601
Pathway
S-Adenosyl-L-Methionine Biosynthesis
S-adenosyl-L-methionine biosynthesis(SAM) is synthesized in the cytosol of the cell from L-methionine and ATP. This reaction is catalyzed by methionine adenosyltransferase. L methione is taken up from the environment through a complex reaction coupled transport and then proceeds too synthesize the s adenosylmethionine through a adenosylmethionine synthase. The S-adenosylmethionine then interacts with a hydrogen ion through a adenosylmethionine decarboxylase resulting in a carbon dioxide and a S-adenosyl 3-methioninamine.This compound interacts with a putrescine through a spermidine synthase resulting in a spermidine, a hydrogen ion and a S-methyl-5'-thioadenosine. The latter compound is degraded by interacting with a water molecule through a 5' methylthioadenosine nucleosidase resulting in a adenine and a S-methylthioribose which is then release into the environment
Metabolic
PW000837
Center
PathwayVisualizationContext1124
2398
2602
#000099
PathwayVisualization585
601
S-Adenosyl-L-Methionine Biosynthesis
S-adenosyl-L-methionine biosynthesis(SAM) is synthesized in the cytosol of the cell from L-methionine and ATP. This reaction is catalyzed by methionine adenosyltransferase. L methione is taken up from the environment through a complex reaction coupled transport and then proceeds too synthesize the s adenosylmethionine through a adenosylmethionine synthase. The S-adenosylmethionine then interacts with a hydrogen ion through a adenosylmethionine decarboxylase resulting in a carbon dioxide and a S-adenosyl 3-methioninamine.This compound interacts with a putrescine through a spermidine synthase resulting in a spermidine, a hydrogen ion and a S-methyl-5'-thioadenosine. The latter compound is degraded by interacting with a water molecule through a 5' methylthioadenosine nucleosidase resulting in a adenine and a S-methylthioribose which is then release into the environment
Metabolic
3
109727
578
SubPathway
109226
548
Compound
117
2262
10762064
Lu SC: S-Adenosylmethionine. Int J Biochem Cell Biol. 2000 Apr;32(4):391-5.
601
Pathway
1
Cell
CL:0000000
2
Platelet
CL:0000233
5
Hepatocyte
CL:0000182
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
7
Epithelial Cell
CL:0000066
6
Myocyte
CL:0000187
1
Homo sapiens
9606
Eukaryote
Human
17
Rattus norvegicus
10116
Eukaryote
Rat
3
Escherichia coli
562
Prokaryote
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
23
Pseudomonas aeruginosa
287
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
5
Cytoplasm
GO:0005737
1
Cytosol
GO:0005829
31
Periplasmic Space
GO:0005620
11
Extracellular Space
GO:0005615
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
14
Mitochondrial Outer Membrane
GO:0005741
15
Nucleus
GO:0005634
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
7
Endoplasmic Reticulum Membrane
GO:0005789
10
Cell Membrane
GO:0005886
27
Peroxisome Membrane
GO:0005778
35
Chloroplast
GO:0009507
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
24
Mitochondrial Intermembrane Space
GO:0005758
17
Nucleoplasm
GO:0005654
39
Mitochondrial membrane
GO:0031966
26
Golgi apparatus membrane
GO:0000139
8
Smooth Endoplasmic Reticulum
GO:0005790
33
Outer Membrane
GO:0043165
2
Endothelium
BTO:0000393
1
Liver
BTO:0000759
72
9
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
25
Intestine
BTO:0000648
8
Blood Vessel
BTO:0001102
74
11
4
Adrenal Medulla
BTO:0000049
71
8
28
Stomach
BTO:0001307
155
26
11
Heart
BTO:0000562
73
10
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
5
cardiocyte
BTO:0001539
8
5
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L-Methionine
HMDB0000696
Methionine is an essential amino acid (there are 9 essential amino acids) required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, it is an intermediate in transmethylation reactions, serving as the major methyl group donor in vivo, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyltransferase (methionine synthase), the only reaction that allows for the recycling of this form of folate, and is also a methyl acceptor for the catabolism of betaine. Methionine is the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine (PMID: 16702340). There is a general consensus concerning normal sulfur amino acid (SAA) requirements. WHO recommendations amount to 13 mg/kg per 24 h in healthy adults. This amount is roughly doubled in artificial nutrition regimens. In disease or after trauma, requirements may be altered for methionine, cysteine, and taurine. Although in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function, hypermethioninemia or hyperhomocysteinemia may occur, SAA supplementation can be considered safe in amounts exceeding 2-3 times the minimum recommended daily intake. Apart from some very specific indications (e.g. acetaminophen poisoning) the usefulness of SAA supplementation is not yet established (PMID: 16702341). Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, but there is no evidence of similar effects in healthy subjects. The role of methionine as a precursor of homocysteine is the most notable cause for concern. Acute doses of methionine can lead to acute increases in plasma homocysteine, which can be used as an index of the susceptibility to cardiovascular disease. Sufficiently high doses of methionine can actually result in death. Longer-term studies in adults have indicated no adverse consequences of moderate fluctuations in dietary methionine intake, but intakes higher than 5 times the normal amount resulted in elevated homocysteine levels. These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid (PMID: 16702346). When present in sufficiently high levels, methionine can act as an atherogen and a metabotoxin. An atherogen is a compound that when present at chronically high levels causes atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of methionine are associated with at least ten inborn errors of metabolism, including cystathionine beta-synthase deficiency, glycine N-methyltransferase deficiency, homocystinuria, tyrosinemia, galactosemia, homocystinuria-megaloblastic anemia due to defects in cobalamin metabolism, methionine adenosyltransferase deficiency, methylenetetrahydrofolate reductase deficiency, and S-adenosylhomocysteine (SAH) hydrolase deficiency. Chronically elevated levels of methionine in infants can lead to intellectual disability and other neurological problems, delays in motor skills, sluggishness, muscle weakness, and liver problems. Many individuals with these metabolic disorders tend to develop cardiovascular disease later in life. Studies on feeding rodents high levels of methionine have shown that methionine promotes atherosclerotic plaques independently of homocysteine levels (PMID: 26647293). A similar study in Finnish men showed the same effect (PMID: 16487911).
63-68-3
C00073
6137
16643
MET
5907
DB00134
CSCC[C@H](N)C(O)=O
C5H11NO2S
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
FFEARJCKVFRZRR-BYPYZUCNSA-N
(2S)-2-amino-4-(methylsulfanyl)butanoic acid
149.211
149.051049291
-0.80
2
L-methionine
0
0
DBMET00506
FDB012683
(2s)-2-amino-4-(methylsulfanyl)butanoate;(2s)-2-amino-4-(methylsulfanyl)butanoic acid;(l)-methionine;(s)-(+)-methionine;(s)-2-amino-4-(methylthio)butanoate;(s)-2-amino-4-(methylthio)butanoic acid;(s)-2-amino-4-(methylthio)-butanoate;(s)-2-amino-4-(methylthio)-butanoic acid;(s)-2-amino-4-(methylthio)butyric acid;(s)-methionine;2-amino-4-(methylthio)butyrate;2-amino-4-(methylthio)butyric acid;2-amino-4-methylthiobutanoate;2-amino-4-methylthiobutanoic acid;A-amino-g-methylmercaptobutyrate;A-amino-g-methylmercaptobutyric acid;Acimethin;Cymethion;G-methylthio-a-aminobutyrate;G-methylthio-a-aminobutyric acid;H-met-h;H-met-oh;L(-)-amino-alpha-amino-alpha-aminobutyric acid;L(-)-amino-gamma-methylthiobutyric acid;L-(-)-methionine;L-2-amino-4-(methylthio)butyric acid;L-2-amino-4-methylthiobutyric acid;L-methionin;L-methionine;L-methioninum;L-a-amino-g-methylthiobutyrate;L-a-amino-g-methylthiobutyric acid;L-alpha-amino-gamma-methylmercaptobutyric acid;L-alpha-amino-gamma-methylthiobutyrate;L-alpha-amino-gamma-methylthiobutyric acid;L-gamma-methylthio-alpha-aminobutyric acid;Liquimeth;Met;Mepron;Methilanin;Methionine;Methioninum;Metionina;Neo-methidin;Poly-l-methionine;Polymethionine;S-methionine;S-methyl-l-homocysteine;Toxin war;Alpha-amino-alpha-aminobutyric acid;Alpha-amino-gamma-methylmercaptobutyrate;Alpha-amino-gamma-methylmercaptobutyric acid;Gamma-methylthio-alpha-aminobutyrate;Gamma-methylthio-alpha-aminobutyric acid;M;(2s)-2-amino-4-(methylsulphanyl)butanoate;(2s)-2-amino-4-(methylsulphanyl)butanoic acid;(s)-2-amino-4-(methylthio)butyrate;L-a-amino-g-methylmercaptobutyrate;L-a-amino-g-methylmercaptobutyric acid;L-alpha-amino-gamma-methylmercaptobutyrate;L-α-amino-γ-methylmercaptobutyrate;L-α-amino-γ-methylmercaptobutyric acid
PW_C000548
Met
568
8
1825
2
5597
135
5680
107
5681
108
5875
105
8267
151
12033
222
42550
315
42565
318
42693
320
76985
224
77609
111
78106
132
120478
122
122152
124
124704
118
125858
297
126311
299
127320
205
127873
388
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
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
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
1104
Phosphate
HMDB0001429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
[O-]P([O-])([O-])=O
O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3
NBIIXXVUZAFLBC-UHFFFAOYSA-K
phosphoric acid
94.9714
94.95342
3
phosphoric acid
0
-2
DBMET00532
FDB022617
Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ion
PW_C001104
Pi
24
4
84
8
814
5
818
18
831
2
980
3
1763
14
1767
49
2500
10
2729
47
2737
46
3129
29
3166
72
3636
61
3851
23
4249
22
4475
31
5031
27
5158
7
5207
97
5216
100
5317
111
5351
112
5381
103
5447
120
5543
129
5573
133
5605
135
5625
108
5693
6
5848
143
5855
146
5911
147
5941
151
6040
155
6100
161
6294
107
6487
178
6691
101
6714
117
6842
188
6889
160
7161
205
7189
206
7212
211
7306
198
7389
210
7402
212
7436
163
7475
222
8196
225
8258
227
10118
241
10134
257
11748
132
11761
115
11773
213
11904
170
11927
164
12014
281
12728
290
13263
223
34819
17
42255
304
42350
315
42435
318
43692
322
77018
253
77194
293
77217
134
77940
336
77966
130
78048
332
78057
329
78245
353
78669
331
80022
368
89279
308
93831
383
94796
384
110558
390
110640
391
113235
94
115845
398
116206
109
119982
406
120069
122
120699
407
121057
124
121216
125
121268
429
121352
121
121409
123
121423
382
121852
405
123304
119
123621
118
123786
136
123838
464
123968
447
123981
399
124405
376
124948
472
125362
479
125446
297
125774
481
125954
299
126221
478
126594
300
126604
298
126723
484
126904
501
127413
388
127783
209
128166
395
128177
513
128315
389
40034
Hydrogen Ion
HMDB0059597
Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])
C00080
1038
15378
1010
[H+]
H
InChI=1S/p+1
GPRLSGONYQIRFK-UHFFFAOYSA-N
hydron
1.0079
1.007825032
0
hydron
1
0
H+;H(+);Hydrogen cation;Hydron;Proton
PW_C040034
H+
215
4
670
8
753
15
788
31
848
3
1116
2
1463
26
1464
54
2231
49
2780
17
4250
22
4254
42
4547
10
4576
18
4694
70
5241
103
5327
111
5353
112
5626
108
5639
107
5699
100
5720
105
5742
117
5963
147
6037
155
6070
157
6093
161
6130
159
6232
166
6483
178
6601
152
6692
101
6843
188
6910
187
7100
163
7168
205
7191
206
7453
219
7454
220
7472
222
7525
213
7532
210
7558
212
7572
160
7590
170
8195
225
8218
151
8243
226
8413
162
8420
224
9139
195
9155
249
11915
164
12015
281
12181
285
12246
286
12266
287
12521
227
13257
223
13325
294
15330
308
42329
315
42354
318
42401
322
42405
312
42454
320
76912
293
77136
133
77210
134
77372
331
77804
114
77955
132
77990
327
77991
347
78379
345
79929
130
80019
368
80387
310
80388
304
80722
119
93823
124
94823
383
110550
388
112855
94
113280
390
115537
398
115539
118
115856
336
116205
109
119973
406
120193
407
120549
122
120593
409
121170
424
121171
425
122569
418
122615
384
122687
125
122758
120
123183
135
123218
137
123742
459
123743
460
125141
454
125188
121
125273
136
125359
479
125550
481
125730
483
125736
297
125809
299
126517
495
126717
489
126766
480
126823
300
126902
501
127213
208
128308
506
128361
391
128430
395
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
[O-]P([O-])(=O)OP([O-])([O-])=O
O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4
XPPKVPWEQAFLFU-UHFFFAOYSA-J
(phosphonooxy)phosphonic acid
173.9433
173.911925378
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
921
S-Adenosylmethionine
HMDB0001185
S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.
485-80-3
C00019
24762165
15414
S-ADENOSYLMETHIONINE
31983
DB00118
C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
C15H23N6O5S
InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1
MEFKEPWMEQBLKI-AIRLBKTGSA-O
[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
399.445
399.145063566
-2.56
5
SAMe
1
1
FDB022473
(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine;2-s-adenosyl-l-methionine;5'-deoxyadenosine-5'-l-methionine disulfate ditosylate;Active methionine;Ademetionine;Adenosylmethionine;Adomet;Donamet;L-s-adenosylmethionine;S-(5'-adenosyl)-l-methionine;S-(5'-deoxyadenosin-5'-yl)-l-methionine;S-adenosyl methionine;S-adenosyl-l-methionine disulfate tosylate;S-adenosyl-l-methionine;S-adenosyl-methionine;S-adenosylmethionine;5'-deoxyadenosine-5'-l-methionine disulphate ditosylate;S-adenosyl-l-methionine disulphate tosylate;(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt;[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl][(3s)-3-amino-3-carboxypropyl](methyl)sulfonium;Acylcarnitine;Sam;Same
PW_C000921
SAMe
519
8
633
30
704
20
1220
3
1880
27
2066
2
4681
10
5023
50
5604
135
7136
163
7540
210
7544
213
7632
160
8266
151
9235
195
11874
198
12031
222
12358
225
15293
249
15345
18
15363
309
76897
293
76899
164
76984
224
77488
111
77731
338
77772
341
78099
132
78303
351
78335
346
79155
112
79961
361
80861
22
94830
382
94833
386
113286
389
113288
397
115543
399
115546
401
120393
122
120537
413
120939
407
121052
124
122282
435
123171
449
123505
119
123616
118
124836
470
125859
297
125879
481
126304
299
126447
499
127321
205
127340
206
127595
388
128017
517
1316
Carbon dioxide
HMDB0001967
Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.
124-38-9
C00011
280
16526
274
O=C=O
CO2
InChI=1S/CO2/c2-1-3
CURLTUGMZLYLDI-UHFFFAOYSA-N
methanedione
44.0095
43.989829244
0.63
0
carbon dioxide
0
0
DBMET00423
FDB014084
Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744
PW_C001316
CO2
50
8
121
1
204
4
480
13
503
18
640
3
677
31
695
20
806
5
1133
43
1638
49
1745
2
2551
17
3144
70
5283
103
5320
111
5750
108
5771
101
5968
100
6026
155
6078
161
6471
178
6637
107
6922
190
7017
160
7035
163
7061
188
7163
205
7308
198
7333
213
7461
222
7530
210
8215
225
8223
151
9158
249
11849
277
11908
170
12464
226
12688
290
42626
315
43523
318
76994
293
77122
133
77170
132
77470
333
77739
112
77750
129
77763
341
78077
134
78405
356
78427
334
78941
331
79227
130
80008
368
80675
119
80717
135
94836
384
113291
391
115549
121
119954
406
120089
122
120155
407
120364
412
120556
414
120833
419
120922
124
120991
408
121284
125
121505
383
122744
120
123011
446
123190
450
123418
455
123489
118
123556
374
123855
136
124063
398
125344
479
125460
297
125516
481
125824
490
125870
299
125931
482
126280
480
126887
501
127052
206
127277
507
127331
388
127390
502
783
S-Adenosylmethioninamine
HMDB0000988
S-Adenosylmethioninamine is a biological sulfonium compound known as the major biological methyl donor. It is also a donor of methylene groups, amino groups, ribosyl groups and aminopropyl groups (PMID 15130560). S-Adenosylmethioninamine is a prodcut of enzyme adenosylmethionine decarboxylase [EC 4.1.1.50] in methionine metabolism pathway (KEGG).
22365-13-5
C01137
439415
15625
S-ADENOSYLMETHIONINAMINE
388529
C[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
C14H23N6O3S
InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1
ZUNBITIXDCPNSD-LSRJEVITSA-N
{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium
355.436
355.155234322
-2.49
4
decarboxylated sam
1
2
FDB022353
(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt;Dadomet;Decarboxylated adomet;Decarboxylated s-adenosylmethionine;Decarboxylated sam;S-adenosyl-l-methioninamine;S-adenosylmethioninamine;(5-deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium;(5-deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium cation;(5-deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium salt;[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfonium;S--adenosylmethioninamine;S-adenosyl-(5')-3-methylthiopropylamine;S-adenosyl-3-methylthiopropylamine;(5-deoxy-5-adenosyl)(3-aminopropyl)methylsulphonium
PW_C000783
Dadomet
1204
8
1885
2
6787
108
6788
107
78308
132
78836
111
120914
122
122287
124
123481
135
124841
118
125861
297
126452
299
127323
205
128022
388
164
Pyruvic acid
HMDB0000243
Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).
127-17-3
C00022
1060
32816
PYRUVATE
1031
DB00119
CC(=O)C(O)=O
C3H4O3
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
LCTONWCANYUPML-UHFFFAOYSA-N
2-oxopropanoic acid
88.0621
88.016043994
0.18
1
pyruvic acid
0
-1
FDB008293
2-oxopropanoate;2-oxopropanoic acid;2-oxopropionate;2-oxopropionic acid;Acetylformate;Acetylformic acid;Bts;Pyroracemate;Pyroracemic acid;Pyruvate;A-ketopropionate;A-ketopropionic acid;Alpha-ketopropionate;Alpha-ketopropionic acid;2-ketopropionic acid;2-oxopropansaeure;2-oxopropionsaeure;Acide pyruvique;Alpha-oxopropionsaeure;Brenztraubensaeure;Ch3cocooh;2-ketopropionate;α-ketopropionate;α-ketopropionic acid;A-oxopropionsaeure;α-oxopropionsaeure
PW_C000164
Pyr
17
2
20
4
422
8
1181
3
1449
50
1457
26
5365
103
5405
117
5440
118
5444
120
5566
132
5570
133
5893
95
5920
147
5951
151
6022
155
6067
156
6074
161
6126
160
6383
1
6467
178
6510
177
6532
85
7457
222
7495
220
8200
225
12622
31
15292
249
15349
18
77310
111
77972
346
77978
327
78090
112
80004
368
80042
367
80695
135
112879
94
115683
121
119950
406
120011
124
120175
122
120878
407
121148
423
121154
424
123454
119
123720
458
123726
459
125340
479
125390
299
125534
297
125854
481
126883
501
126931
388
127067
205
127858
206
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
1092
Putrescine
HMDB0001414
Putrescine is a polyamine. Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. Putrescine is also found in semen. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division. Putrescine apparently has specific role in skin physiology and neuroprotection. (PMID: 15009201, 16364196). Pharmacological interventions have demonstrated convincingly that a steady supply of polyamines is a prerequisite for cell proliferation to occur. Genetic engineering of polyamine metabolism in transgenic rodents has shown that polyamines play a role in spermatogenesis, skin physiology, promotion of tumorigenesis and organ hypertrophy as well as neuronal protection. Transgenic activation of polyamine catabolism not only profoundly disturbs polyamine homeostasis in most tissues, but also creates a complex phenotype affecting skin, female fertility, fat depots, pancreatic integrity and regenerative growth. Transgenic expression of ornithine decarboxylase antizyme has suggested that this unique protein may act as a general tumor suppressor. Homozygous deficiency of the key biosynthetic enzymes of the polyamines, ornithine and S-adenosylmethionine decarboxylase is not compatible with murine embryogenesis.
110-60-1
C00134
1045
17148
PUTRESCINE
13837702
DB01917
NCCCCN
C4H12N2
InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2
KIDHWZJUCRJVML-UHFFFAOYSA-N
butane-1,4-diamine
88.1515
88.100048394
0.43
2
putrescine
0
2
FDB001494
1,4-butanediamine;1,4-butylenediamine;1,4-diaminobutane;1,4-tetramethylenediamine;Butylenediamine;Putrescin;Tetramethyldiamine;Tetramethylenediamine;1,4-butanediammonium
PW_C001092
Putrsce
1206
8
1887
2
6711
117
43696
322
78310
132
78837
111
120915
122
122288
124
123482
135
124842
118
125862
297
126453
299
127324
205
128023
388
971
Spermidine
HMDB0001257
Spermidine is a polyamine formed from putrescine. It is found in almost all tissues in association with nucleic acids. It is found as a cation at all pH values, and is thought to help stabilize some membranes and nucleic acid structures. It is a precursor of spermine.
124-20-9
C00315
1102
16610
SPERMIDINE
1071
DB03566
NCCCCNCCCN
C7H19N3
InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2
ATHGHQPFGPMSJY-UHFFFAOYSA-N
(4-aminobutyl)(3-aminopropyl)amine
145.2459
145.157897623
-0.65
3
spermidine
0
3
FDB012039
1,5,10-triazadecane;1,8-diamino-4-azaoctane;4-azaoctamethylenediamine;4-azaoctane-1,8-diamine;Aminopropylbutandiamine;N-(3-aminopropyl)-1,4-butane-diamine;N-(3-aminopropyl)-1,4-butanediamine;N-(3-aminopropyl)-1,4-diamino-butane;N-(3-aminopropyl)-1,4-diaminobutane;N-(3-aminopropyl)-4-aminobutylamine;N-(4-aminobutyl)-1,3-diaminopropane;N-(gamma-aminopropyl)tetramethylenediamine;Spd;Spermidin;Spermidine
PW_C000971
Spermd
1208
8
1889
2
6712
117
43693
322
78312
132
78839
111
120917
122
122290
124
123484
135
124844
118
125864
297
126455
299
127326
205
128025
388
42677
5'-S-methyl-5'-thioadenosine
5'-Methylthioadenosine, also known as 5-mtda, belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. 5'-Methylthioadenosine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa).
CSCC1OC(C(O)C1O)N1C=NC2=C(N)N=CN=C12
C11H15N5O3S
InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)
WUUGFSXJNOTRMR-UHFFFAOYSA-N
2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
297.334
297.089560061
-1.66
3
2-(6-aminopurin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
0
0
PW_C042677
5SM5T
855
5-Methylthioribose
HMDB0001087
5-Methylthioribose belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. 5-Methylthioribose is soluble (in water) and a very weakly acidic compound (based on its pKa). Within the cell, 5-methylthioribose is primarily located in the cytoplasm. 5-Methylthioribose exists in all living organisms, ranging from bacteria to humans. 5-Methylthioribose participates in a number of enzymatic reactions. In particular, 5-Methylthioribose and adenine can be biosynthesized from 5'-S-methyl-5'-thioadenosine through its interaction with the enzyme 5'-methylthioadenosine/s-adenosylhomocysteine nucleosidase. In addition, 5-Methylthioribose and adenine can be biosynthesized from 5'-S-methyl-5'-thioadenosine through its interaction with the enzyme 5'-methylthioadenosine/s-adenosylhomocysteine nucleosidase. Outside of the human body, 5-methylthioribose can be found in a number of food items such as globe artichoke, red raspberry, maitake, and blackcurrant. This makes 5-methylthioribose a potential biomarker for the consumption of these food products. 5-Methylthioribose is a metabolite of 5-methylthioribose-1-phosphate. It is a substrate of methylthioribose kinase [EC 2.7.1.100] in the methionine metabolism pathway (KEGG).
23656-67-9
C03089
439904
16895
CPD-560
388938
CSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O
C6H12O4S
InChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1
OLVVOVIFTBSBBH-KVTDHHQDSA-N
(2R,3R,4S,5S)-5-[(methylsulfanyl)methyl]oxolane-2,3,4-triol
180.222
180.045629562
-0.01
3
5-methylthio-D-ribose
0
0
FDB022418
5-deoxy-5-(methylthio)ribose;5-methylthio-d-ribose;5-methylthioribose;S(5)-methyl-5-thio-d-ribose;S5-methyl-5-thio-d-ribose;S-methyl-5-thio-d-ribose
PW_C000855
5-MTr
6789
107
43748
318
24
Adenine
HMDB0000034
Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (PMID: 17052198, 17520339).
73-24-5
C00147
190
16708
ADENINE
185
DB00173
NC1=C2NC=NC2=NC=N1
C5H5N5
InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
GFFGJBXGBJISGV-UHFFFAOYSA-N
7H-purin-6-amine
135.1267
135.054495185
-1.07
2
vitamin B4
0
0
FDB012266
1,6-dihydro-6-iminopurine;1h-purin-6-amine;1h-purine-6-amine;3,6-dihydro-6-iminopurine;6-amino-1h-purine;6-amino-3h-purine;6-amino-7h-purine;6-amino-9h-purine;6-amino-purine;6-aminopurine;9h-purin-6-amine;9h-purin-6-yl-amin;9h-purin-6-ylamine;9h-purine-6-amine;Ade;Adenin;Adenine;Adeninimine;Vitamin b4;A
PW_C000024
Adenine
1892
8
6760
107
6761
108
11826
198
12524
227
12530
249
43735
318
43736
315
78703
111
121897
122
124450
135
940
Acetyl-CoA
HMDB0001206
The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.
72-89-9
C00024
444493
15351
ACETYL-COA
392413
CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C23H38N7O17P3S
InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1
ZSLZBFCDCINBPY-ZSJPKINUSA-N
{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
809.571
809.125773051
-2.27
9
acetyl-CoA
0
-4
FDB022491
Ac-coa;Ac-coenzyme a;Ac-s-coa;Ac-s-coenzyme a;Acetyl coenzyme-a;Acetyl-coa;Acetyl-coenzyme a;Acetyl-s-coa;Acetyl-s-coenzyme a;Acetylcoenzyme-a;S-acetate coa;S-acetate coenzyme a;S-acetyl coenzyme a;Accoa;Acetyl coenzyme a;S-acetyl-coa;S-acetyl-coenzyme a;Acetylcoenzyme a
PW_C000940
Ac-CoA
213
4
385
8
842
3
2416
2
2446
5
2896
17
3340
11
4840
14
5278
103
5476
124
5733
108
6025
155
6077
161
6386
1
6470
178
6923
160
7106
163
7291
198
7460
222
8245
151
8277
210
12582
226
13012
299
42615
315
77121
133
77291
111
77562
112
77706
132
77994
115
78355
134
78433
334
80007
368
80634
119
80663
376
90124
170
119953
406
120145
405
120304
122
120632
407
122417
408
122626
384
122743
120
122959
135
123137
118
124986
374
125200
121
125343
479
125507
478
125633
297
126564
482
126572
481
126778
480
126886
501
127044
209
127394
205
127665
388
128137
502
128145
206
128374
391
1476
N8-Acetylspermidine
HMDB0002189
N8-Acetylspermidine is a polyamine. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. The polyamines, found in virtually all living organisms, are a ubiquitous group of compounds that appear to play a vital role in many cellular processes involving nucleic acids including cell growth and differentiation. Acetylation on the terminal nitrogen adjacent to the 4-carbon chain produces N8-acetylspermidine. This reaction is catalyzed by spermidine N8-acetyltransferase and does not result in the conversion of spermidine to putrescine but, instead, the product undergoes deacetylation. This acetyltransferase appears to be associated with chromatin in the cell nucleus and has been reported to be the same as (or related to) the enzyme(s) responsible for histone acetylation. N8-Acetylspermidine does not accumulate in tissues but rather appears to be rapidly deacetylated back to spermidine by a relatively specific cytosolic deacetylase, N8-acetylspermidine deacetylase. The function of this N8-acetylation/deacetylation pathway in cellular processes is not understood clearly, but several observations have suggested a role in cell growth and differentiation. (PMID: 12093478).
13431-24-8
C01029
123689
27911
CPD-3462
110264
CC(=O)NCCCCNCCCN
C9H21N3O
InChI=1S/C9H21N3O/c1-9(13)12-8-3-2-6-11-7-4-5-10/h11H,2-8,10H2,1H3,(H,12,13)
FONIWJIDLJEJTL-UHFFFAOYSA-N
N-{4-[(3-aminopropyl)amino]butyl}acetamide
187.2825
187.168462309
-1.63
3
N8-acetylspermidine
0
2
FDB022894
N-[4-[(3-aminopropyl)amino]butyl]-acetamide;N8-acetylspermidine;N(8)-monoacetylspermidine
PW_C001476
N8-Acsp
1099
Coenzyme A
HMDB0001423
Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia).
85-61-0
C00010
6816
1146900
CO-A
6557
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS
C21H36N7O16P3S
InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1
RGJOEKWQDUBAIZ-IBOSZNHHSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
767.534
767.115208365
-2.22
10
coenzyme A
0
-4
FDB022614
Acetoacetyl coenzyme a sodium salt;Coa;Coa hydrate;Coa-sh;Coash;Coenzyme a;Coenzyme a hydrate;Coenzyme a-sh;Coenzyme ash;Coenzymes a;Depot-zeel;Propionyl coa;Propionyl coenzyme a;S-propanoate;S-propanoate coa;S-propanoate coenzyme a;S-propanoic acid;S-propionate coa;S-propionate coenzyme a;Zeel;[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
PW_C001099
CoA
211
4
386
8
845
3
879
22
892
17
2407
59
2414
2
2459
5
2813
29
2862
31
3342
11
3351
18
4618
10
4629
58
4842
14
4865
54
4879
6
5232
102
5247
104
5280
103
5477
124
5734
108
5777
101
6023
155
6075
161
6384
1
6468
178
6930
160
6961
162
6973
199
7083
188
7108
163
7293
198
7347
210
7458
222
8229
151
9081
226
9090
224
9124
170
9215
195
13013
299
15318
249
25488
49
42616
315
76907
293
77119
133
77222
134
77230
329
77292
111
77550
132
77555
334
77563
112
77633
336
77672
129
77996
115
78047
332
78056
350
78413
335
78567
130
79259
333
79974
331
80005
368
80620
118
80627
374
80635
119
80665
376
93828
382
93834
383
98674
288
110555
389
110561
390
115842
399
115847
398
119951
406
120147
405
120231
384
120305
122
120634
407
120762
117
121406
123
121421
433
121521
125
121666
429
121682
408
121714
414
122404
422
122741
120
122904
121
122960
135
123965
447
123979
468
124079
136
124220
464
124265
450
124974
375
125341
479
125509
478
125579
480
125592
484
125634
297
126084
481
126549
491
126560
482
126746
300
126884
501
127046
209
127109
391
127301
205
127540
206
127667
388
128121
508
128133
502
128340
395
7195
Methionine import ATP-binding protein MetN
P30750
Part of the ABC transporter complex MetNIQ involved in methionine import. Responsible for energy coupling to the transport system (Probable). It has also been shown to be involved in formyl-L-methionine transport.
metN
b0199
AP009048
3
3.6.3.-
5682
109
5880
139
6505
D-methionine transport system permease protein metI
P31547
Part of the binding-protein-dependent transport system for D-methionine and the toxic methionine analog alpha-methyl-methionine. Probably responsible for the translocation of the substrate across the membrane.
metI
b0198
AP009048
3
5683
109
5881
139
7430
D-methionine-binding lipoprotein metQ
P28635
Inorganic ion transport and metabolism. This protein is a component of a D-methionine permease, a binding protein-dependent, ATP-driven transport system.
metQ
b0197
AP009048
3
5684
109
5882
139
6064
S-adenosylmethionine synthase
P0A817
Involved in methionine adenosyltransferase activity. Catalyzes the formation of S-adenosylmethionine from methionine and ATP. The overall synthetic reaction is composed of two sequential steps, AdoMet formation and the subsequent tripolyphosphate hydrolysis which occurs prior to release of AdoMet from the enzyme. Is essential for growth.
metK
b2942
AP009048
3
2.5.1.6
8751
101
6056
S-adenosylmethionine decarboxylase proenzyme
P0A7F6
Involved in adenosylmethionine decarboxylase activity. Catalyzes the decarboxylation of S-adenosylmethionine to S-adenosylmethioninamine (dcAdoMet), the propylamine donor required for the synthesis of the polyamines spermine and spermidine from the diamine putrescine.
speD
b0120
AP009048
3
4.1.1.50
5967
Spermidine synthase
P09158
Involved in catalytic activity. Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM), which serves as an aminopropyl donor.
speE
b0121
AP009048
3
2.5.1.-; 2.5.1.79; 2.5.1.16; 2.5.1.22
8752
101
9645
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
P0AF12
Catalyzes the irreversible cleavage of the glycosidic bond in both 5'-methylthioadenosine (MTA) and S-adenosylhomocysteine (SAH/AdoHcy) to adenine and the corresponding thioribose, 5'-methylthioribose and S-ribosylhomocysteine, respectively. Can also use 5'-isobutylthioadenosine, 5'-n-butylthioadenosine, S-adenosyl-D-homocysteine, decarboxylated adenosylhomocysteine, deaminated adenosylhomocysteine and S-2-aza-adenosylhomocysteine as substrates.
mtn
3
3.2.2.9
6101
Spermidine N(1)-acetyltransferase
P0A951
Involved in N-acetyltransferase activity. Regulates polyamine concentration by their degradation. Acts on spermidine, forming N(1)- and N(8)-acetylspermidine.
speG
b1584
AP009048
3
2.3.1.57
8753
101
1458
L-methionine / D-methionine ABC transporter
3
PW_P001458
1713
7195
2
1714
6505
1715
7430
3426
methionine adenosyltransferase
3
PW_P003426
10199
6064
4
3895
adenosylmethionine decarboxylase
3
PW_P003895
10861
6056
8
589
164
590
423
3896
Spermidine synthase
3
PW_P003896
10862
5967
2
3419
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
3
PW_P003419
10189
9645
2
3910
spermidine acetyltransferase
3
PW_P003910
10878
6101
4
5165
false
PW_R005165
Right
20890
921
1
Compound
true
20891
40034
1
Compound
true
20892
1316
1
Compound
true
20893
783
1
Compound
false
5136
3895
4.1.1.50
5166
false
PW_R005166
Right
20894
1092
1
Compound
false
20895
783
1
Compound
false
20896
971
1
Compound
false
20897
40034
1
Compound
false
20898
42677
1
Compound
false
5137
3896
2.5.1.-
5167
false
PW_R005167
Right
20899
42677
1
Compound
false
20900
1420
1
Compound
false
20901
855
1
Compound
false
20902
24
1
Compound
false
5138
3419
3.2.2.9
5186
false
PW_R005186
Right
20992
971
1
Compound
false
20993
940
1
Compound
false
20994
1476
1
Compound
false
20995
1099
1
Compound
false
20996
40034
1
Compound
false
5154
3910
2.3.1.57
3075
false
PW_R003075
Right
12246
548
1
Compound
false
12247
1420
1
Compound
true
12248
414
1
Compound
true
12249
1104
1
Compound
true
12250
170
1
Compound
true
12251
921
1
Compound
false
3044
3426
2.5.1.6
111
PW_RCT000111
Right
673
111
548
Compound
1
107
674
111
414
Compound
1
108
675
111
1420
Compound
1
108
676
111
1034
Compound
1
108
677
111
1104
Compound
1
108
678
111
40034
Compound
1
108
679
111
548
Compound
1
108
111
125
PW_RCT000125
Right
758
125
548
Compound
1
105
759
125
414
Compound
1
107
760
125
1420
Compound
1
107
761
125
1034
Compound
1
107
762
125
170
Compound
1
107
763
125
40034
Compound
1
107
764
125
548
Compound
1
107
125
16482
548
107
3
false
850
442
10
regular
100
100
16483
414
108
42
false
710
752
10
regular
50
30
16484
1420
108
49
false
581
727
10
regular
78
78
16485
1034
108
43
false
1030
759
10
regular
50
30
16486
1104
108
46
false
1118
749
10
regular
44
43
16487
40034
108
55
false
1201
727
10
regular
78
78
16488
548
108
3
false
850
855
10
regular
100
100
16489
548
105
3
false
850
100
10
regular
100
100
16490
414
107
42
false
675
394
10
regular
50
30
16491
1420
107
49
false
566
364
10
regular
78
78
16492
1034
107
43
false
1130
385
10
regular
50
30
16493
170
107
45
false
1213
380
10
regular
63
43
16494
40034
107
55
false
1016
365
10
regular
78
78
61566
1420
49
false
969
956
10
regular
78
78
61567
414
42
false
983
819
10
regular
50
30
61568
1104
46
false
1241
826
10
regular
44
43
61569
170
45
false
1256
954
10
regular
63
43
61570
921
3
false
1348
850
10
regular
100
110
61571
40034
55
false
1474
790
10
regular
78
78
61572
1316
52
false
1759
945
10
regular
78
78
61573
783
3
false
1848
850
10
regular
100
110
61574
164
9
false
1653
872
10
regular
100
25
61575
423
9
false
1568
872
10
regular
100
25
61576
1092
3
false
1953
1005
10
regular
100
100
61577
971
3
false
1704
1230
10
regular
100
100
61578
40034
55
false
1979
1246
10
regular
78
78
61579
42677
3
false
1847
1325
10
regular
100
120
61580
1420
49
false
1764
1461
10
regular
78
78
61581
855
3
false
1847
1770
10
regular
100
110
61582
24
3
false
1742
1655
10
regular
100
100
61732
940
3
false
1599
1125
10
regular
100
100
61733
1476
3
false
1234
1228
10
regular
100
110
61734
1099
85
false
1369
1193
10
regular
50
30
61735
40034
55
false
1355
1343
10
regular
78
78
8151
7195
109
77
false
820
627
10
subunit
regular
160
80
8152
6505
109
76
false
825
587
8
subunit
regular
150
70
8153
7430
109
76
false
825
647
8
subunit
regular
150
70
8154
7195
139
77
false
820
269
12
subunit
regular
160
80
8155
6505
139
76
false
825
244
8
subunit
regular
150
70
8156
7430
139
76
false
825
314
8
subunit
regular
150
70
28680
6064
101
8
false
1083
865
8
subunit
regular
140
85
28681
6056
7
false
1573
867
8
subunit
regular
190
85
28682
5967
101
6
false
1818
1142
8
subunit
regular
160
80
28683
9645
6
false
1817
1552
8
subunit
regular
160
80
28741
6101
101
8
false
1464
1242
8
subunit
regular
140
85
6560
1458
585
109
8057
8151
8058
8152
8059
8153
6561
1458
585
139
8060
8154
8061
8155
8062
8156
24138
3426
585
28368
28680
24139
3895
585
28369
28681
3645
61574
88393
Cofactor
3646
61575
88394
Cofactor
24140
3896
585
28370
28682
24141
3419
585
28371
28683
24172
3910
585
28429
28741
24942
M900 542 C900 580 900 592 900 632
5
false
7
24943
M735 752 C735 716 747 674 820 667
5
false
18
24944
M620 727 C620 704 702 668 820 667
5
false
18
24945
M1055 759 C1050 707 1049 668 980 667
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24946
M1140 749 C1138 713 1098 667 980 667
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24947
M1240 727 C1240 699 1121 669 980 667
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24948
M900 855 C900 825 900 771 900 717
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24949
M900 200 C900 233 900 252 900 269
5
false
7
24950
M700 394 C701 339 780 307 820 309
5
false
18
24951
M605 364 C611 334 632 311 820 309
5
false
18
24952
M1155 385 C1149 321 1086 310 980 309
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24953
M1244.5 380 C1241.5 335 1130 313 980 309
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24954
M1055 365 C1053 332 1046 309 980 309
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24955
M900 442 C900 424 900 424 900 384
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
88389
M1448 905 C1475 905 1535 906 1573 907
5
false
18
88390
M1513 868 C1511 896 1513 905 1573 907
5
false
18
88391
M1798 945 C1798 921 1793 907 1763 907
5
false
18
true
M 706.9468550441649 931.5948896296294 L 692 930.3333333333334 L 698.3808877211858 943.9084676564117
false
88392
M1848 905 C1807 908 1801 908 1763 907
5
false
18
true
M 706.9468550441649 931.5948896296294 L 692 930.3333333333334 L 698.3808877211858 943.9084676564117
false
88393
M1313 942 L1313 992 L1363 942 z
10
true
18
88394
M1313 922 L1313 972 L1363 922 z
10
true
18
88395
M1953 1055 C1914 1057 1897 1099 1898 1142
5
false
18
88396
M1898 960 C1898 990 1898 1112 1898 1142
5
false
18
88397
M1804 1280 C1881 1278 1897 1286 1898 1222
5
false
18
true
M 1706.9468550441647 1447.5948896296293 L 1692 1446.3333333333333 L 1698.380887721186 1459.9084676564116
false
88398
M1979 1285 C1941 1287 1897 1258 1898 1222
5
false
18
true
M 1706.9468550441647 1447.5948896296293 L 1692 1446.3333333333333 L 1698.380887721186 1459.9084676564116
false
88399
M1897 1325 C1898 1295 1898 1252 1898 1222
5
false
18
true
M 1706.9468550441647 1447.5948896296293 L 1692 1446.3333333333333 L 1698.380887721186 1459.9084676564116
false
88400
M1897 1445 C1897 1475 1897 1522 1897 1552
5
false
18
88401
M1842 1500 C1895 1500 1897 1522 1897 1552
5
false
18
88402
M1897 1770 C1897 1740 1897 1662 1897 1632
5
false
18
true
M 1706.9468550441647 1848.9282229629628 L 1692 1847.6666666666667 L 1698.380887721186 1861.2418009897451
false
88403
M1842 1705 C1885 1703 1897 1662 1897 1632
5
false
18
true
M 1706.9468550441647 1848.9282229629628 L 1692 1847.6666666666667 L 1698.380887721186 1861.2418009897451
false
88585
M1704 1280 C1674 1280 1634 1282 1604 1282
5
false
18
88586
M1649 1225 C1649 1274 1634 1282 1604 1282
5
false
18
88587
M1334 1283 C1364 1283 1434 1282 1464 1282
5
false
18
true
M 750.9468550441649 531.5948896296294 L 736 530.3333333333334 L 742.3808877211858 543.9084676564117
false
88588
M1394 1223 C1395 1273 1434 1282 1464 1282
5
false
18
true
M 750.9468550441649 531.5948896296294 L 736 530.3333333333334 L 742.3808877211858 543.9084676564117
false
88589
M1394 1343 C1394 1297 1434 1282 1464 1282
5
false
18
true
M 750.9468550441649 531.5948896296294 L 736 530.3333333333334 L 742.3808877211858 543.9084676564117
false
3657941
M950 905 C995 905 1056 905 1083 905
5
false
18
3657942
M1008 956 C1008 919 1038 905 1083 905
5
false
18
3657943
M1008 849 C1006 871 1022 908 1083 905
5
false
18
3657944
M1263 869 C1263 879 1266 904 1223 905
5
false
18
true
M 614.9468550441649 294.261556296296 L 600 293 L 606.3808877211858 306.5751343230783
false
3657945
M1287.5 954 C1273.5 910 1268 906 1223 905
5
false
18
true
M 614.9468550441649 294.261556296296 L 600 293 L 606.3808877211858 306.5751343230783
false
3657946
M1348 905 C1309 905 1287 905 1223 905
5
false
18
true
M 614.9468550441649 294.261556296296 L 600 293 L 606.3808877211858 306.5751343230783
false
3657947
M850 905 C813 905 786 906 750 907
5
false
18
true
M 1217.1421870608235 582.2228807701849 L 1225 595 L 1232.1364033706143 581.8063747615796
false
17958
585
5165
69131
61570
88389
Left
69132
61571
88390
Left
69133
61572
88391
Right
69134
61573
88392
Right
18158
5136
24139
17959
585
5166
69135
61576
88395
Left
69136
61573
88396
Left
69137
61577
88397
Right
69138
61578
88398
Right
69139
61579
88399
Right
18159
5137
24140
17960
585
5167
69140
61579
88400
Left
69141
61580
88401
Left
69142
61581
88402
Right
69143
61582
88403
Right
18160
5138
24141
17981
585
5186
69235
61577
88585
Left
69236
61732
88586
Left
69237
61733
88587
Right
69238
61734
88588
Right
69239
61735
88589
Right
18178
5154
24172
797181
585
3075
117
3222156
16488
3657941
Left
3222157
61566
3657942
Left
3222158
61567
3657943
Left
3222159
61568
3657944
Right
3222160
61569
3657945
Right
3222161
61570
3657946
Right
752858
3044
24138
217
111
585
1311
16482
24942
Left
1312
16483
24943
Left
1313
16484
24944
Left
1314
16485
24945
Right
1315
16486
24946
Right
1316
16487
24947
Right
1317
16488
24948
Right
221
6560
145
218
125
585
1318
16489
24949
Left
1319
16490
24950
Left
1320
16491
24951
Left
1321
16492
24952
Right
1322
16493
24953
Right
1323
16494
24954
Right
1324
16482
24955
Right
222
6561
159
109390
109727
585
14
false
600
872
16
regular
106093
16488
3657947
Right
186306
513
1084
1.6
1.6
0
2
92
479
481
1069
M123 422 C123 372 173 322 223 322 C876 322 1724 322 2377 322 C2427 322 2477 372 2477 422 C2477 953 2477 1642 2477 2173 C2477 2223 2427 2273 2377 2273 C1724 2273 876 2273 223 2273 C173 2273 123 2223 123 2173 C123 1642 123 953 123 422
1
true
6
2354.0
1951.0
1070
M476 776 C476 726 526 676 576 676 C1014 676 1584 676 2022 676 C2072 676 2122 726 2122 776 C2122 1096 2122 1512 2122 1832 C2122 1882 2072 1932 2022 1932 C1584 1932 1014 1932 576 1932 C526 1932 476 1882 476 1832 C476 1512 476 1096 476 776
1
true
6
1646.0
1256.0