535
Pathway
Lysine Biosynthesis
Lysine is biosynthesized from L-aspartic acid. L-Aspartic acid can be incorporated into the cell through various methods: C4 dicarboxylate/orotate:H+ symporter, glutamate/aspartate:H+ symporter GltP, dicarboxylate transporter, C4 dicarboxylate/C4 monocarboxylate transporter DauA, and glutamate/aspartate ABC transporter. L-Aspartic acid is phosphorylated by an ATP-driven aspartate kinase resulting in ADP and L-aspartyl-4-phosphate. L-Aspartyl-4-phosphate is then dehydrogenated through an NADPH-driven aspartate semialdehyde dehydrogenase resulting in a release of phosphate, NADP, and L-aspartic 4-semialdehyde (involved in methionine biosynthesis). L-Aspartic 4-semialdehyde interacts with a pyruvic acid through a 4-hydroxy-tetrahydrodipicolinate synthase resulting in a release of hydrogen ion, water, and (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate. The latter compound is then reduced by an NADPH-driven 4-hydroxy-tetrahydrodipicolinate reductase resulting in a release of water, NADP, and (S)-2,3,4,5-tetrahydrodipicolinate, This compound interacts with succinyl-CoA and water through a tetrahydrodipicolinate succinylase resulting in a release of coenzyme A and N-succinyl-2-amino-6-ketopimelate. This compound interacts with L-glutamic acid through an N-succinyldiaminopimelate aminotransferase resulting in oxoglutaric acid and N-succinyl-L,L-2,6-diaminopimelate. The latter compound is then desuccinylated by reacting with water through an N-succinyl-L-diaminopimelate desuccinylase resulting in a succinic acid and L,L-diaminopimelate. This compound is then isomerized through a diaminopimelate epimerase resulting in a meso-diaminopimelate (involved in peptidoglycan biosynthesis I). This compound is then decarboxylated by a diaminopimelate decarboxylase resulting in a release of carbon dioxide and L-lysine. L-Lysine is then incorporated into the lysine degradation pathway. Lysine also regulates its own biosynthesis by repressing dihydrodipicolinate synthase and also by repressing lysine-sensitive aspartokinase 3. Diaminopielate is a precursor for lysine as well as other cell wall components. Synthesis of lysine starts by converting L-aspartic acid (L-aspartate) to L-Aspartyl-4-phosphate by aspartate kinase. L-Aspartyl-4-phosphate transforms to form L-aspartic 4-semialdehyde (L-aspartate semialdehyde) by aspartate semialdehyde dehydrogenase with NADPH. L-aspartic 4-semialdehyde can start the metabolic pathway of synthesis of methionine as well as synthesis of threonine. Aspartate kinase can be regulated by its end product: L-Lysine.
Metabolic
PW000771
Center
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PathwayVisualization519
535
Lysine Biosynthesis
Lysine is biosynthesized from L-aspartic acid. L-Aspartic acid can be incorporated into the cell through various methods: C4 dicarboxylate/orotate:H+ symporter, glutamate/aspartate:H+ symporter GltP, dicarboxylate transporter, C4 dicarboxylate/C4 monocarboxylate transporter DauA, and glutamate/aspartate ABC transporter. L-Aspartic acid is phosphorylated by an ATP-driven aspartate kinase resulting in ADP and L-aspartyl-4-phosphate. L-Aspartyl-4-phosphate is then dehydrogenated through an NADPH-driven aspartate semialdehyde dehydrogenase resulting in a release of phosphate, NADP, and L-aspartic 4-semialdehyde (involved in methionine biosynthesis). L-Aspartic 4-semialdehyde interacts with a pyruvic acid through a 4-hydroxy-tetrahydrodipicolinate synthase resulting in a release of hydrogen ion, water, and (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate. The latter compound is then reduced by an NADPH-driven 4-hydroxy-tetrahydrodipicolinate reductase resulting in a release of water, NADP, and (S)-2,3,4,5-tetrahydrodipicolinate, This compound interacts with succinyl-CoA and water through a tetrahydrodipicolinate succinylase resulting in a release of coenzyme A and N-succinyl-2-amino-6-ketopimelate. This compound interacts with L-glutamic acid through an N-succinyldiaminopimelate aminotransferase resulting in oxoglutaric acid and N-succinyl-L,L-2,6-diaminopimelate. The latter compound is then desuccinylated by reacting with water through an N-succinyl-L-diaminopimelate desuccinylase resulting in a succinic acid and L,L-diaminopimelate. This compound is then isomerized through a diaminopimelate epimerase resulting in a meso-diaminopimelate (involved in peptidoglycan biosynthesis I). This compound is then decarboxylated by a diaminopimelate decarboxylase resulting in a release of carbon dioxide and L-lysine. L-Lysine is then incorporated into the lysine degradation pathway. Lysine also regulates its own biosynthesis by repressing dihydrodipicolinate synthase and also by repressing lysine-sensitive aspartokinase 3. Diaminopielate is a precursor for lysine as well as other cell wall components. Synthesis of lysine starts by converting L-aspartic acid (L-aspartate) to L-Aspartyl-4-phosphate by aspartate kinase. L-Aspartyl-4-phosphate transforms to form L-aspartic 4-semialdehyde (L-aspartate semialdehyde) by aspartate semialdehyde dehydrogenase with NADPH. L-aspartic 4-semialdehyde can start the metabolic pathway of synthesis of methionine as well as synthesis of threonine. Aspartate kinase can be regulated by its end product: L-Lysine.
Metabolic
3
80105
671
SubPathway
78082
40841
Compound
117
80106
536
SubPathway
78083
118
Compound
117
109786
578
SubPathway
109295
40837
Compound
2097
15158272
Acord J, Masters M: Expression from the Escherichia coli dapA promoter is regulated by intracellular levels of diaminopimelic acid. FEMS Microbiol Lett. 2004 Jun 1;235(1):131-7. doi: 10.1016/j.femsle.2004.04.022.
535
Pathway
2098
14726201
Alvarez E, Ramon F, Magan C, Diez E: L-cystine inhibits aspartate-beta-semialdehyde dehydrogenase by covalently binding to the essential 135Cys of the enzyme. Biochim Biophys Acta. 2004 Jan 14;1696(1):23-9.
535
Pathway
2099
2241177
Angeles TS, Viola RE: The kinetic mechanisms of the bifunctional enzyme aspartokinase-homoserine dehydrogenase I from Escherichia coli. Arch Biochem Biophys. 1990 Nov 15;283(1):96-101.
535
Pathway
2100
13412646
ANTIA M, HOARE DS, WORK E: The stereoisomers of alpha epsilon-diaminopimelic acid. III. Properties and distribution of diaminopimelic acid racemase, an enzyme causing interconversion of the LL and meso isomers. Biochem J. 1957 Mar;65(3):448-59.
535
Pathway
2101
3056252
Baumann RJ, Bohme EH, Wiseman JS, Vaal M, Nichols JS: Inhibition of Escherichia coli growth and diaminopimelic acid epimerase by 3-chlorodiaminopimelic acid. Antimicrob Agents Chemother. 1988 Aug;32(8):1119-23.
535
Pathway
2102
28752
Bearer CF, Neet KE: Threonine inhibition of the aspartokinase--homoserine dehydrogenase I of Escherichia coli. A slow transient and cooperativity of inhibition of the aspartokinase activity. Biochemistry. 1978 Aug 22;17(17):3523-30.
535
Pathway
2103
4598010
Berg CM, Rossi JJ: Proline excretion and indirect suppression in Escherichia coli and Salmonella typhimurium. J Bacteriol. 1974 Jun;118(3):928-34.
535
Pathway
2104
3700390
Berges DA, DeWolf WE Jr, Dunn GL, Newman DJ, Schmidt SJ, Taggart JJ, Gilvarg C: Studies on the active site of succinyl-CoA:tetrahydrodipicolinate N-succinyltransferase. Characterization using analogs of tetrahydrodipicolinate. J Biol Chem. 1986 May 15;261(14):6160-7.
535
Pathway
2105
6102909
Biellmann JF, Eid P, Hirth C, Jornvall H: Aspartate-beta-semialdehyde dehydrogenase from Escherichia coli. Purification and general properties. Eur J Biochem. 1980 Feb;104(1):53-8.
535
Pathway
2106
6102911
Biellmann JF, Eid P, Hirth C: Affinity labeling of the Escherichia coli aspartate-beta-semialdehyde dehydrogenase with an alkylating coenzyme analogue. Half-site reactivity and competition with the substrate alkylating analogue. Eur J Biochem. 1980 Feb;104(1):65-9.
535
Pathway
2107
112925
Billheimer JT, Shen MY, Carnevale HN, Horton HR, Jones EE: Isolation and characterization of acetylornithine delta-transaminase of wild-type Escherichia coli W. Comparison with arginine-inducible acetylornithine delta-transaminase. Arch Biochem Biophys. 1979 Jul;195(2):401-13.
535
Pathway
2108
8993314
Blickling S, Renner C, Laber B, Pohlenz HD, Holak TA, Huber R: Reaction mechanism of Escherichia coli dihydrodipicolinate synthase investigated by X-ray crystallography and NMR spectroscopy. Biochemistry. 1997 Jan 7;36(1):24-33. doi: 10.1021/bi962272d.
535
Pathway
2109
7832769
Borthwick EB, Connell SJ, Tudor DW, Robins DJ, Shneier A, Abell C, Coggins JR: Escherichia coli dihydrodipicolinate synthase: characterization of the imine intermediate and the product of bromopyruvate treatment by electrospray mass spectrometry. Biochem J. 1995 Jan 15;305 ( Pt 2):521-4.
535
Pathway
2110
22552955
Boughton BA, Dobson RC, Hutton CA: The crystal structure of dihydrodipicolinate synthase from Escherichia coli with bound pyruvate and succinic acid semialdehyde: unambiguous resolution of the stereochemistry of the condensation product. Proteins. 2012 Aug;80(8):2117-22. doi: 10.1002/prot.24106. Epub 2012 Jun 4.
535
Pathway
2111
22386717
Boughton BA, Hor L, Gerrard JA, Hutton CA: 1,3-Phenylene bis(ketoacid) derivatives as inhibitors of Escherichia coli dihydrodipicolinate synthase. Bioorg Med Chem. 2012 Apr 1;20(7):2419-26. doi: 10.1016/j.bmc.2012.01.045. Epub 2012 Feb 10.
535
Pathway
2112
18502871
Bouvier J, Stragier P, Morales V, Remy E, Gutierrez C: Lysine represses transcription of the Escherichia coli dapB gene by preventing its activation by the ArgP activator. J Bacteriol. 2008 Aug;190(15):5224-9. doi: 10.1128/JB.01782-07. Epub 2008 May 23.
535
Pathway
2113
6094578
Bouvier J, Richaud C, Richaud F, Patte JC, Stragier P: Nucleotide sequence and expression of the Escherichia coli dapB gene. J Biol Chem. 1984 Dec 10;259(23):14829-34.
535
Pathway
2114
1644752
Bouvier J, Richaud C, Higgins W, Bogler O, Stragier P: Cloning, characterization, and expression of the dapE gene of Escherichia coli. J Bacteriol. 1992 Aug;174(16):5265-71.
535
Pathway
2115
4404058
Boy E, Patte JC: Multivalent repression of aspartic semialdehyde dehydrogenase in Escherichia coli K-12. J Bacteriol. 1972 Oct;112(1):84-92.
535
Pathway
2116
8152
Boy E, Reinisch F, Richaud C, Patte JC: Role of lysyl-tRNA in the regulation of lysine biosynthesis in Escherichia coli K12. Biochimie. 1976;58(1-2):213-8.
535
Pathway
1
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8
Beta cell
CL:0000639
7
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CL:0000066
6
Myocyte
CL:0000187
1
Homo sapiens
9606
Eukaryote
Human
2
Bacteria
2
Prokaryote
Bacteria
3
Escherichia coli
562
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
17
Rattus norvegicus
10116
Eukaryote
Rat
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
25
Escherichia coli (strain K12)
83333
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49
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220390
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Pseudomonas aeruginosa
287
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60
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0001
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5
Bos taurus
9913
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10
Drosophila melanogaster
7227
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29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
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126
Lactobacillus delbrueckii subsp. bulgaricus LJJ
1585
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92
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1423
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1
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5
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14
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15
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4
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13
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7
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31
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GO:0005615
35
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GO:0009507
12
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GO:0005743
32
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19
sarcoplasmic reticulum
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36
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24
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53
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34
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GO:0005764
16
Lysosomal Lumen
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18
Melanosome Membrane
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25
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20
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21
Synapse
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40
Periplasm
GO:0042597
17
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8
Smooth Endoplasmic Reticulum
GO:0005790
2
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Nervous System
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Blood Vessel
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74
11
5
cardiocyte
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28
Stomach
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155
26
9
Muscle
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141
18
24
Brain
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16
4
Adrenal Medulla
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8
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Heart
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6
1
PW_BS000115
391
12
6
1
PW_BS000112
6
1
3
1
PW_BS000006
241
5
29
PW_BS000024
257
15
29
1
PW_BS000024
298
1
7
10
1
PW_BS000024
513
1
7
6
1
PW_BS000115
482
4
10
1
PW_BS000115
502
4
6
1
PW_BS000115
50
9
5
1
6
PW_BS000050
95
1
7
2
1
PW_BS000095
156
12
24
1
PW_BS000156
177
1
21
1
PW_BS000177
85
24
10
1
1
PW_BS000085
346
9
5
12
6
PW_BS000028
367
1
60
1
PW_BS000028
423
9
5
5
6
PW_BS000115
458
9
5
17
6
PW_BS000115
9
6
1
1
PW_BS000009
28
1
16
1
1
PW_BS000028
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
43
25
1
1
PW_BS000043
24
4
10
1
1
PW_BS000024
60
25
1
PW_BS000060
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
113
6
12
1
PW_BS000113
110
2
3
1
PW_BS000110
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
140
10
3
PW_BS000140
180
2
21
1
PW_BS000180
207
6
6
1
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
65
11
1
PW_BS000065
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
352
25
12
PW_BS000028
356
25
12
1
PW_BS000028
360
4
10
12
1
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
232
40
3
PW_BS000024
415
18
5
1
PW_BS000115
414
1
5
5
1
PW_BS000115
419
25
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
436
25
5
PW_BS000115
443
6
17
1
PW_BS000115
448
1
16
17
1
PW_BS000115
451
18
17
1
PW_BS000115
450
1
5
17
1
PW_BS000115
455
25
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
471
25
17
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
504
18
6
1
PW_BS000115
507
25
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
71
11
1
3
PW_BS000071
289
2
49
1
PW_BS000024
30
17
1
1
PW_BS000030
338
17
12
1
PW_BS000028
413
17
5
1
PW_BS000115
449
17
17
1
PW_BS000115
11
1
8
1
1
PW_BS000011
102
12
3
1
PW_BS000102
288
14
4
1
PW_BS000024
626
5
126
1
PW_BS000503
311
32
2
PW_BS000024
628
32
126
PW_BS000503
649
32
92
PW_BS000508
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
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
7795
L-Aspartyl-4-phosphate
HMDB0012250
L-Aspartyl-4-phosphate is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. In the lysine biosynthesis I pathway, L-Aspartyl-4-phosphate is produced from a reaction between L-aspartate and ATP, with ADP as a byproduct. The reaction is catalyzed by aspartate kinase. L-aspartyl-4-phosphate reacts with NADPH to produce phosphate, L-aspartate-semialdehyde, and NADP+. Aspartate-semialdehyde dehydrogenase catalyzes this reaction. In the homoserine biosynthesis pathway, L-Aspartyl-4-phosphate is produced from a reaction between L-aspartate and ATP, with ADP as a byproduct. The reaction is catalyzed by aspartate kinase. L-aspartyl-4-phosphate reacts with NADPH to produce phosphate, L-aspartate-semialdehyde, and NADP+. Aspartate-semialdehyde dehydrogenase catalyzes this reaction.
22138-53-0
C03082
832
L-BETA-ASPARTYL-P
809
NC(CC(=O)OP(O)(O)=O)C(O)=O
C4H8NO7P
InChI=1S/C4H8NO7P/c5-2(4(7)8)1-3(6)12-13(9,10)11/h2H,1,5H2,(H,7,8)(H2,9,10,11)
IXZNKTPIYKDIGG-UHFFFAOYSA-N
2-amino-4-oxo-4-(phosphonooxy)butanoic acid
213.0826
213.003838127
-1.21
4
aspartyl phosphate
0
-2
C03082
4-phospho-l-aspartate;L-4-aspartyl phosphate;L-aspartyl-4-p;L-aspartyl-b-phosphate;L-aspartyl-beta-phosphate;L-b-aspartyl-p;L-b-aspartyl-phosphate;L-beta-aspartyl-p;L-beta-aspartyl-phosphate
PW_C007795
LA4P
8188
225
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1
ACFIXJIJDZMPPO-NCHANQSKSA-N
{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
745.4209
745.091102105
-2.14
9
[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
0
-4
FDB021909
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
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
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
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
744.4129
744.083277073
-2.27
9
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-3
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
40837
L-aspartic 4-semialdehyde
L-Aspartate-semialdehyde, also known as aspartic acid b-semialdehyde, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Aspartate-semialdehyde is soluble (in water) and a moderately acidic compound (based on its pKa). Outside of the human body, L-aspartate-semialdehyde can be found in a number of food items such as capers, chervil, tamarind, and grapefruit. This makes L-aspartate-semialdehyde a potential biomarker for the consumption of these food products.
537519
N[C@@H](CC=O)C(O)=O
C4H7NO3
InChI=1S/C4H7NO3/c5-3(1-2-6)4(7)8/h2-3H,1,5H2,(H,7,8)/t3-/m0/s1
HOSWPDPVFBCLSY-VKHMYHEASA-N
(2S)-2-amino-4-oxobutanoic acid
117.1033
117.042593095
0.28
2
L-aspartic 4-semialdehyde
0
0
L-aspartic 4-semialdehyde, l-aspartate-4-semialdehyde, l-aspartate β-semialdehyde
PW_C040837
LA4S
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
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
40838
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate
4-Hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. 4-Hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate is soluble (in water) and a weakly acidic compound (based on its pKa).
67139
OC1CC(N=C(C1)C([O-])=O)C([O-])=O
C7H7NO5
InChI=1S/C7H9NO5/c9-3-1-4(6(10)11)8-5(2-3)7(12)13/h3-4,9H,1-2H2,(H,10,11)(H,12,13)/p-2
DVTPRYHENFBCII-UHFFFAOYSA-L
4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate
185.136
185.033519489
-1.04
1
4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate
-2
-2
(4s)-4-hydroxy-2,3,4,5-tetrahydro-(2s)-dipicolinate
PW_C040838
thpcol
8202
225
40839
(S)-2,3,4,5-tetrahydrodipicolinate
(S)-2,3,4,5-Tetrahydrodipicolinate belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof (S)-2,3,4,5-Tetrahydrodipicolinate is slightly soluble (in water) and a weakly acidic compound (based on its pKa) (S)-2,3,4,5-Tetrahydrodipicolinate may be a unique E.coli metabolite (S)-2,3,4,5-Tetrahydrodipicolinate participates in a number of enzymatic reactions. In particular, (S)-2,3,4,5-Tetrahydrodipicolinate can be biosynthesized from (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate; which is catalyzed by the enzyme 4-hydroxy-tetrahydrodipicolinate reductase. In addition, (S)-2,3,4,5-Tetrahydrodipicolinate and succinyl-CoA can be converted into N-succinyl-2-amino-6-ketopimelate through the action of the enzyme tetrahydrodipicolinate succinylase. Outside of the human body, (S)-2,3,4,5-tetrahydrodipicolinate can be found in a number of food items such as olive, jerusalem artichoke, brussel sprouts, and angelica. This makes (S)-2,3,4,5-tetrahydrodipicolinate a potential biomarker for the consumption of these food products.
16845
[O-]C(=O)C1CCCC(=N1)C([O-])=O
C7H7NO4
InChI=1S/C7H9NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h4H,1-3H2,(H,9,10)(H,11,12)/p-2
CXMBCXQHOXUCEO-UHFFFAOYSA-L
2,3,4,5-tetrahydropyridine-2,6-dicarboxylate
169.137
169.038604869
-1.50
0
2,3,4,5-tetrahydrodipicolinate
-2
-2
2,3,4,5-tetrahydrodipicolinate, (s)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate, Δ1-piperideine-2,6-dicarboxylate, tetrahydrodipicolinate, tetrahydropyridine-2,6-dicarboxylate, l-2,3,4,5-tetrahydrodipicolinate
PW_C040839
Sthdp
8205
225
808
Succinyl-CoA
HMDB0001022
Succinyl-CoA is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase (EC 1.2.4.2) through decarboxylation, and is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (EC 6.2.1.5). Succinyl-CoA may be an end product of peroxisomal beta-oxidation of dicarboxylic fatty acids; the identification of an apparently specific succinyl-CoA thioesterase (ACOT4, EC 3.1.2.3, hydrolyzes succinyl-CoA) in peroxisomes strongly suggests that succinyl-CoA is formed in peroxisomes. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A, thereby regulating levels of these compounds. (PMID: 16141203).
604-98-8
C00091
439161
15380
3-METHYLBENZYLSUCCINYL-COA
388307
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(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O
C25H40N7O19P3S
InChI=1S/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t13-,18-,19-,20?,24-/m1/s1
VNOYUJKHFWYWIR-FZEDXVDRSA-N
4-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-4-oxobutanoic acid
867.607
867.131252359
-2.35
10
4-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-4-oxobutanoic acid
0
-5
FDB022375
Coa s-(hydrogen succinate);Coa s-succinate;Coenzyme a s-(hydrogen succinate);Coenzyme a s-succinate;S-(hydrogen butanedioate;S-(hydrogen butanedioate) coa;S-(hydrogen butanedioate) coenzyme a;S-(hydrogen butanedioic acid;S-succinoylcoenzyme a;Suc-co-a;Suc-coa;Succ-coa;Succ-coenzyme a;Succ-s-coa;Succ-s-coenzyme a;Succ-s-coenzyme-a;Succ-coenzyme-a;Succino-1-yl-coenzyme a;Succinyl coa;Succinyl coenzyme a;Succinyl-s-coa;Succinyl-s-coenzyme a;Succinyl-s-coenzyme-a;Succinylcoenzyme-a;Succinylcoenzyme a
PW_C000808
Suc-CoA
233
4
1055
3
3669
2
5378
103
6039
155
6097
161
6485
178
7015
160
7361
163
7474
222
77140
133
78101
112
78576
132
80021
368
119978
406
120769
407
122014
124
122763
120
123365
119
124568
118
125358
479
126164
299
126306
481
126901
501
127868
206
7810
N-Succinyl-2-amino-6-ketopimelate
HMDB0012266
N-Succinyl-2-amino-6-ketopimelate is an intermediate in lysine biosynthesis. It is the fourth to last step in the synthesis of lysine and is converted. from tetrahydrodipicolinate via the enzyme tetrahydrodipicolinate N-succinyltransferase (EC 2.3.1.117). It is then converted to N-succinyl-L,L-2,6-diaminopimelate via the enzyme Succinyldiaminopimelate transferase (EC 2.6.1.17).
C04462
440349
35266
N-SUCCINYL-2-AMINO-6-KETOPIMELATE
389314
OC(=O)CCC(=O)N[C@@H](CCCC(=O)C(O)=O)C(O)=O
C11H15NO8
InChI=1S/C11H15NO8/c13-7(11(19)20)3-1-2-6(10(17)18)12-8(14)4-5-9(15)16/h6H,1-5H2,(H,12,14)(H,15,16)(H,17,18)(H,19,20)/t6-/m0/s1
SDVXSCSNVVZWDD-LURJTMIESA-N
(2S)-2-(3-carboxypropanamido)-6-oxoheptanedioic acid
289.2387
289.079766461
-2.31
4
(2S)-2-(3-carboxypropanamido)-6-oxoheptanedioic acid
0
-3
C04462
(2s)-2-(3-carboxypropanamido)-6-oxoheptanedioate;(2s)-2-(3-carboxypropanamido)-6-oxoheptanedioic acid;(s)-2-(succinylamino)-6-oxoheptanedioate;(s)-2-(succinylamino)-6-oxoheptanedioic acid;L-2-succinylamino-6-oxoheptanedioate;L-2-succinylamino-6-oxoheptanedioic acid;N-succinyl-2-l-amino-6-oxoheptanedioate;N-succinyl-2-l-amino-6-oxoheptanedioic acid;N-succinyl-2-amino-6-oxo-l-pimelic acid;N-succinyl-l-2-amino-6-oxoheptanedioate;N-succinyl-l-2-amino-6-oxoheptanedioic acid;N-succinyl-l-2-amino-6-oxopimelate;N-succinyl-epsilon-keto-l-aminopimelic acid;Succinyl-epsilon-keto-alpha-aminopimelate;1,7-heptanedioate;1,7-heptanedioic acid;6-carboxyhexanoate;6-carboxyhexanoic acid;Heptandioate;Heptandioic acid;Heptane-1,7-dioate;Heptane-1,7-dioic acid;Heptanedioate;Heptanedioic acid;Pilerate;Pileric acid;Pimelate;Pimelic acid;N-succinyl-2-amino-6-oxo-l-pimelate;N-succinyl-2-amino-6-ketopimelic acid;N-succinyl-epsilon-keto-l-aminopimelate
PW_C007810
NS2A6K
95
L-Glutamic acid
HMDB0000148
Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid).
56-86-0
C00025
33032
16015
GLT
30572
DB00142
N[C@@H](CCC(O)=O)C(O)=O
C5H9NO4
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
WHUUTDBJXJRKMK-VKHMYHEASA-N
(2S)-2-aminopentanedioic acid
147.1293
147.053157781
-0.26
3
L-glutamic acid
0
-1
FDB012535
(2s)-2-aminopentanedioate;(2s)-2-aminopentanedioic acid;(s)-(+)-glutamate;(s)-(+)-glutamic acid;(s)-2-aminopentanedioate;(s)-2-aminopentanedioic acid;(s)-glutamate;(s)-glutamic acid;1-amino-propane-1,3-dicarboxylate;1-amino-propane-1,3-dicarboxylic acid;1-aminopropane-1,3-dicarboxylate;1-aminopropane-1,3-dicarboxylic acid;2-aminoglutarate;2-aminoglutaric acid;2-aminopentanedioate;2-aminopentanedioic acid;Aciglut;Aminoglutarate;Aminoglutaric acid;E;Glt;Glu;Glusate;Glut;Glutacid;Glutamicol;Glutamidex;Glutaminate;Glutaminic acid;Glutaminol;Glutaton;L-(+)-glutamate;L-(+)-glutamic acid;L-glu;L-glutamate;L-glutaminate;L-glutaminic acid;L-a-aminoglutarate;L-a-aminoglutaric acid;L-alpha-aminoglutarate;L-alpha-aminoglutaric acid;A-aminoglutarate;A-aminoglutaric acid;A-glutamate;A-glutamic acid;Alpha-aminoglutarate;Alpha-aminoglutaric acid;Alpha-glutamate;Alpha-glutamic acid;Acide glutamique;Acido glutamico;Acidum glutamicum;Glutamate;Glutamic acid;L-glutaminsaeure
PW_C000095
Glu
16
2
44
3
65
8
119
1
138
4
164
14
969
9
1105
42
1448
50
1456
26
1462
54
5323
111
5344
113
5415
117
5439
118
5565
132
5631
107
5632
108
5859
105
6006
147
6071
157
6191
94
6531
85
6838
187
6844
188
7092
72
7093
71
7165
205
7182
207
7514
224
7518
151
8208
225
8373
220
11792
198
11855
161
12004
222
12621
31
12683
289
12697
290
42348
315
42349
318
42845
320
77020
253
77332
133
77525
112
77971
346
77977
327
77981
347
78291
345
80649
135
120023
124
120040
122
120086
407
120347
406
120692
126
120816
418
121147
423
121153
424
121157
425
122833
119
122997
120
123299
443
123401
454
123719
458
123725
459
123729
460
125401
299
125418
297
125457
481
125667
479
125769
301
125802
489
126941
388
126995
206
127162
501
127257
506
134
Oxoglutaric acid
HMDB0000208
Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207).
328-50-7
C00026
51
30915
2-KETOGLUTARATE
50
DB02926
OC(=O)CCC(=O)C(O)=O
C5H6O5
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
KPGXRSRHYNQIFN-UHFFFAOYSA-N
2-oxopentanedioic acid
146.0981
146.021523302
-0.44
2
oxoglutarate
0
-2
FDB003361
2-ketoglutarate;2-ketoglutaric acid;2-oxo-1,5-pentanedioate;2-oxo-1,5-pentanedioic acid;2-oxoglutarate;2-oxoglutaric acid;2-oxopentanedioate;2-oxopentanedioic acid;Oxoglutarate;Alpha-ketoglutaric acid;Oxoglutaric acid;A-ketoglutarate;A-ketoglutaric acid;Alpha-ketoglutarate;α-ketoglutarate;α-ketoglutaric acid
PW_C000134
AKG
15
2
42
3
141
4
146
8
499
18
673
31
1108
42
1263
5
1447
50
1455
26
1467
54
5375
103
5414
117
5438
118
5564
132
6008
147
6036
155
6069
157
6092
161
6482
178
6530
85
7471
222
7515
224
7519
151
8209
225
8374
220
11863
198
12681
289
77054
253
77135
133
77481
111
77523
112
77746
129
77967
345
77970
346
77976
327
77984
347
78425
334
80018
368
80694
135
113162
94
119972
406
120022
124
120084
407
120174
122
120552
414
120814
418
120989
408
121146
423
121152
424
121160
425
122757
120
122831
119
123186
450
123399
454
123554
374
123718
458
123724
459
123732
460
125357
479
125400
299
125455
481
125533
297
125800
489
125929
482
126900
501
126940
388
126993
206
127066
205
127255
506
127388
502
7811
N-Succinyl-L,L-2,6-diaminopimelate
HMDB0012267
N-Succinyl-L,L-2,6-diaminopimelate is an intermediate in lysine biosynthesis. It is the third to last step in the synthesis of lysine and is converted. from N-Succinyl-2-amino-6-ketopimelate via the enzyme succinyldiaminopimelate transferase (EC 2.6.1.17). It is then converted to L,L-diaminopimelate via the enzyme succinyl-diaminopimelate desuccinylase (EC 3.5.1.18).
26605-36-7
C04421
25202447
N-SUCCINYLLL-2-6-DIAMINOPIMELATE
NC(CCC[C@H](NC(=O)CCC(O)=O)C(O)=O)C(O)=O
C11H18N2O7
InChI=1S/C11H18N2O7/c12-6(10(17)18)2-1-3-7(11(19)20)13-8(14)4-5-9(15)16/h6-7H,1-5,12H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)/t6?,7-/m0/s1
GLXUWZBUPATPBR-MLWJPKLSSA-N
(6S)-2-amino-6-(3-carboxypropanamido)heptanedioic acid
290.2698
290.11140094
-1.70
5
(6S)-2-amino-6-(3-carboxypropanamido)heptanedioic acid
0
-2
C04421
L,l-sdap;N-succinyl-l-2,6-diaminoheptanedioate;N-succinyl-l-2,6-diaminoheptanedioic acid;N-succinyl-ll-2,6-diaminoheptanedioate;N-succinyl-ll-2,6-diaminoheptanedioic acid;N-succinyl-ll-2,6-diaminopimelate
PW_C007811
N-Succi
174
Succinic acid
HMDB0000254
Succinic acid is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle. The succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate. (PMID 16143825) Mutations in the four genes encoding the subunits of the mitochondrial respiratory chain succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntington's disease. (PMID 11803021).
110-15-6
C00042
1110
15741
SUC
1078
DB00139
OC(=O)CCC(O)=O
C4H6O4
InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
KDYFGRWQOYBRFD-UHFFFAOYSA-N
butanedioic acid
118.088
118.02660868
0.25
2
succinic acid
0
-2
FDB001931
1,2-ethanedicarboxylate;1,2-ethanedicarboxylic acid;1,4-butanedioate;1,4-butanedioic acid;Amber acid;Asuccin;Dihydrofumarate;Dihydrofumaric acid;Katasuccin;Succinate;Wormwood acid;Acide butanedioique;Acide succinique;Acidum succinicum;Bernsteinsaeure;Butandisaeure;Butanedionic acid;E363;Ethylenesuccinic acid;Hooc-ch2-ch2-cooh;Spirit of amber;Butanedionate;Ethylenesuccinate
PW_C000174
Succini
152
3
239
4
502
18
507
8
676
31
1265
5
4255
17
5383
103
6042
155
6102
161
6454
107
6455
108
6489
178
6764
117
6836
166
7362
163
7455
219
7456
220
7477
222
11866
198
12142
151
13259
223
42368
318
42369
315
42402
322
77143
133
77213
134
77483
111
77738
112
77749
129
78426
334
80024
368
80721
119
112846
308
113428
1
119984
406
120192
407
120385
122
120555
414
120990
408
122565
384
122767
120
123029
135
123189
450
123555
374
125138
121
125364
479
125549
481
125930
482
126713
480
126906
501
127082
206
127389
502
128304
391
40840
L,L-diaminopimelate
2,6-Diaminopimelic acid, also known as LL-2,6-diaminopimelate or L,L-a2PM, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 2,6-Diaminopimelic acid exists as a solid, soluble (in water), and a moderately acidic compound (based on its pKa). 2,6-Diaminopimelic acid has been detected in multiple biofluids, such as feces, urine, and blood. Within the cell, 2,6-diaminopimelic acid is primarily located in the cytoplasm. 2,6-Diaminopimelic acid can be converted into N-acetyl-LL-2,6-diaminopimelic acid and N-succinyl-LL-2,6-diaminopimelic acid. Outside of the human body, 2,6-diaminopimelic acid can be found in a number of food items such as nopal, pine nut, swiss chard, and borage. This makes 2,6-diaminopimelic acid a potential biomarker for the consumption of these food products.
57609
N[C@@H](CCC[C@H](N)C(O)=O)C(O)=O
C7H14N2O4
InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1
GMKMEZVLHJARHF-WHFBIAKZSA-N
(2S,6S)-2,6-diaminoheptanedioic acid
190.1971
190.095356946
-1.13
4
diamino-pimelic acid
0
0
L,l-a2pm, l,l-dap, l,l-2,6-diaminopimelate, l,l-2,6-diaminoheptanedioate
PW_C040840
LLD
40841
meso-diaminopimelate
Meso-2,6-diaminopimelic acid, also known as meso-diaminoheptanedioate or meso-a2PM, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Meso-2,6-diaminopimelic acid is soluble (in water) and a moderately acidic compound (based on its pKa).
57791
[H][C@](N)(CCC[C@@]([H])(N)C(O)=O)C(O)=O
C7H14N2O4
InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5+
GMKMEZVLHJARHF-SYDPRGILSA-N
(2R,6S)-2,6-diaminoheptanedioic acid
190.1971
190.095356946
-1.13
4
diaminopimelic acid
0
0
Meso-2,6-diaminopimelate, meso-a2pm, meso-diaminoheptanedioate, meso-2,6-diaminoheptanedioate, meso-1-α,ε-diaminopimelate, d,l-diaminopimelate, d,l-dap, d,l-meso-diaminoheptanedioate, m-dap
PW_C040841
meso-di
8212
225
118
L-Lysine
HMDB0000182
L-lysine is an essential amino acid. Normal requirements for lysine have been found to be about 8 g per day or 12 mg/kg in adults. Children and infants need more- 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. Lysine is highly concentrated in muscle compared to most other amino acids. Lysine is high in foods such as wheat germ, cottage cheese and chicken. Of meat products, wild game and pork have the highest concentration of lysine. Fruits and vegetables contain little lysine, except avocados. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Excess arginine antagonizes lysine. Several inborn errors of lysine metabolism are known. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Lysine also may be a useful adjunct in the treatment of osteoporosis. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine may be an adjunct therapy because it reduces calcium losses in urine. Lysine deficiency also may result in immunodeficiency. Requirements for this amino acid are probably increased by stress. Lysine toxicity has not occurred with oral doses in humans. Lysine dosages are presently too small and may fail to reach the concentrations necessary to prove potential therapeutic applications. Lysine metabolites, amino caproic acid and carnitine have already shown their therapeutic potential. Thirty grams daily of amino caproic acid has been used as an initial daily dose in treating blood clotting disorders, indicating that the proper doses of lysine, its precursor, have yet to be used in medicine. Low lysine levels have been found in patients with Parkinson's, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize the level and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) and herpes simplex. It stops the growth of herpes simplex in culture, and has helped to reduce the number and occurrence of cold sores in clinical studies. Dosing has not been adequately studied, but beneficial clinical effects occur in doses ranging from 100 mg to 4 g a day. Higher doses may also be useful, and toxicity has not been reported in doses as high as 8 g per day. Diets high in lysine and low in arginine can be useful in the prevention and treatment of herpes. Some researchers think herpes simplex virus is involved in many other diseases related to cranial nerves such as migraines, Bell's palsy and Meniere's disease. Herpes blister fluid will produce fatal encephalitis in the rabbit. (http://www.dcnutrition.com).
56-87-1
C00047
5962
18019
LYS
5747
DB00123
NCCCC[C@H](N)C(O)=O
C6H14N2O2
InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1
KDXKERNSBIXSRK-YFKPBYRVSA-N
(2S)-2,6-diaminohexanoic acid
146.1876
146.105527702
-0.14
3
L-lysine
0
1
FDB000474
(+)-s-lysine;(s)-2,6-diaminohexanoate;(s)-2,6-diaminohexanoic acid;(s)-2,6-diamino-hexanoate;(s)-2,6-diamino-hexanoic acid;(s)-lysine;(s)-a,e-diaminocaproate;(s)-a,e-diaminocaproic acid;2,6-diaminohexanoate;2,6-diaminohexanoic acid;6-amino-aminutrin;6-amino-l-norleucine;Aminutrin;L-(+)-lysine;L-2,6-diainohexanoate;L-2,6-diainohexanoic acid;L-2,6-diaminocaproate;L-2,6-diaminocaproic acid;L-lys;Lys;Lysine;Lysine acid;A-lysine;Alpha-lysine;H-lys-oh;(s)-alpha,epsilon-diaminocaproic acid;6-ammonio-l-norleucine;K;L-lysin;(s)-a,epsilon-diaminocaproate;(s)-a,epsilon-diaminocaproic acid;(s)-alpha,epsilon-diaminocaproate;(s)-α,epsilon-diaminocaproate;(s)-α,epsilon-diaminocaproic acid
PW_C000118
Lys
581
15
632
30
1065
3
1091
8
5299
105
5303
107
5304
108
5552
114
8214
225
42370
318
42371
315
77730
338
78275
112
78287
111
120504
409
120536
413
120780
407
120807
122
123110
137
123170
449
123372
119
123392
135
125719
483
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
123
L-Aspartic acid
HMDB0000191
Aspartic acid (Asp, D), also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong (Wikipedia). Aspartic acid is a nonessential amino acid that is made from glutamic acid by enzymes using vitamin B6. The amino acid has important roles in the urea cycle and DNA metabolism. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, with the amino acid phenylalanine, is a part of a new natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners, and is probably safe in normal doses to all except phenylketonurics. The jury is still out on the long-term effects it has on many brain neurohormones. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Many claims have been made for the special value of administering aspartic acid in the form of potassium and magnesium salts. Since aspartic acid is relatively nontoxic, studies are now in progress to elucidate its pharmacological and therapeutic roles (http://www.dcnutrition.com/AminoAcids).
56-84-8
C00049
44367445
17053
L-ASPARTATE
5745
DB00128
N[C@@H](CC(O)=O)C(O)=O
C4H7NO4
InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1
CKLJMWTZIZZHCS-REOHCLBHSA-N
(2S)-2-aminobutanedioic acid
133.1027
133.037507717
0.03
3
L-aspartic acid
0
-1
FDB012567
Asp;(+)-aspartate;(+)-aspartic acid;(2s)-aspartate;(2s)-aspartic acid;(l)-aspartate;(l)-aspartic acid;(r)-2-aminosuccinate;(s)-(+)-aspartate;(s)-(+)-aspartic acid;(s)-2-aminosuccinate;(s)-2-aminosuccinic acid;(s)-aminobutanedioate;(s)-aminobutanedioic acid;(s)-aspartate;(s)-aspartic acid;(s)-amino-butanedioate;(s)-amino-butanedioic acid;2-amino-3-methylsuccinate;2-amino-3-methylsuccinic acid;2-aminosuccinate;2-aminosuccinic acid;Aminosuccinate;Asparagate;Asparagic acid;Asparaginate;Asparaginic acid;Asparatate;Aspartate;H-asp-oh;L-(+)-aspartate;L-(+)-aspartic acid;L-aminosuccinate;L-aminosuccinic acid;L-asparagate;L-asparagic acid;L-asparaginate;L-asparaginic acid;L-aspartate;Alpha-aminosuccinate;Alpha-aminosuccinic acid;(s)-2-aminobutanedioic acid;Aspartic acid;D;L-asparaginsaeure;(s)-2-aminobutanedioate
PW_C000123
Asp
48
8
93
9
1101
3
1103
4
1104
42
1994
2
5663
107
5664
108
6851
188
7570
160
8185
225
11802
198
12686
290
12704
291
42363
318
42364
315
77323
111
77510
132
77532
113
78288
133
78289
345
79307
112
80699
135
119878
232
119881
117
120037
122
120421
124
120809
406
120813
418
123057
118
123394
120
123398
454
125415
297
125795
479
125799
489
126955
205
127250
501
127254
506
127555
388
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
5952
Lysine-sensitive aspartokinase 3
P08660
Involved in amino acid binding. ATP + L-aspartate = ADP + 4-phospho-L- aspartate.
lysC
b4024
AP009048
3
2.7.2.4
6138
Aspartate-semialdehyde dehydrogenase
P0A9Q9
Involved in aspartate-semialdehyde dehydrogenase activity. L-aspartate 4-semialdehyde + phosphate + NADP(+) = L-4-aspartyl phosphate + NADPH.
asd
b3433
AP009048
3
1.2.1.11
6002
Dihydrodipicolinate synthase
P0A6L2
Involved in catalytic activity. L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O.
dapA
b2478
AP009048
3
4.3.3.7
8575
101
135742
100
135757
626
5867
Dihydrodipicolinate reductase
P04036
Involved in dihydrodipicolinate reductase activity. 2,3,4,5-tetrahydrodipicolinate + NAD(P)(+) = 2,3-dihydrodipicolinate + NAD(P)H.
dapB
b0031
AP009048
3
1.17.1.8
8576
101
135743
100
135758
626
6117
2,3,4,5-tetrahydropyridine-2,6-dicarboxylate N-succinyltransferase
P0A9D8
Involved in 2,3,4,5-tetrahydropyridine-2,6-dicarboxylate N-succinyltransferase activity. Succinyl-CoA + (S)-2,3,4,5-tetrahydropyridine- 2,6-dicarboxylate + H(2)O = CoA + N-succinyl-L-2-amino-6- oxoheptanedioate.
dapD
b0166
AP009048
3
2.3.1.117
8577
101
135744
100
135759
626
6372
Acetylornithine/succinyldiaminopimelate aminotransferase
P18335
Involved in transaminase activity. Involved in both the arginine and lysine biosynthetic pathways.
argD
b3359
AP009048
3
2.6.1.11; 2.6.1.17
8578
101
135745
100
135760
626
6234
Succinyl-diaminopimelate desuccinylase
P0AED7
Involved in metallopeptidase activity. Catalyzes the hydrolysis of N-succinyl-L,L- diaminopimelic acid (SDAP), forming succinate and LL-2,6- diaminoheptanedioate (DAP), an intermediate involved in the bacterial biosynthesis of lysine and meso-diaminopimelic acid, an essential component of bacterial cell walls.
dapE
b2472
AP009048
3
3.5.1.18
5998
Diaminopimelate epimerase
P0A6K1
Involved in diaminopimelate epimerase activity. LL-2,6-diaminoheptanedioate = meso- diaminoheptanedioate.
dapF
b3809
AP009048
3
5.1.1.7
8579
101
135746
100
135761
626
5835
Diaminopimelate decarboxylase
P00861
Involved in catalytic activity. Meso-2,6-diaminoheptanedioate = L-lysine + CO(2).
lysA
b2838
AP009048
3
4.1.1.20
7325
Aerobic C4-dicarboxylate transport protein
P0A830
Involved in symporter activity. Responsible for the aerobic transport of the dicarboxylates fumarate, L- and D-malate and to a lesser extent succinate, from the periplasm across the inner membrane.
dctA
b3528
AP009048
3
8580
109
135756
311
135771
628
7203
Proton glutamate symport protein
P21345
Involved in sodium:dicarboxylate symporter activity. This carrier protein is part of the Na(+)-independent, binding-protein-independent glutamate-aspartate transport system.
gltP
b4077
AP009048
3
8570
109
135755
311
135770
628
6864
Anaerobic C4-dicarboxylate transporter dcuC
P0ABP4
Involved in C4-dicarboxylate transmembrane transporter activity. Responsible for the transport of C4-dicarboxylates during anaerobic growth.
dcuC
AE005174
3
8581
109
135752
311
135767
628
7031
Anaerobic C4-dicarboxylate transporter dcuA
P0ABN5
Involved in C4-dicarboxylate transmembrane transporter activity. Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane.
dcuA
b4138
AP009048
3
8582
109
135753
311
135768
628
6863
Anaerobic C4-dicarboxylate transporter dcuB
P0ABP1
Involved in C4-dicarboxylate transmembrane transporter activity. Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane.
dcuB
AE005174
3
8583
109
135754
311
135769
628
7069
Putative sulfate transporter ychM
P0AFR2
Involved in secondary active sulfate transmembrane transporter activity. Possible sulfate transporter.
ychM
b1206
AP009048
3
8584
109
135751
311
135766
628
7346
Glutamate/aspartate transport ATP-binding protein gltL
P0AAG3
Involved in nucleotide binding. Part of the binding-protein-dependent transport system for glutamate and aspartate. Probably responsible for energy coupling to the transport system.
gltL
b0652
AP009048
3
5633
109
135747
311
135762
628
136119
649
7047
Glutamate/aspartate transport system permease protein gltK
P0AER5
Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane.
gltK
b0653
AP009048
3
5634
109
135748
311
135763
628
136120
649
7046
Glutamate/aspartate transport system permease protein gltJ
P0AER3
Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane.
gltJ
b0654
AP009048
3
5635
109
135749
311
135764
628
136121
649
7489
Glutamate/aspartate periplasmic-binding protein
P37902
Part of the binding-protein-dependent transport system for glutamate and aspartate. Binds to both aspartate and glutamate.
gltI
b0655
AP009048
3
5636
109
135750
311
135765
628
136122
649
1237
Aspartate kinase
3
PW_P001237
1430
5952
2
1238
aspartate semialdehyde dehydrogenase
3
PW_P001238
1431
6138
2
1239
4-hydroxy-tetrahydrodipicolinate synthase
3
PW_P001239
1432
6002
4
1240
4-hydroxy-tetrahydrodipicolinate reductase
3
PW_P001240
1433
5867
4
1241
tetrahydrodipicolinate succinylase
3
PW_P001241
1434
6117
2
1242
N-succinyldiaminopimelate aminotransferase
3
PW_P001242
1435
6372
2
1243
N-succinyl-L-diaminopimelate desuccinylase
3
PW_P001243
1436
6234
4
1244
diaminopimelate epimerase
3
PW_P001244
1437
5998
2
1245
diaminopimelate decarboxylase
3
PW_P001245
1438
5835
4
3776
C4 dicarboxylate / orotate:H+ symporter
3
PW_P003776
10688
7325
1662
glutamate / aspartate : H+ symporter GltP
3
PW_P001662
1957
7203
3777
dicarboxylate transporter
3
PW_P003777
10689
6864
10690
7031
10691
6863
3781
C4 dicarboxylate / C4 monocarboxylate transporter DauA
3
PW_P003781
10695
7069
1436
glutamate / aspartate ABC transporter
3
PW_P001436
1674
7346
1675
7047
1676
7046
1677
7489
2533
false
PW_R002533
Right
9839
40841
1
Compound
false
9840
40034
1
Compound
false
9841
118
1
Compound
false
9842
1316
1
Compound
false
2500
1245
4.1.1.20
2525
false
PW_R002525
Right
9803
123
1
Compound
false
9804
414
1
Compound
false
9805
1034
1
Compound
false
9806
7795
1
Compound
false
2492
1237
2.7.2.4
2526
false
PW_R002526
Right
9807
7795
1
Compound
false
9808
146
1
Compound
false
9809
40034
1
Compound
false
9810
1104
1
Compound
false
9811
143
1
Compound
false
9812
40837
1
Compound
false
2493
1238
1.2.1.11
2527
false
PW_R002527
Right
9813
40837
1
Compound
false
9814
164
1
Compound
false
9815
40034
1
Compound
false
9816
1420
1
Compound
false
9817
40838
1
Compound
false
2494
1239
4.3.3.7
2528
false
PW_R002528
Right
9818
40838
1
Compound
false
9819
40034
1
Compound
false
9820
146
1
Compound
false
9821
1420
1
Compound
false
9822
143
1
Compound
false
9823
40839
1
Compound
false
2495
1240
1.17.1.8
2529
false
PW_R002529
Right
9824
40839
1
Compound
false
9825
808
1
Compound
false
9826
1420
1
Compound
false
9827
1099
1
Compound
false
9828
7810
1
Compound
false
2496
1241
2.3.1.117
2530
false
PW_R002530
Right
9829
7810
1
Compound
false
9830
95
1
Compound
false
9831
7811
1
Compound
false
9832
134
1
Compound
false
2497
1242
2531
false
PW_R002531
Right
9833
7811
1
Compound
false
9834
1420
1
Compound
false
9835
174
1
Compound
false
9836
40840
1
Compound
false
2498
1243
3.5.1.18
2532
false
PW_R002532
Right
9837
40840
1
Compound
false
9838
40841
1
Compound
false
2499
1244
5.1.1.7
108
PW_RCT000108
Right
652
108
123
Compound
1
107
653
108
414
Compound
1
108
654
108
1420
Compound
1
108
655
108
1034
Compound
1
108
656
108
1104
Compound
1
108
657
108
40034
Compound
1
108
658
108
123
Compound
1
108
108
455
PW_T000455
566
123
1
Compound
107
108
Right
390
3781
2015-06-17T13:25:16-06:00
2015-06-17T13:25:16-06:00
109
454
PW_T000454
564
123
1
Compound
107
108
Right
565
174
1
Compound
107
108
Left
389
3777
2015-06-17T12:10:55-06:00
2015-06-17T12:10:55-06:00
109
453
PW_T000453
562
123
1
Compound
107
108
Right
563
40034
2
Compound
107
108
Right
388
1662
2015-06-17T12:03:05-06:00
2015-06-17T12:03:05-06:00
109
452
PW_T000452
560
123
1
Compound
107
108
Right
561
40034
1
Compound
107
108
Right
387
3776
2015-06-17T11:59:01-06:00
2015-06-17T11:59:01-06:00
109
987
Inhibition
PW_I000987
1973
118
Compound
1
1974
1239
ProteinComplex
1
988
Inhibition
PW_I000988
1975
118
Compound
1
1976
1237
ProteinComplex
1
13313
414
42
false
920
904
10
regular
50
30
13314
1034
43
false
930
1104
10
regular
50
30
13316
7795
3
false
1000
1189
10
regular
100
110
13317
146
62
false
935
1354
10
regular
50
30
13318
40034
55
false
1115
1325
10
regular
78
78
13319
1104
46
false
936
1537
10
regular
44
43
13320
143
61
false
1120
1539
10
regular
50
30
13322
40837
3
false
997
1634
10
regular
100
110
13323
164
3
false
1137
1794
10
regular
100
100
13324
40034
55
false
895
2080
10
regular
78
78
13325
1420
49
false
1103
2075
10
regular
78
78
13327
40838
3
false
1000
2234
10
regular
100
130
13328
40034
55
false
905
2361
10
regular
78
78
13329
146
62
false
1103
2384
10
regular
50
30
13330
1420
49
false
903
2656
10
regular
78
78
13331
143
61
false
1111
2679
10
regular
50
30
13333
40839
3
false
1000
2824
10
regular
100
110
13334
808
3
false
1375
2959
10
regular
100
100
13335
1420
49
false
1385
2726
10
regular
78
78
13338
7810
3
false
2000
2824
10
regular
100
120
13339
95
3
false
1860
2579
10
regular
100
110
13341
134
3
false
1860
2314
10
regular
100
110
13342
7811
3
false
2000
2179
10
regular
100
120
13343
1420
49
false
1891
2091
10
regular
78
78
13344
174
3
false
1875
1784
10
regular
100
100
13346
40840
3
false
2000
1634
10
regular
100
110
13348
40841
3
false
2000
1234
10
regular
100
110
13349
40034
55
false
1887
1141
10
regular
78
78
13350
118
3
false
1500
979
10
regular
100
100
13351
1316
52
false
1812
906
10
regular
78
78
22640
123
107
3
false
553
206
10
regular
100
110
22642
40034
107
55
false
438
297
10
regular
78
78
22643
40034
108
55
false
468
572
10
regular
78
78
22644
123
107
3
false
798
196
10
regular
100
110
22646
40034
107
55
false
708
317
10
regular
78
78
22647
40034
108
55
false
913
582
10
regular
78
78
22648
123
107
3
false
1228
195
10
regular
100
110
22650
174
107
3
false
1108
280
10
regular
100
100
22651
174
108
3
false
1298
560
10
regular
100
100
22652
123
107
3
false
1523
200
10
regular
100
110
22653
123
108
3
false
998
725
10
regular
100
110
22657
1034
108
43
false
2003
675
10
regular
50
30
22658
1104
108
46
false
1753
593
10
regular
44
43
22659
40034
108
55
false
1992
536
10
regular
78
78
2109998
1099
117
85
false
1775
2994
10
regular
50
30
2111196
123
107
3
false
1850
195
10
regular
100
110
2111197
414
108
42
false
1805
330
10
regular
50
30
2111198
1420
108
49
false
1970
306
10
regular
78
78
7131
5952
6
false
972
989
8
subunit
regular
160
80
7132
6138
6
false
969
1419
8
subunit
regular
160
80
7133
6002
101
8
false
982
1939
8
subunit
regular
140
85
7134
5867
101
8
false
981
2509
8
subunit
regular
140
85
7135
6117
101
6
false
1519
2839
8
subunit
regular
160
80
7136
6372
101
6
false
1970
2439
8
subunit
regular
160
80
7137
6234
8
false
1980
1944
8
subunit
regular
140
85
7138
5998
101
6
false
1970
1444
8
subunit
regular
160
80
7139
5835
8
false
1980
989
8
subunit
regular
140
85
10839
7325
109
76
false
527
421
8
subunit
regular
150
70
10840
7203
109
76
false
772
421
8
subunit
regular
150
70
10841
6864
109
76
false
1118
420
8
subunit
regular
150
70
10842
7031
109
76
false
1303
420
9
subunit
regular
150
70
10843
6863
109
76
false
1203
420
8
subunit
regular
150
70
10844
7069
109
76
false
1498
420
8
subunit
regular
150
70
746126
7346
109
76
false
1694
420
8
subunit
regular
150
70
746127
7047
109
76
false
2089
420
8
subunit
regular
150
70
746128
7046
109
76
false
1959
420
8
subunit
regular
150
70
746129
7489
109
76
false
1824
420
8
subunit
regular
150
70
5751
1237
519
7034
7131
5752
1238
519
7035
7132
5753
1239
519
7036
7133
5754
1240
519
7037
7134
5755
1241
519
7038
7135
5756
1242
519
7039
7136
5757
1243
519
7040
7137
5758
1244
519
7041
7138
5759
1245
519
7042
7139
8458
3776
519
10661
10839
8459
1662
519
10662
10840
8460
3777
519
10663
10841
10664
10842
10665
10843
8461
3781
519
10666
10844
633034
1436
519
109
744609
746126
744610
746127
744611
746128
744612
746129
20755
M2050 1234 C2050 1204 2050 1104 2050 1074
5
false
18
20756
M1965 1180 C2050 1179 2050 1104 2050 1074
5
false
18
20757
M1600 1029 C1681 1028 1909 1029 1980 1029
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
20758
M1851 984 C1850 1033 1891 1027 1980 1029
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
33611
M1573 310 C1573 340 1573 390 1573 420
83
false
18
33612
M1098 780 C1331 782 1561 749 1573 490
83
false
18
true
M 25.946855044164835 664.9282229629626 L 11 663.6666666666666 L 17.380887721185843 677.241800989745
false
2863690
M1278 305 C1278 335 1278 390 1278 420
83
false
18
2863691
M1048 725 C1225 727 1275 588 1278 490
83
false
18
true
M 347.94685504416486 790.261556296296 L 333 789 L 339.38088772118584 802.5751343230784
false
2863692
M1208 330 C1278 340 1278 390 1278 420
83
false
18
true
M 347.94685504416486 790.261556296296 L 333 789 L 339.38088772118584 802.5751343230784
false
2863693
M1298 610 C1265 581 1279 522 1278 490
83
false
18
2863748
M848 306 C846 355 849 403 847 421
83
false
18
2863749
M998 780 C845 777 850 758 847 491
83
false
18
true
M 346.94685504416486 790.261556296296 L 332 789 L 338.38088772118584 802.5751343230784
false
2863750
M786 356 C816 356 843 354 847 421
83
false
18
2863751
M913 621 C849 603 853 514 847 491
83
false
18
true
M 346.94685504416486 790.261556296296 L 332 789 L 338.38088772118584 802.5751343230784
false
2863765
M603 316 C604 360 602 384 602 421
83
false
18
2863766
M998 780 C706 780 600 795 602 491
83
false
18
true
M 346.94685504416486 790.261556296296 L 332 789 L 338.38088772118584 802.5751343230784
false
2863767
M516 336 C546 336 605 345 602 421
83
false
18
2863768
M546 611 C620 637 601 520 602 491
83
false
18
true
M 346.94685504416486 790.261556296296 L 332 789 L 338.38088772118584 802.5751343230784
false
2864438
M1048 835 C1048 865 1052 959 1052 989
5
false
18
2864439
M970 919 C1051 915 1052 961 1052 989
5
false
18
2864440
M985 1124 C1058 1126 1052 1099 1052 1069
5
false
18
true
M 362.94685504416486 1386.261556296296 L 348 1385 L 354.38088772118584 1398.5751343230784
false
2864441
M1050 1189 C1050 1159 1052 1099 1052 1069
5
false
18
true
M 362.94685504416486 1386.261556296296 L 348 1385 L 354.38088772118584 1398.5751343230784
false
2866116
M1050 1299 C1050 1329 1049 1389 1049 1419
5
false
18
2866117
M989 1369 C1027 1368 1049 1389 1049 1419
5
false
18
2866118
M1115 1364 C1070 1366 1054 1388 1049 1419
5
false
18
2866119
M975 1553.5 C1008 1551.5 1049 1529 1049 1499
5
false
18
true
M 427.94685504416486 1755.261556296296 L 413 1754 L 419.38088772118584 1767.5751343230784
false
2866120
M1120 1554 C1067 1559 1049 1521 1049 1499
5
false
18
true
M 427.94685504416486 1755.261556296296 L 413 1754 L 419.38088772118584 1767.5751343230784
false
2866121
M1047 1634 C1047 1604 1049 1529 1049 1499
5
false
18
true
M 427.94685504416486 1755.261556296296 L 413 1754 L 419.38088772118584 1767.5751343230784
false
2866298
M1047 1744 C1047 1774 1052 1909 1052 1939
5
false
18
2866299
M1137 1844 C1071 1838 1052 1909 1052 1939
5
false
18
2866300
M978 2119 C1016 2109 1052 2054 1052 2024
5
false
18
true
M 434.94685504416486 2147.261556296296 L 420 2146 L 426.38088772118584 2159.575134323078
false
2866301
M1108 2114 C1061 2093 1052 2054 1052 2024
5
false
18
true
M 434.94685504416486 2147.261556296296 L 420 2146 L 426.38088772118584 2159.575134323078
false
2866302
M1050 2234 C1050 2204 1052 2054 1052 2024
5
false
18
true
M 434.94685504416486 2147.261556296296 L 420 2146 L 426.38088772118584 2159.575134323078
false
2866442
M1050 2364 C1050 2394 1051 2479 1051 2509
5
false
18
2866443
M983 2400 C1039 2401 1051 2479 1051 2509
5
false
18
2866444
M1103 2399 C1051 2403 1051 2479 1051 2509
5
false
18
2866445
M981 2695 C1057 2702 1051 2624 1051 2594
5
false
18
true
M 498.94685504416486 2734.261556296296 L 484 2733 L 490.38088772118584 2746.575134323078
false
2866446
M1111 2694 C1049 2708 1051 2624 1051 2594
5
false
18
true
M 498.94685504416486 2734.261556296296 L 484 2733 L 490.38088772118584 2746.575134323078
false
2866447
M1050 2824 C1050 2794 1051 2624 1051 2594
5
false
18
true
M 498.94685504416486 2734.261556296296 L 484 2733 L 490.38088772118584 2746.575134323078
false
2866531
M1100 2879 C1227 2880 1405 2876 1519 2879
5
false
18
2866532
M1425 2959 C1423 2923 1433 2877 1519 2879
5
false
18
2866533
M1424 2804 C1417 2843 1443 2878 1519 2879
5
false
18
2866534
M1800 2994 C1800 2917 1774 2880 1679 2879
5
false
18
true
M 498.94685504416486 3220.261556296296 L 484 3219 L 490.38088772118584 3232.575134323078
false
2866535
M2000 2884 C1937 2884 1752 2879 1679 2879
5
false
18
true
M 498.94685504416486 3220.261556296296 L 484 3219 L 490.38088772118584 3232.575134323078
false
2866967
M2050 2824 C2049 2737 2050 2617 2050 2519
5
false
18
2866968
M1960 2634 C1990 2634 2049 2623 2050 2519
5
false
18
2866969
M2050 2299 C2050 2342 2050 2384 2050 2439
5
false
18
true
M 804.9468550441649 3728.261556296296 L 790 3727 L 796.3808877211858 3740.575134323078
false
2866970
M1960 2369 C2014 2368 2051 2393 2050 2439
5
false
18
true
M 804.9468550441649 3728.261556296296 L 790 3727 L 796.3808877211858 3740.575134323078
false
2867134
M2050 2179 C2049 2122 2050 2098 2050 2029
5
false
18
2867135
M1969 2130 C1992 2129 2048 2106 2050 2029
5
false
18
2867136
M1975 1834 C2028 1845 2049 1871 2050 1944
5
false
18
true
M 946.9468550441649 3931.261556296296 L 932 3930 L 938.3808877211858 3943.575134323078
false
2867137
M2050 1744 C2051 1845 2050 1834 2050 1944
5
false
18
true
M 946.9468550441649 3931.261556296296 L 932 3930 L 938.3808877211858 3943.575134323078
false
2867223
M2050 1634 C2050 1604 2050 1554 2050 1524
5
false
18
2867224
M2050 1344 C2050 1374 2050 1414 2050 1444
5
false
18
true
M 948.9468550441649 3743.261556296296 L 934 3742 L 940.3808877211858 3755.575134323078
false
2867370
M2100 1289 C2130 1289 2155 1289 2185 1289
5
false
18
true
M 1924.0096189432334 3567.5 L 1937 3560 L 1924.0096189432334 3552.5
false
2867473
M1550 979 C1549 957 1548 961 1550 909
5
false
18
true
M 1954.0096189432334 2842.5 L 1967 2835 L 1954.0096189432334 2827.5
false
2867745
M1500 1029 C1500 1213 1505.5 1877.5 1503.5 1982.5
148
false
18
2867746
M1122 1979 C1152 1979 1472.5 1979.5 1502.5 1979.5
148
false
18
false
true
M 873.565967322979 2365.686421973218 L 865 2378 L 856.434032677021 2390.313578026782
2867976
M1500 1029 C1457 1029 1372 1028.5 1349 1028.5
148
false
18
2867977
M1132 1029 C1189 1029 1263 1029.5 1350 1028.5
148
false
18
false
true
M 868.565967322979 1248.6864219732176 L 860 1261 L 851.434032677021 1273.3135780267824
2868362
M1900 305 C1900 335 1899 390 1899 420
5
false
18
2868363
M1855 345 C1892 358 1899 390 1899 420
5
false
18
2868364
M1970 345 C1909 354 1899 392 1899 420
5
false
18
2868365
M2003 690 C1947 691 1901 651 1899 490
5
false
18
true
M 988.9468550441649 883.261556296296 L 974 882 L 980.3808877211858 895.5751343230784
false
2868366
M1797 614.5 C1859 607.5 1901 608 1899 490
5
false
18
true
M 988.9468550441649 883.261556296296 L 974 882 L 980.3808877211858 895.5751343230784
false
2868367
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2868368
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3659572
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3634
519
2533
12055
13348
20755
Left
12056
13349
20756
Left
12057
13350
20757
Right
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13351
20758
Right
3835
2500
5759
637174
519
2525
117
2573979
22653
2864438
Left
2573980
13313
2864439
Left
2573981
13314
2864440
Right
2573982
13316
2864441
Right
595213
2492
5751
637502
519
2526
117
2575318
13316
2866116
Left
2575319
13317
2866117
Left
2575320
13318
2866118
Left
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13319
2866119
Right
2575322
13320
2866120
Right
2575323
13322
2866121
Right
595546
2493
5752
637541
519
2527
117
2575484
13322
2866298
Left
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13323
2866299
Left
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13324
2866300
Right
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13325
2866301
Right
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13327
2866302
Right
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2494
5753
637569
519
2528
117
2575593
13327
2866442
Left
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13328
2866443
Left
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13329
2866444
Left
2575596
13330
2866445
Right
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13331
2866446
Right
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13333
2866447
Right
595614
2495
5754
637585
519
2529
117
2575659
13333
2866531
Left
2575660
13334
2866532
Left
2575661
13335
2866533
Left
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2109998
2866534
Right
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13338
2866535
Right
595630
2496
5755
637669
519
2530
117
2575998
13338
2866967
Left
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13339
2866968
Left
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13342
2866969
Right
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13341
2866970
Right
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2497
5756
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519
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117
2576132
13342
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Left
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13343
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Left
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13344
2867136
Right
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13346
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Right
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5757
637720
519
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117
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13346
2867223
Left
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13348
2867224
Right
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2499
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1146
108
519
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2111196
2868362
Left
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2111197
2868363
Left
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2111198
2868364
Left
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22657
2868365
Right
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22658
2868366
Right
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22659
2868367
Right
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22653
2868368
Right
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633034
142
820
455
519
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22652
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Left
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Right
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8461
390
50282
454
519
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22648
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Left
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Right
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22650
2863692
Left
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22651
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Right
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8460
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50287
453
519
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Left
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Right
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22646
2863750
Left
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22647
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Right
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388
50288
452
519
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22640
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Left
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22653
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Right
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Left
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22643
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Right
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2485
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519
117
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13350
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Left
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5753
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Right
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988
519
117
769
13350
2867976
Left
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5751
2867977
Right
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519
14
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2185
1254
16
regular
76525
13348
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Left
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80106
519
14
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1475
839
16
regular
76526
13350
2867473
Left
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109786
519
14
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1167
1654
16
regular
106153
13322
3659572
Left
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1210
2105
1.3
1.3
0
2
92
479
481
910
M424 557 C424 507 474 457 524 457 C1070 457 1780 457 2326 457 C2376 457 2426 507 2426 557 C2426 1318 2426 2308 2426 3069 C2426 3119 2376 3169 2326 3169 C1780 3169 1070 3169 524 3169 C474 3169 424 3119 424 3069 C424 2308 424 1318 424 557
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2002.0
2712.0
911
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1
true
6
2603.0
3301.0