1821
Pathway
Polymyxin Resistance
UDP-glucuronic acid compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate.
The compound 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate hypothetically reacts with water and results in the release of a formic acid and 4-amino-4-deoxy-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate which in turn reacts with a KDO2-lipid A through a 4-amino-4-deoxy-L-arabinose transferase resulting in the release of a di-trans,octa-cis-undecaprenyl phosphate and a L-Ara4N-modified KDO2-Lipid A
Metabolic
PW002052
Center
PathwayVisualizationContext2339
1604
2449
#000099
PathwayVisualization1805
1821
Polymyxin Resistance
UDP-glucuronic acid compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate.
The compound 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate hypothetically reacts with water and results in the release of a formic acid and 4-amino-4-deoxy-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate which in turn reacts with a KDO2-lipid A through a 4-amino-4-deoxy-L-arabinose transferase resulting in the release of a di-trans,octa-cis-undecaprenyl phosphate and a L-Ara4N-modified KDO2-Lipid A
Metabolic
3
3805
19076233
Barchiesi J, Espariz M, Checa SK, Soncini FC: Downregulation of RpoN-controlled genes protects Salmonella cells from killing by the cationic antimicrobial peptide polymyxin B. FEMS Microbiol Lett. 2009 Feb;291(1):73-9. doi: 10.1111/j.1574-6968.2008.01437.x. Epub 2008 Dec 3.
1821
Pathway
3806
16226890
Bretscher LE, Morrell MT, Funk AL, Klug CS: Purification and characterization of the L-Ara4N transferase protein ArnT from Salmonella typhimurium. Protein Expr Purif. 2006 Mar;46(1):33-9. doi: 10.1016/j.pep.2005.08.028. Epub 2005 Sep 28.
1821
Pathway
3807
17686460
Fu W, Yang F, Kang X, Zhang X, Li Y, Xia B, Jin C: First structure of the polymyxin resistance proteins. Biochem Biophys Res Commun. 2007 Oct 5;361(4):1033-7. doi: 10.1016/j.bbrc.2007.07.144. Epub 2007 Aug 2.
1821
Pathway
3808
15939024
Gatzeva-Topalova PZ, May AP, Sousa MC: Structure and mechanism of ArnA: conformational change implies ordered dehydrogenase mechanism in key enzyme for polymyxin resistance. Structure. 2005 Jun;13(6):929-42. doi: 10.1016/j.str.2005.03.018.
1821
Pathway
3809
9371451
Groisman EA, Kayser J, Soncini FC: Regulation of polymyxin resistance and adaptation to low-Mg2+ environments. J Bacteriol. 1997 Nov;179(22):7040-5.
1821
Pathway
3810
18467098
Gunn JS: The Salmonella PmrAB regulon: lipopolysaccharide modifications, antimicrobial peptide resistance and more. Trends Microbiol. 2008 Jun;16(6):284-90. doi: 10.1016/j.tim.2008.03.007. Epub 2008 May 6.
1821
Pathway
3811
18187325
Kline T, Trent MS, Stead CM, Lee MS, Sousa MC, Felise HB, Nguyen HV, Miller SI: Synthesis of and evaluation of lipid A modification by 4-substituted 4-deoxy arabinose analogs as potential inhibitors of bacterial polymyxin resistance. Bioorg Med Chem Lett. 2008 Feb 15;18(4):1507-10. doi: 10.1016/j.bmcl.2007.12.061. Epub 2007 Dec 27.
1821
Pathway
3812
10775270
Kox LF, Wosten MM, Groisman EA: A small protein that mediates the activation of a two-component system by another two-component system. EMBO J. 2000 Apr 17;19(8):1861-72. doi: 10.1093/emboj/19.8.1861.
1821
Pathway
3813
21114395
Lim LM, Ly N, Anderson D, Yang JC, Macander L, Jarkowski A 3rd, Forrest A, Bulitta JB, Tsuji BT: Resurgence of colistin: a review of resistance, toxicity, pharmacodynamics, and dosing. Pharmacotherapy. 2010 Dec;30(12):1279-91. doi: 10.1592/phco.30.12.1279.
1821
Pathway
3814
7565089
Nummila K, Kilpelainen I, Zahringer U, Vaara M, Helander IM: Lipopolysaccharides of polymyxin B-resistant mutants of Escherichia coli are extensively substituted by 2-aminoethyl pyrophosphate and contain aminoarabinose in lipid A. Mol Microbiol. 1995 Apr;16(2):271-8.
1821
Pathway
3815
19767429
Pilonieta MC, Erickson KD, Ernst RK, Detweiler CS: A protein important for antimicrobial peptide resistance, YdeI/OmdA, is in the periplasm and interacts with OmpD/NmpC. J Bacteriol. 2009 Dec;191(23):7243-52. doi: 10.1128/JB.00688-09. Epub 2009 Sep 18.
1821
Pathway
3816
12045108
Raetz CR, Whitfield C: Lipopolysaccharide endotoxins. Annu Rev Biochem. 2002;71:635-700. doi: 10.1146/annurev.biochem.71.110601.135414. Epub 2001 Nov 9.
1821
Pathway
3817
11535605
Trent MS, Ribeiro AA, Doerrler WT, Lin S, Cotter RJ, Raetz CR: Accumulation of a polyisoprene-linked amino sugar in polymyxin-resistant Salmonella typhimurium and Escherichia coli: structural characterization and transfer to lipid A in the periplasm. J Biol Chem. 2001 Nov 16;276(46):43132-44. doi: 10.1074/jbc.M106962200. Epub 2001 Sep 4.
1821
Pathway
3818
11051552
Wosten MM, Kox LF, Chamnongpol S, Soncini FC, Groisman EA: A signal transduction system that responds to extracellular iron. Cell. 2000 Sep 29;103(1):113-25.
1821
Pathway
3819
17928292
Yan A, Guan Z, Raetz CR: An undecaprenyl phosphate-aminoarabinose flippase required for polymyxin resistance in Escherichia coli. J Biol Chem. 2007 Dec 7;282(49):36077-89. doi: 10.1074/jbc.M706172200. Epub 2007 Oct 10.
1821
Pathway
3820
10373459
Zhou Z, Lin S, Cotter RJ, Raetz CR: Lipid A modifications characteristic of Salmonella typhimurium are induced by NH4VO3 in Escherichia coli K12. Detection of 4-amino-4-deoxy-L-arabinose, phosphoethanolamine and palmitate. J Biol Chem. 1999 Jun 25;274(26):18503-14.
1821
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
6
Myocyte
CL:0000187
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
7
Epithelial Cell
CL:0000066
1
Homo sapiens
9606
Eukaryote
Human
2
Bacteria
2
Prokaryote
Bacteria
12
Mus musculus
10090
Eukaryote
Mouse
19
Schizosaccharomyces pombe
4896
Eukaryote
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
3
Escherichia coli
562
Prokaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
21
Xenopus laevis
8355
Eukaryote
African clawed frog
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
25
Escherichia coli (strain K12)
83333
Prokaryote
5
Cytoplasm
GO:0005737
7
Endoplasmic Reticulum Membrane
GO:0005789
1
Cytosol
GO:0005829
6
Lysosome
GO:0005764
13
Endoplasmic Reticulum
GO:0005783
20
Endoplasmic Reticulum Lumen
GO:0005788
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
25
Golgi apparatus
GO:0005794
4
Peroxisome
GO:0005777
12
Mitochondrial Inner Membrane
GO:0005743
16
Lysosomal Lumen
GO:0043202
35
Chloroplast
GO:0009507
31
Periplasmic Space
GO:0005620
11
Extracellular Space
GO:0005615
10
Cell Membrane
GO:0005886
24
Mitochondrial Intermembrane Space
GO:0005758
14
Mitochondrial Outer Membrane
GO:0005741
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
18
Melanosome Membrane
GO:0033162
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
40
Periplasm
GO:0042597
1
Liver
BTO:0000759
72
9
25
Intestine
BTO:0000648
4
Adrenal Medulla
BTO:0000049
71
8
28
Stomach
BTO:0001307
155
26
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
8
Blood Vessel
BTO:0001102
74
11
7
Nervous System
BTO:0001484
11
Heart
BTO:0000562
73
10
8
5
1
1
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PW_BS000010
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1
PW_BS000036
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PW_BS000092
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PW_BS000115
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PW_BS000100
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PW_BS000120
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PW_BS000115
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PW_BS000024
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PW_BS000170
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PW_BS000024
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PW_BS000129
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PW_BS000028
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PW_BS000115
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PW_BS000014
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PW_BS000042
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746
Uridine diphosphate glucuronic acid
HMDB0000935
Uridine diphosphate glucuronic acid is a nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP Iduronic acid, which donates Iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones. The transfer of glucuronic acid from UDP-alpha-D-glucuronic acid onto a terminal galactose residue is done by beta1,3-glucuronosyltransferases, responsible for the completion of the protein-glycosaminoglycan linkage region of proteoglycans and of the HNK1 epitope of glycoproteins and glycolipids. In humans the enzyme galactose-beta-1,3-glucuronosyltransferase I completes the synthesis of the common linker region of glycosaminoglycans (GAGs) by transferring glucuronic acid (GlcA) onto the terminal galactose of the glycopeptide primer of proteoglycans. The GAG chains of proteoglycans regulate major biological processes such as cell proliferation and recognition, extracellular matrix deposition, and morphogenesis. (PMID: 16815917).
2616-64-0
C00167
17473
17200
UDP-GLUCURONATE
16522
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O
C15H22N2O18P2
InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1
HDYANYHVCAPMJV-LXQIFKJMSA-N
(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
580.2853
580.034284934
-1.51
9
udp-α-D-glucuronic acid
0
-3
FDB022325
Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphate;Udp glucuronate;Udp glucuronic acid;Udp-d-glucuronate;Udp-d-glucuronic acid;Udp-glcua;Udp-glucuronate;Udp-glucuronic acid;Udp-alpha-d-glucuronate;Udp-alpha-delta-glucuronate;Udp-delta-glucuronate;Udp-delta-glucuronic acid;Udpga;Udpglucuronate;Uga;Uridine 5'-[3-(d-glucopyranosyloxyuronic acid) dihydrogen diphosphate];Uridine 5'-diphospho-a-d-glucuronate;Uridine 5'-diphospho-a-d-glucuronic acid;Uridine 5'-diphospho-alpha-delta-glucuronate;Uridine 5'-diphospho-alpha-delta-glucuronic acid;Uridine 5'-diphospho-glucuronic acid;Uridine 5'-diphosphoglucuronate;Uridine 5'-diphosphoglucuronic acid;Uridine diphosphate glucuronate;Uridine diphosphate glucuronic acid;Uridine diphosphate-glucuronate;Uridine diphospho-d-glucuronate;Uridine diphospho-d-glucuronic acid;Uridine diphospho-delta-glucuronate;Uridine diphospho-delta-glucuronic acid;Uridine diphosphoglucuronate;Uridine diphosphoglucuronic acid;Uridine pyrophosphoglucuronate;Uridine pyrophosphoglucuronic acid;Uridinediphosphoglucuronic acid;A-d-glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate);A-d-glucopyranuronic acid ester with uridine 5'-pyrophosphate;Alpha-d-glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate);Alpha-delta-glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate);Alpha-delta-glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate);Alpha-delta-glucopyranuronic acid ester with uridine 5'-pyrophosphate;Uridine-5'-diphosphate-glucuronic acid;Udp-a-d-glucuronate;Udp-a-d-glucuronic acid;Udp-α-d-glucuronate;Udp-α-d-glucuronic acid;Udpglucuronic acid;Uridine diphosphoric acid glucuronic acid;Uridine-5'-diphosphate-glucuronate;Uridine-5'-diphosphoric acid-glucuronic acid
PW_C000746
UDPGlcA
1129
8
2219
49
2303
2
2351
9
4479
18
4516
10
4844
36
4944
92
5176
95
5525
130
5832
141
7055
160
77358
331
78403
111
78615
132
120830
122
122049
124
122338
383
123415
135
124603
118
124889
398
125821
297
126201
299
126506
495
127274
205
128078
390
721
NAD
HMDB0000902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H28N7O14P2
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
664.433
664.116946663
-2.59
8
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-1
FDB022309
3-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nad
PW_C000721
NAD
140
4
150
3
353
8
651
10
1114
2
1134
43
1273
5
1466
54
2229
49
2779
17
2835
29
3107
9
4807
18
4813
18
4819
28
4902
6
4960
31
5167
95
5238
103
5334
111
5360
112
5469
123
5482
125
5590
135
5610
118
5696
100
5738
108
5827
141
5912
147
5942
151
6024
155
6072
157
6076
161
6385
1
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
7459
222
8241
226
8359
225
9085
224
11819
216
12322
249
13006
298
13018
300
13256
223
42404
322
42619
315
77104
132
77120
133
77209
134
77370
331
77650
336
77667
334
77702
332
77709
130
77915
113
77983
347
78406
356
80006
368
80690
119
93825
124
110552
388
112750
166
112853
94
119929
122
119952
406
120171
407
120834
419
120984
408
121159
425
121242
126
121259
429
121817
383
122614
384
122742
120
123130
447
123141
136
123419
455
123549
374
123731
460
123812
443
123829
464
124370
398
125187
121
125319
297
125342
479
125530
481
125806
299
125825
490
125924
482
126515
495
126765
480
126885
501
127278
507
127383
502
128089
390
128360
391
128428
395
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
1144
NADH
HMDB0001487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
665.441
665.124771695
-2.35
8
NADH
0
-2
FDB022649
1,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotide
PW_C001144
NADH
143
4
153
3
490
8
648
10
1115
2
1275
5
1469
54
2230
49
2781
17
2836
29
3109
9
4806
18
4812
18
4821
28
4904
6
4959
31
5169
95
5240
103
5332
111
5358
112
5466
123
5479
125
5593
135
5698
100
5737
108
5829
141
5915
147
5945
151
6027
155
6079
161
6387
1
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
7462
222
8244
226
8360
225
9086
224
11809
198
11821
216
12320
249
13003
298
13015
300
13255
223
42403
322
42618
315
77107
132
77123
133
77208
134
77371
331
77651
336
77668
334
77700
332
77707
130
77917
113
77986
347
80009
368
80691
119
93822
124
110549
388
112854
94
115838
118
119955
406
120172
407
120378
122
120986
408
121162
425
121244
126
121693
429
121818
383
122616
384
122745
120
123127
447
123138
136
123551
374
123734
460
123814
443
124242
464
124371
398
125189
121
125345
479
125531
481
125762
297
125808
299
125926
482
126516
495
126767
480
126888
501
127385
502
128090
390
128362
391
128429
395
42899
UDP-β-L-threo-pentapyranos-4-ulose
UDP-β-L-threo-pentapyranos-4-ulose, also known as UDP-4''-ketopentose or UDP-L-ara4O, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. UDP-β-L-threo-pentapyranos-4-ulose is soluble (in water) and a moderately acidic compound (based on its pKa). UDP-β-L-threo-pentapyranos-4-ulose may be a unique E.coli metabolite.
47028
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2OCC(=O)[C@H](O)[C@H]2O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O
C14H20N2O16P2
InChI=1S/C14H20N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,6,8-13,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t6-,8+,9-,10-,11-,12-,13-/m1/s1
URJZIQLTPCJVMW-QNSCKLTRSA-N
[({[(2R,3R,4R)-3,4-dihydroxy-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
534.26
534.028806568
-1.55
7
udp-L-ara4O
0
-2
Udp-4-keto-pyranose, uridine 5'-β-l-threo-pentapyranosyl-4''-ulose diphosphate, udp-4-ketopentose, udp-l-ara4o
PW_C042899
UβLTP4U
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
42900
UDP-4-amino-4-deoxy-β-L-arabinopyranose
Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose, also known as udp-4-amino-4-deoxy-beta-L-arabinose, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose is soluble (in water) and a moderately acidic compound (based on its pKa). Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose may be a unique E.coli metabolite.
58708
[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OC[C@]([H])(N)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC([O-])=NC2=O)[C@]([H])(O)[C@]1([H])O
C14H22N3O15P2
InChI=1S/C14H23N3O15P2/c15-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)17-2-1-7(18)16-14(17)23/h1-2,5-6,8-13,19-22H,3-4,15H2,(H,24,25)(H,26,27)(H,16,18,23)/p-1/t5-,6+,8-,9+,10+,11+,12+,13+/m0/s1
GWBAKYBSWHQNMQ-IAZOVDBXSA-M
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-olate
534.2831
534.052615073
-1.28
7
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-oxopyrimidin-4-olate
-1
-1
Uridine 5''-diphospho-{β}-4-deoxy-4-amino-l-arabinose, udp-4-amino-4-deoxy-l-arabinose
PW_C042900
U4A4DbL
774
10-Formyltetrahydrofolate
HMDB0000972
10-Formyltetrahydrofolate (10-CHO-THF) is form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. In particular, 10-CHO-THF is used as a substrate in a number of formyltransferase reactions. It plays an important role in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase, as well as in the formylation of the methionyl initiator tRNA (fMet-tRNA), when 10-CHO-THF is a substrate for methionyl-tRNA formyltransferase. 10-Formyltetrahydrofolate is a substrate for Trifunctional purine biosynthetic protein adenosine-3, Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), 10-formyltetrahydrofolate dehydrogenase, Folylpolyglutamate synthase (mitochondrial), Bifunctional purine biosynthesis protein PURH and C-1-tetrahydrofolate synthase (cytoplasmic).
2800-34-2
C00234
122347
15637
10-FORMYL-THF
109092
NC1=NC(=O)C2=C(NCC(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1
C20H23N7O7
InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1
AUFGTPPARQZWDO-YUZLPWPTSA-N
(2S)-2-[(4-{N-[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
473.4393
473.165896125
-3.15
7
(2S)-2-[(4-{N-[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
0
-2
FDB022345
10-formyl-(6rs)-tetrahydrofolic acid;10-formyl-h4pteglu1;10-formyl-thf;10-formyl-tetrahydrofolate;10-formyltetrahydrofolate;10-formyltetrahydrofolic acid;10-formyltetrahydropteroylglutamate;10-formyltetrahydropteroylglutamic acid;10-fthf;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamate;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamic acid;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-l-glutamate;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-l-glutamic acid;N10-formyl-5,6,7,8-tetrahydrofolate;N10-formyl-5,6,7,8-tetrahydrofolic acid;N10-formyltetrahydrofolate;N10-formyltetrahydrofolic acid;N10-formyltetrahydropteroylglutamate;N10-formyl-h4f;N10-formyl-thf
PW_C000774
10-FTHF
947
8
979
3
1918
2
5316
111
5350
112
7160
205
7188
206
7440
166
11796
198
78322
132
120671
122
120698
407
122301
124
123285
135
123303
119
124853
118
125754
297
125773
481
126467
299
128037
388
42901
UDP-4-deoxy-4-formamido-β-L-arabinopyranose
UDP-4-Deoxy-4-formamido-beta-L-arabinose, also known as UDP-beta-L-ara4fn or UDP-4-deoxy-4-formamido-β-L-arabinopyranose, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. UDP-4-Deoxy-4-formamido-beta-L-arabinose is soluble (in water) and a moderately acidic compound (based on its pKa). UDP-4-Deoxy-4-formamido-beta-L-arabinose may be a unique E.coli metabolite.
47027
[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])OC[C@]([H])(N=CO)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])O
C15H23N3O16P2
InChI=1S/C15H23N3O16P2/c19-5-16-6-3-30-14(12(24)9(6)21)33-36(28,29)34-35(26,27)31-4-7-10(22)11(23)13(32-7)18-2-1-8(20)17-15(18)25/h1-2,5-7,9-14,21-24H,3-4H2,(H,16,19)(H,26,27)(H,28,29)(H,17,20,25)/t6-,7+,9-,10+,11+,12+,13+,14+/m0/s1
QGYFHZBDXXNYAX-RTXATJJPSA-N
N-[(3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxyoxan-3-yl]carboximidic acid
563.3011
563.055354727
-1.73
8
udp-L-ara4FN
0
-1
Udp-l-ara4fn, udp-β-l-ara4fn, udp-l-ara4-formyl-n, udp-β-(4-deoxy-4-formamido-l-arabinose), uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-l-arabinose
PW_C042901
U4D4FβL
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
40918
Tetrahydrofolate
Tetrahydrofolic acid, also known as tetrahydrofolate, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. Tetrahydrofolic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. Tetrahydrofolic acid has been found throughout most human tissues, and has also been detected in multiple biofluids, such as urine and blood. Tetrahydrofolic acid can be found anywhere throughout the human cell, such as in myelin sheath, lysosome, cytoplasm, and membrane (predicted from logP). In humans, tetrahydrofolic acid is involved in pterine biosynthesis pathway, the azathioprine action pathway, the sarcosine oncometabolite pathway, and the folate malabsorption, hereditary pathway. Tetrahydrofolic acid is also involved in several metabolic disorders, some of which include dihydropyrimidine dehydrogenase deficiency (DHPD), molybdenum cofactor deficiency, cystathionine Beta-synthase deficiency, and dimethylglycine dehydrogenase deficiency.
C03541
NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1
C19H23N7O6
InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12?/m0/s1
MSTNYGQPCMXVAQ-PXYINDEMSA-N
2-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
445.4292
445.170981503
-3.22
8
2-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
0
-2
PW_C040918
tethf
6012
147
12007
222
42617
di-trans,octa-cis-undecaprenyl phosphate
Undecaprenyl phosphate belongs to the class of organic compounds known as bactoprenol monophosphates. These are polyprenyl compounds consisting of a monophosphate group substituted by a bactoprenyl moiety. Undecaprenyl phosphate is considered to be a practically insoluble (in water) and relatively neutral molecule.
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/COP(O)(O)=O
C55H91O4P
InChI=1S/C55H91O4P/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-59-60(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H2,56,57,58)/b46-25+,47-27+,48-29-,49-31-,50-33-,51-35-,52-37-,53-39-,54-41-,55-43-
UFPHFKCTOZIAFY-NTDVEAECSA-N
{[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy}phosphonic acid
847.2824
846.665497912
-6.29
2
undecaprenyl phosphate
0
-2
PW_C042617
DTOCUP
40980
UDP
Also known uridine 5'-diphosphate or uridine diphosphoric acid, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. Uridine 5'-diphosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Uridine 5'-diphosphate has been found in human prostate, endocrine gland and placenta tissues, and has also been primarily detected in blood. Uridine 5'-diphosphate can be found anywhere throughout the human cell, such as in endoplasmic reticulum, nucleus, mitochondria, and lysosome. Uridine 5'-diphosphate exists in all living organisms, ranging from bacteria to humans. Uridine 5'-diphosphate participates in a number of enzymatic reactions. In particular, Uridine 5'-diphosphate can be biosynthesized from uridine 5'-monophosphate; which is catalyzed by the enzyme UMP kinase. Furthermore, Uridine 5'-diphosphate can be converted into uridine triphosphate through the action of the enzyme nucleoside diphosphate kinase. Finally, Uridine 5'-diphosphate and trehalose 6-phosphate can be biosynthesized from uridine diphosphate glucose and alpha-D-glucose 6-phosphate through the action of the enzyme trehalose-6-phosphate synthase. In humans, uridine 5'-diphosphate is involved in the morphine metabolism pathway, the androstenedione metabolism pathway, the mycophenolic Acid metabolism pathway, and the tramadol metabolism pathway. Uridine 5'-diphosphate is also involved in several metabolic disorders, some of which include 17-Beta hydroxysteroid dehydrogenase III deficiency, the mucopolysaccharidosis vi. sly syndrome pathway, glycogen synthetase deficiency, and UMP synthase deficiency (orotic aciduria). Outside of the human body, uridine 5'-diphosphate can be found in a number of food items such as hickory nut, cocoa bean, sunburst squash (pattypan squash), and sorghum. This makes uridine 5'-diphosphate a potential biomarker for the consumption of these food products.
58223
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
C9H14N2O12P2
InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
XCCTYIAWTASOJW-XVFCMESISA-N
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
404.1612
404.002196946
-1.66
6
UDP
0
-2
Uridine-diphosphate, uridine-5'-diphosphate
PW_C040980
UDP
5984
147
42902
4-deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate
4-Deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate is considered to be a practically insoluble (in water) and relatively neutral molecule. 4-Deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate may be a unique E.coli metabolite. 4-Deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate participates in a number of enzymatic reactions. In particular, UDP and 4-deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate can be biosynthesized from UDP-4-deoxy-4-formamido-β-L-arabinopyranose and di-trans,octa-cis-undecaprenyl phosphate; which is mediated by the enzyme undecaprenyl phosphate-L-ara4fn transferase. In addition, UDP and 4-deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate can be biosynthesized from UDP-4-deoxy-4-formamido-β-L-arabinopyranose and di-trans,octa-cis-undecaprenyl phosphate through the action of the enzyme undecaprenyl phosphate-L-ara4fn transferase. A polyprenyl glycosyl phosphate consisting of 4-deoxy-4-formamido-α-L-arabinopyranose attached at the 1-position to di-trans,poly-cis-undecaprenyl phosphate.
53028
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/COP(O)(=O)OC1OCC(NC=O)C(O)C1O
C61H100NO8P
InChI=1S/C61H100NO8P/c1-47(2)23-13-24-48(3)25-14-26-49(4)27-15-28-50(5)29-16-30-51(6)31-17-32-52(7)33-18-34-53(8)35-19-36-54(9)37-20-38-55(10)39-21-40-56(11)41-22-42-57(12)43-44-69-71(66,67)70-61-60(65)59(64)58(45-68-61)62-46-63/h23,25,27,29,31,33,35,37,39,41,43,46,58-61,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44-45H2,1-12H3,(H,62,63)(H,66,67)/b48-25+,49-27+,50-29-,51-31-,52-33-,53-35-,54-37-,55-39-,56-41-,57-43-
KDTATMYQJZYGGT-QTBHONTMSA-N
[(5-formamido-3,4-dihydroxyoxan-2-yl)oxy]({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphinic acid
1006.444
1005.718656182
-6.19
4
(5-formamido-3,4-dihydroxyoxan-2-yl)oxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxyphosphinic acid
0
-1
Undecaprenyl phosphate-l-ara4-formyl-n, undecaprenyl phosphate-α-l-ara4fn, 4-deoxy-4-formamido-α-l-arabinopyranosyl undecaprenyl phosphate
PW_C042902
4D4FαLA
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
92
Formic acid
HMDB0000142
Formic acid is the simplest carboxylic acid. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a byproduct in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer.
64-18-6
C00058
18971002
30751
FORMATE
278
DB01942
OC=O
CH2O2
InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
BDAGIHXWWSANSR-UHFFFAOYSA-N
formic acid
46.0254
46.005479308
1.02
1
formic acid
0
-1
DBMET00489
FDB012804
Add-f;Ameisensaure;Aminate;Aminic acid;Bilorin;Collo-bueglatt;Collo-didax;Formate;Formira;Formisoton;Formylate;Formylic acid;Hydrogen carboxylate;Hydrogen carboxylic acid;Methanoate;Methanoic acid;Methanoic acid monomer;Myrmicyl;Sodium formate;Sybest;Wonderbond hardener m 600l
PW_C000092
Formate
946
8
977
3
1629
49
1943
2
5314
111
5348
112
6636
107
7158
205
7186
206
7325
213
7616
160
8287
210
11982
151
43522
318
76963
225
78652
132
78934
331
120670
122
120697
407
121496
383
121751
124
123284
135
123302
119
124054
398
124302
118
125753
297
125772
481
126478
299
126821
495
127637
388
128426
390
42606
4-Amino-4-deoxy-α-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate
4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate, also known as undecaprenyl phosphoric acid a-L-ara4fn, belongs to the class of organic compounds known as bactoprenol monophosphates. These are polyprenyl compounds consisting of a monophosphate group substituted by a bactoprenyl moiety. 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate is considered to be a practically insoluble (in water) and relatively neutral molecule. 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate may be a unique E.coli metabolite. 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate and (kdo)2-lipid a can be converted into di-trans,octa-cis-undecaprenyl diphosphate and L-ara4n-modified kdo2-lipid a through the action of the enzyme 4-amino-4-deoxy-L-arabinose (L-ara4n) transferase.
OC=N[C@@]1([H])CO[C@@]([H])(OP(O)(=O)OC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@@](O)([H])[C@]1(O)[H]
C61H100NO8P
InChI=1S/C61H100NO8P/c1-47(2)23-13-24-48(3)25-14-26-49(4)27-15-28-50(5)29-16-30-51(6)31-17-32-52(7)33-18-34-53(8)35-19-36-54(9)37-20-38-55(10)39-21-40-56(11)41-22-42-57(12)43-44-69-71(66,67)70-61-60(65)59(64)58(45-68-61)62-46-63/h23,25,27,29,31,33,35,37,39,41,43,46,58-61,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44-45H2,1-12H3,(H,62,63)(H,66,67)/b48-25+,49-27+,50-29-,51-31-,52-33-,53-35-,54-37-,55-39-,56-41-,57-43-/t58-,59-,60+,61-/m0/s1
KDTATMYQJZYGGT-CRHUQJHVSA-N
N-[(3S,4S,5R,6S)-4,5-dihydroxy-6-{[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy}oxan-3-yl]carboximidic acid
1006.4224
1005.718655693
-6.13
4
N-[(3S,4S,5R,6S)-4,5-dihydroxy-6-({hydroxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxyphosphoryl}oxy)oxan-3-yl]carboximidic acid
0
-1
Udp-ara4fn
PW_C042606
A4DLTO
40740
(KDO)2-lipid A
(KDO)2-lipid a belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group (KDO)2-lipid a is considered to be a practically insoluble (in water) and relatively neutral molecule (KDO)2-lipid a may be a unique E.coli metabolite (KDO)2-lipid a participates in a number of enzymatic reactions. In particular, (Kdo)2-lipid a and ADP-L-glycero-beta-D-manno-heptose can be converted into heptosyl-kdo2-lipid a through the action of the enzyme ADP-heptose:lps heptosyltransferase i. Furthermore, (Kdo)2-lipid a can be biosynthesized from (kdo)2-(lauroyl)-lipid iva; which is catalyzed by the enzyme myristoyl-acyl carrier protein (acp)-dependent acyltransferase. Furthermore, (Kdo)2-lipid a and ADP-L-glycero-beta-D-manno-heptose can be converted into heptosyl-kdo2-lipid a through the action of the enzyme ADP-heptose:lps heptosyltransferase i. Furthermore, (Kdo)2-lipid a can be biosynthesized from (kdo)2-(lauroyl)-lipid iva through the action of the enzyme myristoyl-acyl carrier protein (acp)-dependent acyltransferase. Furthermore, (Kdo)2-lipid a and ADP-L-glycero-beta-D-manno-heptose can be converted into heptosyl-kdo2-lipid a; which is mediated by the enzyme ADP-heptose:lps heptosyltransferase i. Finally, (Kdo)2-lipid a can be biosynthesized from (kdo)2-(lauroyl)-lipid iva through the action of the enzyme myristoyl-acyl carrier protein (acp)-dependent acyltransferase. (KDO)2-lipid A is an intermediate in the synthesis of LPS. It has two 3-deoxy-D-manno-octulosonic acid (KDO) sugar residues in place of the core, and has no O-antigen.
C06026
58540
[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])O[C@]([H])(CO[C@@]3(C[C@@]([H])(O[C@@]4(C[C@@]([H])(O)[C@@]([H])(O)[C@]([H])(O4)[C@]([H])(O)CO)C([O-])=O)[C@@]([H])(O)[C@]([H])(O3)[C@]([H])(O)CO)C([O-])=O)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(OC(=O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC
C110H196N2O39P2
InChI=1S/C110H202N2O39P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-92(123)142-82(66-60-54-48-42-35-29-23-17-11-5)72-94(125)146-104-96(112-90(121)71-81(65-59-53-47-41-34-28-22-16-10-4)141-91(122)67-61-55-49-43-36-30-24-18-12-6)105(144-88(102(104)150-152(133,134)135)78-140-109(107(129)130)74-86(98(127)101(148-109)85(119)76-114)147-110(108(131)132)73-83(117)97(126)100(149-110)84(118)75-113)139-77-87-99(128)103(145-93(124)70-80(116)64-58-52-46-40-33-27-21-15-9-3)95(106(143-87)151-153(136,137)138)111-89(120)69-79(115)63-57-51-45-39-32-26-20-14-8-2/h79-88,95-106,113-119,126-128H,7-78H2,1-6H3,(H,111,120)(H,112,121)(H,129,130)(H,131,132)(H2,133,134,135)(H2,136,137,138)/p-6/t79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,109-,110-/m1/s1
DIXUKJUHGLIZGU-OIPVZEHTSA-H
(2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxylato-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-5-hydroxyoxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylate
2232.704
2231.292339975
-4.95
12
(2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxylato-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-5-hydroxyoxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylate
-6
-6
PW_C040740
K2LA
42616
di-trans,octa-cis-undecaprenyl diphosphate
Di-trans,poly-cis-undecaprenyl diphosphate, also known as bactoprenyl diphosphate, belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety. Di-trans,poly-cis-undecaprenyl diphosphate is considered to be a practically insoluble (in water) and relatively neutral molecule.
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/COP(O)(=O)OP(O)(O)=O
C55H92O7P2
InChI=1S/C55H92O7P2/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-61-64(59,60)62-63(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H,59,60)(H2,56,57,58)/b46-25+,47-27+,48-29-,49-31-,50-33-,51-35-,52-37-,53-39-,54-41-,55-43-
NTXGVHCCXVHYCL-NTDVEAECSA-N
{[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid
927.2623
926.631828322
-6.40
3
{hydroxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxyphosphoryl}oxyphosphonic acid
0
-2
PW_C042616
DTOCUD
41467
L-Ara4N-modified KDO2-Lipid A
L-Ara4n-modified kdo2-lipid a belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. L-Ara4n-modified kdo2-lipid a is considered to be a practically insoluble (in water) and relatively neutral molecule. L-Ara4n-modified kdo2-lipid a may be a unique E.coli metabolite. Di-trans,octa-cis-undecaprenyl diphosphate and L-ara4n-modified kdo2-lipid a can be biosynthesized from 4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate and (kdo)2-lipid a; which is mediated by the enzyme 4-amino-4-deoxy-L-arabinose (L-ara4n) transferase.
656478
CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(OP(O)(=O)OC2OCC(N)C(O)C2O)C(COC2(CC(OC3(CC(O)C(O)C(O3)C(O)CO)C(O)=O)C(O)C(O2)C(O)CO)C(O)=O)OC(OCC2OC(OP(O)(=O)OC3OCC(N)C(O)C3O)C(N=C(O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)C1N=C(O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
C120H220N4O45P2
InChI=1S/C120H220N4O45P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(135)158-84(66-60-54-48-42-35-29-23-17-11-5)72-98(137)162-112-100(124-94(133)71-83(65-59-53-47-41-34-28-22-16-10-4)157-95(134)67-61-55-49-43-36-30-24-18-12-6)113(160-92(110(112)166-170(149,150)168-115-106(143)101(138)85(121)77-153-115)80-156-119(117(145)146)74-90(104(141)109(164-119)89(131)76-126)163-120(118(147)148)73-87(129)103(140)108(165-120)88(130)75-125)155-79-91-105(142)111(161-97(136)70-82(128)64-58-52-46-40-33-27-21-15-9-3)99(123-93(132)69-81(127)63-57-51-45-39-32-26-20-14-8-2)114(159-91)167-171(151,152)169-116-107(144)102(139)86(122)78-154-116/h81-92,99-116,125-131,138-144H,7-80,121-122H2,1-6H3,(H,123,132)(H,124,133)(H,145,146)(H,147,148)(H,149,150)(H,151,152)
RYVJLJVPSMBXLB-UHFFFAOYSA-N
2-{[3-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-6-{[6-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-5-[(1,3-dihydroxytetradecylidene)amino]-3-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl]methoxy}-5-{[3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-{[2-carboxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-hydroxyoxane-2-carboxylic acid
2500.9781
2499.452484074
-4.52
22
2-[(3-{[(5-amino-3,4-dihydroxyoxan-2-yl)oxy(hydroxy)phosphoryl]oxy}-6-[(6-{[(5-amino-3,4-dihydroxyoxan-2-yl)oxy(hydroxy)phosphoryl]oxy}-5-[(1,3-dihydroxytetradecylidene)amino]-3-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl)methoxy]-5-{[3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl)methoxy]-4-{[2-carboxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-hydroxyoxane-2-carboxylic acid
0
-2
α-kdo-(2→4)-α6)-lipid ii<sub>a</sub>;Alpha-kdo-(2->4)-alpha-kdo-(2->6)-lipid a;L-ara4n-modified (kdo)<sub>2</sub>-lipid a
PW_C041467
L-ArlpA
6772
Bifunctional polymyxin resistance protein ArnA
P77398
Involved in hydroxymethyl-, formyl- and related transferase activity. Bifunctional enzyme that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto- arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4- amino-4-deoxy-L-arabinose (UDP-L-Ara4N) to form UDP-L-4-formamido- arabinose (UDP-L-Ara4FN). The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides.
arnA
b2255
AP009048
3
2.1.2.13; 1.1.1.305
6797
UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase
P77690
Involved in transaminase activity. Catalyzes the conversion of UDP-4-keto-arabinose (UDP- Ara4O) to UDP-4-amino-4-deoxy-L-arabinose (UDP-L-Ara4N). The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides.
arnB
b2253
AF527386
3
2.6.1.87
6800
Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase
P77757
Involved in phosphotransferase activity, for other substituted phosphate groups. Catalyzes the transfer of 4-deoxy-4-formamido-L- arabinose from UDP to undecaprenyl phosphate. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides.
arnC
b2254
AP009048
3
2.4.2.53
8762
109
6837
Undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase
P76473
Involved in transferase activity, transferring pentosyl groups. Catalyzes the transfer of the L-Ara4N moiety of the glycolipid undecaprenyl phosphate-alpha-L-Ara4N to lipid A. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides.
arnT
b2257
AP009048
3
2.4.2.43
8885
109
3582
UDP-L-Ara4N formyltransferase / UDP-GlcA C-4"-decarboxylase
3
PW_P003582
10421
6772
6
3583
UDP-L-Ara4O C-4" transaminase
3
PW_P003583
10422
6797
3584
undecaprenyl phosphate-L-Ara4FN transferase
3
PW_P003584
10423
6800
4030
4-amino-4-deoxy-L-arabinose (L-Ara4N) transferase
3
PW_P004030
11031
6837
3356
false
PW_R003356
Right
13390
746
1
Compound
false
13391
721
1
Compound
false
13392
1316
1
Compound
false
13393
1144
1
Compound
false
13394
42899
1
Compound
false
3325
3582
2.1.2.13
3357
false
PW_R003357
Right
13395
42899
1
Compound
false
13396
95
1
Compound
false
13397
134
1
Compound
false
13398
42900
1
Compound
false
3326
3583
2.6.1.87
3358
false
PW_R003358
Right
13399
42900
1
Compound
false
13400
774
1
Compound
false
13401
42901
1
Compound
false
13402
40034
1
Compound
false
13403
40918
1
Compound
false
3327
3582
2.1.2.13
3359
false
PW_R003359
Right
13404
42901
1
Compound
false
13405
42617
1
Compound
false
13406
40980
1
Compound
false
13407
42902
1
Compound
false
3328
3584
2.4.2.53
5994
PW_R005994
Right
24489
42902
2
Compound
false
24490
1420
2
Compound
false
24491
92
1
Compound
false
24492
42606
1
Compound
false
5995
false
PW_R005995
Right
24493
42606
2
Compound
false
24494
40740
1
Compound
false
24495
42616
2
Compound
false
24496
41467
1
Compound
false
5956
4030
2.4.2.43
70537
746
3
false
315
377
10
regular
100
130
70538
721
59
false
450
487
10
regular
50
30
70539
1316
52
false
781
321
10
regular
78
78
70540
1144
60
false
760
489
10
regular
50
30
70541
42899
3
false
890
379
10
regular
100
130
70542
95
3
false
1010
494
10
regular
100
110
70543
134
3
false
1335
286
10
regular
100
110
70544
42900
3
false
1460
381
10
regular
100
120
70547
774
3
false
1595
291
10
regular
100
110
70548
42901
3
false
2036
376
10
regular
100
130
70549
40034
55
false
1921
492
10
regular
78
78
70550
40918
3
false
1919
291
10
regular
100
100
70551
42617
3
false
1935
621
10
regular
100
140
70552
40980
3
false
1936
901
10
regular
100
100
70553
42902
3
false
2036
1021
10
regular
100
160
70554
1420
49
false
1933
1157
10
regular
78
78
70555
92
3
false
1746
971
10
regular
100
100
70556
42606
3
false
1606
1016
10
regular
100
170
70557
40740
3
false
1461
961
10
regular
100
100
70558
42616
3
false
971
1031
10
regular
100
140
70559
41467
3
false
1106
1151
10
regular
100
120
32369
6772
17
false
535
404
8
subunit
regular
180
85
32370
6797
2
false
1150
409
8
subunit
regular
150
70
32372
6772
17
false
1715
403
8
subunit
regular
180
85
32373
6800
109
2
false
2011
801
8
subunit
regular
150
70
32374
6837
109
2
false
1251
1066
8
subunit
regular
150
70
27231
3582
1805
32050
32369
27232
3583
1805
32051
32370
27234
3582
1805
32053
32372
27235
3584
1805
32054
32373
27236
4030
1805
32055
32374
100277
M415 442 C445 442 505 444 535 444
5
false
18
100278
M475 487 C476 448 505 444 535 444
5
false
18
100279
M820 399 C817 450 745 444 715 444
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100280
M785 489 C786 434 745 444 715 444
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100281
M890 444 C860 444 745 444 715 444
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100282
M990 444 C1020 444 1120 444 1150 444
5
false
18
100283
M1060 494 C1061 433 1120 444 1150 444
5
false
18
100284
M1385 396 C1384 448 1330 444 1300 444
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100285
M1460 441 C1430 441 1330 444 1300 444
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100291
M1560 441 C1605 441 1648 443 1715 443
5
false
18
100292
M1645 401 C1644 442 1674 444 1715 443
5
false
18
100293
M2036 441 C1999 442 1920 443 1895 443
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100294
M1960 492 C1961 434 1928 444 1895 443
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100295
M1969 391 C1972 421 1945 443 1895 443
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100296
M2086 506 C2086 578 2086 706 2086 801
5
false
18
100297
M2035 691 C2061 691 2086 685 2086 801
5
false
18
100298
M2036 951 C2077 951 2086 914 2086 871
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100299
M2086 1021 C2086 944 2087 950 2086 871
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100300
M1706 1101 C1736 1103 1990 1100 2036 1101
5
false
18
100301
M1972 1157 C1973 1120 1938.5 1100 1878.5 1101
5
false
18
100302
M1796 1071 C1796 1089 1836.5 1101 1881.5 1101
5
false
18
true
M 25.946855044164835 566.261556296296 L 11 565 L 17.380887721185843 578.5751343230784
false
100303
M1706 1101 C1741 1103 1999 1100 2036 1101
5
true
18
true
M 25.946855044164835 566.261556296296 L 11 565 L 17.380887721185843 578.5751343230784
false
100304
M1606 1101 C1576 1100 1442 1106 1401 1101
5
false
18
100305
M1511 1061 C1511 1104 1468 1102 1401 1101
5
false
18
100306
M1071 1101 C1112 1101 1205 1100 1251 1101
5
false
18
true
M 653.6135217108315 1331.5948896296293 L 638.6666666666666 1330.3333333333333 L 645.0475543878524 1343.9084676564116
false
100307
M1156 1151 C1156 1121 1153 1105 1251 1101
5
false
18
true
M 653.6135217108315 1331.5948896296293 L 638.6666666666666 1330.3333333333333 L 645.0475543878524 1343.9084676564116
false
20520
1805
3356
79727
70537
100277
Left
79728
70538
100278
Left
79729
70539
100279
Right
79730
70540
100280
Right
79731
70541
100281
Right
20693
3325
27231
20521
1805
3357
79732
70541
100282
Left
79733
70542
100283
Left
79734
70543
100284
Right
79735
70544
100285
Right
20694
3326
27232
20523
1805
3358
79739
70544
100291
Left
79740
70547
100292
Left
79741
70548
100293
Right
79742
70549
100294
Right
79743
70550
100295
Right
20696
3327
27234
20524
1805
3359
79744
70548
100296
Left
79745
70551
100297
Left
79746
70552
100298
Right
79747
70553
100299
Right
20697
3328
27235
20525
1805
5994
79748
70553
100300
Left
79749
70554
100301
Left
79750
70555
100302
Right
79751
70556
100303
Right
20526
1805
5995
79752
70556
100304
Left
79753
70557
100305
Left
79754
70558
100306
Right
79755
70559
100307
Right
20698
5956
27236
186451
400
588
1.1
1.1
0
2
92
479
481
3525
M125 225 C125 175 175 125 225 125 C831 125 1618 125 2224 125 C2274 125 2324 175 2324 225 C2324 575 2324 1029 2324 1379 C2324 1429 2274 1479 2224 1479 C1618 1479 831 1479 225 1479 C175 1479 125 1429 125 1379 C125 1029 125 575 125 225
1
true
6
2199.0
1354.0
3526
M224 325 C224 275 274 225 324 225 C871 225 1581 225 2128 225 C2178 225 2228 275 2228 325 C2228 613 2228 986 2228 1274 C2228 1324 2178 1374 2128 1374 C1581 1374 871 1374 324 1374 C274 1374 224 1324 224 1274 C224 986 224 613 224 325
1
true
6
2004.0
1149.0