2211
Pathway
Phenylalanine Metabolism
The biosynthesis of phenylalanine begins with chorismate interacting with chorismate mutase resulting in a prephenate. Prephenate reacts with a hydrogen ion through a prephenate dehydratase resulting in the release of water, carbon dioxide and 2-oxo-3-phenylpropanoate. The latter compound can be turn into phenylalanine through two different reversible reactions a) 2-oxo-3-phenylpropanoate reacts with alanine through a aromatic amino acid aminotransferase 2 resulting in the release of pyruvate and phenylalanine. b) 2-oxo-3-phenylpropanoate reacts with glutamic acid through a amino aci aminotransferase 1 resulting in the release of oxoglutaric acid and phenylalanine.
The degradation of phenylalanine begins with the two previous reactions turning phenylalanine back ino 2-oxo-3-phenylpropanoate. The latter compound reacts with a phenylpyruvate carboxy lyase resulting in the release of phenylacetaldehyde. This latter compound reacts with a 2-phenylethanol dehydrogenase resulting in the release of 2-phenylethanol.
Metabolic
PW002437
Center
PathwayVisualizationContext2723
1641
2498
#000099
PathwayVisualization2194
2211
Phenylalanine Metabolism
The biosynthesis of phenylalanine begins with chorismate interacting with chorismate mutase resulting in a prephenate. Prephenate reacts with a hydrogen ion through a prephenate dehydratase resulting in the release of water, carbon dioxide and 2-oxo-3-phenylpropanoate. The latter compound can be turn into phenylalanine through two different reversible reactions a) 2-oxo-3-phenylpropanoate reacts with alanine through a aromatic amino acid aminotransferase 2 resulting in the release of pyruvate and phenylalanine. b) 2-oxo-3-phenylpropanoate reacts with glutamic acid through a amino aci aminotransferase 1 resulting in the release of oxoglutaric acid and phenylalanine.
The degradation of phenylalanine begins with the two previous reactions turning phenylalanine back ino 2-oxo-3-phenylpropanoate. The latter compound reacts with a phenylpyruvate carboxy lyase resulting in the release of phenylacetaldehyde. This latter compound reacts with a 2-phenylethanol dehydrogenase resulting in the release of 2-phenylethanol.
Metabolic
18
5138
1943992
Braus GH: Aromatic amino acid biosynthesis in the yeast Saccharomyces cerevisiae: a model system for the regulation of a eukaryotic biosynthetic pathway. Microbiol Rev. 1991 Sep;55(3):349-70.
2211
Pathway
5139
9491083
Iraqui I, Vissers S, Cartiaux M, Urrestarazu A: Characterisation of Saccharomyces cerevisiae ARO8 and ARO9 genes encoding aromatic aminotransferases I and II reveals a new aminotransferase subfamily. Mol Gen Genet. 1998 Jan;257(2):238-48.
2211
Pathway
5140
9642265
Schnappauf G, Krappmann S, Braus GH: Tyrosine and tryptophan act through the same binding site at the dimer interface of yeast chorismate mutase. J Biol Chem. 1998 Jul 3;273(27):17012-7.
2211
Pathway
5141
9491082
Urrestarazu A, Vissers S, Iraqui I, Grenson M: Phenylalanine- and tyrosine-auxotrophic mutants of Saccharomyces cerevisiae impaired in transamination. Mol Gen Genet. 1998 Jan;257(2):230-7.
2211
Pathway
5142
6763508
Kradolfer P, Niederberger P, Hutter R: Tryptophan degradation in Saccharomyces cerevisiae: characterization of two aromatic aminotransferases. Arch Microbiol. 1982 Dec 11;133(3):242-8.
2211
Pathway
5144
12499363
Dickinson JR, Salgado LE, Hewlins MJ: The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae. J Biol Chem. 2003 Mar 7;278(10):8028-34. doi: 10.1074/jbc.M211914200. Epub 2002 Dec 23.
2211
Pathway
5148
12902239
Vuralhan Z, Morais MA, Tai SL, Piper MD, Pronk JT: Identification and characterization of phenylpyruvate decarboxylase genes in Saccharomyces cerevisiae. Appl Environ Microbiol. 2003 Aug;69(8):4534-41.
2211
Pathway
5149
15933030
Vuralhan Z, Luttik MA, Tai SL, Boer VM, Morais MA, Schipper D, Almering MJ, Kotter P, Dickinson JR, Daran JM, Pronk JT: Physiological characterization of the ARO10-dependent, broad-substrate-specificity 2-oxo acid decarboxylase activity of Saccharomyces cerevisiae. Appl Environ Microbiol. 2005 Jun;71(6):3276-84. doi: 10.1128/AEM.71.6.3276-3284.2005.
2211
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
6
Myocyte
CL:0000187
3
Escherichia coli
562
Prokaryote
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
23
Pseudomonas aeruginosa
287
Prokaryote
1
Homo sapiens
9606
Eukaryote
Human
12
Mus musculus
10090
Eukaryote
Mouse
2
Bacteria
2
Prokaryote
Bacteria
24
Solanum lycopersicum
4081
Eukaryote
Tomato
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
17
Rattus norvegicus
10116
Eukaryote
Rat
5
Bos taurus
9913
Eukaryote
Cattle
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
19
Schizosaccharomyces pombe
4896
Eukaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
7
Chlamydomonas reinhardtii
3055
Eukaryote
35
Chloroplast
GO:0009507
1
Cytosol
GO:0005829
3
Mitochondrial Matrix
GO:0005759
5
Cytoplasm
GO:0005737
11
Extracellular Space
GO:0005615
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
12
Mitochondrial Inner Membrane
GO:0005743
14
Mitochondrial Outer Membrane
GO:0005741
24
Mitochondrial Intermembrane Space
GO:0005758
13
Endoplasmic Reticulum
GO:0005783
31
Periplasmic Space
GO:0005620
4
Peroxisome
GO:0005777
10
Cell Membrane
GO:0005886
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
25
Golgi apparatus
GO:0005794
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
40
Periplasm
GO:0042597
1
Liver
BTO:0000759
72
9
28
Stomach
BTO:0001307
155
26
8
Blood Vessel
BTO:0001102
74
11
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
7
Nervous System
BTO:0001484
11
Heart
BTO:0000562
73
10
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
94
3
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14
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PW_BS000028
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PW_BS000028
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7748
Chorismate
HMDB0012199
Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for the aromatic amino acids phenylalanine and tyrosine,indole, indole derivatives and tryptophan,2,3-dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis,the plant hormone salicylic acid and many alkaloids and other aromatic metabolites. -- Wikipedia.
617-12-9
C00251
12039
17333
CPD-9517
11542
O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O
C10H10O6
InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1
WTFXTQVDAKGDEY-HTQZYQBOSA-N
(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
226.1828
226.047738052
-1.41
3
chorismic acid
0
-2
C00251
Chorismic acid;(3r,4r)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid;(3r-trans)-3-((1-carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid;(3r,4r)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate;(3r-trans)-3-((1-carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylate
PW_C007748
Chorism
5164
94
8325
225
8329
151
42309
313
7823
Prephenate
HMDB0012283
Prephenate, also known as prephenic acid, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Prephenate is soluble (in water) and a moderately acidic compound (based on its pKa). Prephenate exists in all living organisms, ranging from bacteria to humans. Prephenate participates in a number of enzymatic reactions. In particular, Prephenate can be biosynthesized from chorismate; which is catalyzed by the enzyme chorismate mutase:phea. Furthermore, Prephenate can be converted into phenylpyruvic acid through its interaction with the enzyme chorismate mutase:phea. Furthermore, Prephenate can be biosynthesized from chorismate through the action of the enzyme chorismate mutase:phea. Furthermore, Prephenate can be converted into phenylpyruvic acid; which is catalyzed by the enzyme chorismate mutase:phea. Furthermore, Prephenate can be biosynthesized from chorismate through the action of the enzyme chorismate mutase:tyra. Finally, Prephenate can be converted into 4-hydroxyphenylpyruvic acid through its interaction with the enzyme chorismate mutase:tyra. Outside of the human body, prephenate can be found in a number of food items such as garden tomato (var.), vaccinium (blueberry, cranberry, huckleberry), sacred lotus, and alpine sweetvetch. This makes prephenate a potential biomarker for the consumption of these food products. Prephenic acid, more commonly known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine.
126-49-8
C00254
1028
16666
PREPHENATE
1001
OC1C=CC(CC(=O)C(O)=O)(C=C1)C(O)=O
C10H10O6
InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)
FPWMCUPFBRFMLH-UHFFFAOYSA-N
1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
226.1828
226.047738052
-0.80
3
prephenic acid
0
-2
C00254
1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid;Pre;Prephenic acid;1-carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid;1-carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvate;1-carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoate;1-carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoic acid;1-carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoate;1-carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoate;1-carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acid
PW_C007823
Prephen
8326
225
8330
151
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
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
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
12810
2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto)
HMDB0031629
2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto) is a flavouring ingredient
2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto) belongs to the family of Phenylpyruvic Acid Derivatives. These are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
156-06-9
C00166
997
30851
972
DB03884
OC(=O)C(=O)CC1=CC=CC=C1
C9H8O3
InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)
BTNMPGBKDVTSJY-UHFFFAOYSA-N
2-oxo-3-phenylpropanoic acid
164.158
164.047344122
-2.25
1
phenylpyruvic acid
0
-1
C00166
2-hydroxy-3-phenyl-2-propenoic acid, 9ci;Fema 3892;Phenylpyruvic acid;A-hydroxycinnamic acid;A-oxobenzenepropanoic acid, 9ci;3-phenyl-2-oxopropanoate;3-phenyl-2-oxopropanoic acid;3-phenylpyruvic acid;Alpha-ketohydrocinnamic acid;Alpha-oxo-benzenepropanoic acid;Beta-phenylpyruvic acid;Keto-phenylpyruvate;Phenylbrenztraubensaeure;Phenylpyruvate;2-oxo-3-phenylpropanoate;3-phenylpyruvate;A-ketohydrocinnamate;A-ketohydrocinnamic acid;Alpha-ketohydrocinnamate;α-ketohydrocinnamate;α-ketohydrocinnamic acid;A-oxo-benzenepropanoate;A-oxo-benzenepropanoic acid;Alpha-oxo-benzenepropanoate;α-oxo-benzenepropanoate;α-oxo-benzenepropanoic acid;B-phenylpyruvate;B-phenylpyruvic acid;Beta-phenylpyruvate;β-phenylpyruvate;β-phenylpyruvic acid;Keto-phenylpyruvic acid;2-oxo-3-phenylpropanoic acid (mixture oxo and keto);Phenylpyroracemate;Phenylpyroracemic acid
PW_C012810
2Oxo3
8335
225
77062
253
105
L-Alanine
HMDB0000161
Alanine is a non-essential amino acid made in the body from either the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (branched-chain amino acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine, and glycine, is an inhibitory neurotransmitter in the brain (http://www.dcnutrition.com/AminoAcids/). L-Alanine has been found to be associated with glucagon deficiency, which is an inborn error of metabolism.
56-41-7
C00041
5950
16977
L-ALPHA-ALANINE
5735
DB00160
C[C@H](N)C(O)=O
C3H7NO2
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
QNAYBMKLOCPYGJ-REOHCLBHSA-N
(2S)-2-aminopropanoic acid
89.0932
89.047678473
0.70
2
L-alanine
0
0
FDB000556
(2s)-2-aminopropanoate;(2s)-2-aminopropanoic acid;(s)-(+)-alanine;(s)-2-aminopropanoate;(s)-2-aminopropanoic acid;(s)-2-amino-propanoate;(s)-2-amino-propanoic acid;(s)-alanine;2-aminopropanoate;2-aminopropanoic acid;2-aminopropionate;2-aminopropionic acid;2-ammoniopropanoate;2-ammoniopropanoic acid;Ala;Alanine;L-(+)-alanine;L-2-aminopropanoate;L-2-aminopropanoic acid;L-2-aminopropionate;L-2-aminopropionic acid;L-a-alanine;L-a-aminopropionate;L-a-aminopropionic acid;L-alpha-alanine;L-alpha-aminopropionate;L-alpha-aminopropionic acid;A-alanine;A-aminopropionate;A-aminopropionic acid;Alpha-alanine;Alpha-aminopropanoate;Alpha-aminopropanoic acid;Alpha-aminopropionate;Alpha-aminopropionic acid;A;L-alanin;L-α-alanine
PW_C000105
Ala
10
2
29
4
316
8
1446
50
1453
51
1454
26
3022
15
3439
3
5407
117
5418
103
5431
118
5452
120
5557
132
5578
133
5637
107
5638
108
5883
105
6529
85
8350
225
12271
151
12620
31
12627
18
15230
222
42452
320
42453
318
42534
315
77969
346
77975
327
77988
326
78008
111
78092
112
79165
114
80693
135
119910
122
120015
124
120026
406
121145
423
121151
424
121164
416
121220
409
122139
407
123717
458
123723
459
123736
452
123790
137
124691
119
125300
297
125393
299
125404
479
126296
481
126850
205
126933
388
126944
501
127860
206
164
Pyruvic acid
HMDB0000243
Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).
127-17-3
C00022
1060
32816
PYRUVATE
1031
DB00119
CC(=O)C(O)=O
C3H4O3
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
LCTONWCANYUPML-UHFFFAOYSA-N
2-oxopropanoic acid
88.0621
88.016043994
0.18
1
pyruvic acid
0
-1
FDB008293
2-oxopropanoate;2-oxopropanoic acid;2-oxopropionate;2-oxopropionic acid;Acetylformate;Acetylformic acid;Bts;Pyroracemate;Pyroracemic acid;Pyruvate;A-ketopropionate;A-ketopropionic acid;Alpha-ketopropionate;Alpha-ketopropionic acid;2-ketopropionic acid;2-oxopropansaeure;2-oxopropionsaeure;Acide pyruvique;Alpha-oxopropionsaeure;Brenztraubensaeure;Ch3cocooh;2-ketopropionate;α-ketopropionate;α-ketopropionic acid;A-oxopropionsaeure;α-oxopropionsaeure
PW_C000164
Pyr
17
2
20
4
422
8
1181
3
1449
50
1457
26
5365
103
5405
117
5440
118
5444
120
5566
132
5570
133
5893
95
5920
147
5951
151
6022
155
6067
156
6074
161
6126
160
6383
1
6467
178
6510
177
6532
85
7457
222
7495
220
8200
225
12622
31
15292
249
15349
18
77310
111
77972
346
77978
327
78090
112
80004
368
80042
367
80695
135
112879
94
115683
121
119950
406
120011
124
120175
122
120878
407
121148
423
121154
424
123454
119
123720
458
123726
459
125340
479
125390
299
125534
297
125854
481
126883
501
126931
388
127067
205
127858
206
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
104
L-Phenylalanine
HMDB0000159
Phenylalanine is an essential amino acid and the precursor of the amino acid tyrosine. Like tyrosine, phenylalanine is also a precursor for catecholamines including tyramine, dopamine, epinephrine, and norepinephrine. Catecholamines are neurotransmitters that act as adrenalin-like substances. Interestingly, several psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper, and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in a number of high protein foods, such as meat, cottage cheese, and wheat germ. An additional dietary source of phenylalanine is artificial sweeteners containing aspartame. As a general rule, aspartame should be avoided by phenylketonurics and pregnant women. When present in sufficiently high levels, phenylalanine can act as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of phenylalanine are associated with at least five inborn errors of metabolism, including Hartnup disorder, hyperphenylalaninemia due to guanosine triphosphate cyclohydrolase deficiency, phenylketonuria (PKU), tyrosinemia type 2 (or Richner-Hanhart syndrome), and tyrosinemia type III (TYRO3). Phenylketonurics have elevated serum plasma levels of phenylalanine up to 400 times normal. High plasma concentrations of phenylalanine influence the blood-brain barrier transport of large neutral amino acids. The high plasma phenylalanine concentrations increase phenylalanine entry into the brain and restrict the entry of other large neutral amino acids (PMID: 19191004). Phenylalanine has been found to interfere with different cerebral enzyme systems. Untreated phenylketonuria (PKU) can lead to intellectual disability, seizures, behavioural problems, and mental disorders. It may also result in a musty smell and lighter skin. Classic PKU dramatically affects myelination and white matter tracts in untreated infants; this may be one major cause of neurological disorders associated with phenylketonuria. Mild phenylketonuria can act as an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. It has been recently suggested that PKU may resemble amyloid diseases, such as Alzheimer's disease and Parkinson's disease, due to the formation of toxic amyloid-like assemblies of phenylalanine (PMID: 22706200). Phenylalanine also has some potential benefits. Phenylalanine can act as an effective pain reliever. Its use in premenstrual syndrome and Parkinson's may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-DOPA, produce a catecholamine-like effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. For instance, some tumours use more phenylalanine than others (particularly melatonin-producing tumours called melanomas).
63-91-2
C00079
6140
17295
PHE
5910
DB00120
N[C@@H](CC1=CC=CC=C1)C(O)=O
C9H11NO2
InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1
COLNVLDHVKWLRT-QMMMGPOBSA-N
(2S)-2-amino-3-phenylpropanoic acid
165.1891
165.078978601
-1.60
2
L-phenylalanine
0
0
FDB014705
(-)-beta-phenylalanine;(l)-phenylalanine;(s)-(-)-phenylalanine;(s)-2-amino-3-phenylpropionate;(s)-2-amino-3-phenylpropionic acid;(s)-2-amino-3-phenylpropanoate;(s)-2-amino-3-phenylpropanoic acid;(s)-phenylalanine;(s)-alpha-amino-benzenepropanoate;(s)-alpha-amino-benzenepropanoic acid;(s)-alpha-amino-beta-phenylpropionate;(s)-alpha-amino-beta-phenylpropionic acid;(s)-alpha-aminobenzenepropanoate;(s)-alpha-aminobenzenepropanoic acid;(s)-alpha-aminohydrocinnamate;(s)-alpha-aminohydrocinnamic acid;3-phenyl-l-alanine;L-2-amino-3-phenylpropionate;L-2-amino-3-phenylpropionic acid;Phe;Phenyl-alanine;Phenylalamine;Phenylalanine;Alpha-aminohydrocinnamate;Alpha-aminohydrocinnamic acid;Beta-phenyl-l-alanine;Beta-phenyl-alpha-alanine;Beta-phenylalanine;F;(s)-a-amino-b-phenylpropionate;(s)-a-amino-b-phenylpropionic acid;(s)-α-amino-β-phenylpropionate;(s)-α-amino-β-phenylpropionic acid;B-phenyl-l-alanine;β-phenyl-l-alanine
PW_C000104
Phe
1279
8
5669
107
5670
108
5888
105
8340
225
8341
151
42458
315
42459
318
77061
253
78463
111
120997
122
123562
135
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
2680
Phenylacetaldehyde
HMDB0006236
Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form. (PMID: 16910727, 7818768, 15606130).
122-78-1
C00601
998
16424
HYDRPHENYLAC-CPD
13876539
DB02178
O=CCC1=CC=CC=C1
C8H8O
InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2
DTUQWGWMVIHBKE-UHFFFAOYSA-N
2-phenylacetaldehyde
120.1485
120.057514878
-1.76
0
phenylacetaldehyde
0
0
FDB012238
.alpha.-toluic aldehyde;1-oxo-2-phenylethane;2-phenylacetaldehyde;2-phenylethanal;Benzenacetaldehyde;Benzeneacetaldehyde;Benzylcarboxaldehyde;Fema no. 2974;Hyacinthin;Oxophenylethane;Phenacetaldehyde;Phenyl-acetaldehyde;Phenylacetaldehyde;Phenylacetic aldehyde;Phenylethanal;A-phenylacetaldehyde;A-tolualdehyde;A-toluic aldehyde;Alpha-phenylacetaldehyde;Alpha-tolualdehyde;Alpha-toluic aldehyde;α-tolualdehyde
PW_C002680
Phenyla
6698
108
8352
151
43670
315
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
15002
2-Phenylethanol
HMDB0033944
2-Phenylethanol, also known as benzeneethanol or phenethyl alcohol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 2-Phenylethanol exists as a solid, soluble (in water), and an extremely weak acidic (essentially neutral) compound (based on its pKa). 2-Phenylethanol has been primarily detected in feces. Within the cell, 2-phenylethanol is primarily located in the cytoplasm. 2-Phenylethanol is also a parent compound for other transformation products, including but not limited to, 2-(4-hydroxyphenyl)ethanol, phenethyl acetate, and 2-(2-hydroxyphenyl)ethanol. 2-Phenylethanol is a bitter, floral, and honey tasting compound that can be found in a number of food items such as swede, towel gourd, mountain yam, and alaska blueberry. This makes 2-phenylethanol a potential biomarker for the consumption of these food products. 2-Phenylethanol has been found to be associated with several diseases known as pervasive developmental disorder not otherwise specified, autism, and ulcerative colitis; 2-phenylethanol has also been linked to the inborn metabolic disorders including celiac disease. 2-Phenylethanol is found in almond. 2-Phenylethanol is a flavouring ingredient. 2-Phenylethanol is a component of ylang-ylang oil.
60-12-8
C05853
6054
49000
5830
DB02192
OCCC1=CC=CC=C1
C8H10O
InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
WRMNZCZEMHIOCP-UHFFFAOYSA-N
2-phenylethan-1-ol
122.1644
122.073164942
-1.03
1
phenylethanol
0
0
C05853
1-phenyl-2-ethanol;2-hydroxyethylbenzene;2-phenethanol;2-phenethyl alcohol;2-phenyiethanol;2-phenyl-ethanol;2-phenylethyl alcohol;Benzeneethanol;Benzeneethanol, 9ci;Benzenethanol;Benzyl carbinol;Benzyl ethyl alcohol;Benzyl-methanol;Benzylcarbinol;Benzylmethanol;Fema 2858;Hydroxyethylbenzene;Phenethanol;Phenethyl alcohol;Phenethyl alcohol, 8ci, ban;Phenyl ethyl alcohol;Phenyl-ethanol;Phenylethanol;Phenylethyl alcohol, usan;B-hydroxyethylbenzene;Beta -hydroxyethylbenzene;Beta-phenylethanol;Beta-phenylethyl alcohol;2-phenylethanol
PW_C015002
2Pheny
8356
151
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
C21H28N7O14P2
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)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
664.433
664.116946663
-2.59
8
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-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
10758
chorismate mutase
P32178
ARO7
29
5.4.99.5
7915
160
10759
Putative prephenate dehydratase
P32452
PHA2
29
4.2.1.51
7916
160
10551
aromatic amino acid aminotransferase II
P38840
General aromatic amino acid transaminase involved in several otherwise unrelated metabolic pathways. Mainly involved in tryptophan degradation. Active with phenylalanine, tyrosine and tryptophan as amino donors and with phenylpyruvate, hydroxyphenylpyruvate and pyruvate as amino acceptors. Does not accept glutamate or 2-oxoglutarate as substrates. Also active with methionine, leucine, glutamine and kynurenine. Catalyzes the formation of methionine from 2-keto-4-methylthiobutyrate (KMTB) in the methionine salvage pathway primarily using aromatic amino acids (tyrosine, phenylalanine and tryptophan) as the amino donors. Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA) with pyruvate as amino acceptor.
ARO9
29
2.6.1.57; 2.6.1.7
7871
160
10760
Aromatic/aminoadipate aminotransferase 1
P53090
General aromatic amino acid transaminase involved in several otherwise unrelated metabolic pathways. Responsible for phenylalanine and tyrosine biosynthesis. Active with glutamate, phenylalanine, tyrosine and tryptophan as amino donors and with phenylpyruvate, hydroxyphenylpyruvate, 2-oxoglutarate and pyruvate as amino acceptors. Also active with methionine, alpha-aminoadipate and leucine as amino donors when phenylpyruvate is the amino acceptor and in the reverse reactions with the corresponding oxo acids and phenylalanine as amino donor. Catalyzes the formation of methionine from 2-keto-4-methylthiobutyrate (KMTB) in the methionine salvage pathway primarily using aromatic amino acids (tyrosine, phenylalanine and tryptophan) as the amino donors. Catalyzes the formation of alpha-aminoadipate from alpha-ketoadipate in the lysine biosyntheic pathway.
ARO8
29
2.6.1.39; 2.6.1.57
7917
160
10761
Pyruvate decarboxylase isozyme 1
P06169
Major of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-ketoacids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins.
PDC1
29
4.1.1.-; 4.1.1.1
7752
160
137085
708
10762
pyruvate decarboxylase 2
P16467
Second most abundant of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-keto-acids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins.
PDC5
29
4.1.1.-; 4.1.1.1
7754
160
136091
644
137086
708
10763
Pyruvate decarboxylase isozyme 3
P26263
Minor of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-keto-acids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins. The expression level of this protein in the presence of fermentable carbon sources is so low that it can not compensate for the other two pyruvate decarboxylases to sustain fermentation.
PDC6
29
4.1.1.1
7753
160
136092
644
137087
708
10641
alcohol dehydrogenase subunit I
P25377
NADP-dependent alcohol dehydrogenase with a broad substrate specificity.
ADH7
29
1.1.1.2
7755
160
136093
644
137088
708
10642
alcohol dehydrogenase subunit 2
Q04894
NADP-dependent alcohol dehydrogenase with a broad substrate specificity.
ADH6
29
1.1.1.2
7756
160
136094
644
137089
708
4405
chorismate mutase
18
PW_P004405
11492
10758
4406
prephenate dehydratase
18
PW_P004406
11493
10759
4255
aromatic amino acid aminotransferase II
18
PW_P004255
11307
10551
4407
Aromatic/aminoadipate aminotransferase 1
18
PW_P004407
11494
10760
4408
pyruvate decarboxylase
18
PW_P004408
11495
10761
11496
10762
11497
10763
4337
alcohol dehydrogenase
18
PW_P004337
11398
10641
11399
10642
6516
false
PW_R006516
Right
26758
7748
1
Compound
false
26759
7823
1
Compound
false
6436
4405
5.4.99.5
6517
false
PW_R006517
Right
26760
7823
1
Compound
false
26761
40034
1
Compound
false
26762
1420
1
Compound
false
26763
1316
1
Compound
false
26764
12810
1
Compound
false
6437
4406
4.2.1.51
6519
false
PW_R006519
Right
26769
12810
1
Compound
false
26770
95
1
Compound
false
26771
104
1
Compound
false
26772
134
1
Compound
false
6439
4407
2.6.1.39,2.6.1.57
6520
false
PW_R006520
Right
26773
12810
1
Compound
false
26774
40034
1
Compound
false
26775
1316
1
Compound
false
26776
2680
1
Compound
false
6440
4408
4.1.1.-,4.1.1.1
6521
false
PW_R006521
Right
26777
2680
1
Compound
false
26778
40034
1
Compound
false
26779
1144
1
Compound
false
26780
15002
1
Compound
false
26781
721
1
Compound
false
6441
4337
1.1.1.1
6518
false
PW_R006518
Both
26765
12810
1
Compound
false
26766
105
1
Compound
false
26767
164
1
Compound
false
26768
104
1
Compound
false
6438
4255
78890
7748
3
false
297
380
10
regular
100
100
78891
7823
3
false
697
380
10
regular
100
100
78892
40034
55
false
843
317
10
regular
78
78
78893
1420
49
false
1138
305
10
regular
78
78
78894
1316
52
false
1143
473
10
regular
78
78
78895
12810
3
false
1247
366
10
regular
100
130
78896
105
3
false
1327
556
10
regular
100
100
78897
164
3
false
1637
551
10
regular
100
100
78899
95
3
false
1377
286
10
regular
100
110
78900
104
3
false
1797
381
10
regular
100
100
78901
134
3
false
1652
281
10
regular
100
110
78903
105
3
false
1702
956
10
regular
100
100
78904
164
3
false
1702
731
10
regular
100
100
78905
12810
3
false
1797
1141
10
regular
100
130
78906
95
3
false
2072
831
10
regular
100
110
78907
134
3
false
2072
591
10
regular
100
110
78908
40034
55
false
1688
1238
10
regular
78
78
78909
1316
52
false
1378
1240
10
regular
78
78
78910
2680
3
false
1247
1153
10
regular
100
100
78911
40034
55
false
1168
1070
10
regular
78
78
78912
1144
60
false
1157
1243
10
regular
50
30
78913
15002
3
false
752
1156
10
regular
100
100
78914
721
59
false
877
1246
10
regular
50
30
37745
10758
160
2
false
472
395
8
subunit
regular
150
70
37746
10759
160
2
false
952
395
8
subunit
regular
150
70
37747
10551
160
2
false
1452
658
8
subunit
regular
150
70
37748
10760
160
2
false
1492
396
8
subunit
regular
150
70
37749
10551
160
2
false
1777
863
8
subunit
regular
150
70
37750
10760
160
2
false
1952
716
8
subunit
regular
150
70
37751
10761
160
2
false
1547
1134
8
subunit
regular
150
70
37752
10762
160
2
false
1432
1144
8
subunit
regular
150
70
37753
10763
160
2
false
1507
1169
8
subunit
regular
150
70
37754
10641
160
2
false
907
1133
8
subunit
regular
150
70
37755
10642
160
2
false
962
1168
8
subunit
regular
150
70
30770
4405
2194
37082
37745
30771
4406
2194
37083
37746
30772
4255
2194
37084
37747
30773
4407
2194
37085
37748
30774
4255
2194
37086
37749
30775
4407
2194
37087
37750
30776
4408
2194
37088
37751
37089
37752
37090
37753
30777
4337
2194
37091
37754
37092
37755
113441
M397 430 C427 430 442 430 472 430
5
false
18
113442
M697 430 C667 430 652 430 622 430
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113443
M797 430 C827 430 922 430 952 430
5
false
18
113444
M882 395 C884 430 922 430 952 430
5
false
18
113445
M1177 383 C1176 438 1132 430 1102 430
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113446
M1182 473 C1180 426 1132 430 1102 430
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113447
M1247 431 C1217 431 1132 430 1102 430
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113452
M1347 431 C1381 431 1468 431 1492 431
5
false
18
true
M 1653.5031999261191 367.5317372693074 L 1640 361 L 1641.0949495569937 375.9599828030529
false
113453
M1427 396 C1427 426 1437 430 1492 431
5
false
18
113454
M1797 431 C1750 431 1688 431 1642 431
5
false
18
true
M 1198.9468550441647 147.26155629629605 L 1184 146 L 1190.380887721186 159.57513432307834
false
113455
M1702 391 C1702 419 1685 431 1642 431
5
false
18
true
M 1198.9468550441647 147.26155629629605 L 1184 146 L 1190.380887721186 159.57513432307834
false
113460
M1897 1206 C1937 1207 2001 1206 2025 1206 C2025 1162 2027 886 2027 786
5
false
18
true
M 1627.5 1328.0096189432334 L 1635 1341 L 1642.5 1328.0096189432334
false
113461
M2072 886 C2027 885 2027 816 2027 786
5
false
18
113462
M1897 431 C1928 432 2003 433 2027 433 C2027 533 2027 615 2027 716
5
false
18
true
M 760.9468550441649 612.261556296296 L 746 611 L 752.3808877211858 624.5751343230784
false
113463
M2072 646 C2038 646 2027 686 2027 716
5
false
18
true
M 760.9468550441649 612.261556296296 L 746 611 L 752.3808877211858 624.5751343230784
false
113464
M1797 1206 C1767 1206 1687 1204 1657 1204
5
false
18
113465
M1727 1238 C1726 1203 1687 1204 1657 1204
5
false
18
113466
M1417 1240 C1416 1202 1477 1204 1507 1204
5
false
18
true
M 1079.9468550441647 895.261556296296 L 1065 894 L 1071.380887721186 907.5751343230784
false
113467
M1347 1203 C1377 1203 1477 1204 1507 1204
5
false
18
true
M 1079.9468550441647 895.261556296296 L 1065 894 L 1071.380887721186 907.5751343230784
false
113468
M1247 1203 C1217 1203 1142 1203 1112 1203
5
false
18
113469
M1207 1148 C1206 1208 1142 1203 1112 1203
5
false
18
113470
M1182 1243 C1183 1197 1142 1203 1112 1203
5
false
18
113471
M852 1206 C882 1206 932 1203 962 1203
5
false
18
true
M 453.94685504416486 1035.261556296296 L 439 1034 L 445.38088772118584 1047.5751343230784
false
113472
M902 1246 C905 1203 932 1203 962 1203
5
false
18
true
M 453.94685504416486 1035.261556296296 L 439 1034 L 445.38088772118584 1047.5751343230784
false
3665925
M1847 1141 C1847 1111 1852 963 1852 933
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3665926
M1802 1006 C1834 1006 1852 963 1852 933
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3665927
M1802 781 C1832 781 1852 833 1852 863
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3665928
M1847 481 C1847 511 1852 833 1852 863
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3665929
M1297 496 C1297 526 1297 662 1297 692 C1354 693 1422 693 1452 693
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3665930
M1377 656 C1377 687 1410 694 1452 693
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3665931
M1687 651 C1688 677 1680 692 1602 693
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3665932
M1797 431 C1797 497 1797 638 1796 692 C1741 692 1639 692 1602 693
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
23289
2194
6516
89634
78890
113441
Left
89635
78891
113442
Right
23095
6436
30770
23290
2194
6517
89636
78891
113443
Left
89637
78892
113444
Left
89638
78893
113445
Right
89639
78894
113446
Right
89640
78895
113447
Right
23096
6437
30771
23292
2194
6519
89645
78895
113452
Left
89646
78899
113453
Left
89647
78900
113454
Right
89648
78901
113455
Right
23098
6439
30773
23294
2194
6519
89653
78905
113460
Left
89654
78906
113461
Left
89655
78900
113462
Right
89656
78907
113463
Right
23100
6439
30775
23295
2194
6520
89657
78905
113464
Left
89658
78908
113465
Left
89659
78909
113466
Right
89660
78910
113467
Right
23101
6440
30776
23296
2194
6521
89661
78910
113468
Left
89662
78911
113469
Left
89663
78912
113470
Left
89664
78913
113471
Right
89665
78914
113472
Right
23102
6441
30777
798532
2194
6518
3227344
78905
3665925
Left
3227345
78903
3665926
Left
3227346
78904
3665927
Right
3227347
78900
3665928
Right
754105
6438
30774
798533
2194
6518
3227348
78895
3665929
Left
3227349
78896
3665930
Left
3227350
78897
3665931
Right
3227351
78900
3665932
Right
754106
6438
30772
186765
288
527
1.3
1.3
0
2
90
484
497
4283
M125 225 C125 175 175 125 225 125 C846 125 1652 125 2273 125 C2323 125 2373 175 2373 225 C2373 573 2373 1025 2373 1373 C2373 1423 2323 1473 2273 1473 C1652 1473 846 1473 225 1473 C175 1473 125 1423 125 1373 C125 1025 125 573 125 225
1
true
6
2248.0
1348.0
4284
M225 325 C225 275 275 225 325 225 C886 225 1614 225 2175 225 C2225 225 2275 275 2275 325 C2275 613 2275 987 2275 1275 C2275 1325 2225 1375 2175 1375 C1614 1375 886 1375 325 1375 C275 1375 225 1325 225 1275 C225 987 225 613 225 325
1
true
6
2050.0
1150.0