893
Right
3232533
2686737
3673894
Right
755495
861
805880
799986
85
199
8
3232534
2686735
3673896
Left
3232535
2686739
3673897
Left
3232536
2686740
3673898
Right
3232537
2686741
3673899
Right
755496
863
805881
799987
85
124
8
3232538
2686729
3673901
Left
3232539
2686743
3673902
Left
3232540
2686744
3673903
Left
3232541
2686740
3673904
Right
3232542
2686745
3673905
Right
3232543
2686746
3673906
Right
755497
866
805882
202
163
85
14
false
1145
1635
16
regular
175
3583
5335
Left
878
787
85
14
false
1425
1395
16
regular
821
3583
14719
Left
187219
3725
2058
2.5
2.5
0
2
90
484
497
479676
965
731
1.3
1.3
0
2
1
490
240
479677
1698
1174
1.0
1.0
0
2
1
490
240
218
M2372 1179 C2372 1129 2422 1079 2472 1079 C2550 1079 2651 1079 2729 1079 C2779 1079 2829 1129 2829 1179 C2829 1251 2829 1345 2829 1417 C2829 1467 2779 1517 2729 1517 C2651 1517 2550 1517 2472 1517 C2422 1517 2372 1467 2372 1417 C2372 1345 2372 1251 2372 1179
95
true
6
457.0
438.0
219
M2870 2019 C2870 1969 2920 1919 2970 1919 C3064 1919 3187 1919 3281 1919 C3331 1919 3381 1969 3381 2019 C3381 2095 3381 2193 3381 2269 C3381 2319 3331 2369 3281 2369 C3187 2369 3064 2369 2970 2369 C2920 2369 2870 2319 2870 2269 C2870 2193 2870 2095 2870 2019
95
true
6
511.0
450.0
220
M2940 2760 C2940 2710 2990 2660 3040 2660 C3141 2660 3271 2660 3372 2660 C3422 2660 3472 2710 3472 2760 C3472 2795 3472 2840 3472 2875 C3472 2925 3422 2975 3372 2975 C3271 2975 3141 2975 3040 2975 C2990 2975 2940 2925 2940 2875 C2940 2840 2940 2795 2940 2760
95
true
6
532.0
315.0
229
M126 399 C126 349 176 299 226 299 C1771 299 3780 299 5325 299 C5375 299 5425 349 5425 399 C5425 1286 5425 2438 5425 3325 C5425 3375 5375 3425 5325 3425 C3780 3425 1771 3425 226 3425 C176 3425 126 3375 126 3325 C126 2438 126 1286 126 399
1
true
6
5299.0
3126.0
207
235
Cytosol
855
285
20
2.2
2.2
200
15
208
235
Extracellular space
900
110
20
2.0
2.0
200
15
890819
235
Melanosome
2500
1045
20
1.0
1.0
200
15
890820
235
Melanosome
2965
1865
20
1.3
1.3
200
15
890821
235
Melanosome
3016
2605
20
1.3
1.3
200
15
Alkaptonuria
Alkaptonuria (Homogentisic acid oxidase deficiency) is an autosomal recessive disease caused by a mutation in the HGD gene which codes for homogentisate 1,2-dioxygenase. A mutation in this enzyme results in accumulation of homogentisic acid in urine. Symptoms, which present in adulthood, include arthritis, black or brown urine, and urolithiasis. Treatment includes a low-protein diet with vitamin C.
Disease
PW_X000042
Context42
233
787
Protein
Mutated
234
84
Compound
Increased
695
11
Tissue
Damaged
696
15
Tissue
Damaged
697
14
Tissue
Damaged
471
Engelke, U., van der Graaf, M., Heerschap, A., Hoenderop, S., Moolenaar, S., Morava, E., Wevers, R. Handbook of 1H-NMR spectroscopy in inborn errors of metabolism: body fluid NMR spectroscopy and in vivo MR spectroscopy (2nd ed) (2007) p.22 Heilbronn: SPS Verlagsgesellschaft
42
Context
472
[Uniprot: Q93099](http://www.uniprot.org/uniprot/Q93099)
42
Context
473
[OMIM: Entry 203500](http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=203500)
42
Context
474
[Wikipedia: Alkaptonuria](http://en.wikipedia.org/wiki/Alkaptonuria)
42
Context
475
Alcaptonuria.In: Stanbury, J. B.; Wyngaarden, J. B.; Fredrickson, D. S. The Metabolic Basis of Inherited Disease. New York: McGraw-Hill (pp. 268-282) (4th ed.) 1978.
42
Context
476
Engelke, U., van der Graaf, M., Heerschap, A., Hoenderop, S., Moolenaar, S., Morava, E., Wevers, R. Handbook of 1H-NMR spectroscopy in inborn errors of metabolism: body fluid NMR spectroscopy and in vivo MR spectroscopy (2nd ed) (2007) p.24 Heilbronn: SPS Verlagsgesellschaft
42
Context
477
9529363
Beltran-Valero de Bernabe D, Granadino B, Chiarelli I, Porfirio B, Mayatepek E, Aquaron R, Moore MM, Festen JJ, Sanmarti R, Penalva MA, de Cordoba SR: Mutation and polymorphism analysis of the human homogentisate 1, 2-dioxygenase gene in alkaptonuria patients. Am J Hum Genet. 1998 Apr;62(4):776-84.
42
Context
478
12872815
Elcioglu NH, Aytug AF, Muller CR, Gurbuz O, Ergun T, Kotiloglu E, Elcioglu M: Alkaptonuria caused by compound heterozygote mutations. Genet Couns. 2003;14(2):207-13.
42
Context
479
8782815
Fernandez-Canon JM, Granadino B, Beltran-Valero de Bernabe D, Renedo M, Fernandez-Ruiz E, Penalva MA, Rodriguez de Cordoba S: The molecular basis of alkaptonuria. Nat Genet. 1996 Sep;14(1):19-24. doi: 10.1038/ng0996-19.
42
Context
480
9154114
Gehrig A, Schmidt SR, Muller CR, Srsen S, Srsnova K, Kress W: Molecular defects in alkaptonuria. Cytogenet Cell Genet. 1997;76(1-2):14-6. doi: 10.1159/000134501.
42
Context
481
12501223
Phornphutkul C, Introne WJ, Perry MB, Bernardini I, Murphey MD, Fitzpatrick DL, Anderson PD, Huizing M, Anikster Y, Gerber LH, Gahl WA: Natural history of alkaptonuria. N Engl J Med. 2002 Dec 26;347(26):2111-21. doi: 10.1056/NEJMoa021736.
42
Context
278305
20301627
Introne WJ, Gahl WA: Alkaptonuria
42
Context
279354
23511227
Preston AJ, Keenan CM, Sutherland H, Wilson PJ, Wlodarski B, Taylor AM, Williams DP, Ranganath LR, Gallagher JA, Jarvis JC: Ochronotic osteoarthropathy in a mouse model of alkaptonuria, and its inhibition by nitisinone. Ann Rheum Dis. 2014 Jan;73(1):284-9. doi: 10.1136/annrheumdis-2012-202878. Epub 2013 Mar 19.
42
Context