1
Pathway
Selenoamino Acid Metabolism
Phospholipids are membrane components in P. aeruginosa. The major phospholipids of P. aeruginosa are phosphatidylethanolamine, phosphatidylglycerol, and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions. The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed into an sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH-driven glycerol-3-phosphate dehydrogenase. sn-Glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid). This can be achieved by an sn-glycerol-3-phosphate acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate (phosphatidic acid) through a 1-acylglycerol-3-phosphate O-acyltransferase. This compound is then converted into a CPD-diacylglycerol through a CTP phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either into an L-1-phosphatidylserine or an L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase, respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase. On the other hand, L-1-phosphatidylglycerol-phosphate gets transformed into an L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combine to produce a cardiolipin and an ethanolamine. The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin.
Metabolic
PW000007
Center
PathwayVisualizationContext7
3000
2700
#000099
PathwayVisualization10
1
Selenoamino Acid Metabolism
Phospholipids are membrane components in P. aeruginosa. The major phospholipids of P. aeruginosa are phosphatidylethanolamine, phosphatidylglycerol, and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions. The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed into an sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH-driven glycerol-3-phosphate dehydrogenase. sn-Glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid). This can be achieved by an sn-glycerol-3-phosphate acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate (phosphatidic acid) through a 1-acylglycerol-3-phosphate O-acyltransferase. This compound is then converted into a CPD-diacylglycerol through a CTP phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either into an L-1-phosphatidylserine or an L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase, respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase. On the other hand, L-1-phosphatidylglycerol-phosphate gets transformed into an L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combine to produce a cardiolipin and an ethanolamine. The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin.
Metabolic
1
238
4
SubPathway
362
105
Compound
8
239
7
SubPathway
363
105
Compound
8
240
3
SubPathway
364
105
Compound
8
241
28
SubPathway
365
105
Compound
8
110304
Internal digestion and absorption
SubPathway
73
Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.
1
Pathway
74
Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.
1
Pathway
279613
28574376
Lazard M, Dauplais M, Blanquet S, Plateau P: Recent advances in the mechanism of selenoamino acids toxicity in eukaryotic cells. Biomol Concepts. 2017 May 24;8(2):93-104. doi: 10.1515/bmc-2017-0007.
1
Pathway
280364
27166256
McDermott JR, Geng X, Jiang L, Galvez-Peralta M, Chen F, Nebert DW, Liu Z: Zinc- and bicarbonate-dependent ZIP8 transporter mediates selenite uptake. Oncotarget. 2016 Jun 7;7(23):35327-40. doi: 10.18632/oncotarget.9205.
1
Pathway
1
Cell
CL:0000000
6
Myocyte
CL:0000187
5
Hepatocyte
CL:0000182
3
Neuron
CL:0000540
2
Platelet
CL:0000233
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
7
Epithelial Cell
CL:0000066
10
Glial cell
CL:0000125
18
Erythrocyte
CL:0000232
28
Macrophage
CL:0000235
1
Homo sapiens
9606
Eukaryote
Human
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
3
Escherichia coli
562
Prokaryote
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
23
Pseudomonas aeruginosa
287
Prokaryote
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
2
Bacteria
2
Prokaryote
Bacteria
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
196
Homo
1924
Eukaryote
Human
157
Acinetobacter baumannii
107673
Prokaryote
280
Bacteroides fragilis
55247009
Prokaryote
5
Cytoplasm
GO:0005737
11
Extracellular Space
GO:0005615
1
Cytosol
GO:0005829
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
31
Periplasmic Space
GO:0005620
10
Cell Membrane
GO:0005886
35
Chloroplast
GO:0009507
13
Endoplasmic Reticulum
GO:0005783
24
Mitochondrial Intermembrane Space
GO:0005758
7
Endoplasmic Reticulum Membrane
GO:0005789
14
Mitochondrial Outer Membrane
GO:0005741
15
Nucleus
GO:0005634
4
Peroxisome
GO:0005777
27
Peroxisome Membrane
GO:0005778
12
Mitochondrial Inner Membrane
GO:0005743
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
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
19
Sarcoplasmic Reticulum
GO:0016529
37
Basolateral cell membrane
GO:0016323
49
Nuclear Envelope
GO:0005635
39
Mitochondrial membrane
GO:0031966
56
Basal Cell Membrane
GO:0009925
38
Apical cell membrane
GO:0016324
9
Muscle
BTO:0000887
141
18
8
Blood Vessel
BTO:0001102
74
11
1
Liver
BTO:0000759
72
9
24
Brain
BTO:0000142
89
16
3
Sympathetic Nervous System
BTO:0001832
4
Adrenal Medulla
BTO:0000049
71
8
2
Endothelium
BTO:0000393
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
25
Intestine
BTO:0000648
28
Stomach
BTO:0001307
155
26
11
Heart
BTO:0000562
73
10
6
Kidney
BTO:0000671
71
8
8
5
1
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PW_BS000135
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75
25
10
1
7
PW_BS000075
1065
32
196
PW_BS000578
1143
1
14
1
5
PW_BS000583
961
1
2
1
5
PW_BS000564
1148
1
49
1
5
PW_BS000583
1168
8
10
1
28
PW_BS000583
1184
1
280
1
PW_BS000588
810
10
157
4
PW_BS000548
231
39
1
PW_BS000024
80
11
1
1
PW_BS000080
1829
Selenocysteine
HMDB0003288
Selenocysteine is an amino acid that is present in several enzymes (for example glutathione peroxidases, tetraiodothyronine 5' deiodinases, thioredoxin reductases, formate dehydrogenases, glycine reductases and some hydrogenases). Selenocysteine has a structure similar to cysteine, but with an atom of selenium taking the place of the usual sulfur. Proteins that include a selenocysteine residue are called selenoproteins (Wikipedia). Selenocysteine is a naturally occurring amino acid in both eukaryotic and prokaryotic organisms. It is found in tRNAs and in the catalytic site of some enzymes. The genes for glutathione peroxidase and formate dehydrogenase contain the TGA codon, which codes for this amino acid (Pubchem).
10236-58-5
C05688
25076
16633
L-SELENOCYSTEINE
23436
DB02345
N[C@@H](C[SeH])C(O)=O
C3H7NO2Se
InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
ZKZBPNGNEQAJSX-REOHCLBHSA-N
(2R)-2-amino-3-selanylpropanoic acid
168.05
168.964200301
0.29
3
L-selenocysteine
0
0
FDB002262
(2r)-2-amino-3-selanylpropanoate;(2r)-2-amino-3-selanylpropanoic acid;3-seleno-alanine;3-selenoalanine;3-selenyl-l-alanine;L-selenocystein;L-selenocysteine;L-selenozystein;U
PW_C001829
SelCys
315
8
375
15
78813
111
119909
122
122710
135
125299
297
126849
205
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
6752
Hydrogen selenide
HMDB0011110
Hydrogen selenide is a metabolite of selenium which could have potential antiangiogenic effect in the chemoprevention of cancer. The hydrogen selenide is a key intermediate in the selenium methylation metabolism of inorganic and organic selenium compounds. Accumulation of the hydrogen selenide resulting from inhibition of the selenium methylation metabolism, detoxification metabolic pathway of selenium, is found in animals following repeated administration of a toxic dose of selenocystine. The excess of the hydrogen selenide produced by inhibition of the selenium methylation metabolism contributes to the hepatotoxicity caused by selenocystine. (PMID: 9414580, 11799926).
7783-07-5
C01528
533
16503
518
[SeH2]
H2Se
InChI=1S/H2Se/h1H2
SPVXKVOXSXTJOY-UHFFFAOYSA-N
hydrogen selenide
80.98
81.932171892
1
hydrogen selenide
0
-1
C01528
Dihydrogen monoselenide;Dihydrogen selenide;Hydrogen selenide;Selane;Selenium dihydride;Selenium hydride;Selenium hydride (seh2);[seh2];H2se;Hydroselenic acid;Hydroselenate
PW_C006752
HygSlnd
317
8
12635
31
78814
111
119911
122
122711
135
125301
297
126851
205
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
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
140770
891
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
32
Adenosine monophosphate
HMDB0000045
Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable.
61-19-8
C00020
6083
16027
AMP
5858
DB00131
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
C10H14N5O7P
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
UDMBCSSLTHHNCD-KQYNXXCUSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
347.2212
347.063084339
-2.02
5
adenylate
0
-2
DBMET00485
FDB021806
5'-amp;5'-adenosine monophosphate;5'-adenylate;5'-adenylic acid;Amp;Adenosine 5'-monophosphate;Adenosine 5'-phosphate;Adenosine 5'-phosphorate;Adenosine 5'-phosphoric acid;Adenosine phosphate;Adenosine-5'-monophosphorate;Adenosine-5'-monophosphoric acid;Adenosine-5-monophosphorate;Adenosine-5-monophosphoric acid;Adenosine-monophosphate;Adenosine-phosphate;Adenovite;Adenylate;Adenylic acid;Cardiomone;Lycedan;Muscle adenylate;Muscle adenylic acid;My-b-den;My-beta-den;Phosaden;Phosphaden;Phosphentaside;5'-o-phosphonoadenosine;Adenosine 5'-(dihydrogen phosphate);Adenosine monophosphate;Adenosine-5'p;Adenosini phosphas;Ado5'p;Fosfato de adenosina;Pa;Pado;Phosphate d'adenosine;5'-adenosine monophosphoric acid;Adenosine phosphoric acid;Adenosine 5'-(dihydrogen phosphoric acid);Adenosine 5'-monophosphoric acid;Adenosine monophosphoric acid;Adenosine-5'-monophosphate;Phosphoric acid d'adenosine
PW_C000032
AMP
11
2
34
4
62
8
270
16
734
32
881
22
1189
14
4572
5
4867
54
5033
89
5251
104
5408
117
5423
103
5432
118
5457
120
5558
132
5583
133
5779
101
5795
108
6977
199
7072
188
11789
198
11868
161
11988
151
12003
222
12580
226
12636
31
12694
290
13331
225
42266
3
42646
315
77234
329
77325
111
78392
334
78809
115
79320
112
80399
1
80684
135
80900
7
119916
122
120016
124
120031
406
120246
382
120888
405
121954
408
122920
399
123464
376
124507
374
125306
297
125394
299
125409
479
125596
484
126853
205
126934
388
126949
501
127124
389
127311
209
127711
502
140771
891
1977
Phosphoroselenoic acid
HMDB0003840
Phosphoroselenoic acid, H3SePO3, is the activated selenium donor compound required for the biosynthesis of selenocysteyl-tRNA, the precursor of specific selenocysteine residues in bacterial and mammalian selenoproteins. Selenocysteine is the 21st amino acid, because Sec has a specific tRNA and codon UGA, and shares a major stop codon UGA. A number of enzymes have selenocysteine, residues and in some cases at their active sites. Proteins containing the 21st amino acid, selenocysteine (Sec), have been described in all three domains of life. (PMID: 18156471).
25758-66-1
C05172
1092
29269
1061
OP(O)(O)=[Se]
H3O3PSe
InChI=1S/H3O3PSe/c1-4(2,3)5/h(H3,1,2,3,5)
JRPHGDYSKGJTKZ-UHFFFAOYSA-N
hydroxy(selanylidene)phosphonous acid
160.96
161.898502302
3
selenophosphoric acid
0
-3
FDB023234
Monoselenophosphoric acid;Sepo3;Selenophosphoric acid;Trihydroxidoselenidophosphorus;[p(oh)3se];Selenophosphate
PW_C001977
PhSelnA
321
8
12637
31
78816
111
119917
122
122713
135
125307
297
126854
205
1441
Phosphoric acid
HMDB0002142
Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a mineral acid with the chemical formula H3PO4. Alternatively, orthophosphoric acid molecules can combine with themselves to form a variety of compounds referred to as phosphoric acids in a more general way. For a discussion of these, see Phosphoric acids and Phosphates. Appears to exist only as a food additive and produced synthetically. --Wikipedia.
7664-38-2
C00009
1004
26078
979
OP(O)(O)=O
H3O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)
NBIIXXVUZAFLBC-UHFFFAOYSA-N
phosphoric acid
97.9952
97.976895096
3
phosphoric acid
0
-2
FDB013380
Acide phosphorique (french);Acido fosforico [italian];Acidum phosphoricum;Diphosphate tetrasodium;Fosforzuuroplossingen [dutch];Marphos;Nfb;Ortho- phosphoric acid;Orthophosphoric acid;Phosphoric acid (acd/name 4.0);Phosphorsaeure;Phosphorsaeureloesungen [german];Sodium pyrophosphate;Sodium pyrophosphate decahydrate;Sodium pyrophosphate decahydrate biochemica;Sonac;Tetra-sodium pyrophosphate;Tetrasodium pyrophosphate decahydrate;Tetrasodium pyrophosphate 10-hydrate;White phosphoric acid;[po(oh)3];Acide phosphorique;H3po4;Phosphate;Phosphorsaeureloesungen;Orthophosphate
PW_C001441
PhosfrA
171
8
440
4
483
13
1592
43
1678
2
1902
49
1910
5
4856
3
5913
147
5943
151
6891
160
11782
198
11828
213
11829
216
11852
277
12638
31
77105
132
77330
133
77473
333
77779
111
78000
112
78272
356
78706
331
78707
334
80671
135
80677
119
119918
122
120126
124
120157
407
120344
406
120367
412
121383
419
121900
383
121902
408
122858
118
122994
120
123014
446
123942
455
124453
398
124455
374
125308
297
125493
299
125518
481
125664
479
126056
490
126855
205
127030
388
127053
206
127159
501
127508
507
2727
Selenocystathionine
HMDB0006343
Selenocystathionine is formed from Selenohomocysteine by the enzyme cystathionine beta-synthase (EC 4.2.1.22), as a by-product of cystathionine synthesis. Selenocystathionine is consumed in the diet, and is one of the main compounds present in plants that tend to hyperaccumulate selenium and use it as an elemental plant defense mechanism. (PMID: 10026151, 6456763, 16920881).
2196-58-9
C05699
98223
26630
88693
NC(CC[Se]CC(N)C(O)=O)C(O)=O
C7H14N2O4Se
InChI=1S/C7H14N2O4Se/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)
ZNWYDQPOUQRDLY-UHFFFAOYSA-N
2-amino-4-[(2-amino-2-carboxyethyl)selanyl]butanoic acid
269.16
270.011878774
-0.49
4
selenocystathionine
0
0
FDB023895
2-amino-4-((2-amino-2-carboxyethyl)seleno)-butanoate;2-amino-4-((2-amino-2-carboxyethyl)seleno)-butanoic acid;2-amino-4-((2-amino-2-carboxyethyl)seleno)butanoate;2-amino-4-((2-amino-2-carboxyethyl)seleno)butanoic acid;Selenocystathionine;2-amino-4-[(2-amino-2-carboxyethyl)selanyl]butyric acid;Selenocystathionines
PW_C002727
SelC
336
8
78817
111
119920
122
122715
135
125310
297
126857
205
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
3
2-Ketobutyric acid
HMDB0000005
2-Ketobutyric acid is a substance that is involved in the metabolism of many amino acids (glycine, methionine, valine, leucine, serine, threonine, isoleucine) as well as propanoate metabolism and C-5 branched dibasic acid metabolism. More specifically, alpha-ketobutyric acid is a product of the lysis of cystathionine. It is also one of the degradation products of threonine. It can be converted into propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted into succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle.
600-18-0
C00109
58
30831
2-OXOBUTANOATE
57
DB04553
CCC(=O)C(O)=O
C4H6O3
InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
TYEYBOSBBBHJIV-UHFFFAOYSA-N
2-oxobutanoic acid
102.0886
102.031694058
-0.11
1
2-oxobutanoic acid
0
-1
FDB003359
2-ketobutanoate;2-ketobutanoic acid;2-ketobutyrate;2-oxo-butanoate;2-oxo-butanoic acid;2-oxo-butyrate;2-oxo-butyric acid;2-oxo-n-butyrate;2-oxo-n-butyric acid;2-oxobutanoate;2-oxobutanoic acid;2-oxobutyrate;2-oxobutyric acid;3-methylpyruvate;3-methylpyruvic acid;Methyl-pyruvate;Methyl-pyruvic acid;Propionyl-formate;Propionyl-formic acid;A-keto-n-butyrate;A-keto-n-butyric acid;A-ketobutyrate;A-ketobutyric acid;A-oxo-n-butyrate;A-oxo-n-butyric acid;A-oxobutyrate;A-oxobutyric acid;Alpha-keto-n-butyrate;Alpha-keto-n-butyric acid;Alpha-ketobutric acid;Alpha-ketobutyrate;Alpha-ketobutyric acid;Alpha-oxo-n-butyrate;Alpha-oxo-n-butyric acid;Alpha-oxobutyrate;Alpha-oxobutyric acid;2-ketobutyric acid;3-methyl pyruvic acid;3-methyl pyruvate;α-ketobutyrate;α-ketobutyric acid;α-oxo-n-butyrate;α-oxo-n-butyric acid
PW_C000003
2KBA
337
8
1868
2
2692
3
8274
151
8383
225
42272
4
78126
132
78163
111
78643
133
79027
112
119922
122
122176
124
122274
406
122577
407
122716
135
124728
118
124829
120
125149
119
125312
297
126333
299
126438
479
126726
481
126858
205
127896
388
128007
501
128319
206
120
L-Serine
HMDB0000187
Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373).
56-45-1
C00065
5951
17115
SER
5736
DB00133
N[C@@H](CO)C(O)=O
C3H7NO3
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
MTCFGRXMJLQNBG-REOHCLBHSA-N
(2S)-2-amino-3-hydroxypropanoic acid
105.0926
105.042593095
0.66
3
L-serine
0
0
FDB012739
(-)-serine;(s)-2-amino-3-hydroxypropanoate;(s)-2-amino-3-hydroxypropanoic acid;(s)-2-amino-3-hydroxy-propanoate;(s)-2-amino-3-hydroxy-propanoic acid;(s)-serine;(s)-a-amino-b-hydroxypropionate;(s)-a-amino-b-hydroxypropionic acid;(s)-alpha-amino-beta-hydroxypropionate;(s)-alpha-amino-beta-hydroxypropionic acid;(s)-b-amino-3-hydroxypropionate;(s)-b-amino-3-hydroxypropionic acid;(s)-beta-amino-3-hydroxypropionate;(s)-beta-amino-3-hydroxypropionic acid;2-amino-3-hydroxypropanoate;2-amino-3-hydroxypropanoic acid;3-hydroxy-l-alanine;L-(-)-serine;L-3-hydroxy-2-aminopropionate;L-3-hydroxy-2-aminopropionic acid;L-3-hydroxy-alanine;L-ser;Serine;B-hydroxy-l-alanine;Beta-hydroxy-l-alanine;Beta-hydroxyalanine;(2s)-2-amino-3-hydroxypropanoic acid;(s)-(-)-serine;L-2-amino-3-hydroxypropionic acid;L-serin;S;Ser;(2s)-2-amino-3-hydroxypropanoate;(s)-α-amino-β-hydroxypropionate;(s)-α-amino-β-hydroxypropionic acid;β-hydroxy-l-alanine;B-hydroxyalanine;β-hydroxyalanine;L-2-amino-3-hydroxypropionate
PW_C000120
Ser
344
8
1810
2
2617
4
5642
107
5643
108
5884
105
6011
147
6907
163
7086
201
7087
202
7090
71
7091
72
7202
160
7438
3
7443
15
7444
166
7522
224
8357
225
9154
249
12173
151
12625
18
15379
49
42335
318
42336
315
77320
111
78088
133
78112
132
79979
331
94858
383
115752
398
119924
122
122056
124
122136
406
122718
135
124667
118
124688
120
125314
297
126209
299
126293
479
126860
205
127771
388
127856
501
2066
Selenohomocysteine
HMDB0004119
Selenohomocysteine is the precursor of selenocysteine, which is synthesized by catalysis of cystathionine beta-synthase (EC 4.2.1.22) and cystathionine gamma-lyase (EC 4.4.1.1), in mammalian systems (both enzymes require pyridoxal phosphate). Selenohomocysteine (lactone) has been found to be a competitive and irreversible inhibitor of lysyl oxidase; this may relate to the development of connective tissue defects seen in homocystinuria. L-Selenohomocysteine also can serve as a substituent donor in the beta-replacement reaction to yield selenocystathionine. (PMID: 10609891, 9405445, 6456763, 3338973).
29412-93-9
C05698
440763
SELENOHOMOCYSTEINE
389632
NC(CC[SeH])C(O)=O
C4H9NO2Se
InChI=1S/C4H9NO2Se/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)
RCWCGLALNCIQNM-UHFFFAOYSA-N
2-amino-4-selanylbutanoic acid
182.08
182.979850365
0.06
2
2-amino-4-selanylbutanoic acid
0
0
FDB023315
2-amino-4-selanyl-butanoate;2-amino-4-selanyl-butanoic acid;Se-selenocysteine
PW_C002066
Selhcys
345
8
78819
111
119925
122
122719
135
125315
297
126861
205
6759
Se-Adenosylselenohomocysteine
HMDB0011117
Se-Adenosylselenohomocysteine is an intermediate in Selenoamino acid metabolism. Se-Adenosylselenohomocysteine is the second to last step in the synthesis of Selenohomocystine and is converted from Se-Adenosylselenomethionine via the enzyme Transferases (EC 2.1.1.-). It is then. converted to Selenohomocysteine via the enzyme adenosylhomocysteinase (EC 3.3.1.1).
C05692
16682731
17615371
NC(CC[Se]C[C@H]1O[C@@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O
C14H20N6O5Se
InChI=1S/C14H20N6O5Se/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+/m1/s1
UVSMMLABJBJNGH-WWJIDFMMSA-N
2-amino-4-({[(2S,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}selanyl)butanoic acid
431.31
432.066039608
-1.71
5
se-adenosylselenohomocysteine
0
0
C05692
PW_C006759
S-Adnsc
351
8
78821
111
119927
122
122721
135
125317
297
126863
205
34
Adenosine
HMDB0000050
Adenosine is a nucleoside that is composed of adenine and D-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously adenosine causes transient heart block in the AV node. Due to the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Overdoses of adenosine intake (as a drug) can lead to several side effects including chest pain, feeling faint, shortness of breath, and tingling of the senses. Serious side effects include a worsening dysrhythmia and low blood pressure. When present in sufficiently high levels, adenosine 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 adenosine are associated with adenosine deaminase deficiency. Adenosine is a precursor to deoxyadenosine, which is a precursor to dATP. A buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes.
58-61-7
C00212
60961
16335
ADENOSINE
54923
DB00640
NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1
C10H13N5O4
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
OIRDTQYFTABQOQ-KQYNXXCUSA-N
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
267.2413
267.096753929
-1.28
4
adenosine
0
0
FDB003554
1-(6-amino-9h-purin-9-yl)-1-deoxy-beta-d-ribofuranose;1-(6-amino-9h-purin-9-yl)-1-deoxy-beta-delta-ribofuranose;6-amino-9beta-d-ribofuranosyl-9h-purine;6-amino-9beta-delta-ribofuranosyl-9h-purine;9-beta-d-arabinofuranosyladenine;9-beta-d-ribofuranosidoadenine;9-beta-d-ribofuranosyl-9h-purin-6-amine;9-beta-d-ribofuranosyladenine;9-beta-delta-arabinofuranosyladenine;9-beta-delta-ribofuranosidoadenine;9-beta-delta-ribofuranosyl-9h-purin-6-amine;9-beta-delta-ribofuranosyladenine;9beta-d-ribofuranosyladenine;9beta-d-ribofuranosyl-9h-purin-6-amine;9beta-delta-ribofuranosyladenine;9beta-delta-ribofuranosyl-9h-purin-6-amine;Adenine nucleoside;Adenine riboside;Adenine-9beta-d-ribofuranoside;Adenine-9beta-delta-ribofuranoside;Adenocard;Adenocor;Adenoscan;Adenosin;Boniton;Myocol;Nucleocardyl;Sandesin;B-d-adenosine;Beta-adenosine;Beta-d-adenosine;Beta-delta-adenosine;(2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;6-amino-9-beta-d-ribofuranosyl-9h-purine;Ade-rib;Adenine deoxyribonucleoside;Adenyldeoxyriboside;Ado;Deoxyadenosine;Desoxyadenosine;6-amino-9-b-d-ribofuranosyl-9h-purine;6-amino-9-β-d-ribofuranosyl-9h-purine;9-b-d-ribofuranosidoadenine;9-β-d-ribofuranosidoadenine;9-b-d-ribofuranosyl-9h-purin-6-amine;9-β-d-ribofuranosyl-9h-purin-6-amine;β-d-adenosine
PW_C000034
Adenosi
352
8
1896
2
4013
15
5609
118
6769
107
6770
108
11825
198
12526
249
43737
315
43738
318
77612
132
78702
111
119928
122
120487
124
122722
135
125318
297
126459
299
126864
205
128029
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
6760
Se-Adenosylselenomethionine
HMDB0011118
Se-Adenosylselenomethionine is an intermediate in Selenoamino acid metabolism. Se-Adenosylselenomethionine is converted from Selenomethionine via the enzyme S-adenosylmethionine synthetase (EC 2.5.1.6). It is then. converted to Se-Adenosylselenohomocysteine via the enzyme Transferases (EC 2.1.1.-).
C05691
24892761
C[Se+](CCC(N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
C15H23N6O5Se
InChI=1S/C15H22N6O5Se/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?/m1/s1
GGJFWMOVUFBSIN-YDBXVIPQSA-O
(3-amino-3-carboxypropyl)({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylselanium
446.34
447.089514704
-2.43
5
se-adenosylselenomethionine
1
1
C05691
PW_C006760
S-Adnsm
358
8
78822
111
119931
122
122724
135
125321
297
126866
205
2019
Selenomethionine
HMDB0003966
Selenomethionine is an amino acid containing selenium that cannot be synthesized by higher animals, but can be obtained from plant material. Selenomethionine is the major seleno-compound in cereal grains (wheat grain, maize and rice), soybeans and enriched yeast. Seleno-compounds present in plants may have a profound effect upon the health of animals and human subjects. It is now known that the total Se content cannot be used as an indication of its efficacy, but knowledge of individual selenocompounds is necessary to fully assess the significance. Thus, speciation of the seleno-compounds has moved to the forefront. Since animals and man are dependent upon plants for their nutritional requirements, this makes the types of seleno-compounds in plants even more critical. Se enters the food chain through incorporation into plant proteins, mostly as selenocysteine and selenomethionine at normal Se levels. There are two possible pathways for the catabolism of selenomethionine. One is the transsulfuration pathway via selenocystathionine to produce selenocysteine, which in turn is degraded to H2Se by the enzyme b-lyase. The other pathway is the transamination-decarboxylation pathway. It was estimated that 90% of methionine is metabolized through this pathway and thus could be also the major route for selenomethionine catabolism. (PMID: 14748935, Br J Nutr. 2004 Jan;91(1):11-28.).
1464-42-2
C05335
15103
27585
SELENOMETHIONINE
14375
C[Se]CCC(N)C(O)=O
C5H11NO2Se
InChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
RJFAYQIBOAGBLC-UHFFFAOYSA-N
2-amino-4-(methylselanyl)butanoic acid
196.11
196.995500429
-0.25
2
(+,-)-selenomethionine
0
0
FDB012156
(+-)-selenomethionine;(2s)-2-amino-4-(methylseleno)butanoate;(2s)-2-amino-4-(methylseleno)butanoic acid;(s)-2-amino-4-(methylseleno)butanoate;(s)-2-amino-4-(methylseleno)butanoic acid;(s)-2-amino-4-(methylseleno)butyric acid;(s)-2-amino-4-(methylseleno)-butanoate;(s)-2-amino-4-(methylseleno)-butanoic acid;2-amino-4-(methylseleno)butanoate;2-amino-4-(methylseleno)butanoic acid;2-amino-4-(methylselenyl)butyrate;2-amino-4-(methylselenyl)butyric acid;Dl-selenomethionine;L(+)-selenomethionine;L-2-amino-4-(methylselenyl)-butyric acid;L-selenomethionine;L-selenomethioninum;Mse;Semet;Selenium methionine;Selenium-l-methionine;Seleno-d,l-methionine;Seleno-dl-methionine;Seleno-l-methionine;Selenomethionine se 75;Sethotope
PW_C002019
SelMet
360
8
78824
111
119933
122
122726
135
125323
297
126868
205
170
Pyrophosphate
HMDB0000250
The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.
14000-31-8
C00013
644102
18361
PPI
559142
DB04160
OP(O)(=O)OP(O)(O)=O
H4O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)
XPPKVPWEQAFLFU-UHFFFAOYSA-N
(phosphonooxy)phosphonic acid
177.9751
177.943225506
4
pyrophosphoric acid
0
-3
FDB021918
(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ion
PW_C000170
Ppi
12
2
35
4
63
8
429
23
735
32
882
22
1217
3
1620
49
2410
59
2815
29
4175
14
4868
54
5034
89
5252
104
5294
101
5409
117
5424
103
5433
118
5458
120
5548
111
5559
132
5584
133
5606
135
5655
108
5879
107
6239
166
6978
199
7073
188
7134
163
7272
160
7312
198
7318
213
8275
151
8283
210
11869
161
12002
222
12041
164
12315
225
12323
249
12512
288
12579
226
12695
290
15219
306
15375
18
34760
17
42561
315
42697
318
77235
329
77317
128
77635
336
78416
335
78928
331
79153
112
79950
134
79958
130
80047
372
80417
170
85630
1
94786
384
94814
125
94819
382
98678
223
110634
391
113270
395
113275
389
115527
136
115532
399
119934
122
120017
124
120032
406
120330
410
120936
407
121261
429
121341
121
121486
383
122407
422
122985
444
123502
119
123831
464
124044
398
124977
375
125324
297
125395
299
125410
479
125597
484
125656
485
125876
481
126552
491
126869
205
126935
388
126950
501
127337
206
128124
508
140772
891
40445
Selenic acid
HMDB0060694
Selenate, also known as sodium selenate or [seo2(OH)2], belongs to the class of inorganic compounds known as non-metal selenates. These are inorganic non-metallic compounds containing a selenate as its largest oxoanion. Selenate has been primarily detected in urine. Selenate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, selenate can be found in a number of food items such as turmeric, roman camomile, savoy cabbage, and other soy product. This makes selenate a potential biomarker for the consumption of these food products. Selenate is a potentially toxic compound.
7783-08-6
C05697
1089
18170
1058
O[Se](O)(=O)=O
H2O4Se
InChI=1S/H2O4Se/c1-5(2,3)4/h(H2,1,2,3,4)
QYHFIVBSNOWOCQ-UHFFFAOYSA-N
selenic acid
144.97
145.91183038
2
selenic acid
0
-2
[seo2(oh)2];H2seo4;Selenate
PW_C040445
Selenic
368
8
6652
107
6653
108
42489
318
42490
315
78828
111
119940
122
122732
135
125330
297
126874
205
2063
Adenylylselenate
HMDB0004112
Adenylylselenate is an intermediate in selenoamino acid metabolism. Adenylylselenate is produced from selenate via the enzyme sulfate adenylyltransferase [EC:2.7.7.4] and then converted to selenite via the enzyme adenylylsulfate reductase [EC:1.8.99.2]. The reaction between adenylselenate and adenylylsulfate kinase [EC:2.7.1.25] also gives rise to the 3'-Phosphoadenylylselenate.
C05686
440758
2485
389628
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)O[Se](O)(=O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
C10H14N5O10PSe
InChI=1S/C10H14N5O10PSe/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-26(18,19)25-27(20,21)22/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H,20,21,22)/t4-,6-,7-,10-/m1/s1
XCADVMZZFPIERR-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]selenonic acid
474.18
474.964350033
-2.30
5
adenylylselenate
0
-2
FDB023314
Adenosine-5'-phosphoselenate;Adenylylselenic acid;Adenylylselenate;Adenosine-5'-phosphoselenic acid
PW_C002063
AdenylS
369
8
78829
111
119941
122
122733
135
125331
297
126875
205
6747
3-Phosphoadenylylselenate
HMDB0011104
3-Phosphoadenylylselenate belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. 3-Phosphoadenylylselenate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). 3-Phosphoadenylylselenate exists in all living organisms, ranging from bacteria to humans. In humans, 3-phosphoadenylylselenate is involved in the selenoamino acid metabolism pathway. 3-Phosphoadenylylselenate participates in selenoamino acid metabolism. 3-phosphoadenylylselenate is converted from adenylylselenate via adenylylsulfate kinase (EC: 2.7.1.25).
C05696
24892762
28450
30785505
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)O[Se](O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1
C10H15N5O13P2Se
InChI=1S/C10H15N5O13P2Se/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6-,7-,10-/m1/s1
AZRLZPIFEZUZLW-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]selenonic acid
554.16
554.930680443
-2.28
6
3'-phosphoadenylylselenate
0
-3
C05696
3'-phosphoadenosine-5'-phosphoselanate;3'-phosphoadenosine-5'-phosphoselenate;3'-phosphoadenylylselenate;3'-phosphoadenosine-5'-phosphoselanic acid;3-phosphoadenylylselenic acid;3'-phosphoadenosine-5'-phosphoselenic acid;3'-phosphoadenylylselenic acid
PW_C006747
3PAdns
371
8
78830
111
119943
122
122735
135
125333
297
126877
205
1034
Adenosine diphosphate
HMDB0001341
Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.
58-64-0
C00008
6022
16761
ADP
5800
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
XTWYTFMLZFPYCI-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
427.2011
427.029414749
-2.12
6
adenosine-diphosphate
0
-2
FDB021817
Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid
PW_C001034
ADP
23
4
134
8
415
22
482
13
801
5
963
15
978
3
1061
14
1518
2
1901
49
2104
18
2113
10
2161
58
2408
59
2435
27
2728
47
2736
46
2855
29
3165
72
3635
61
4400
23
4476
31
4770
91
5036
26
5157
7
5208
97
5217
100
5315
111
5349
112
5392
103
5446
120
5544
129
5572
133
5624
108
5741
117
5764
101
5849
143
5856
146
5878
107
5899
147
5926
151
6050
155
6111
161
6231
166
6495
178
6700
94
6841
188
6872
160
7159
205
7187
206
7208
210
7226
213
7231
211
7300
198
7303
216
7391
217
7410
218
7433
163
7483
222
8187
225
11851
277
11905
170
12013
281
12180
285
13262
223
15329
308
42328
315
42398
313
42622
322
42696
318
77029
253
77087
132
77216
134
77306
329
77472
333
77663
336
78039
332
78043
350
78170
128
78215
351
78244
353
78414
335
78495
115
78705
331
78849
130
78920
334
80030
368
80622
118
80651
135
80676
119
94827
124
113283
388
116204
109
119944
122
119994
406
120156
407
120318
382
120366
412
121248
429
121394
123
121399
433
121472
408
121899
383
121976
410
122064
125
122085
405
122405
422
122445
435
122973
399
123013
446
123818
464
123953
447
123958
468
124030
374
124452
398
124529
444
124615
136
124636
376
124947
472
124975
375
125012
470
125334
297
125373
479
125492
299
125517
481
125645
484
126125
485
126219
300
126235
495
126242
478
126550
491
126597
499
126915
501
127733
516
127780
395
127797
390
127803
209
128122
508
128168
517
128313
389
2064
Se-Methylselenocysteine
HMDB0004113
Se-Methylselenocysteine (SeMSC) is a naturally occurring seleno-amino acid that is synthesized by plants such as garlic, astragalus, onions and broccoli. Unlike selenomethionine, which is incorporated into proteins in place of methionine, SeMSC is not incorporated into any proteins, thereby being fully available for the synthesis of selenium-containing enzymes such as glutathione peroxidase.
26046-90-2
C05689
147004
27812
129633
C[Se]C[C@H](N)C(O)=O
C4H9NO2Se
InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
XDSSPSLGNGIIHP-VKHMYHEASA-N
(2R)-2-amino-3-(methylselanyl)propanoic acid
182.08
182.979850365
-0.07
2
methylselenocysteine
0
0
FDB012599
3-(methylseleno)-l-alanine;Methylselenocysteine;Se-methyl-l-selenocysteine;Selenium-methylselenocystine;L-methylselenocysteine;Methyl-l-selenocysteine;Se-methyl-seleno-l-cysteine;Se-methyl-selenocysteine;Se-methylselenocysteine;Selenium methyl cysteine;Selenohomocysteine;Selenomethylselenocysteine;(2r)-2-amino-3-methylselanylpropanoate
PW_C002064
Selenoh
310
14
372
15
373
8
78831
111
119945
122
122736
135
125335
297
126878
205
6724
γ-Glutamyl-Se-methylselenocysteine
HMDB0010716
Gamma-Glutamyl-se-methylselenocysteine, also known as gamma-glutamyl-semc or GGMSC CPD, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Gamma-Glutamyl-se-methylselenocysteine is soluble (in water) and a moderately acidic compound (based on its pKa). Gamma-Glutamyl-se-methylselenocysteine exists in all living organisms, ranging from bacteria to humans. In humans, Gamma-glutamyl-se-methylselenocysteine is involved in the selenoamino acid metabolism pathway. gamma-Glutamyl-Se-methylselenocysteine is an intermediate in selenoamino acid metabolism(KEGG ID C05695). It is generated from Se-methyl-selenocysteine via the enzyme gamma-glutamyltranspeptidase [EC:2.3.2.2].
C05695
440760
389629
C[Se]CC(NC(=O)CCC(N)C(O)=O)C(O)=O
C9H16N2O5Se
InChI=1S/C9H16N2O5Se/c1-17-4-6(9(15)16)11-7(12)3-2-5(10)8(13)14/h5-6H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)
IEFQLTYCECVOLL-UHFFFAOYSA-N
2-amino-4-{[1-carboxy-2-(methylselanyl)ethyl]carbamoyl}butanoic acid
311.19
312.02244346
-1.00
4
2-amino-4-{[1-carboxy-2-(methylselanyl)ethyl]carbamoyl}butanoic acid
0
-1
C05695
PW_C006724
γGSM
311
14
78832
115
98611
8
119946
405
122737
376
125336
478
126879
209
2067
Selenocystine
HMDB0004122
Selenocystine belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Selenocystine is soluble (in water) and an extremely strong acidic compound (based on its pKa). Selenocystine has been primarily detected in blood. Within the cell, selenocystine is primarily located in the cytoplasm. In humans, selenocystine is involved in the selenoamino acid metabolism pathway. Selenocystine is a substrate for glutathione peroxidase 1.
1464-43-3
C05704
15104
28553
14376
NC(C[Se][Se]CC(N)C(O)=O)C(O)=O
C6H12N2O4Se2
InChI=1S/C6H12N2O4Se2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)
JULROCUWKLNBSN-UHFFFAOYSA-N
2-amino-3-[(2-amino-2-carboxyethyl)diselanyl]propanoic acid
334.09
335.912750538
-0.82
4
selenocystine
0
0
FDB023316
3,3'-diselenobisalanine;3,3'-diselenodialanine;D,l-selenocystine;Dl-selenocystine;Selenium cystine;Seleno-dl-cystine
PW_C002067
SlnoCys
328
8
78835
111
119949
122
122740
135
125339
297
126882
205
6761
Selenite
HMDB0011119
The selenite anion is a selenium oxoanion with the chemical formula SeO32−. A selenite (compound) is a compound that contains this ion. In slightly acid conditions, the hydrogenselenite ion, HSeO3−, is formed; in more acidic conditions selenous acid, H2SeO3, exists. Most selenite salts can be formed by heating the relevant metal oxide with selenium dioxide, e.g.:Na2O + SeO2 → Na2SeO3. Selenite is an inorganic form of selenium which may also be useful in cancer chemotherapy.(Wikipedia).
14124-67-5
C05684
1090
18212
1059
O[Se](O)=O
H2O3Se
InChI=1S/H2O3Se/c1-4(2)3/h(H2,1,2,3)
MCAHWIHFGHIESP-UHFFFAOYSA-N
selenous acid
128.97
129.916915758
2
selenious acid
0
-2
C05684
Selenite (seo32-);Selenite ion (seo32-);Selenite ion(2-);Selenite(2-);[seo3](2-);Selenit
PW_C006761
Selenit
367
8
374
15
6650
107
6651
108
42487
318
42488
315
78834
111
119948
122
122739
135
125338
297
126881
205
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
457
Potassium
HMDB0000586
Potassium is an essential electrolyte. Potassium balance is crucial for regulating the excitability of nerves and muscles and so critical for regulating contractility of cardiac muscle. Although the most important changes seen in the presence of deranged potassium are cardiac, smooth muscle is also affected with increasing muscle weakness, a feature of both hyperkalaemia and hypokalaemia. Physiologically, it exists as an ion in the body. Potassium (K+) is a positively charged electrolyte, cation, which is present throughout the body in both intracellular and extracellular fluids. The majority of body potassium, >90%, are intracellular. It moves freely from intracellular fluid (ICF) to extracellular fluid (ECF) and vice versa when adenosine triphosphate increases the permeability of the cell membrane. It is mainly replaced inside or outside the cells by another cation, sodium (Na+). The movement of potassium into or out of the cells is linked to certain body hormones and also to certain physiological states. Standard laboratory tests measure ECF potassium. Potassium enters the body rapidly during food ingestion. Insulin is produced when a meal is eaten; this causes the temporary movement of potassium from ECF to ICF. Over the ensuing hours, the kidneys excrete the ingested potassium and homeostasis is returned. In the critically ill patient, suffering from hyperkalaemia, this mechanism can be manipulated beneficially by administering high concentration (50%) intravenous glucose. Insulin can be added to the glucose, but glucose alone will stimulate insulin production and cause movement of potassium from ECF to ICF. The stimulation of alpha receptors causes increased movement of potassium from ICF to ECF. A noradrenaline infusion can elevate serum potassium levels. An adrenaline infusion, or elevated adrenaline levels, can lower serum potassium levels. Metabolic acidosis causes a rise in extracellular potassium levels. In this situation, excess of hydrogen ions (H+) are exchanged for intracellular potassium ions, probably as a result of the cellular response to a falling blood pH. Metabolic alkalosis causes the opposite effect, with potassium moving into the cells. (PMID: 17883675).
24203-36-9
C00238
813
29103
K%2b
791
DB01345
[K+]
K
InChI=1S/K/q+1
NPYPAHLBTDXSSS-UHFFFAOYSA-N
potassium(1+) ion
39.0983
38.963706861
0
potassium(1+) ion
1
1
FDB003521
K+;Kalium;Potassium;Potassium (k+);Potassium (ion);Potassium cation;Potassium ion;Potassium ion (k+);Potassium ion (k1+);Potassium ion(+);Potassium ion(1+);Potassium monocation;Potassium(+);Potassium(1+);Potassium(1+) ion;Potassium(i) cation;K(+)
PW_C000457
K+
573
8
931
19
1926
2
2095
15
3033
66
3161
72
3162
71
3613
51
3614
61
5921
147
5952
151
6902
160
11810
198
15222
306
77023
225
77115
132
77610
111
78241
326
78246
353
120484
122
121198
124
123105
135
123768
118
124944
452
124949
472
125860
297
125965
299
127322
205
127421
388
140680
834
140681
790
140687
781
8
R
Compound
PW_EC000008
17792
ChEBI
R
9
CH3-R
Compound
PW_EC000009
3274
ChEBI
CH3-R
1
Organic halide
Compound
PW_EC000001
17792
ChEBI
OH
9
tRNA(Met)
RNA
PW_NA000009
29173
TRNAMET
363
8
1913
2
78319
132
78826
111
119937
122
122298
124
122729
135
124850
118
125327
297
126464
299
126871
205
128034
388
139352
225
10
Selenomethionyl-tRNA(Met)
RNA
PW_NA000010
9100
STM
364
8
78827
111
119938
122
122730
135
125328
297
126872
205
139353
225
2426
Selenocysteine lyase
Q96I15
Catalyzes the decomposition of L-selenocysteine to L-alanine and elemental selenium (By similarity).
HMDBP04824
SCLY
2q37.3
CH471063
1
4.4.1.16
318
8
624
Selenide, water dikinase 2
Q99611
Synthesizes selenophosphate from selenide and ATP.
HMDBP00658
SEPHS2
16p11.2
U43286
1
2.7.9.3
322
8
12639
31
511
Cystathionine gamma-lyase
P32929
Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
HMDBP00538
CTH
1p31.1
BC015807
1
4.4.1.1
338
8
1869
2
98631
7
724
Cystathionine beta-synthase
P35520
Only known pyridoxal phosphate-dependent enzyme that contains heme. Important regulator of hydrogen sulfide, especially in the brain, utilizing cysteine instead of serine to catalyze the formation of hydrogen sulfide. Hydrogen sulfide is a gastratransmitter with signaling and cytoprotective effects such as acting as a neuromodulator in the brain to protect neurons against hypoxic injury (By similarity).
HMDBP00779
CBS
21q22.3
BC011381
1
4.2.1.22
346
8
1829
2
627
Adenosylhomocysteinase
P23526
Adenosylhomocysteine is a competitive inhibitor of S-adenosyl-L-methionine-dependent methyl transferase reactions; therefore adenosylhomocysteinase may play a key role in the control of methylations via regulation of the intracellular concentration of adenosylhomocysteine.
HMDBP00662
AHCY
20q11.22
AK290422
1
3.3.1.1
354
8
1897
2
143011
1076
5470
Methyltransferase-like protein 6
Q8TCB7
Probable methyltransferase (By similarity).
HMDBP11825
METTL6
AC027125
1
2.1.1.-
359
8
397
S-adenosylmethionine synthase isoform type-2
P31153
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
HMDBP00405
MAT2A
2p11.2
BC001686
1
2.5.1.6
361
8
1927
2
143006
1076
2387
Methionine adenosyltransferase 2 subunit beta
Q9NZL9
Non-catalytic regulatory subunit of S-adenosylmethionine synthetase 2 (MAT2A), an enzyme that catalyzes the formation of S-adenosylmethionine from methionine and ATP. Regulates the activity of S-adenosylmethionine synthetase 2 by changing its kinetic properties, rendering the enzyme more susceptible to S-adenosylmethionine inhibition.
HMDBP03965
MAT2B
AK312365
1
362
8
1928
2
143007
1076
590
Methionine--tRNA ligase, cytoplasmic
P56192
HMDBP00623
MARS
12q13
X94754
1
6.1.1.10
366
8
1912
3
1915
2
338
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1
O43252
Bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS: activated sulfate donor used by sulfotransferase). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. Also involved in the biosynthesis of sulfated L-selectin ligands in endothelial cells.
HMDBP00345
PAPSS1
4q24
AF097716
1
2.7.7.4; 2.7.1.25
370
8
691
Gamma-glutamyltranspeptidase 1
P19440
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
HMDBP00730
GGT1
22q11.23
BC069504
1
2.3.2.2; 3.4.19.13; 3.4.19.14
166
14
231
8
5586
Zinc transporter ZIP8
Q9C0K1
Acts as a zinc-influx transporter.
HMDBP11941
SLC39A8
4q22-q24
AF193052
1
9013
228
10207
Unknown
Unknown
1
2.3.1.85; 2.3.1.38; 2.3.1.39; 2.3.1.41; 1.1.1.100; 4.2.1.59; 1.3.1.39; 3.1.2.14; 3.5.99.5; 1.1.1.-
6404
10
6429
31
6434
53
9166
17
9170
4
9182
22
11678
3
11685
2
12124
8
12129
14
12133
229
135973
51
136178
7
140020
308
140156
768
140576
309
140589
832
140864
60
140933
48
140954
184
141261
831
141275
877
141432
931
141584
958
141585
959
141586
828
142155
26
142194
15
142265
372
142332
23
142671
29
142673
996
142683
973
142813
787
143272
811
143273
52
143355
75
143398
1065
143474
1143
143476
13
143478
961
143515
1148
143934
1168
143951
1184
143959
810
144094
231
80
Selenocysteine lyase
1
PW_P000080
94
2426
2
44
1148
1
81
Selenide, water dikinase 2
1
PW_P000081
95
624
1
82
Cystathionine gamma-lyase
1
PW_P000082
96
511
4
45
1148
1
335
8
83
Cystathionine beta-synthase
1
PW_P000083
97
724
4
46
1148
1
343
8
84
Adenosylhomocysteinase
1
PW_P000084
98
627
4
47
721
4
350
8
85
Methyltransferase-like protein 6
1
PW_P000085
99
5470
1
86
S-adenosylmethionine synthase
1
PW_P000086
100
397
2
101
2387
1
150
423
6
151
457
3
87
Methionine--tRNA ligase, cytoplasmic
1
PW_P000087
102
590
1
365
8
88
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1
1
PW_P000088
103
338
1
47
Gamma-glutamyltranspeptidase 1
1
PW_P000047
48
691
1
160
14
13576
Zinc transporter ZIP8
1
PW_P013576
23448
5586
137108
308
13578
Unknown transport protein
1
PW_P013578
23450
10207
613
false
PW_R000613
Right
2552
1829
1
Compound
false
2553
105
1
Compound
false
2554
6752
1
Compound
false
97
80
4.4.1.16
520
false
PW_R000520
Both
2171
414
1
Compound
true
2172
6752
1
Compound
false
2173
1420
1
Compound
true
2174
32
1
Compound
true
2175
1977
1
Compound
false
2176
1441
1
Compound
true
98
81
2.7.9.3
615
false
PW_R000615
Right
2557
2727
1
Compound
false
2558
1420
1
Compound
true
2559
1829
1
Compound
false
2560
35
1
Compound
true
2561
3
1
Compound
true
99
82
4.4.1.1
616
false
PW_R000616
Right
2562
120
1
Compound
true
2563
2066
1
Compound
false
2564
2727
1
Compound
false
2565
1420
1
Compound
true
100
83
4.2.1.22
617
false
PW_R000617
Right
2566
6759
1
Compound
false
2567
1420
1
Compound
true
2568
2066
1
Compound
false
2569
34
1
Compound
true
101
84
3.3.1.1
618
false
PW_R000618
Right
2570
6760
1
Compound
false
2571
8
1
ElementCollection
false
2572
6759
1
Compound
false
2573
9
1
ElementCollection
false
102
85
2.1.1.-
619
false
PW_R000619
Right
2574
2019
1
Compound
false
2575
414
1
Compound
true
2579
1420
1
Compound
true
2576
6760
1
Compound
false
2577
1441
1
Compound
true
2578
170
1
Compound
true
103
86
2.5.1.6
620
false
PW_R000620
Right
2580
2019
1
Compound
false
2581
414
1
Compound
true
2582
9
1
NucleicAcid
false
2583
10
1
NucleicAcid
false
2584
32
1
Compound
true
2585
170
1
Compound
true
104
87
6.1.1.10
622
false
PW_R000622
Right
2588
414
1
Compound
true
2589
40445
1
Compound
false
2590
2063
1
Compound
false
2591
170
1
Compound
true
105
88
623
false
PW_R000623
Right
2592
414
1
Compound
true
2593
2063
1
Compound
false
2594
6747
1
Compound
false
2595
1034
1
Compound
true
106
88
612
false
PW_R000612
Right
2550
2064
1
Compound
false
2551
6724
1
Compound
false
96
47
614
true
PW_R000614
Right
2555
1829
1
Compound
false
2556
2067
1
Compound
false
2297
true
PW_R002297
Right
8461
2066
1
Compound
false
8462
2019
1
Compound
false
621
true
PW_R000621
Right
2586
6761
1
Compound
false
2587
40445
1
Compound
false
10394
PW_T010394
10766
6761
1
Compound
80
8
Unknown
1559
13576
2019-07-31T14:04:34-06:00
2019-07-31T14:04:34-06:00
308
10395
PW_T010395
10767
2064
1
Compound
80
8
Unknown
1560
13578
2019-08-01T11:46:14-06:00
2019-08-01T11:46:14-06:00
308
10396
PW_T010396
10768
1829
1
Compound
80
8
Unknown
1561
13578
2019-08-01T11:53:33-06:00
2019-08-01T11:54:02-06:00
308
390
1829
8
81
false
1980
910
10
regular
200
190
391
105
8
81
false
1520
740
10
regular
200
190
392
6752
8
81
false
1520
1185
10
regular
200
190
393
1148
8
9
false
1755
955
10
regular
100
35
395
414
8
42
false
1495
1405
10
regular
50
30
396
1420
8
49
false
1695
1390
10
regular
78
78
397
32
8
44
false
1500
1555
10
regular
50
30
398
1977
8
81
false
1520
1610
10
regular
200
190
399
1441
8
46
false
1695
1555
10
regular
44
43
410
2727
8
81
false
1979
1475
10
regular
200
190
411
1420
8
49
false
2154
1375
10
regular
78
78
412
35
8
63
false
1933
1166
10
regular
78
78
413
3
8
81
false
2145
1105
10
regular
200
190
414
1148
8
9
false
2029
1277
19
regular
100
35
425
120
8
81
false
2184
1830
10
regular
200
190
426
2066
8
81
false
1979
1960
10
regular
200
190
427
1420
8
49
false
1934
1680
10
regular
78
78
428
1148
8
9
false
2034
1775
19
regular
100
35
434
6759
8
81
false
1199
1960
10
regular
200
190
435
1420
8
49
false
1529
1910
10
regular
78
78
436
34
8
81
false
1744
1795
10
regular
200
190
437
721
8
9
false
1649
2010
10
regular
100
25
442
6760
8
81
false
1199
2335
10
regular
200
190
447
2019
8
81
false
1979
2334
10
regular
200
190
448
414
8
42
false
1794
2324
10
regular
50
30
449
1420
8
49
false
1789
2519
10
regular
78
78
450
1441
8
81
false
1449
2522
10
regular
200
190
451
170
8
45
false
1527
2320
10
regular
63
43
452
414
8
42
false
2369
2419
10
regular
50
30
453
32
8
44
false
2362
2579
10
regular
50
30
454
170
8
45
false
2185
2582
10
regular
63
43
457
40445
8
81
false
800
1205
10
regular
200
190
458
414
8
42
false
730
1200
10
regular
50
30
459
2063
8
81
false
228
1205
10
regular
200
190
460
170
8
45
false
446
1193
10
regular
63
43
461
414
8
42
false
408
1430
10
regular
50
30
462
6747
8
81
false
228
1675
10
regular
200
190
463
1034
8
43
false
408
1610
10
regular
50
30
467
2064
8
81
false
795
805
10
regular
200
190
468
6724
14
81
false
195
800
10
regular
200
200
472
2067
8
81
false
2305
910
10
regular
200
190
2686928
6761
80
81
false
1105
1205
10
regular
200
190
2686929
6761
8
81
false
1100
240
10
regular
200
190
2686932
2064
80
81
false
795
255
10
regular
200
190
2686933
1829
80
81
false
1975
205
10
regular
200
190
13
8
37
8
true
1119
2300
12
regular
100
90
14
9
37
8
true
1124
2110
12
regular
100
90
15669
1
37
false
492
396
12
regular
100
90
14
9
96
8
false
2234
2269
14
120
nucleic_acid
regular
120
115
15
10
96
8
false
2235
2644
14
120
nucleic_acid
regular
120
115
130
2426
8
6
false
1730
965
8
subunit
regular
160
80
132
624
8
2
false
1545
1465
8
subunit
regular
150
70
139
511
8
8
false
2009
1287
8
subunit
regular
140
85
145
724
8
8
false
2009
1780
8
subunit
regular
140
85
149
627
8
2
false
1624
2020
8
subunit
regular
150
70
153
5470
8
2
false
1224
2215
8
subunit
regular
150
70
156
397
8
6
false
1619
2349
8
subunit
regular
160
80
157
2387
8
97
false
1624
2429
8
subunit
regular
150
70
158
590
8
2
false
2219
2476
8
subunit
regular
150
70
159
338
8
2
false
545
1265
8
subunit
regular
150
70
160
338
8
2
false
253
1500
8
subunit
regular
150
70
161
691
14
2
false
515
480
8
subunit
regular
150
70
951957
5586
76
false
1125
480
8
subunit
regular
150
70
951960
10207
76
false
820
480
8
subunit
regular
150
70
951961
10207
76
false
2000
480
8
subunit
regular
150
70
107
80
10
8
130
130
59
393
498
Cofactor
109
81
10
8
132
132
116
82
10
8
139
139
63
414
529
Cofactor
122
83
10
8
145
145
68
428
550
Cofactor
126
84
10
8
149
149
71
437
563
Cofactor
130
85
10
8
153
153
132
86
10
8
156
156
157
157
133
87
10
8
158
158
134
88
10
8
159
159
135
88
10
8
160
160
136
47
10
14
161
161
805957
13576
10
947725
951957
805960
13578
10
947728
951960
805961
13578
10
947729
951961
495
M1980 1005 C1950 1005 1920 1005 1890 1005
5
false
18
496
M1620 930 C1618 997 1689 1005 1730 1005
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
497
M1620 1185 C1620 1134 1612 1004 1730 1005
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
498
M1445 1450 L1445 1500 L1495 1450 z
10
true
18
501
M1545 1420 C1575 1420 1620 1435 1620 1465
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
502
M1620 1375 C1620 1405 1620 1435 1620 1465
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
503
M1695 1429 C1665 1429 1620 1435 1620 1465
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
504
M1550 1570 C1578 1570 1620 1565 1620 1535
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
505
M1620 1610 C1620 1580 1620 1565 1620 1535
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
506
M1695 1576.5 C1671 1577.5 1620 1565 1620 1535
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
524
M2079 1475 C2079 1445 2079 1402 2079 1372
5
false
18
525
M2154 1414 C2120 1414 2079 1402 2079 1372
5
false
18
526
M2080 1100 C2080 1130 2079 1257 2079 1287
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
527
M2011 1205 C2051 1204 2079 1257 2079 1287
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
528
M2145 1200 C2094 1200 2079 1257 2079 1287
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
529
M150 650 L150 700 L200 650 z
10
true
18
546
M2184 1925 C2139 1917 2079 1895 2079 1865
5
false
18
547
M2079 1960 C2079 1930 2079 1895 2079 1865
5
false
18
548
M2079 1665 C2079 1695 2079 1750 2079 1780
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
549
M2012 1719 C2044 1718 2079 1750 2079 1780
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
550
M150 650 L150 700 L200 650 z
10
true
18
559
M1399 2055 C1429 2055 1594 2055 1624 2055
5
false
18
560
M1568 1988 C1568 2014 1594 2055 1624 2055
5
false
18
561
M1979 2055 C1949 2055 1804 2055 1774 2055
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
562
M1844 1985 C1844 2015 1804 2055 1774 2055
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
563
M150 650 L150 700 L200 650 z
10
true
18
571
M1299 2335 C1299 2305 1299 2315 1299 2285
5
false
18
572
M1299 2150 C1299 2180 1299 2185 1299 2215
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
573
M1219 2350 C1250 2350 1299 2307 1299 2285
5
true
18
574
M1224 2160 C1258 2160 1299 2192 1299 2215
5
true
18
true
M 1111.9903810567666 1591.5 L 1099 1599 L 1111.9903810567666 1606.5
false
580
M1979 2429 C1949 2429 1729 2429 1699 2429
5
false
7
581
M1819 2354 C1819 2379 1808 2428 1699 2429
5
false
7
582
M1828 2519 C1828 2491 1827 2430 1699 2429
5
false
7
583
M1399 2430 C1429 2430 1669 2429 1699 2429
5
false
7
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
584
M1549 2522 C1549 2495 1568 2430 1699 2429
5
false
7
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
585
M1558.5 2363 C1558.5 2396 1584 2427 1699 2429
5
false
7
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
586
M2179 2429 C2212 2429 2294 2446 2294 2476
5
false
18
587
M2369 2434 C2343 2434 2294 2446 2294 2476
5
false
18
588
M2362 2594 C2336 2594 2294 2576 2294 2546
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
589
M2248 2603.5 C2280 2602.5 2294 2576 2294 2546
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
590
M2294 2376 C2294 2406 2294 2446 2294 2476
5
false
18
591
M2295 2649 C2295 2619 2294 2576 2294 2546
5
false
18
596
M755 1230 C754 1261 738 1299 695 1300
5
false
18
597
M800 1300 C744 1301 737 1299 695 1300
5
false
18
598
M428 1300 C467 1300 522 1300 545 1300
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
599
M477.5 1236 C476.5 1271 509 1300 545 1300
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
600
M408 1445 C379 1446 328 1470 328 1500
5
false
18
601
M328 1395 C328 1425 328 1470 328 1500
5
false
18
602
M328 1675 C328 1645 328 1600 328 1570
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
603
M408 1625 C380 1625 328 1600 328 1570
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
608
M795 900 C769 900 750 899 725 899 C725 847 728 572 728 516 C702 516 691 514 665 515
5
false
18
609
M395 900 C411 900 422 900 452 900 C450 842 450 589 450 516 C471 516 496 515 515 515
5
false
18
true
M 403.07211192945806 533.8835670024241 L 398 548 L 412.76124555145066 545.3343612829608
false
616
M2180 1005 C2210 1005 2248 1005 2305 1005
5
false
18
true
M 2267.0096189432334 607.5 L 2280 600 L 2267.0096189432334 592.5
false
617
M2305 1005 C2275 1005 63 593 87 610
5
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
7395
M1620 740 C1620 693 1619 701 1620 655
5
false
18
true
M 1392.9903810567666 422.5 L 1380 430 L 1392.9903810567666 437.5
false
true
M 1552.0096189432334 502.5 L 1565 495 L 1552.0096189432334 487.5
false
7396
M1720 835 C1752 835 1802 836 1845 835
5
false
18
true
M 1407.9903810567666 487.5 L 1395 495 L 1407.9903810567666 502.5
false
true
M 1552.0096189432334 502.5 L 1565 495 L 1552.0096189432334 487.5
false
7401
M1520 835 C1490 835 1405 835 1375 835
5
false
18
true
M 1392.9903810567666 487.5 L 1380 495 L 1392.9903810567666 502.5
false
true
M 1552.0096189432334 502.5 L 1565 495 L 1552.0096189432334 487.5
false
7402
M1520 835 C1443 834 1350 901 1350 955
5
false
18
true
M 1551.0096189432334 542.5 L 1564 535 L 1551.0096189432334 527.5
false
true
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613
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397
390
495
Left
398
391
496
Right
399
392
497
Right
105
97
107
112
10
520
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402
395
501
Left
403
392
502
Left
404
396
503
Left
405
397
504
Right
406
398
505
Right
407
399
506
Right
107
98
109
120
10
615
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422
410
524
Left
423
411
525
Left
424
390
526
Right
425
412
527
Right
426
413
528
Right
114
99
116
127
10
616
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439
425
546
Left
440
426
547
Left
441
410
548
Right
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427
549
Right
120
100
122
131
10
617
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449
434
559
Left
450
435
560
Left
451
426
561
Right
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436
562
Right
124
101
126
135
10
618
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459
442
571
Left
460
434
572
Right
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13
573
Left
13
14
574
Right
128
102
130
137
10
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447
580
Left
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Left
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449
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Left
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442
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Right
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450
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Right
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451
585
Right
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103
132
138
10
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447
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Left
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452
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Left
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453
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Right
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454
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Right
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14
590
Left
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15
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Right
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133
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10
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458
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457
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Left
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459
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Right
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460
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Right
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105
134
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Left
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459
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Left
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462
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463
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Right
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106
135
143
10
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467
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Left
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468
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Right
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145
10
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390
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Left
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472
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Right
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10
2297
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16131
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Right
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Right
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regular
68742
3674291
68743
3674292
68744
3674293
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1785
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1
true
6
2444.0
2358.0
20
235
Extracellular Space
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390
20
1.0
1.0
200
15
21
235
Intracellular Space
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1035
20
1.3
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200
15
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235
Extracellular Space
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20
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