2208
Pathway
Biosynthesis of Unsaturated Fatty Acids (Icosanoyl-CoA)
The biosynthesis of unsaturated fatty acids begins with palmitic acid interacting with ATP and Coenzyme A through an acyl-CoA synthetase resulting in the release of AMP, diphosphate and palmitoyl-CoA. This compound then enters the cycle of unsaturated fatty acid elongation This cycle starts with the acyl-CoA reacting with a hydrogen ion and a malonyl-CoA through a 3-oxo-stearoyl-CoA synthase resulting in the release of a coenzyme A, a carbon dioxide molecule and a 3-oxoacyl-CoA. The 3-oxoacyl-CoA then reacts with a hydrogen ion and an NADPH through a 3-oxoacyl-CoA reductase resulting in the release of an NADP and a (3R)-3-hydroxy-acyl-CoA. The resulting compound then reacts with a trans-2-enoyl-CoA hydratase 2 resulting in the release of water and trans-2,3-dehydroacyl-CoA. This compound then reacts with a hydrogen ion and a NADPH through a enoyl-CoA reductase resulting in the release of a NADP and a new acyl-CoA. The cycle goes from palmitoyl-CoA-->stearoyl-CoA-->eicosanoyl-CoA-->docosanoyl-CoA-->tetracosanoyl-CoA-->hexacosanoyl-CoA.
The long chain fatty acids are then incorporated into the sphingolipid pathway. The long chain fatty acid reacts with a phytosphingosine through a ceramide synthase resulting in the release of a hydrogen ion, a coenzyme A and a N-acyl-phytosphinganine.
Metabolic
PW002434
Center
PathwayVisualizationContext2720
2450
2900
#000099
PathwayVisualization2191
2208
Biosynthesis of Unsaturated Fatty Acids (Icosanoyl-CoA)
The biosynthesis of unsaturated fatty acids begins with palmitic acid interacting with ATP and Coenzyme A through an acyl-CoA synthetase resulting in the release of AMP, diphosphate and palmitoyl-CoA. This compound then enters the cycle of unsaturated fatty acid elongation This cycle starts with the acyl-CoA reacting with a hydrogen ion and a malonyl-CoA through a 3-oxo-stearoyl-CoA synthase resulting in the release of a coenzyme A, a carbon dioxide molecule and a 3-oxoacyl-CoA. The 3-oxoacyl-CoA then reacts with a hydrogen ion and an NADPH through a 3-oxoacyl-CoA reductase resulting in the release of an NADP and a (3R)-3-hydroxy-acyl-CoA. The resulting compound then reacts with a trans-2-enoyl-CoA hydratase 2 resulting in the release of water and trans-2,3-dehydroacyl-CoA. This compound then reacts with a hydrogen ion and a NADPH through a enoyl-CoA reductase resulting in the release of a NADP and a new acyl-CoA. The cycle goes from palmitoyl-CoA-->stearoyl-CoA-->eicosanoyl-CoA-->docosanoyl-CoA-->tetracosanoyl-CoA-->hexacosanoyl-CoA.
The long chain fatty acids are then incorporated into the sphingolipid pathway. The long chain fatty acid reacts with a phytosphingosine through a ceramide synthase resulting in the release of a hydrogen ion, a coenzyme A and a N-acyl-phytosphinganine.
Metabolic
18
5125
12452424
Bagnat M, Simons K: Lipid rafts in protein sorting and cell polarity in budding yeast Saccharomyces cerevisiae. Biol Chem. 2002 Oct;383(10):1475-80. doi: 10.1515/BC.2002.169.
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Pathway
5126
12069845
Dickson RC, Lester RL: Sphingolipid functions in Saccharomyces cerevisiae. Biochim Biophys Acta. 2002 Jun 13;1583(1):13-25.
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Pathway
5127
12484746
Funato K, Vallee B, Riezman H: Biosynthesis and trafficking of sphingolipids in the yeast Saccharomyces cerevisiae. Biochemistry. 2002 Dec 24;41(51):15105-14.
2208
Pathway
5128
16730802
Dickson RC, Sumanasekera C, Lester RL: Functions and metabolism of sphingolipids in Saccharomyces cerevisiae. Prog Lipid Res. 2006 Nov;45(6):447-65. doi: 10.1016/j.plipres.2006.03.004. Epub 2006 Apr 21.
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Pathway
5129
16980694
Gaigg B, Toulmay A, Schneiter R: Very long-chain fatty acid-containing lipids rather than sphingolipids per se are required for raft association and stable surface transport of newly synthesized plasma membrane ATPase in yeast. J Biol Chem. 2006 Nov 10;281(45):34135-45. doi: 10.1074/jbc.M603791200. Epub 2006 Sep 15.
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Pathway
5130
11113186
Kohlwein SD, Eder S, Oh CS, Martin CE, Gable K, Bacikova D, Dunn T: Tsc13p is required for fatty acid elongation and localizes to a novel structure at the nuclear-vacuolar interface in Saccharomyces cerevisiae. Mol Cell Biol. 2001 Jan;21(1):109-25. doi: 10.1128/MCB.21.1.109-125.2001.
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Pathway
5131
16950653
Tehlivets O, Scheuringer K, Kohlwein SD: Fatty acid synthesis and elongation in yeast. Biochim Biophys Acta. 2007 Mar;1771(3):255-70. doi: 10.1016/j.bbalip.2006.07.004. Epub 2006 Jul 21.
2208
Pathway
5132
7962057
Johnson DR, Knoll LJ, Levin DE, Gordon JI: Saccharomyces cerevisiae contains four fatty acid activation (FAA) genes: an assessment of their role in regulating protein N-myristoylation and cellular lipid metabolism. J Cell Biol. 1994 Nov;127(3):751-62.
2208
Pathway
5133
8027063
Johnson DR, Knoll LJ, Rowley N, Gordon JI: Genetic analysis of the role of Saccharomyces cerevisiae acyl-CoA synthetase genes in regulating protein N-myristoylation. J Biol Chem. 1994 Jul 8;269(27):18037-46.
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Pathway
5134
10092594
Jones JM, Nau K, Geraghty MT, Erdmann R, Gould SJ: Identification of peroxisomal acyl-CoA thioesterases in yeast and humans. J Biol Chem. 1999 Apr 2;274(14):9216-23.
2208
Pathway
5135
11330035
Kal AJ, Hettema EH, van den Berg M, Koerkamp MG, van Ijlst L, Distel B, Tabak HF: In silicio search for genes encoding peroxisomal proteins in Saccharomyces cerevisiae. Cell Biochem Biophys. 2000;32 Spring:1-8.
2208
Pathway
5136
8206942
Knoll LJ, Johnson DR, Gordon JI: Biochemical studies of three Saccharomyces cerevisiae acyl-CoA synthetases, Faa1p, Faa2p, and Faa3p. J Biol Chem. 1994 Jun 10;269(23):16348-56.
2208
Pathway
5137
22493507
van Roermund CW, Ijlst L, Majczak W, Waterham HR, Folkerts H, Wanders RJ, Hellingwerf KJ: Peroxisomal fatty acid uptake mechanism in Saccharomyces cerevisiae. J Biol Chem. 2012 Jun 8;287(24):20144-53. doi: 10.1074/jbc.M111.332833. Epub 2012 Apr 9.
2208
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
2
Platelet
CL:0000233
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
7
Epithelial Cell
CL:0000066
10
Glial cell
CL:0000125
1
Homo sapiens
9606
Eukaryote
Human
3
Escherichia coli
562
Prokaryote
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
2
Bacteria
2
Prokaryote
Bacteria
24
Solanum lycopersicum
4081
Eukaryote
Tomato
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
19
Schizosaccharomyces pombe
4896
Eukaryote
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
7
Chlamydomonas reinhardtii
3055
Eukaryote
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
2
Mitochondrion
GO:0005739
14
Mitochondrial Outer Membrane
GO:0005741
12
Mitochondrial Inner Membrane
GO:0005743
10
Cell Membrane
GO:0005886
7
Endoplasmic Reticulum Membrane
GO:0005789
1
Cytosol
GO:0005829
13
Endoplasmic Reticulum
GO:0005783
5
Cytoplasm
GO:0005737
3
Mitochondrial Matrix
GO:0005759
11
Extracellular Space
GO:0005615
24
Mitochondrial Intermembrane Space
GO:0005758
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
4
Peroxisome
GO:0005777
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
25
Golgi apparatus
GO:0005794
27
Peroxisome Membrane
GO:0005778
8
Smooth Endoplasmic Reticulum
GO:0005790
15
Nucleus
GO:0005634
19
sarcoplasmic reticulum
GO:0016529
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
40
Periplasm
GO:0042597
1
Liver
BTO:0000759
72
9
28
Stomach
BTO:0001307
155
26
8
Blood Vessel
BTO:0001102
74
11
4
Adrenal Medulla
BTO:0000049
71
8
2
Endothelium
BTO:0000393
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
25
Intestine
BTO:0000648
5
cardiocyte
BTO:0001539
11
Heart
BTO:0000562
73
10
3
2
1
1
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PW_BS000119
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17
PW_BS000053
447
1
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PW_BS000115
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1
PW_BS000118
480
12
10
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PW_BS000161
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PW_BS000159
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PW_BS000166
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PW_BS000152
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PW_BS000024
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291
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PW_BS000024
292
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PW_BS000024
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PW_BS000028
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2
60
1
PW_BS000028
228
36
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PW_BS000024
232
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3
PW_BS000024
415
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5
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PW_BS000115
434
4
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PW_BS000115
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6
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448
1
16
17
1
PW_BS000115
451
18
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PW_BS000115
469
4
10
17
1
PW_BS000115
471
25
17
PW_BS000115
487
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PW_BS000115
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1
PW_BS000115
515
4
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PW_BS000024
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1
3
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PW_BS000024
254
5
18
PW_BS000024
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PW_BS000508
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2
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1
PW_BS000508
693
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1
PW_BS000512
708
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29
1
PW_BS000512
1031
Palmityl-CoA
HMDB0001338
Palmityl-CoA, also known as palmitoyl CoA or CoA, palmitoyl, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Palmityl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Palmityl-CoA has been found throughout most human tissues, and has also been primarily detected in urine. Within the cell, palmityl-CoA is primarily located in the cytoplasm and mitochondria. In humans, palmityl-CoA is involved in cardiolipin biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) pathway, cardiolipin biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, cardiolipin biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, and cardiolipin biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) pathway. Palmityl-CoA is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/16:0/14:1(9Z)) pathway, de novo triacylglycerol biosynthesis TG(16:0/14:1(9Z)/14:1(9Z)) pathway, de novo triacylglycerol biosynthesis TG(a-25:0/i-14:0/16:0) pathway, and de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)) pathway. Palmityl-CoA is a fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis.
1763-10-6
C00154
15667
15525
PALMITYL-COA
14902
CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C37H66N7O17P3S
InChI=1S/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/t26-,30-,31-,32?,36-/m1/s1
MNBKLUUYKPBKDU-TZIIWEFPSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
1005.943
1005.344873947
-2.76
9
palmitoyl-coa
0
-4
FDB022562
Hexadecanoyl coa;Hexadecanoyl coenzyme a;Palmitoyl coa;Palmitoyl coenzyme a;Palmitoyl-coa;Palmitoyl-coenzyme a;Palmityl-coa;Palmityl-coenzyme a;S-hexadecanoate;S-hexadecanoate coa;S-hexadecanoate coenzyme a;S-hexadecanoic acid;S-palmitoylcoenzyme a;CoA(16:0)
PW_C001031
COA16:0
875
3
880
22
890
17
1647
14
2090
10
2096
2
5229
102
5244
104
6958
162
6970
199
7129
163
7201
160
9123
170
9129
188
9214
195
25503
49
77219
134
77227
329
77893
112
78045
332
78049
132
78549
115
79257
333
81844
331
90767
210
95706
383
97120
382
108597
288
111103
389
114205
390
120228
384
120664
407
121356
405
121404
123
121411
124
122901
121
122914
399
123278
119
123915
376
123963
447
123970
118
125576
480
125589
484
126026
481
126028
478
126208
299
127106
391
127478
206
127480
209
127770
388
128847
398
911
Malonyl-CoA
HMDB0001175
Malonyl-CoA, also known as malonyl CoA or CoA, malonyl, belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Malonyl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Malonyl-CoA has been found throughout most human tissues, and has also been primarily detected in urine. Within the cell, malonyl-CoA is primarily located in the mitochondria, peroxisome and cytoplasm. In humans, malonyl-CoA is involved in fatty acid biosynthesis pathway, the pyruvate metabolism pathway, and the propanoate metabolism pathway. Malonyl-CoA is also involved in several metabolic disorders, some of which include the primary hyperoxaluria II, PH2 pathway, pyruvate decarboxylase E1 component deficiency (pdhe1 deficiency), malonyl-CoA decarboxylase deficiency, and pyruvate dehydrogenase complex deficiency. Malonyl-CoA is a coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems.
524-14-1
C00083
10663
15531
MALONYL-COA
10213
DB04524
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)CC(O)=O
C24H38N7O19P3S
InChI=1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19?,23-/m1/s1
LTYOQGRJFJAKNA-VFLPNFFSSA-N
3-{[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}-3-oxopropanoic acid
853.58
853.115602295
-2.35
10
3-({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)-3-oxopropanoic acid
0
-5
FDB001606
Malonyl coa;Malonyl coenzyme a;Malonyl-coa;Malonyl-coenzyme a;Omega-carboxyacyl-coa;Omega-carboxyacyl-coenzyme a;S-(hydrogen malonyl)coenzyme a;S-(hydrogen propanedioate;S-(hydrogen propanedioate) coa;S-(hydrogen propanedioate) coenzyme a;S-(hydrogen propanedioic acid
PW_C000911
MalyCoA
1788
8
2268
4
4263
2
6924
160
12138
151
77830
132
78629
133
78777
111
121454
122
122257
406
122454
124
124012
135
124810
120
125021
118
126082
297
126420
479
126606
299
127538
205
127987
501
128180
388
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
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
2775
3-Oxooctadecanoyl-CoA
HMDB0006498
3-Oxooctadecanoyl-CoA is a metabolite intermediate in the microsomal fatty acid chain elongation system. Microsomal electron-transport components NADPH-cytochrome P450 reductase (EC 1.6.2.4) and cytochrome b5 (EC 1.6.2.2) participate in the conversion from 3-Oxooctadecanoyl-CoA to beta-hydroxystearoyl-CoA, the first reductive step of the microsomal chain elongating system initiated by NADPH. (PMID: 6404652).
86370-20-9
C16216
22833663
17216373
CCCCCCCCCCCCCCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C39H68N7O18P3S
InChI=1S/C39H68N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-26,28,32-34,38,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)
LGOGWHDPDVAUNY-UHFFFAOYSA-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-[(3-oxooctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
1047.99
1047.355440546
-2.81
9
3-oxooctadecanoyl-coa
0
-4
FDB023942
3-ketostearoyl-coa;3-ketostearoyl-coenzyme a;3-oxostearoyl-coa;3-oxostearoyl-coenzyme a;Beta-ketostearoyl-coa;Beta-ketostearoyl-coenzyme a
PW_C002775
3OOACoA
2893
4
78353
133
122625
406
125199
120
126777
479
128373
501
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
145
Palmitic acid
HMDB0000220
Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent.
57-10-3
C00249
985
15756
CPD-8475
960
DB03796
CCCCCCCCCCCCCCCC(O)=O
C16H32O2
InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)
IPCSVZSSVZVIGE-UHFFFAOYSA-N
hexadecanoic acid
256.4241
256.240230268
-5.80
1
palmitic acid
0
-1
FDB011679
1-hexyldecanoate;1-hexyldecanoic acid;1-pentadecanecarboxylic acid;C16 fatty acid;Cetylic acid;Edenor c16;Emersol 140;Emersol 143;Glycon p-45;Hexadecanoate;Hexadecanoic acid;Hexadecanoic acid palmitic acid;Hexadecoate;Hexadecoic acid;Hexadecylic acid;Hexaectylic acid;Hydrofol;Hydrofol acid 1690;Hystrene 8016;Hystrene 9016;Industrene 4516;Kortacid 1698;Loxiol ep 278;Lunac p 95;Lunac p 95kc;Lunac p 98;N-hexadecanoate;N-hexadecanoic acid;N-hexadecoate;N-hexadecoic acid;Pam;Plm;Palmitate;Palmitic acid;Palmitinate;Palmitinic acid;Palmitinsaeure;Palmitoate;Palmitoic acid;Pentadecanecarboxylate;Pentadecanecarboxylic acid;Prifac 2960;Prifrac 2960;Pristerene 4934;Univol u332;C16:0;Ch3-[ch2]14-cooh;1-pentadecanecarboxylate;Cetylate;Hexadecylate;Hexaectylate;Hexadecanoate (n-c16:0);FA(16:0)
PW_C000145
16:0
876
3
878
22
2177
14
2181
2
2185
15
2843
29
2898
8
5249
104
6447
105
6448
107
6515
108
6957
160
6975
199
7130
163
8311
210
9223
170
12916
151
12918
226
42523
320
42524
318
42525
315
77232
329
77655
336
77861
132
77894
112
78060
115
78061
114
120244
382
120665
407
121427
405
121429
409
121431
124
121699
429
122918
399
123279
119
123985
376
123987
137
123989
118
124249
464
125594
484
126637
299
127122
389
128213
388
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
32
Adenosine monophosphate
HMDB0000045
Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable.
61-19-8
C00020
6083
16027
AMP
5858
DB00131
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
C10H14N5O7P
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
UDMBCSSLTHHNCD-KQYNXXCUSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
347.2212
347.063084339
-2.02
5
adenylate
0
-2
DBMET00485
FDB021806
5'-amp;5'-adenosine monophosphate;5'-adenylate;5'-adenylic acid;Amp;Adenosine 5'-monophosphate;Adenosine 5'-phosphate;Adenosine 5'-phosphorate;Adenosine 5'-phosphoric acid;Adenosine phosphate;Adenosine-5'-monophosphorate;Adenosine-5'-monophosphoric acid;Adenosine-5-monophosphorate;Adenosine-5-monophosphoric acid;Adenosine-monophosphate;Adenosine-phosphate;Adenovite;Adenylate;Adenylic acid;Cardiomone;Lycedan;Muscle adenylate;Muscle adenylic acid;My-b-den;My-beta-den;Phosaden;Phosphaden;Phosphentaside;5'-o-phosphonoadenosine;Adenosine 5'-(dihydrogen phosphate);Adenosine monophosphate;Adenosine-5'p;Adenosini phosphas;Ado5'p;Fosfato de adenosina;Pa;Pado;Phosphate d'adenosine;5'-adenosine monophosphoric acid;Adenosine phosphoric acid;Adenosine 5'-(dihydrogen phosphoric acid);Adenosine 5'-monophosphoric acid;Adenosine monophosphoric acid;Adenosine-5'-monophosphate;Phosphoric acid d'adenosine
PW_C000032
AMP
11
2
34
4
62
8
270
16
734
32
881
22
1189
14
4572
5
4867
54
5033
89
5251
104
5408
117
5423
103
5432
118
5457
120
5558
132
5583
133
5779
101
5795
108
6977
199
7072
188
11789
198
11868
161
11988
151
12003
222
12580
226
12636
31
12694
290
13331
225
42266
3
42646
315
77234
329
77325
111
78392
334
78809
115
79320
112
80399
1
80684
135
80900
7
119916
122
120016
124
120031
406
120246
382
120888
405
121954
408
122920
399
123464
376
124507
374
125306
297
125394
299
125409
479
125596
484
126853
205
126934
388
126949
501
127124
389
127311
209
127711
502
170
Pyrophosphate
HMDB0000250
The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.
14000-31-8
C00013
644102
18361
PPI
559142
DB04160
[O-]P([O-])(=O)OP([O-])([O-])=O
O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4
XPPKVPWEQAFLFU-UHFFFAOYSA-J
(phosphonooxy)phosphonic acid
173.9433
173.911925378
4
pyrophosphoric acid
0
-3
FDB021918
(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ion
PW_C000170
Ppi
12
2
35
4
63
8
429
23
735
32
882
22
1217
3
1620
49
2410
59
2815
29
4175
14
4868
54
5034
89
5252
104
5294
101
5409
117
5424
103
5433
118
5458
120
5548
111
5559
132
5584
133
5606
135
5655
108
5879
107
6239
166
6978
199
7073
188
7134
163
7272
160
7312
198
7318
213
8275
151
8283
210
11869
161
12002
222
12041
164
12315
225
12323
249
12512
288
12579
226
12695
290
15219
306
15375
18
34760
17
42561
315
42697
318
77235
329
77317
128
77635
336
78416
335
78928
331
79153
112
79950
134
79958
130
80047
372
80417
170
85630
1
94786
384
94814
125
94819
382
98678
223
110634
391
113270
395
113275
389
115527
136
115532
399
119934
122
120017
124
120032
406
120330
410
120936
407
121261
429
121341
121
121486
383
122407
422
122985
444
123502
119
123831
464
124044
398
124977
375
125324
297
125395
299
125410
479
125597
484
125656
485
125876
481
126552
491
126869
205
126935
388
126950
501
127337
206
128124
508
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
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
44536
(3R)-3-hydroxy-stearoyl-CoA
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carboximidato)ethyl]-3,3-dimethylbutanecarboximidate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa).
76374
CCCCCCCCCCCCCCCC(O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OCC1OC(C(O)C1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N
C39H66N7O18P3S
InChI=1S/C39H70N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-28,32-34,38,47,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-4
WZMAIEGYXCOYSH-UHFFFAOYSA-J
3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropyl ({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate
1045.97
1045.341984801
-2.96
6
3-hydroxy-3-{[2-({2-[(3-hydroxyoctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropyl {[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate
-4
-4
(3r)-3-hydroxyoctadecanoyl-coa, β-hydroxystearoyl-coa
PW_C044536
3RhsCoA
2796
(2E)-Octadecenoyl-CoA
HMDB0006529
trans-Octadec-2-enoyl-CoA, also known as (2e)-octadecenoyl-coa, belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms. trans-Octadec-2-enoyl-CoA is considered to be a practically insoluble (in water) and relatively neutral molecule. trans-Octadec-2-enoyl-CoA has been primarily detected in urine. Within the cell, trans-octadec-2-enoyl-CoA is primarily located in the cytoplasm, membrane (predicted from logP) and mitochondria. In humans, trans-octadec-2-enoyl-CoA is involved in the metabolic disorder called the mitochondrial Beta-oxidation OF long chain saturated fatty acids pathway. trans-Octadec-2-enoyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. trans-Octadec-2-enoyl-CoA is produced from 3-Hydroxyoctadecanoyl-CoA and then converted to Stearoyl-CoA via enzymatic reaction.
C16218
53477850
CCCCCCCCCCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H](C(O)[C@H]1OP(=O)(O)O)N1C=NC2=C1N=CN=C2N
C39H68N7O17P3S
InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h18-19,26-28,32-34,38,49-50H,4-17,20-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b19-18+/t28-,32?,33+,34+,38-/m1/s1
NBCCUIHOHUKBMK-XCRBYWPRSA-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-[(2E)-octadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
1031.98
1031.360524011
-3.10
9
trans-octadec-2-enoyl-coa
0
-4
FDB023960
(2e)-octadecenoyl-coa;(2e)-octadecenoyl-coenzyme a
PW_C002796
tO2eCoA
2891
4
78348
133
122623
406
125197
120
126775
479
128370
501
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
871
Stearoyl-CoA
HMDB0001114
Stearoyl-CoA is a long-chain acyl CoA ester that acts as an intermediate metabolite in the biosynthesis of monounsaturated fatty acids; a critical committed step in the reaction is the introduction of the cis-configuration double bond into acyl-CoAs (between carbons 9 and 10). This oxidative reaction is catalyzed by the iron-containing, microsomal enzyme, stearoyl-CoA desaturase (SCD, EC 1.14.19.1). NADH supplies the reducing equivalents for the reaction, the flavoprotein is cytochrome b5-reductase and the electron carrier is the heme protein cytochrome b5. Stearoyl-CoA is converted into oleoyl-CoA and then used as a major substrate for the synthesis of various kinds of lipids including phospholipids, triglycerides, cholesteryl esters and wax esters. Oleic acid is the preferred substrate for acyl-CoA cholesterol acyltransferase (ACAT, EC 2.3.1.26) and diacylglycerol acyltransferase (DGAT, EC 2.3.1.20), the enzymes responsible for cholesteryl esters and triglycerides synthesis, respectively. In addition oleate is the major monounsaturated fatty acid in human adipose tissue and in the phospholipid of the red-blood-cell membrane. In the biosynthesis of sphinganine, stearoyl-CoA proceeds through the acyl-CoA + serine -> 3-keto-sphinganine -> sphinganine pathway, with the key enzyme being acyl-CoA serine acyltransferase (EC 2.3.1.50) to yield C20-(3-ketosphinganine) long-chain base. There is growing recognition that acyl-CoA esters could act as signaling molecules in cellular metabolism. (PMID: 12538075, 10998569, Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):113-21.).
362-66-3
C00412
439229
15541
STEAROYL-COA
388366
CCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C39H70N7O17P3S
InChI=1S/C39H70N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h26-28,32-34,38,49-50H,4-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/t28-,32-,33-,34?,38-/m1/s1
SIARJEKBADXQJG-KBEKLFCESA-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-(octadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
1033.996
1033.376174075
-3.04
9
stearoyl-coa
0
-4
FDB022431
Octadecanoyl-coa;Octadecanoyl-coenzyme a;S-octadecanoate;S-octadecanoate coa;S-octadecanoate coenzyme a;S-octadecanoic acid;S-stearate coa;S-stearate coenzyme a;S-stearoylcoenzyme a;Stearoyl coenzyme a;Stearoyl coenzyme a ester;Stearoyl-coa;Stearoyl-coenzyme a;Stearyl coenzyme a;Stearyl-coa;Stearyl-coenzyme a;CoA(18:0)
PW_C000871
COA18:0
2882
22
2889
17
25504
49
78338
329
78344
134
81850
331
95710
383
97899
382
108753
288
111309
389
114211
390
122620
384
125190
399
125194
121
126768
484
126772
480
128367
391
128851
398
661
Stearic acid
HMDB0000827
Stearic acid, also called octadecanoic acid, is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. It is a waxy solid, and its chemical formula is CH3(CH2)16COOH. Its name comes from the Greek word stear, which means tallow. Its IUPAC name is octadecanoic acid. -- Wikipedia.
57-11-4
C01530
5281
28842
STEARIC_ACID
5091
DB03193
CCCCCCCCCCCCCCCCCC(O)=O
C18H36O2
InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)
QIQXTHQIDYTFRH-UHFFFAOYSA-N
octadecanoic acid
284.4772
284.271530396
-6.63
1
stearic acid
0
-1
FDB002941
1-heptadecanecarboxylate;1-heptadecanecarboxylic acid;N-octadecanoate;N-octadecanoic acid;Octadecanoate;Octadecanoic acid;Stearate;Stearex beads;Stearic acid;Stearic acid cherry;Stearophanate;Stearophanic acid;FA(18:0)
PW_C000661
18:0
2884
22
2890
8
3315
5
12928
151
12979
226
78342
111
78563
334
122596
408
122619
122
125168
374
125193
135
126742
482
126771
297
128336
502
128366
205
44540
(2E)-eicosenoyl-CoA
HMDB0062227
trans-2-Icosenoyl-CoA(4-), also known as (e)-2-eicosenoyl-CoA(4-) or (2E)-arachidoenoyl-CoA, belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms. trans-2-Icosenoyl-CoA(4-) is considered to be a practically insoluble (in water) and relatively neutral molecule.
71627315
[H]\C(CCCCCCCCCCCCCCCCC)=C(\[H])C(=O)SCCN=C([O-])CCN=C([O-])[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP([O-])([O-])=O
C41H68N7O17P3S
InChI=1S/C41H72N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h20-21,28-30,34-36,40,51-52H,4-19,22-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/p-4/b21-20+/t30-,34-,35-,36+,40-/m1/s1
ROOFWBIMBMJYGA-DSAUMYHJSA-J
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-(2-{[2-(icos-2-enoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidic acid
1056.01
1055.362720245
-3.90
9
4-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-(2-{[2-(icos-2-enoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidic acid
0
-4
(2e)-eicosenoyl-coa;(2e)-arachidoenoyl-coa;Trans-arachido-2-enoyl-coa;Trans-2-eicosenoyl-coa(4-);(e)-2-icosenoyl-coa(4-);(e)-2-eicosenoyl-coa(4-)
PW_C044540
2ECoA
44538
3-oxoicosanoyl-CoA
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-5-methyl-3-(phosphonatooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-oxoicosanoyl)sulfanyl]ethyl}carboximidato)ethyl]butanecarboximidate belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms. 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-5-methyl-3-(phosphonatooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-oxoicosanoyl)sulfanyl]ethyl}carboximidato)ethyl]butanecarboximidate is considered to be a practically insoluble (in water) and relatively neutral molecule.
70678676
CCCCCCCCCCCCCCCCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OCC1OC(C)(C(O)C1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N
C42H70N7O18P3S
InChI=1S/C42H74N7O18P3S/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-30(50)25-33(52)71-24-23-44-32(51)21-22-45-40(55)37(54)41(2,3)27-64-70(61,62)67-69(59,60)63-26-31-35(66-68(56,57)58)36(53)42(4,65-31)49-29-48-34-38(43)46-28-47-39(34)49/h28-29,31,35-37,53-54H,5-27H2,1-4H3,(H,44,51)(H,45,55)(H,59,60)(H,61,62)(H2,43,46,47)(H2,56,57,58)/p-4
XTEYONNNQURLOI-UHFFFAOYSA-J
(3-oxoicosanoyl)-CoA
1086.04
1085.37328493
-3.47
5
(3-oxoicosanoyl)-CoA
-4
-4
PW_C044537
3OIyCoA
44539
(3R)-3-hydroxy-arachidoyl-CoA
(R)-3-Hydroxyicosanoyl-CoA(4-), also known as (3R)-hydroxyeicosanoyl-CoA or (R)-3-OH-C20:0-CoA(4-), belongs to the class of organic compounds known as long-chain (3r)-3-hydroxyacyl coas. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative, to which the acyl chain carries between 13 and 21 carbon atoms (R)-3-Hydroxyicosanoyl-CoA(4-) is considered to be a practically insoluble (in water) and relatively neutral molecule.
72193813
[H][C@@](O)(CCCCCCCCCCCCCCCCC)CC(=O)SCCN=C([O-])CCN=C([O-])[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP([O-])([O-])=O
C41H70N7O18P3S
InChI=1S/C41H74N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-29(49)24-32(51)70-23-22-43-31(50)20-21-44-39(54)36(53)41(2,3)26-63-69(60,61)66-68(58,59)62-25-30-35(65-67(55,56)57)34(52)40(64-30)48-28-47-33-37(42)45-27-46-38(33)48/h27-30,34-36,40,49,52-53H,4-26H2,1-3H3,(H,43,50)(H,44,54)(H,58,59)(H,60,61)(H2,42,45,46)(H2,55,56,57)/p-4/t29-,30-,34-,35-,36+,40-/m1/s1
KNSVYMFEJLUJST-AFMYZWIISA-J
(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(3R)-3-hydroxyicosanoyl]sulfanyl}ethyl)carboximidato]ethyl}-3,3-dimethylbutanecarboximidate
1074.03
1073.37328493
-3.39
6
(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-{2-[(2-{[(3R)-3-hydroxyicosanoyl]sulfanyl}ethyl)carboximidato]ethyl}-3,3-dimethylbutanecarboximidate
-4
-4
(r)-3-hydroxyeicosanoyl-coa;(3r)-hydroxyeicosanoyl-coa;(r)-3-hydroxyicosanoyl-coenzyme a(4-)
PW_C044539
3RHArCA
1065
Oxygen
HMDB0001377
Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).
7782-44-7
C00007
977
15379
CPD-6641
952
O=O
O2
InChI=1S/O2/c1-2
MYMOFIZGZYHOMD-UHFFFAOYSA-N
oxidanone
31.9988
31.989829244
0
singlet oxygen
0
0
FDB022589
Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948
PW_C001065
O2
95
9
110
5
245
16
500
18
505
8
549
14
625
28
638
3
649
10
674
31
688
20
754
15
763
4
769
33
836
2
1375
49
2016
24
2531
22
2803
29
4260
42
4747
13
5467
123
5480
125
5493
126
5508
127
5809
108
5973
147
6129
159
7006
188
7032
163
7050
160
7319
213
7533
210
7560
212
8395
151
11816
216
11864
198
11883
215
11894
211
12057
225
12063
164
12247
286
12279
226
12325
249
12706
291
12716
292
13004
298
13016
300
13026
301
13038
302
13260
223
42276
17
42657
315
76910
293
77044
294
77214
134
77350
111
77363
130
77377
331
77395
332
77497
113
77512
115
77537
334
77626
336
77723
337
77736
112
77747
129
77756
341
77805
114
77812
133
78070
329
78151
132
78381
345
78805
343
79111
360
120047
408
120383
122
120426
405
120542
407
120553
414
120594
409
120601
406
120883
415
121045
124
121104
383
121605
434
121656
429
122117
382
122573
418
122689
384
122798
374
122822
443
123027
135
123060
376
123128
447
123139
136
123163
448
123176
119
123187
450
123219
137
123226
120
123459
451
123609
118
123669
398
124163
469
124214
464
124669
399
125145
454
125275
121
125425
482
125706
478
125731
483
125737
297
125740
479
125884
481
126100
299
126272
484
126522
495
126721
489
126825
480
126964
502
126986
207
127198
209
127214
208
127219
205
127222
501
127305
504
127345
206
127557
388
127574
515
127835
389
128081
395
128095
390
128312
506
128432
391
184
Sphinganine
HMDB0000269
Sphinganine is a blocker postlysosomal cholesterol transport by inhibition of low-density lipoprotein-induced esterification of cholesterol and cause unesterified cholesterol to accumulate in perinuclear vesicles. It has been suggested the possibility that endogenous sphinganine may inhibit cholesterol transport in Niemann-Pick Type C (NPC) disease. (PMID 1817037).
764-22-7
C00836
91486
16566
82609
CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO
C18H39NO2
InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1
OTKJDMGTUTTYMP-ZWKOTPCHSA-N
(2S,3R)-2-aminooctadecane-1,3-diol
301.5078
301.298079497
-4.82
3
sphinganine
0
1
FDB021924
2-amino-d-erythro-1,3-octadecanediol;C18-dihydrosphingosine;C18-dihydro-sphingosine;D-erythro-1,3-dihydroxy-2-aminooctadecane;D-erythro-2-amino-1,3-octadecanediol;D-erythro-c18-dihydrosphingosine;D-erythro-sphinganine;Dihydro-c18-sphingosine;Dihydrosphingosine;Erythro-sphinganine;Octadecasphinganine;Sphinganine;[r-(r*,s*)]-2-amino-1,3-octadecanediol;(2s,3r)-2-amino-1,3-octadecanediol;(r-(r*,s*))-2-aminooctadecane-1,3-diol;2-amino-1,3-dihydroxyoctadecane;C18-sphinganine;D18:0;Safingol
PW_C000184
d18:0
2100
2
2123
10
4468
18
7204
160
78845
132
122060
124
124610
118
126213
299
127775
388
2151
Phytosphingosine
HMDB0004610
Phytosphingosine is a phospholipid. Phospholipids are a class of lipids and a major component of all biological membranes; sphingolipid metabolites, such as sphingosine and ceramide, are highly bioactive compounds and are involved in diverse cell processes, including cell-cell interaction, cell proliferation, differentiation, and apoptosis. Phytosphingosine is also one of the most widely distributed natural sphingoid bases, which is abundant in fungi and plants, and also found in animals including humans. Phytosphingosine is structurally similar to sphingosine; phytosphingosine possesses a hydroxyl group at C-4 of the sphingoid long-chain base. The physiological roles of phytosphingosine are largely unknown. Phytosphingosine induces apoptosis in human T-cell lymphoma and non-small cell lung cancer cells, and induces caspase-independent cytochrome c release from mitochondria. In the presence of caspase inhibitors, phytosphingosine-induced apoptosis is almost completely suppressed, suggesting that phytosphingosine-induced apoptosis is largely dependent on caspase activities. (PMID: 12576463, 12531554, 8046331, 8048941,8706124).
554-62-1
C12144
122121
46961
PHYTOSPINGOSINE
108921
CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO
C18H39NO3
InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1
AERBNCYCJBRYDG-KSZLIROESA-N
(2S,3S,4R)-2-aminooctadecane-1,3,4-triol
317.5072
317.292994119
-3.85
4
phytosphingosine
0
1
FDB023381
(+)-d-ribo-phytosphingosine;4-d-hydroxy-sphinganine;4-d-hydroxysphinganine;4d-hydroxysphinganine;C18-phytosphingosine;D-ribo-1,3,4-trihydroxy-2-aminooctadecane;D-ribo-2-amino-1,3,4-octadecanetriol;[2s-(2r*,3r*,4s*)]-2-amino-1,3,4-octadecanetriol;4-r-hydroxyoctadecasphinganine
PW_C002151
Phytosp
1139
3-Dehydrosphinganine
HMDB0001480
3-Dehydrosphinganine, also known as ketodihydrosphingosine or KDHS, belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group. Thus, 3-dehydrosphinganine is considered to be a sphingoid base lipid molecule. 3-Dehydrosphinganine is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, 3-dehydrosphinganine is primarily located in the cytoplasm, membrane (predicted from logP) and mitochondria. In humans, 3-dehydrosphinganine is involved in the globoid cell leukodystrophy pathway, the sphingolipid metabolism pathway, and the metachromatic leukodystrophy (MLD) pathway. 3-Dehydrosphinganine is also involved in a few metabolic disorders, which include the fabry disease pathway, the gaucher disease pathway, and the krabbe disease pathway. 3-Dehydrosphinganine is an intermediate in the metabolism of Glycosphingolipids. It is a substrate for Serine palmitoyltransferase 1 and Serine palmitoyltransferase 2.
16105-69-4
C02934
439853
17862
DEHYDROSPHINGANINE
388895
CCCCCCCCCCCCCCCC(=O)[C@@H](N)CO
C18H37NO2
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17,20H,2-16,19H2,1H3/t17-/m0/s1
KBUNOSOGGAARKZ-KRWDZBQOSA-N
(2S)-2-amino-1-hydroxyoctadecan-3-one
299.4919
299.282429433
-5.36
2
3-ketosphinganine
0
1
FDB022645
(2s)-2-amino-1-hydroxyoctadecan-3-one;1-hydroxy-2-amino-3-oxo-octadecane;2-amino-1-hydroxy-3-octadecanone;3-dehydro-d-sphinganine;3-dehydrosphinganine;3-ketodihydrosphingosine;3-ketosphinganine;Kdhs;Ketodihydrosphingosine
PW_C001139
3-DHPG
2097
2
7203
160
78842
132
122057
124
124611
118
126210
299
127772
388
2111
Eicosanoyl-CoA
HMDB0004258
Eicosanoyl-CoA is an intermediate metabolite in the synthesis of phosphatidic acid, a substrate of lysophosphatidic acid acyltransferase with high specificity as an acyl donor. Cells and membranes of mammalian cells synthesize their glycerophospholipids and triglycerides to maintain the cellular integrity and to provide energy for cellular functions. The phospholipids are synthesized de novo in cells through an evolutionary conserved process involving serial acylations of glycerol-3-phosphate. Several isoforms of the enzyme 1-acylglycerol-3-phosphate-O-acyltransferase (EC 2.3.1.51, AGPAT) acylate lysophosphatidic acid at the sn-2 position to produce phosphatidic acid. Bile acid-CoA:amino acid N-acyltransferase (EC 2.3.1.65, BACAT) catalyzes the conjugation of bile acids to glycine and taurine for excretion into bile and can utilize Eicosanoyl-CoA as an acyl donor as well; this may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids. (PMID: 17535882, 12810727).
15895-27-9
C02041
16061151
15527
ICOSANOYL-COA
17220830
CCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C41H74N7O17P3S
InChI=1S/C41H74N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h28-30,34-36,40,51-52H,4-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/t30-,34-,35-,36+,40-/m1/s1
JYLSVNBJLYCSSW-IBYUJNRCSA-N
{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-[(2-{[2-(icosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
1062.06
1061.407476119
-3.34
9
[(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy((3R)-3-hydroxy-3-[(2-{[2-(icosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
0
-4
FDB023354
Arachidinoyl-coa;Arachidinoyl-coenzyme a;Arachidoyl coenzyme a;Arachidoyl-coa;Arachidoyl-coenzyme a;Arachidyl coa;Arachidyl coenzyme a;Eicosanethioate;Eicosanethioic acid;Eicosanethioic acid s-ester with coenzyme a;Eicosanoyl coenzyme a;Eicosyl-coenzyme a;Icosanoyl-coa;S-eicosanoate;S-eicosanoate coa;S-eicosanoate coenzyme a;S-eicosanoic acid;CoA(20:0)
PW_C002111
Eicosan
3308
5
25506
49
25582
22
78558
334
81864
331
86108
329
95724
383
99885
382
109034
288
111647
389
114223
390
122589
408
125161
374
126735
482
128329
502
128865
398
44563
N-icosanoylphytosphingosine
Cer(t18:0/20:0), also known as phc-b 18:0/20:0, belongs to the class of organic compounds known as phytoceramides. These are n-acylated 4-hydroxysphinganine. Thus, cer(t18:0/20:0) is considered to be a ceramide lipid molecule. Cer(t18:0/20:0) is considered to be a practically insoluble (in water) and relatively neutral molecule.
70678852
[H][C@@](O)(CCCCCCCCCCCCCC)[C@@]([H])(O)[C@]([H])(CO)N=C(O)CCCCCCCCCCCCCCCCCCC
C38H77NO4
InChI=1S/C38H77NO4/c1-3-5-7-9-11-13-15-17-18-19-20-21-23-25-27-29-31-33-37(42)39-35(34-40)38(43)36(41)32-30-28-26-24-22-16-14-12-10-8-6-4-2/h35-36,38,40-41,43H,3-34H2,1-2H3,(H,39,42)/t35-,36+,38-/m0/s1
HFJJUTILDZFUOE-BEAALGTASA-N
N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]icosanimidic acid
612.037
611.585259963
-6.79
4
N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]icosanimidic acid
0
0
PW_C044563
N-Icspg
120
L-Serine
HMDB0000187
Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373).
56-45-1
C00065
5951
17115
SER
5736
DB00133
N[C@@H](CO)C(O)=O
C3H7NO3
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
MTCFGRXMJLQNBG-REOHCLBHSA-N
(2S)-2-amino-3-hydroxypropanoic acid
105.0926
105.042593095
0.66
3
L-serine
0
0
FDB012739
(-)-serine;(s)-2-amino-3-hydroxypropanoate;(s)-2-amino-3-hydroxypropanoic acid;(s)-2-amino-3-hydroxy-propanoate;(s)-2-amino-3-hydroxy-propanoic acid;(s)-serine;(s)-a-amino-b-hydroxypropionate;(s)-a-amino-b-hydroxypropionic acid;(s)-alpha-amino-beta-hydroxypropionate;(s)-alpha-amino-beta-hydroxypropionic acid;(s)-b-amino-3-hydroxypropionate;(s)-b-amino-3-hydroxypropionic acid;(s)-beta-amino-3-hydroxypropionate;(s)-beta-amino-3-hydroxypropionic acid;2-amino-3-hydroxypropanoate;2-amino-3-hydroxypropanoic acid;3-hydroxy-l-alanine;L-(-)-serine;L-3-hydroxy-2-aminopropionate;L-3-hydroxy-2-aminopropionic acid;L-3-hydroxy-alanine;L-ser;Serine;B-hydroxy-l-alanine;Beta-hydroxy-l-alanine;Beta-hydroxyalanine;(2s)-2-amino-3-hydroxypropanoic acid;(s)-(-)-serine;L-2-amino-3-hydroxypropionic acid;L-serin;S;Ser;(2s)-2-amino-3-hydroxypropanoate;(s)-α-amino-β-hydroxypropionate;(s)-α-amino-β-hydroxypropionic acid;β-hydroxy-l-alanine;B-hydroxyalanine;β-hydroxyalanine;L-2-amino-3-hydroxypropionate
PW_C000120
Ser
344
8
1810
2
2617
4
5642
107
5643
108
5884
105
6011
147
6907
163
7086
201
7087
202
7090
71
7091
72
7202
160
7438
3
7443
15
7444
166
7522
224
8357
225
9154
249
12173
151
12625
18
15379
49
42335
318
42336
315
77320
111
78088
133
78112
132
79979
331
94858
383
115752
398
119924
122
122056
124
122136
406
122718
135
124667
118
124688
120
125314
297
126209
299
126293
479
126860
205
127771
388
127856
501
260
ferrocytochrome b5
ProteinComplex
ProteinComplex
PW_EC000260
FB
259
ferricytochrome b5
Compound
Compound
PW_EC000259
FB
9969
Unknown
Unknown
18
1.3.1.71
6083
161
6121
162
6845
189
6885
160
7036
163
7063
188
7210
210
7213
211
7217
212
7223
213
7237
214
7241
215
7283
190
7301
198
7305
216
7392
217
7412
218
9275
254
11854
277
136087
644
136098
646
136985
253
136986
226
136987
693
136988
249
137079
708
10631
Ceramide synthase subunit LIP1
A6ZN14
Component of the ceramide synthase complex required for synthesis of ceramides.
LIP1
41
7655
160
137731
170
10614
Serine palmitoyltransferase 1
P25045
Component of serine palmitoyltransferase (SPT), which catalyzes the committed step in the synthesis of sphingolipids, the condensation of serine with palmitoyl CoA to form the long chain base 3-ketosphinganine.
LCB1
29
2.3.1.50
7657
160
10618
3-ketoacyl-CoA synthase ELO1
P39540
Component of a microsomal membrane bound medium-chain fatty acid elongation system, which extends medium-chain-length fatty acids to long-chain fatty acids. Component of elongase I, which extends 12-16-carbon fatty acyl-CoAs such as lauroyl-CoA to 14-18-carbon fatty acids by incorporation of malonyl-CoA.
ELO1
29
2.3.1.199
7653
160
8980
244
10619
Long-chain-fatty-acid--CoA ligase 2
P39518
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Preferentially acts on C9:0-C13:0 fatty acids although C7:0-C17:0 fatty acids are tolerated.
FAA2
29
6.2.1.3
10620
Very long-chain fatty acid transport protein
P38225
May be involved in long-chain fatty acids uptake, and thus may play a pivotal role in regulating their accessibility prior to metabolic utilization. May play an important role in uptake of these hydrophobic compounds under conditions where fatty acid synthesis is compromised.
FAT1
29
8981
242
10621
long chain fatty acyl:CoA synthetase
P47912
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Contributes, with FAA1, to the activation of imported myristate.
FAA4
29
6.2.1.3
10622
Long-chain-fatty-acid--CoA ligase 1
P30624
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It may supplement intracellular myristoyl-CoA pools from exogenous myristate. Preferentially acts on C12:0-C16:0 fatty acids with myristic and pentadecanic acid (C15:0) having the highest activities.
FAA1
29
6.2.1.3
10623
Long-chain-fatty-acid--CoA ligase 3
P39002
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. This enzyme acts preferentially on C16 and C18 fatty acids with a cis-double bond at C-9-C-10.
FAA3
29
6.2.1.3
10624
3-oxoacyl-[acyl-carrier-protein] reductase
P35731
Involved in biosynthesis of fatty acids in mitochondria.
OAR1
29
1.1.1.100
7650
160
8982
243
10625
Peroxisomal hydratase-dehydrogenase-epimerase
Q02207
Second trifunctional enzyme acting on the beta-oxidation pathway for fatty acids, possessing hydratase-dehydrogenase-epimerase activities. Converts trans-2-enoyl-CoA via D-3-hydroxyacyl-CoA to 3-ketoacyl-CoA.
FOX2
29
4.2.1.119; 1.1.1.n12
7651
160
8983
245
10626
2-enoyl thioester reductase
P38071
Required for respiration and the maintenance of the mitochondrial compartment. Oxidoreductase with a preference for short and medium chain substrates, including trans-2-hexenoyl-CoA (C6), trans-2-decenoyl-CoA (C10), and trans-2-hexadecenoyl-CoA (C16). May play a role in mitochondrial fatty acid synthesis.
ETR1
29
1.3.1.10; 1.3.1.38
7652
160
8984
239
10627
Peroxisomal acyl-coenzyme A thioester hydrolase 1
P41903
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH.
TES1
29
3.1.2.2
8985
245
10628
dihydrosphingosine C-4 hydroxylase
P38992
Required for hydroxylation of C-4 in the sphingoid moiety of ceramide. Involved in the response to syringomycin.
SUR2
29
1.-.-.-
7654
160
10629
3-ketosphinganine reductase
P38342
Catalyzes the reduction of 3-ketodihydrosphingosine (KDS) to dihydrosphingosine (DHS).
TSC10
29
1.1.1.102
7656
160
4325
3-ketoacyl-CoA synthase ELO1
18
PW_P004325
11382
10618
4326
Acyl-CoA synthase
18
PW_P004326
11383
10619
11384
10620
11385
10621
11386
10622
11387
10623
4327
3-oxoacyl-[acyl-carrier-protein] reductase
18
PW_P004327
11388
10624
4328
Peroxisomal hydratase-dehydrogenase-epimerase
18
PW_P004328
11389
10625
4329
2-enoyl thioester reductase
18
PW_P004329
11390
10626
4330
acyl-CoA thioesterase
18
PW_P004330
11391
10627
4331
dihydrosphingosine C-4 hydroxylase
18
PW_P004331
11392
10628
4332
3-ketosphinganine reductase
18
PW_P004332
11393
10629
4334
Ceramide synthase
18
PW_P004334
11395
10631
4333
Serine palmitoyltransferase 1
18
PW_P004333
11394
10614
6386
false
PW_R006386
Right
26161
1031
1
Compound
false
26162
911
1
Compound
false
26163
40034
1
Compound
false
26164
1316
1
Compound
false
26165
2775
1
Compound
false
26166
1099
1
Compound
false
6312
4325
2.3.1.199
6387
false
PW_R006387
Right
26167
145
1
Compound
false
26168
414
1
Compound
true
26169
1099
1
Compound
true
26170
32
1
Compound
true
26171
170
1
Compound
true
26172
1031
1
Compound
false
6313
4326
6.2.1.3
6388
false
PW_R006388
Right
26173
2775
1
Compound
false
26174
40034
1
Compound
false
26175
146
1
Compound
false
26176
143
1
Compound
false
26177
44536
1
Compound
false
6314
4327
1.1.1.100
6389
false
PW_R006389
Right
26178
44536
1
Compound
false
26179
2796
1
Compound
false
26180
1420
1
Compound
false
6315
4328
4.2.1.119,1.1.1.n12
6390
false
PW_R006390
Right
26181
2796
1
Compound
false
26182
40034
1
Compound
false
26183
146
1
Compound
false
26184
871
1
Compound
false
26185
143
1
Compound
false
6316
4329
1.3.1.10,1.3.1.38
6391
false
PW_R006391
Right
26186
871
1
Compound
false
26187
1420
1
Compound
false
26188
40034
1
Compound
false
26189
1099
1
Compound
false
26190
661
1
Compound
false
6317
4330
3.1.2.2
6412
false
PW_R006412
Right
26290
871
1
Compound
false
26291
40034
1
Compound
false
26292
911
1
Compound
false
26293
44538
1
Compound
false
26294
1099
1
Compound
false
26295
1316
1
Compound
false
6340
4325
6413
false
PW_R006413
Right
26296
44538
1
Compound
false
26297
146
1
Compound
false
26298
40034
1
Compound
false
26299
44539
1
Compound
false
26300
143
1
Compound
false
6341
4327
6408
false
PW_R006408
Right
26267
40034
2
Compound
false
26268
1065
1
Compound
false
26269
260
1
ElementCollection
false
26270
184
1
Compound
false
26271
1420
1
Compound
false
26272
2151
1
Compound
false
26273
259
1
ElementCollection
false
6336
4331
1.-.-.-
6409
false
PW_R006409
Right
26274
40034
1
Compound
false
26275
146
1
Compound
false
26276
1139
1
Compound
false
26277
143
1
Compound
false
26278
184
1
Compound
false
6337
4332
1.1.1.102
6515
false
PW_R006515
Right
26753
2111
1
Compound
false
26754
2151
1
Compound
false
26755
40034
1
Compound
false
26756
1099
1
Compound
false
26757
44563
1
Compound
false
6435
4334
6410
PW_R006410
Unknown
26279
1031
1
Compound
false
26280
120
1
Compound
false
26281
40034
1
Compound
false
26282
1099
1
Compound
false
26283
1316
1
Compound
false
26284
1139
1
Compound
false
6338
4333
2.3.1.50
6395
false
PW_R006395
Right
26205
44540
1
Compound
false
26206
40034
1
Compound
false
26207
146
1
Compound
false
26208
2111
1
Compound
false
26209
143
1
Compound
false
6321
4329
6394
false
PW_R006394
Right
26202
44539
1
Compound
false
26203
1420
1
Compound
false
26204
44540
1
Compound
false
6320
4328
78734
1031
3
false
853
402
10
regular
100
100
78735
911
3
false
973
492
10
regular
100
100
78736
40034
55
false
998
348
10
regular
78
78
78737
1316
52
false
1286
333
10
regular
78
78
78738
2775
3
false
1394
392
10
regular
100
120
78739
1099
85
false
1309
497
10
regular
50
30
78740
145
3
false
288
400
10
regular
100
100
78741
414
42
false
418
385
10
regular
50
30
78742
1099
85
false
428
485
10
regular
50
30
78743
32
44
false
758
504
10
regular
50
30
78744
170
45
false
771
364
10
regular
63
43
78745
40034
55
false
1520
329
10
regular
78
78
78746
146
62
false
1534
492
10
regular
50
30
78747
143
61
false
1819
360
10
regular
50
30
78748
44536
3
false
1879
395
10
regular
100
120
78749
2796
3
false
2404
390
10
regular
100
120
78750
1420
49
false
2279
336
10
regular
78
78
78751
40034
55
false
2495
522
10
regular
78
78
78752
146
62
false
2349
565
10
regular
50
30
78753
871
3
false
2404
848
10
regular
100
100
78754
143
61
false
2504
758
10
regular
50
30
78755
1420
49
false
2300
780
10
regular
78
78
78756
40034
55
false
2005
785
10
regular
78
78
78757
1099
85
false
2019
933
10
regular
50
30
78758
661
3
false
1889
848
10
regular
100
100
78760
1420
49
false
1532
1244
10
regular
78
78
78761
44540
3
false
1398
1297
10
regular
100
120
78762
40034
55
false
1295
1408
10
regular
78
78
78763
146
62
false
1318
1287
10
regular
50
30
78765
143
61
false
1048
1402
10
regular
50
30
78781
40034
55
false
2331
989
10
regular
78
78
78782
911
3
false
2494
968
10
regular
100
100
78783
44538
3
false
2405
1303
10
regular
100
120
78784
1099
85
false
2355
1203
10
regular
50
30
78785
1316
52
false
2525
1209
10
regular
78
78
78786
146
62
false
2322
1298
10
regular
50
30
78787
40034
55
false
2307
1409
10
regular
78
78
78788
44539
3
false
1901
1293
10
regular
100
130
78789
143
61
false
2036
1403
10
regular
50
30
78790
40034
55
false
694
1805
10
regular
78
78
78791
1065
65
false
872
1810
10
regular
78
78
78792
184
3
false
774
1983
10
regular
100
100
78793
1420
49
false
878
1585
10
regular
78
78
78794
2151
3
false
773
1419
10
regular
100
100
78795
40034
55
false
1190
1900
10
regular
78
78
78796
146
62
false
1189
2093
10
regular
50
30
78797
1139
3
false
1309
1978
10
regular
100
110
78798
143
61
false
924
1963
10
regular
50
30
78886
2111
3
false
888
1304
10
regular
100
100
78887
40034
55
false
474
1223
10
regular
78
78
78888
1099
85
false
507
1404
10
regular
50
30
78889
44563
3
false
347
1306
10
regular
100
110
84079
1031
160
3
false
1848
1983
10
regular
100
100
84080
120
160
3
false
1733
2078
10
regular
100
100
84081
40034
160
55
false
1748
1919
10
regular
78
78
84082
1099
160
85
false
1451
1973
10
regular
50
30
84083
1316
160
52
false
1431
2089
10
regular
78
78
1569
260
144
false
614
1914
12
regular
150
70
1570
259
144
false
628
1579
12
regular
150
70
37699
9969
160
2
false
1112
417
8
protein
regular
150
70
37700
9969
160
2
false
598
428
8
protein
regular
150
70
37701
9969
160
2
false
598
383
8
protein
regular
150
70
37702
9969
160
2
false
493
388
8
protein
regular
150
70
37703
9969
160
2
false
543
338
8
protein
regular
150
70
37704
9969
160
2
false
523
418
8
protein
regular
150
70
37705
9969
160
2
false
1624
417
8
protein
regular
150
70
37706
9969
160
2
false
2094
420
8
protein
regular
150
70
37707
9969
160
2
false
2379
645
8
protein
regular
150
70
37708
9969
160
2
false
2109
868
8
protein
regular
150
70
37709
9969
160
2
false
1651
1323
8
protein
regular
150
70
37710
9969
160
2
false
1121
1322
8
protein
regular
150
70
37715
9969
160
2
false
2379
1093
8
protein
regular
150
70
37716
9969
160
2
false
2118
1325
8
protein
regular
150
70
37717
9969
160
2
false
748
1704
8
protein
regular
150
70
37718
9969
160
2
false
984
2001
8
protein
regular
150
70
37744
10631
160
2
false
598
1321
8
subunit
regular
150
70
39653
10614
160
2
false
1547
2000
8
subunit
regular
150
70
30732
4325
2191
37036
37699
30733
4326
2191
37037
37700
37038
37701
37039
37702
37040
37703
37041
37704
30734
4327
2191
37042
37705
30735
4328
2191
37043
37706
30736
4329
2191
37044
37707
30737
4330
2191
37045
37708
30738
4328
2191
37046
37709
30739
4329
2191
37047
37710
30744
4325
2191
37052
37715
30745
4327
2191
37053
37716
30746
4331
2191
37054
37717
30747
4332
2191
37055
37718
30769
4334
2191
37081
37744
32231
4333
2191
160
38951
39653
113249
M953 452 C990 452 1060 452 1112 452
5
false
18
113250
M1023 492 C1023 462 1047 452 1112 452
5
false
18
113251
M1037 426 C1038 452 1078 453 1112 452
5
false
18
113252
M1325 411 C1325 440 1325 452 1262 452
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113253
M1394 452 C1357 453 1290 453 1262 452
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113254
M1334 497 C1334 469 1326 452 1262 452
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113255
M388 450 C418 450 493 453 523 453
5
false
18
113256
M443 415 C444 455 486 453 523 453
5
false
18
113257
M453 485 C453 452 478 452 523 453
5
false
18
113258
M783 504 C783 464 728 453 673 453
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113259
M802.5 407 C803.5 454 738 453 673 453
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113260
M853 452 C823 452 703 453 673 453
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
113261
M1494 452 C1524 452 1594 452 1624 452
5
false
18
113262
M1559 407 C1558 444 1583 453 1624 452
5
false
18
113263
M1559 492 C1558 460 1594 452 1624 452
5
false
18
113264
M1844 390 C1843 433 1804 452 1774 452
5
false
18
true
M 25.946855044164835 399.261556296296 L 11 398 L 17.380887721185843 411.5751343230783
false
113265
M1879 452 C1849 452 1804 452 1774 452
5
false
18
true
M 25.946855044164835 399.261556296296 L 11 398 L 17.380887721185843 411.5751343230783
false
113266
M1979 450 C1999 450 2076 451 2094 450
5
false
18
113267
M2404 452 C2365 453 2287 454 2246 452
5
false
18
true
M 546.9468550441649 268.261556296296 L 532 267 L 538.3808877211858 280.5751343230783
false
113268
M2318 414 C2318 438 2307 455 2244 455
5
false
18
true
M 546.9468550441649 268.261556296296 L 532 267 L 538.3808877211858 280.5751343230783
false
113269
M2454 510 C2453 542 2454 601 2454 645
5
false
18
113270
M2495 561 C2458 561 2453 584 2454 645
5
false
18
113271
M2403 580 C2448 580 2454 593 2454 645
5
false
18
113272
M2454 848 C2455 803 2454 736 2454 715
5
false
18
true
M 985.9468550441649 102.26155629629604 L 971 101 L 977.3808877211858 114.57513432307834
false
113273
M2504 773 C2471 774 2454 757 2454 715
5
false
18
true
M 985.9468550441649 102.26155629629604 L 971 101 L 977.3808877211858 114.57513432307834
false
113274
M2404 898 C2380 898 2292 903 2259 903
5
false
18
113275
M2339 858 C2336 887 2302 903 2259 903
5
false
18
113276
M2044 863 C2044 896 2075 903 2109 903
5
false
18
true
M 1221.9468550441647 102.26155629629604 L 1207 101 L 1213.380887721186 114.57513432307834
false
113277
M2044 933 C2044 894 2076 902 2109 903
5
false
18
true
M 1221.9468550441647 102.26155629629604 L 1207 101 L 1213.380887721186 114.57513432307834
false
113278
M1989 898 C2076 898 2072 903 2109 903
5
false
18
true
M 1221.9468550441647 102.26155629629604 L 1207 101 L 1213.380887721186 114.57513432307834
false
113306
M2454 948 C2454 978 2454 1063 2454 1093
5
false
18
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