1321
Pathway
Phospholipid Biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycw7/19:0cycw7)
Phospholipids are membrane components in E. coli. The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol, and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions. The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed into an sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH-driven glycerol-3-phosphate dehydrogenase. sn-Glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid). This can be achieved by an sn-glycerol-3-phosphate acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate (phosphatidic acid) through a 1-acylglycerol-3-phosphate O-acyltransferase. This compound is then converted into a CPD-diacylglycerol through a CTP phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either into an L-1-phosphatidylserine or an L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase, respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase. On the other hand, L-1-phosphatidylglycerol-phosphate gets transformed into an L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combine to produce a cardiolipin and an ethanolamine. The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin.
Metabolic
PW001557
Center
PathwayVisualizationContext1844
2049
2799
#000099
PathwayVisualization1305
1321
Phospholipid Biosynthesis CL(16:1(9Z)/16:1(9Z)/19:0cycw7/19:0cycw7)
Phospholipids are membrane components in E. coli. The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol, and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions. The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed into an sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH-driven glycerol-3-phosphate dehydrogenase. sn-Glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid). This can be achieved by an sn-glycerol-3-phosphate acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate (phosphatidic acid) through a 1-acylglycerol-3-phosphate O-acyltransferase. This compound is then converted into a CPD-diacylglycerol through a CTP phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either into an L-1-phosphatidylserine or an L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase, respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase. On the other hand, L-1-phosphatidylglycerol-phosphate gets transformed into an L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combine to produce a cardiolipin and an ethanolamine. The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin.
Metabolic
3
111017
549
SubPathway
110629
1134
Compound
3028
26443744
Cronan JE Jr, Rock CO: Biosynthesis of Membrane Lipids. EcoSal Plus. 2008 Sep;3(1). doi: 10.1128/ecosalplus.3.6.4.
1321
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
10
Glial cell
CL:0000125
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
1
Homo sapiens
9606
Eukaryote
Human
3
Escherichia coli
562
Prokaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
23
Pseudomonas aeruginosa
287
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
2
Bacteria
2
Prokaryote
Bacteria
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
19
Schizosaccharomyces pombe
4896
Eukaryote
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
5
Cytoplasm
GO:0005737
1
Cytosol
GO:0005829
4
Peroxisome
GO:0005777
24
Mitochondrial Intermembrane Space
GO:0005758
3
Mitochondrial Matrix
GO:0005759
11
Extracellular Space
GO:0005615
2
Mitochondrion
GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
12
Mitochondrial Inner Membrane
GO:0005743
14
Mitochondrial Outer Membrane
GO:0005741
13
Endoplasmic Reticulum
GO:0005783
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
10
Cell Membrane
GO:0005886
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
32
Inner Membrane
GO:0070258
19
sarcoplasmic reticulum
GO:0016529
27
Peroxisome Membrane
GO:0005778
8
Smooth Endoplasmic Reticulum
GO:0005790
15
Nucleus
GO:0005634
26
Golgi apparatus membrane
GO:0000139
39
Mitochondrial membrane
GO:0031966
25
Golgi apparatus
GO:0005794
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
5
cardiocyte
BTO:0001539
7
Nervous System
BTO:0001484
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
11
Heart
BTO:0000562
73
10
8
5
1
1
PW_BS000008
2
1
1
1
PW_BS000002
5
4
1
1
PW_BS000005
42
24
1
1
PW_BS000042
108
1
3
PW_BS000108
147
1
24
1
PW_BS000147
151
1
4
1
PW_BS000151
160
1
18
1
PW_BS000160
315
1
23
PW_BS000024
132
1
12
1
PW_BS000132
111
5
12
1
PW_BS000111
345
24
12
1
PW_BS000028
334
4
12
1
PW_BS000028
124
1
5
1
PW_BS000124
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1
6
1
PW_BS000112
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1
17
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PW_BS000118
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5
5
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PW_BS000122
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24
5
1
PW_BS000115
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PW_BS000115
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17
1
PW_BS000135
454
24
17
1
PW_BS000115
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4
17
1
PW_BS000053
297
5
10
1
PW_BS000024
299
1
10
1
PW_BS000024
489
24
10
1
PW_BS000115
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4
10
1
PW_BS000115
205
5
6
1
PW_BS000024
506
24
6
1
PW_BS000115
502
4
6
1
PW_BS000115
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3
1
1
PW_BS000004
15
11
1
PW_BS000015
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1
5
1
1
PW_BS000031
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2
1
1
PW_BS000003
26
1
1
1
5
PW_BS000026
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1
3
1
5
PW_BS000054
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7
1
1
PW_BS000049
17
12
1
1
PW_BS000017
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14
1
1
PW_BS000022
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1
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1
1
PW_BS000010
18
13
1
1
PW_BS000018
70
28
5
1
1
PW_BS000070
103
3
3
1
PW_BS000103
112
2
12
1
PW_BS000112
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31
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PW_BS000107
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PW_BS000100
105
11
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PW_BS000105
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1
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PW_BS000117
155
3
24
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PW_BS000155
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2
24
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PW_BS000157
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3
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PW_BS000161
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PW_BS000159
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PW_BS000166
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3
21
1
PW_BS000178
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8
4
PW_BS000152
101
5
3
1
PW_BS000101
188
1
18
PW_BS000024
187
31
18
PW_BS000024
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2
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PW_BS000163
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2
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PW_BS000024
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31
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PW_BS000024
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PW_BS000024
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PW_BS000024
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PW_BS000170
225
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12
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PW_BS000162
224
2
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1
PW_BS000024
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13
18
PW_BS000024
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13
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PW_BS000024
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PW_BS000164
281
1
25
1
PW_BS000024
285
10
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PW_BS000024
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36
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PW_BS000024
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34
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PW_BS000024
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PW_BS000024
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PW_BS000024
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31
23
PW_BS000024
322
1
23
1
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
293
4
1
PW_BS000024
133
3
12
1
PW_BS000133
134
12
12
1
PW_BS000134
331
7
12
1
PW_BS000028
114
11
12
PW_BS000114
327
1
1
12
5
PW_BS000028
347
1
3
12
5
PW_BS000028
130
13
12
1
PW_BS000130
368
3
60
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
119
2
17
1
PW_BS000119
383
7
5
1
PW_BS000100
94
3
PW_BS000094
390
7
6
1
PW_BS000112
398
7
17
1
PW_BS000113
336
1
12
1
PW_BS000028
109
32
3
PW_BS000109
406
3
5
1
PW_BS000115
407
2
5
1
PW_BS000115
409
11
5
PW_BS000115
424
1
1
5
5
PW_BS000115
425
1
3
5
5
PW_BS000115
384
12
5
1
PW_BS000100
125
13
5
1
PW_BS000125
120
3
17
1
PW_BS000120
137
11
17
PW_BS000137
459
1
1
17
5
PW_BS000115
460
1
3
17
5
PW_BS000115
121
12
17
1
PW_BS000121
136
13
17
1
PW_BS000136
479
3
10
1
PW_BS000115
481
2
10
1
PW_BS000115
483
11
10
PW_BS000115
495
7
10
1
PW_BS000115
480
12
10
1
PW_BS000115
300
13
10
1
PW_BS000024
501
3
6
1
PW_BS000115
208
11
6
PW_BS000024
391
12
6
1
PW_BS000112
395
13
6
1
PW_BS000113
29
1
1
1
PW_BS000029
14
10
1
PW_BS000014
35
5
19
1
4
PW_BS000035
198
5
18
1
PW_BS000024
211
10
18
PW_BS000024
332
1
7
12
1
PW_BS000028
115
10
12
PW_BS000115
405
10
5
PW_BS000115
123
1
7
5
1
PW_BS000123
429
1
5
1
PW_BS000115
376
10
17
PW_BS000053
447
1
7
17
1
PW_BS000115
464
1
17
1
PW_BS000115
58
1
14
1
1
PW_BS000058
350
1
14
12
1
PW_BS000028
253
5
4
1
PW_BS000024
433
1
14
5
1
PW_BS000115
468
1
14
17
1
PW_BS000115
329
14
12
1
PW_BS000028
382
14
5
1
PW_BS000100
389
14
6
1
PW_BS000112
399
14
17
1
PW_BS000113
59
27
1
1
PW_BS000059
11
1
8
1
1
PW_BS000011
6
1
3
1
PW_BS000006
102
12
3
1
PW_BS000102
104
14
3
1
PW_BS000104
1
1
PW_BS000001
199
14
18
1
PW_BS000024
129
1
5
12
1
PW_BS000129
335
27
12
1
PW_BS000028
333
1
2
12
PW_BS000028
288
14
4
1
PW_BS000024
414
1
5
5
1
PW_BS000115
422
27
5
1
PW_BS000115
450
1
5
17
1
PW_BS000115
375
27
17
1
PW_BS000053
478
10
10
PW_BS000115
484
14
10
1
PW_BS000115
491
27
10
1
PW_BS000115
209
10
6
PW_BS000024
508
27
6
1
PW_BS000115
189
32
18
PW_BS000024
197
14
18
PW_BS000024
23
15
1
1
PW_BS000023
128
15
12
1
PW_BS000128
410
15
5
1
PW_BS000115
444
15
17
1
PW_BS000115
485
15
10
1
PW_BS000115
32
1
15
1
5
PW_BS000032
89
2
PW_BS000089
290
5
49
1
PW_BS000024
306
35
51
1
PW_BS000024
372
10
2
PW_BS000028
201
7
5
1
10
PW_BS000024
202
7
11
1
10
PW_BS000024
71
11
1
3
PW_BS000071
72
5
1
3
PW_BS000072
56
26
1
1
PW_BS000056
309
39
1
1
PW_BS000024
13
1
2
1
PW_BS000013
20
4
1
1
1
PW_BS000020
43
25
1
1
PW_BS000043
190
11
18
PW_BS000024
277
1
2
18
PW_BS000024
341
4
1
12
1
PW_BS000028
356
25
12
1
PW_BS000028
412
1
2
5
PW_BS000115
419
25
5
1
PW_BS000115
446
1
2
17
PW_BS000115
455
25
17
1
PW_BS000115
490
25
10
1
PW_BS000115
507
25
6
1
PW_BS000115
361
39
12
1
PW_BS000028
386
39
5
1
PW_BS000100
401
39
17
1
PW_BS000113
9
6
1
1
PW_BS000009
28
1
16
1
1
PW_BS000028
33
18
1
1
PW_BS000033
24
4
10
1
1
PW_BS000024
60
25
1
PW_BS000060
46
1
1
4
PW_BS000046
61
25
1
7
PW_BS000061
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
27
15
1
PW_BS000027
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
113
6
12
1
PW_BS000113
110
2
3
1
PW_BS000110
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
140
10
3
PW_BS000140
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
95
1
7
2
1
PW_BS000095
180
2
21
1
PW_BS000180
207
6
6
1
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
216
4
18
1
PW_BS000024
65
11
1
PW_BS000065
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
298
1
7
10
1
PW_BS000024
301
6
10
1
PW_BS000024
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1
16
10
1
PW_BS000024
337
1
16
12
1
PW_BS000028
343
18
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
360
4
10
12
1
PW_BS000028
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2
60
1
PW_BS000028
228
36
1
PW_BS000024
232
40
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PW_BS000024
415
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434
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25
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17
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PW_BS000115
451
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17
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PW_BS000115
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4
10
17
1
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25
17
PW_BS000115
472
25
17
7
PW_BS000115
487
18
10
1
PW_BS000115
504
18
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
513
1
7
6
1
PW_BS000115
47
19
1
4
PW_BS000047
241
5
29
PW_BS000024
257
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29
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PW_BS000024
1134
Dihydroxyacetone phosphate
HMDB0001473
Dihydroxyacetone phosphate, also known as 3-phosphate, dihydroxyacetone or 3-hydroxy-2-oxopropyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Dihydroxyacetone phosphate has been detected in multiple biofluids, such as saliva and blood. Within the cell, dihydroxyacetone phosphate is primarily located in the peroxisome, mitochondria and cytoplasm. Dihydroxyacetone phosphate exists in all living organisms, ranging from bacteria to humans. In humans, dihydroxyacetone phosphate is involved in cardiolipin biosynthesis CL(i-13:0/i-21:0/a-17:0/i-14:0) pathway, cardiolipin biosynthesis CL(i-14:0/a-13:0/i-19:0/a-25:0) pathway, cardiolipin biosynthesis CL(i-12:0/i-13:0/i-17:0/i-12:0) pathway, and cardiolipin biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-20:0/i-22:0) pathway. Dihydroxyacetone phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(8:0/a-21:0/13:0) pathway, de novo triacylglycerol biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(i-20:0/i-21:0/19:0) pathway, and de novo triacylglycerol biosynthesis TG(i-22:0/17:0/i-14:0) pathway. Outside of the human body, dihydroxyacetone phosphate can be found in a number of food items such as towel gourd, boysenberry, jujube, and prunus (cherry, plum). This makes dihydroxyacetone phosphate a potential biomarker for the consumption of these food products. Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.
57-04-5
C00111
668
16108
DIHYDROXY-ACETONE-PHOSPHATE
648
DB04326
OCC(=O)COP(O)(O)=O
C3H7O6P
InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
GNGACRATGGDKBX-UHFFFAOYSA-N
(3-hydroxy-2-oxopropoxy)phosphonic acid
170.0578
169.998024468
-0.89
3
dihydroxyacetone-phosphate
0
-2
FDB001618
1,3-dihydroxy-2-propanone mono(dihydrogen phosphate);1,3-dihydroxy-2-propanone phosphate;1,3-dihydroxyacetone 1-phosphate;1-hydroxy-3-(phosphonooxy)-2-propanone;1-hydroxy-3-(phosphonooxy)acetone;Dhap;Di-oh-acetone-p;Dihydroxy-acetone-p;Dihydroxy-acetone-phosphate;Dihydroxyacetone 3-phosphate;Dihydroxyacetone monophosphate;Dihydroxyacetone phosphate;Dihydroxyacetone-p;Dihydroxyacetone-phosphate;Glycerone phosphate;Glycerone-phosphate;Phosphoric acid ester with 1,3-dihydroxy-2-propanone;1,3-dihydroxy-2-propanone monodihydrogen phosphate;3-hydroxy-2-oxopropyl phosphate;Glycerone monophosphate;1,3-dihydroxy-2-propanone monodihydrogen phosphoric acid;Glycerone phosphoric acid;1,3-dihydroxy-2-propanone phosphoric acid;1,3-dihydroxyacetone 1-phosphoric acid;3-hydroxy-2-oxopropyl phosphoric acid;Dihydroxyacetone monophosphoric acid;Dihydroxyacetone phosphoric acid;Glycerone monophosphoric acid
PW_C001134
Dhapp
1026
8
1474
2
3305
5
4253
42
5813
108
5908
147
5936
151
6884
160
42660
315
77098
132
77934
111
78374
345
78559
334
93824
124
110551
388
115839
118
120733
122
122564
418
122590
408
123333
135
125137
454
125162
374
125787
297
125950
299
126712
489
126736
482
127242
205
128303
506
128330
502
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
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
81
Glycerol 3-phosphate
HMDB0000126
Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia).
17989-41-2
C00093
439162
15978
GLYCEROL-3P
388308
DB02515
OC[C@@H](O)COP(O)(O)=O
C3H9O6P
InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1
AWUCVROLDVIAJX-GSVOUGTGSA-N
[(2R)-2,3-dihydroxypropoxy]phosphonic acid
172.0737
172.013674532
-0.75
4
3-phosphoglycerol
0
-2
FDB021800
1-(dihydrogen phosphate) glycerol;1-glycerophosphate;1-glycerophosphorate;1-glycerophosphoric acid;3-glycerophosphate;Dl-glycerol 1-phosphate;Dl-glycerol 3-phosphate;Dl-a-glycerol phosphate;Dl-a-glycerophosphate;Dl-a-glycerophosphorate;Dl-a-glycerophosphoric acid;Dl-a-glyceryl phosphate;Dl-alpha-glycerol phosphate;Dl-alpha-glycerophosphate;Dl-alpha-glycerophosphorate;Dl-alpha-glycerophosphoric acid;Dl-alpha-glyceryl phosphate;Dihydrogen a-glycerophosphate;Glycerol 1-phosphate;Glycerol a-phosphate;Glycerol monophosphate;Glycerophosphate;Glycerophosphorate;Glycerophosphoric acid;Glycerophosphoric acid i;Glyceryl phosphate;Sn-gro-1-p;Sn-glycerol 3-phosphate;A-glycerophosphate;A-glycerophosphorate;A-glycerophosphoric acid;A-phosphoglycerol;Alpha-glycerophosphate;Alpha-glycerophosphorate;Alpha-glycerophosphoric acid;Alpha-phosphoglycerol;D-glycerol 1-phosphate;Glycerol 3-phosphoric acid;D-glycerol 1-phosphoric acid
PW_C000081
Glyc1P
1043
8
1475
2
1488
42
2115
58
6295
107
6296
108
8412
162
9122
170
10653
188
12546
151
12550
223
15319
249
34814
17
42466
318
42467
315
78030
111
78052
350
78372
345
78378
132
79952
134
81808
253
93826
124
94789
384
110553
388
110636
391
115840
118
120756
122
121297
418
121345
121
121415
433
123353
135
123867
454
123974
468
125788
297
125978
489
125991
299
127243
205
127431
506
2798
Palmitoleyl-CoA
HMDB0006532
Palmitoleyl coenzyme A is a monounsaturated fatty acid, the product of palmitoyl-CoA from a reaction catalyzed by stearoyl-CoA desaturase (EC 1.14.99.5, SCD) in the endoplasmic reticulum, an enzyme that catalyzes the delta9-cis desaturation of saturated fatty acyl-CoAs. These monounsaturated fatty acids are used as substrates for the synthesis of triglycerides, wax esters, cholesteryl esters and membrane phospholipids. The saturated to monounsaturated fatty acid ratio affects membrane phospholipid composition and alteration in this ratio has been implicated in a variety of disease states including cardiovascular disease, obesity, diabetes, neurological disease, skin disorders and cancer. Thus, the expression of SCD is of physiological importance in normal and disease states. Unsaturated fatty acids are the most abundant form of stored fat in the human body and are vital for all living organisms. In addition to their role as an energy source, they are integral constituents of cell membranes, playing a role in membrane fluidity, cell signaling, and membrane integrity. Numerous beneficial physiologic effects have been attributed to unsaturated fatty acids, including protection from obesity, diabetes, cancer, and atherosclerosis. (PMID: 12538075, 16020546).
18198-76-0
53477852
53152
CCCCCC\C=C/CCCCCCCC(=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
C37H64N7O17P3S
InChI=1S/C37H64N7O17P3S/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/h9-10,24-26,30-32,36,47-48H,4-8,11-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/b10-9-/t26-,30-,31-,32+,36-/m1/s1
QBYOCCWNZAOZTL-MDMKAECGSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(9Z)-hexadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
1003.93
1003.329225797
-2.80
9
palmitoleoyl-coa
0
-4
FDB023962
(z)-s-9-hexadecenoate;(z)-s-9-hexadecenoate coa;(z)-s-9-hexadecenoate coenzyme a;(z)-s-9-hexadecenoic acid;(z)-thio-9-hexadecenoate;(z)-thio-9-hexadecenoic acid;(z)-thio-9-hexadecenoic acid s-ester with coenzyme a;Palmitoleoyl coenzyme a;Palmitoleoyl-coa;Palmitoleoyl-coenzyme a;Palmitoleyl coenzyme a;Palmitoleyl-coa;Palmitoleyl-coenzyme a;S-(9z)-9-hexadecenoate;S-(9z)-9-hexadecenoate coa;S-(9z)-9-hexadecenoate coenzyme a;S-(9z)-9-hexadecenoic acid;S-palmitoleate coa;S-palmitoleate coenzyme a;S-cis-9-hexadecenoate;S-cis-9-hexadecenoate coa;S-cis-9-hexadecenoate coenzyme a;S-cis-9-hexadecenoic acid;Cis-9-hexadecenoyl-coenzyme a;CoA(16:1(9Z))
PW_C002798
COA(16:
25508
49
25594
22
81848
331
83722
329
95708
383
97521
382
111213
389
114207
390
128849
398
130553
399
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
42972
LPA(16:1(9Z)/0:0)
LPA(16:1(9Z)/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common.LPA(16:1(9Z)/0:0), in particular, consists of one 9Z-hexadecenoyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes.
C00681
75070
ACYL-SN-GLYCEROL-3P
[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OCC(O)COP(O)(O)=O
C19H37O7P
InChI=1S/C19H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h7-8,18,20H,2-6,9-17H2,1H3,(H2,22,23,24)/b8-7-
GLGQZYWTNAOWHT-FPLPWBNLSA-N
{3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxy}phosphonic acid
408.472
408.227690529
-4.99
3
3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropoxyphosphonic acid
0
-2
Pa(16:1(9z)/0:0);1-palmitoleoyl-sn-glycerol 3-phosphate;1-(9z-hexadecenoyl)-glycero-3-phosphate;1-(9z)-hexadecenoyl-sn-glycerol 3-phosphate;1-hexadec-9-enoyl-sn-glycerol 3-phosphate;1-hexadecanoyl-sn-glycerol 3-phosphate
PW_C042972
PA(16:1
25595
22
25596
49
83723
329
83724
331
97522
382
97523
383
112373
389
114721
390
130554
399
130555
398
55580
PA(16:1(9Z)/16:1(9Z))
PA(16:1(9Z)/16:1(9Z))is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:1(9Z)/16:1(9Z)), in particular, consists of two 9Z-hexadecenoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.
C00416
16337
L-PHOSPHATIDATE
CCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCC
C35H65O8P
InChI=1S/C35H65O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,33H,3-12,17-32H2,1-2H3,(H2,38,39,40)/b15-13-,16-14-/t33-/m1/s1
YLDMPBGXNLGSQO-BFEVMTRQSA-N
[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy]phosphonic acid
644.8596
644.441705568
-6.79
2
(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxyphosphonic acid
0
-2
1-palmitoleoyl-2-palmitoleoyl-sn-glycero-3-phosphate ;1-palmitoleoyl-2-palmitoleoyl-sn-phosphatidic acid ;PA(16:1/16:1) ;PA(16:1n7/16:1n7) ;PA(16:1w7/16:1w7) ;PA(32:2) ;Phosphatidic acid(16:1(9Z)/16:1(9Z)) ;Phosphatidic acid(16:1/16:1) ;Phosphatidic acid(16:1n7/16:1n7) ;Phosphatidic acid(16:1w7/16:1w7) ;Phosphatidic acid(32:2) ;Phosphatidate(16:1(9Z)/16:1(9Z)) ;Phosphatidate(16:1/16:1) ;Phosphatidate(16:1n7/16:1n7) ;Phosphatidate(16:1w7/16:1w7) ;Phosphatidate(32:2)
PW_C055580
PA32:2
11569
189
11570
197
25608
49
38235
22
38236
17
83725
331
88157
329
88158
134
97524
383
101920
382
101921
384
112374
389
112375
391
114722
390
130556
398
57
Cytidine triphosphate
HMDB0000082
Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.
65-47-4
C00063
6176
17677
CTP
5941
DB02431
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C9H16N3O14P3
InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
PCDQPRRSZKQHHS-XVFCMESISA-N
({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
483.1563
482.984511771
-1.64
7
CTP
0
-3
FDB012833
5'-(tetrahydrogen triphosphate) cytidine;5'-ctp;Ctp;Cytidine 3'-triphosphate;Cytidine 5'-(tetrahydrogen triphosphate);Cytidine 5'-triphosphate;Cytidine 5'-triphosphoric acid;Cytidine 5-prime-triphosphate;Cytidine triphosphate;Cytidine mono;Cytidine mono(tetrahydrogen triphosphate) (ester);Cytidine-5'-triphosphate;Deoxycytosine triphosphate;H4ctp
PW_C000057
CTP
427
23
1150
8
2718
2
5766
101
5800
108
7077
188
7593
160
9137
195
9142
213
12194
164
12510
288
15285
151
15317
249
15342
22
15374
18
34759
17
42650
315
77315
128
78448
111
78733
132
79949
134
79957
130
79964
329
80416
170
94784
384
94812
125
94817
382
98677
223
110633
391
113268
395
113273
389
115525
136
115530
399
120328
410
120854
122
121340
121
122212
124
122983
444
123434
135
124764
118
125654
485
125840
297
126374
299
127292
205
127935
388
44266
CDP-DG(16:1(9Z)/16:1(9Z))
CDP-DG(16:1(9Z)/16:1(9Z)) belongs to the family of CDP-diacylglycerols. It is a glycerophospholipid containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. CDP-DG(16:1(9Z)/16:1(9Z)), in particular, consists of two 9Z-hexadecenoyl chain at positions C-1 and C2. In E. coli glycerophospholipid metabolism, The biosynthesis of CDP-diacylglycerol (CDP-DG) involves condensation of phosphatidic acid (PA) and cytidine triphosphate, with elimination of pyrophosphate, catalysed by the enzyme CDP-diacylglycerol synthase. The resulting CDP-diacylglycerol can be utilized immediately for the synthesis of phosphatidylglycerol (PG), and thence cardiolipin (CL), and of phosphatidylinositol (PI). CDP-DG(16:1(9Z)/16:1(9Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.
C00269
17962
CDPDIACYLGLYCEROL
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCC
C44H77N3O15P2
InChI=1S/C44H77N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-39(48)57-33-36(60-40(49)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)34-58-63(53,54)62-64(55,56)59-35-37-41(50)42(51)43(61-37)47-32-31-38(45)46-44(47)52/h13-16,31-32,36-37,41-43,50-51H,3-12,17-30,33-35H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/b15-13-,16-14-/t36-,37-,41+,42?,43-/m1/s1
LBKBJHVQQNUXGQ-HCALIIFQSA-N
{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid
950.054
949.482992787
-5.10
5
[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid
0
-2
1-palmitoleoyl-2-palmitoleoyl-sn-glycero-3-CDP ;1-palmitoleoyl-2-palmitoleoyl-sn-glycero-3-cytidine-5'-diphosphate ;CDP-DG(16:1/16:1) ;CDP-DG(16:1n7/16:1n7) ;CDP-DG(16:1w7/16:1w7) ;CDP-DG(32:2) ;CDP-diacylglycerol(16:1(9Z)/16:1(9Z)) ;CDP-diacylglycerol(16:1/16:1) ;CDP-diacylglycerol(16:1n7/16:1n7) ;CDP-diacylglycerol(16:1w7/16:1w7) ;CDP-diacylglycerol(32:2)
PW_C044266
CDP-DG(
37546
17
87468
134
101232
384
110916
391
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
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
64
Cytidine monophosphate
HMDB0000095
Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].
63-37-6
C00055
6131
17361
CMP
5901
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C9H14N3O8P
InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
IERHLVCPSMICTF-XVFCMESISA-N
{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
323.1965
323.051850951
-1.30
5
cytidine monophosphate
0
-2
FDB011882
5'-cmp;5-cytidylate;5-cytidylic acid;Cmp;Cytidine 5'-monophosphate;Cytidine 5'-monophosphorate;Cytidine 5'-monophosphoric acid;Cytidine 5'-phosphate;Cytidine 5'-phosphorate;Cytidine 5'-phosphoric acid;Cytidine mono(dihydrogen phosphate);Cytidine monophosphate;Cytidylate;Cytidylic acid;Cytidine-5'-monophosphate;Pc;Cytidine-5'-monophosphoric acid
PW_C000064
CMP
1151
8
2512
14
2734
2
3386
18
4972
56
5768
101
5802
108
7079
188
7595
160
9147
249
9151
224
9257
195
12196
164
12210
151
15274
285
15336
308
15373
49
34815
17
42652
315
78449
111
78488
115
78573
130
78736
132
79953
134
79969
331
80421
170
94791
384
94821
383
98680
223
110637
391
113277
390
115535
398
120855
122
121346
121
122216
124
122487
405
122605
125
123435
135
124768
118
125053
376
125177
136
125841
297
126378
299
126641
478
126752
300
127293
205
127940
388
128217
209
128346
395
7895
PS(16:1(9Z)/16:1(9Z))
HMDB0012366
PS(16:1(9Z)/16:1(9Z)) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PS(16:1(9Z)/16:1(9Z)), in particular, consists of two 9Z-hexadecenoyl chains at positions C-1 and C-2. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.
C02737
52926071
18303
L-1-PHOSPHATIDYL-SERINE
13628254
DB00144
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC)C(O)=O
C38H70NO10P
InChI=1S/C38H70NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,34-35H,3-12,17-33,39H2,1-2H3,(H,42,43)(H,44,45)/b15-13-,16-14-/t34-,35+/m1/s1
SYAYTZJXUCQTMJ-XOZMKWGESA-N
(2S)-2-amino-3-({[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid
731.949
731.473734456
-6.82
3
(2S)-2-amino-3-{[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}propanoic acid
0
-1
1,2-dipalmitoleoyl-rac-glycero-3-phosphoserine;Ps(16:1/16:1);Ps(16:1n7/16:1n7);Ps(16:1w7/16:1w7);Ps(32:2);Pser(16:1/16:1);Pser(16:1n7/16:1n7);Pser(16:1w7/16:1w7);Pser(32:2);Phosphatidylserine(16:1/16:1);Phosphatidylserine(16:1n7/16:1n7);Phosphatidylserine(16:1w7/16:1w7);Phosphatidylserine(32:2)
PW_C007895
PS32:2
9314
195
9404
163
16350
309
22582
49
22583
17
90210
134
93897
331
105988
384
110482
383
117041
121
128512
398
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
5005
PE(16:1(9Z)/16:1(9Z))
HMDB0008957
PE(16:1(9Z)/16:1(9Z)) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PE(16:1(9Z)/16:1(9Z)), in particular, consists of two 9Z-hexadecenoyl chains at positions C-1 and C-2. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
C00350
9546809
16337
L-1-PHOSPHATIDYL-ETHANOLAMINE
7825759
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCC
C37H70NO8P
InChI=1S/C37H70NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,35H,3-12,17-34,38H2,1-2H3,(H,41,42)/b15-13-,16-14-/t35-/m1/s1
PGPMCWZMPPZJML-NAFNZUQFSA-N
(2-aminoethoxy)[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy]phosphinic acid
687.94
687.483905216
-6.83
2
2-aminoethoxy((2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy)phosphinic acid
0
0
C00350
1,2-dipalmitoleoyl-rac-glycero-3-phosphoethanolamine;Gpetn(16:1/16:1);Gpetn(16:1n7/16:1n7);Gpetn(16:1w7/16:1w7);Gpetn(32:2);Pe(16:1/16:1);Pe(16:1n7/16:1n7);Pe(16:1w7/16:1w7);Pe(32:2);Phophatidylethanolamine(16:1/16:1);Phophatidylethanolamine(16:1n7/16:1n7);Phophatidylethanolamine(16:1w7/16:1w7);Phophatidylethanolamine(32:2);Phosphatidylethanolamine (1-16:1-2-16:1);16:1-16:1-pe;Phosphatidylethanolamine (dihexadec-9enoyl, n-c16:1)
PW_C005005
PE32:2
9400
163
9701
195
16346
49
16347
309
22584
17
90207
331
90208
134
90209
361
105985
383
105986
384
105987
386
117038
398
117039
121
117040
401
44304
CDP-DG(19:0cycw7/19:0cycw7)
(1R,3S,18R,32R)-4,42-Dihexyl-2,3,36,38-tetrahydroxy-32-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)-17,20,33,35,37,39-hexaoxa-36λ⁵,38λ⁵-diphosphatricyclo[16.15.7.2⁶,³¹]dotetracontane-16,21,36,38-tetrone is considered to be a practically insoluble (in water) and relatively neutral molecule.
C00269
17962
CDPDIACYLGLYCEROL
CCCCCCC1CC2CCCCCCCCCC(=O)OC[C@@H]3COP(O)(=O)OP(O)(=O)OC[C@@H](O[C@H]2N2C=CC(N)=NC2=O)[C@@H](O)[C@@H](O)C(CCCCCC)CC1CCCCCCCCCC(=O)O3
C50H89N3O15P2
InChI=1S/C50H89N3O15P2/c1-3-5-7-19-25-39-34-41-28-22-16-12-10-13-17-23-29-45(54)63-35-42-36-64-69(59,60)68-70(61,62)65-37-43(67-49(41)53-32-31-44(51)52-50(53)58)48(57)47(56)40(27-20-8-6-4-2)33-38(39)26-21-15-11-9-14-18-24-30-46(55)66-42/h31-32,38-43,47-49,56-57H,3-30,33-37H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/t38?,39?,40?,41?,42-,43-,47+,48?,49-/m1/s1
YCSKERKWNMEPTN-ACBZXFSLSA-N
{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,3-bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy](hydroxy)phosphoryl}oxy)phosphinic acid
1034.216
1033.576893174
-5.80
5
[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2,3-bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy(hydroxy)phosphoryl]oxy)phosphinic acid
0
-2
1-11,12-methyleneoctadecanoyl-2-11,12-methyleneoctadecanoyl-sn-glycero-3-CDP;1-11,12-methyleneoctadecanoyl-2-11,12-methyleneoctadecanoyl-sn-glycero-3-cytidine-5'-diphosphate;CDP-DG(19:0/19:0);CDP-DG(19:0cycn7/19:0cycn7);CDP-DG(19:0cycw7/19:0cycw7);CDP-DG(38:0);CDP-diacylglycerol(19:0cycw7/19:0cycw7);CDP-diacylglycerol(19:0/19:0);CDP-diacylglycerol(19:0cycn7/19:0cycn7);CDP-diacylglycerol(38:0)
PW_C044304
CDPDG
44100
PGP(19:0cycw7/19:0cycw7)
[(2S)-3-({[(2R)-2,3-bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. PGP(19:0Cycv8c/19:0cycv8c) has the chemical formula C44H84O13P2, and an average molecular weight of 883.091. PGP(19:0Cycv8c/19:0cycv8c) is involved in the Phospholipid Biosynthesis CL(18:1(9Z)/15:0cyclo/19:0cycv8c/19:0cycv8c) Pathway.
C03892
37393
L-1-PHOSPHATIDYL-GLYCEROL-P
[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC
C44H84O13P2
InChI=1S/C44H84O13P2/c1-3-5-7-19-25-37-31-39(37)27-21-15-11-9-13-17-23-29-43(46)53-35-42(36-56-59(51,52)55-34-41(45)33-54-58(48,49)50)57-44(47)30-24-18-14-10-12-16-22-28-40-32-38(40)26-20-8-6-4-2/h37-42,45H,3-36H2,1-2H3,(H,51,52)(H2,48,49,50)/t37?,38?,39?,40?,41-,42+/m0/s1
YPYGMEOBLOGWTD-HBLNEQHKSA-N
[(2S)-3-({[(2R)-2,3-bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
883.091
882.538716761
-6.33
4
(2S)-3-{[(2R)-2,3-bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
0
-3
1-11,12-methyleneoctadecanoyl-2-11,12-methyleneoctadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate);PGP(19:0/19:0);PGP(19:0cycn7/19:0cycn7);PGP(19:0cycw7/19:0cycw7);PGP(38:0)
PW_C044100
PGP
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
43981
PG(19:0cycw7/19:0cycw7)
[2,3-Bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy](2,3-dihydroxypropoxy)phosphinic acid belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. [2,3-Bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy](2,3-dihydroxypropoxy)phosphinic acid is considered to be a practically insoluble (in water) and relatively neutral molecule.
C00344
17517
L-1-PHOSPHATIDYL-GLYCEROL
CCCCCCC1CC1CCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCC1CC1CCCCCC
C44H83O10P
InChI=1S/C44H83O10P/c1-3-5-7-19-25-37-31-39(37)27-21-15-11-9-13-17-23-29-43(47)51-35-42(36-53-55(49,50)52-34-41(46)33-45)54-44(48)30-24-18-14-10-12-16-22-28-40-32-38(40)26-20-8-6-4-2/h37-42,45-46H,3-36H2,1-2H3,(H,49,50)
ACOSNNHXZDLJJE-UHFFFAOYSA-N
[(2R)-2,3-bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
803.112
802.572385871
-7.09
3
(2R)-2,3-bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
0
-1
1-11,12-methyleneoctadecanoyl-2-11,12-methyleneoctadecanoyl-sn-glycero-3-phospho-(1'-glycerol);1-11,12-methyleneoctadecanoyl-2-11,12-methyleneoctadecanoyl-sn-glycero-3-phosphoglycerol;PG(19:0/19:0);PG(19:0cycn7/19:0cycn7);PG(19:0cycw7/19:0cycw7);PG(38:0);Phosphatidylglycerol(19:0cycw7/19:0cycw7);Phosphatidylglycerol(19:0/19:0);Phosphatidylglycerol(19:0cycn7/19:0cycn7);Phosphatidylglycerol(38:0)
PW_C043981
PG
1104
Phosphate
HMDB0001429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
[O-]P([O-])([O-])=O
O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3
NBIIXXVUZAFLBC-UHFFFAOYSA-K
phosphoric acid
94.9714
94.95342
3
phosphoric acid
0
-2
DBMET00532
FDB022617
Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ion
PW_C001104
Pi
24
4
84
8
814
5
818
18
831
2
980
3
1763
14
1767
49
2500
10
2729
47
2737
46
3129
29
3166
72
3636
61
3851
23
4249
22
4475
31
5031
27
5158
7
5207
97
5216
100
5317
111
5351
112
5381
103
5447
120
5543
129
5573
133
5605
135
5625
108
5693
6
5848
143
5855
146
5911
147
5941
151
6040
155
6100
161
6294
107
6487
178
6691
101
6714
117
6842
188
6889
160
7161
205
7189
206
7212
211
7306
198
7389
210
7402
212
7436
163
7475
222
8196
225
8258
227
10118
241
10134
257
11748
132
11761
115
11773
213
11904
170
11927
164
12014
281
12728
290
13263
223
34819
17
42255
304
42350
315
42435
318
43692
322
77018
253
77194
293
77217
134
77940
336
77966
130
78048
332
78057
329
78245
353
78669
331
80022
368
89279
308
93831
383
94796
384
110558
390
110640
391
113235
94
115845
398
116206
109
119982
406
120069
122
120699
407
121057
124
121216
125
121268
429
121352
121
121409
123
121423
382
121852
405
123304
119
123621
118
123786
136
123838
464
123968
447
123981
399
124405
376
124948
472
125362
479
125446
297
125774
481
125954
299
126221
478
126594
300
126604
298
126723
484
126904
501
127413
388
127783
209
128166
395
128177
513
128315
389
96
Ethanolamine
HMDB0000149
Ethanolamine is a viscous, hygroscopic amino alcohol with an ammoniacal odor. It is widely distributed in biological tissue and is a component of lecithin. It is used as a surfactant, fluorometric reagent, and to remove CO2 and H2S from natural gas and other gases.
141-43-5
C00189
700
16000
ETHANOL-AMINE
13835336
DB03994
NCCO
C2H7NO
InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2
HZAXFHJVJLSVMW-UHFFFAOYSA-N
2-aminoethan-1-ol
61.0831
61.052763851
1.14
2
ethanolamine
0
1
FDB000769
1-amino-2-hydroxyethane;2-amino-1-ethanol;2-aminoethanol;2-aminoethyl alcohol;2-ethanolamine;2-hydroxyethanamine;2-hydroxyethylamine;Aethanolamin;Aminoethanol;Colamine;Envision conditioner pdd 9020;Ethanolamine;Ethylolamine;Glycinol;H-glycinol;Mea;Monoaethanolamin;Monoethanolamine;Olamine;B-aminoethanol;B-aminoethyl alcohol;B-ethanolamine;B-hydroxyethylamine;Beta-aminoethanol;Beta-aminoethyl alcohol;Beta-ethanolamine;Beta-hydroxyethylamine;Eta;2-amino-ethanol;2-aminoethan-1-ol;Hea;β-aminoethanol;β-aminoethyl alcohol;β-ethanolamine;β-hydroxyethylamine
PW_C000096
ETA
1564
8
9146
249
12174
151
15326
2
78542
111
79971
132
94825
124
113281
388
115538
118
121333
122
123903
135
126013
297
127465
205
43608
CL(16:1(9Z)/16:1(9Z)/19:0cycw7/19:0cycw7)
CL(16:1(9Z)/16:1(9Z)/19:0CYCV8C/19:0CYCV8C) belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains. CL(16:1(9Z)/16:1(9Z)/19:0CYCV8C/19:0CYCV8C) is considered to be a practically insoluble (in water) and relatively neutral molecule. CL(16:1(9Z)/16:1(9Z)/19:0CYCV8C/19:0CYCV8C) may be a unique E.coli metabolite. CL(16:1(9Z)/16:1(9Z)/19:0CYCV8C/19:0CYCV8C) and ethanolamine can be biosynthesized from PG(16:1(9Z)/16:1(9Z)) and PE(19:ISO/19:ISO) through the action of the enzyme cardiolipin synthase c.
C05980
28494
CARDIOLIPIN
[H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC
C79H146O17P2
InChI=1S/C79H146O17P2/c1-5-9-13-17-19-21-23-25-27-29-35-41-49-57-76(81)89-65-74(95-78(83)59-51-43-36-30-28-26-24-22-20-18-14-10-6-2)67-93-97(85,86)91-63-73(80)64-92-98(87,88)94-68-75(96-79(84)60-52-44-38-32-34-40-48-56-72-62-70(72)54-46-16-12-8-4)66-90-77(82)58-50-42-37-31-33-39-47-55-71-61-69(71)53-45-15-11-7-3/h21-24,69-75,80H,5-20,25-68H2,1-4H3,(H,85,86)(H,87,88)/b23-21-,24-22-/t69?,70?,71?,72?,73-,74+,75+/m0/s1
IFGWJDJTWBTNGD-ZKPOVZHBSA-N
[(2R)-2,3-bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy][(2R)-3-({[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
1429.968
1429.003527237
-7.51
3
(2R)-2,3-bis({[10-(2-hexylcyclopropyl)decanoyl]oxy})propoxy((2R)-3-{[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
0
-2
CL(16:1/16:1/19:0/19:0);CL(16:1n7/16:1n7/19:0cycn7/19:0cycn7);CL(16:1w7/16:1w7/19:0cycw7/19:0cycw7);CL(70:2);Cardiolipin(16:1(9Z)/16:1(9Z)/19:0cycw7/19:0cycw7);Cardiolipin(16:1/16:1/19:0/19:0);Cardiolipin(16:1n7/16:1n7/19:0cycn7/19:0cycn7);Cardiolipin(16:1w7/16:1w7/19:0cycw7/19:0cycw7);Cardiolipin(70:2)
PW_C043608
CL
6594
PG(16:1(9Z)/16:1(9Z))
HMDB0010586
PG(16:1(9Z)/16:1(9Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(16:1(9Z)/16:1(9Z)), in particular, consists of two 9Z-hexadecenoyl chains at positions C-1 and C-2. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.
C00344
52927230
17517
L-1-PHOSPHATIDYL-GLYCEROL
24768085
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC
C38H71O10P
InChI=1S/C38H71O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,35-36,39-40H,3-12,17-34H2,1-2H3,(H,43,44)/b15-13-,16-14-/t35-,36+/m0/s1
GHQNERCMPIDAAU-NWHZUZAFSA-N
[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
718.95
718.478485484
-6.68
3
(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
0
-1
1,2-di(9z-hexadecenoyl)-rac-glycero-3-phospho-(1'-glycerol);1,2-dipalmitoleoyl-rac-glycero-3-phosphoglycerol;Gpg(16:1/16:1);Gpg(16:1n7/16:1n7);Gpg(16:1w7/16:1w7);Gpg(32:2);Pg(16:1/16:1);Pg(16:1n7/16:1n7);Pg(16:1w7/16:1w7);Pg(32:2);Phosphatidylglycerol(16:1/16:1);Phosphatidylglycerol(16:1n7/16:1n7);Phosphatidylglycerol(16:1w7/16:1w7);Phosphatidylglycerol(32:2)
PW_C006594
PG32:2
38238
17
88160
134
101923
384
112377
391
85
Glycerol
HMDB0000131
Glycerol or glycerin is a colourless, odourless, viscous liquid that is sweet-tasting and mostly non-toxic. It is widely used in the food industry as a sweetener and humectant and in pharmaceutical formulations. Glycerol is an important component of triglycerides (i.e. fats and oils) and of phospholipids. Glycerol is a three-carbon substance that forms the backbone of fatty acids in fats. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. The glycerol component can be converted into glucose by the liver and provides energy for cellular metabolism. Normally, glycerol shows very little acute toxicity and very high oral doses or acute exposures can be tolerated. On the other hand, chronically high levels of glycerol in the blood are associated with glycerol kinase deficiency (GKD). GKD causes the condition known as hyperglycerolemia, an accumulation of glycerol in the blood and urine. There are three clinically distinct forms of GKD: infantile, juvenile, and adult. The infantile form is the most severe and is associated with vomiting, lethargy, severe developmental delay, and adrenal insufficiency. The mechanisms of glycerol toxicity in infants are not known, but it appears to shift metabolism towards chronic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated GKD. Many affected children with organic acidemias experience intellectual disability or delayed development. Patients with the adult form of GKD generally have no symptoms and are often detected fortuitously.
56-81-5
C00116
753
17522
GLYCEROL
733
DB04077
OCC(O)CO
C3H8O3
InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2
PEDCQBHIVMGVHV-UHFFFAOYSA-N
propane-1,2,3-triol
92.0938
92.047344122
1.10
3
glycerol
0
0
FDB000756
1,2,3-trihydroxypropane;Bulbold;Cristal;E 422;Emery 916;Glyceol opthalgan;Glycerin;Glycerine;Glyceritol;Glycerol;Glycyl alcohol;Glyrol;Glysanin;Ifp;Incorporation factor;Mackstat h 66;Osmoglyn;Pricerine 9091;Propanetriol;Rg-s;Trihydroxypropane;Tryhydroxypropane;1,2,3-propanetriol;Glycerolum;Glyzerin;Gro;Oelsuess
PW_C000085
Ifp
2063
8
2216
15
3093
9
6297
108
6298
107
9232
170
12545
151
42448
318
42449
315
77903
113
78035
111
78064
114
121229
126
121389
122
121435
409
123799
443
123948
135
123993
137
151
acyl-[acp]
ProteinComplex
ProteinComplex
PW_EC000151
ACYLACP
86
a holo-[acyl-carrier protein]
Compound
PW_EC000086
AHACP
6009
Glycerol-3-phosphate dehydrogenase [NAD(P)+]
P0A6S7
Involved in oxidation-reduction process. sn-glycerol 3-phosphate + NAD(P)(+) = glycerone phosphate + NAD(P)H.
gpsA
b3608
AP009048
3
1.1.1.94
8797
101
6043
Glycerol-3-phosphate acyltransferase
P0A7A7
Involved in transferase activity, transferring acyl groups. Catalyzes the transfer of an acyl group from acyl-ACP to glycerol-3-phosphate (G3P) to form lysophosphatidic acid (LPA). This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor.
plsB
b4041
AF106625
3
2.3.1.15
8843
109
6458
1-acyl-sn-glycerol-3-phosphate acyltransferase
P26647
Involved in transferase activity, transferring acyl groups. Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the 2 position. This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor.
plsC
b3018
AP009048
3
2.3.1.51; 2.3.1.n4
8844
109
135919
293
137189
101
6177
Phosphatidate cytidylyltransferase
P0ABG1
Involved in transferase activity, transferring phosphorus-containing groups. CTP + phosphatidate = diphosphate + CDP- diacylglycerol.
cdsA
b0175
AP009048
3
2.7.7.41
8845
109
7470
CDP-diacylglycerol--serine O-phosphatidyltransferase
P23830
Involved in phosphotransferase activity, for other substituted phosphate groups. CDP-diacylglycerol + L-serine = CMP + (3-sn- phosphatidyl)-L-serine.
pssA
b2585
AP009048
3
2.7.8.8
6084
Phosphatidylserine decarboxylase proenzyme
P0A8K1
Involved in phosphatidylserine decarboxylase activity. Phosphatidyl-L-serine = phosphatidylethanolamine + CO(2).
psd
b4160
AP009048
3
4.1.1.65
8848
140
6176
CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase
P0ABF8
Involved in phosphotransferase activity, for other substituted phosphate groups. This protein catalyzes the committed step to the synthesis of the acidic phospholipids.
pgsA
b1912
AP009048
3
2.7.8.5
8846
109
6098
Phosphatidylglycerophosphatase B
P0A924
Involved in catalytic activity. Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location.
pgpB
b1278
AP009048
3
3.1.3.27; 3.1.3.81; 3.1.3.4; 3.6.1.27
137185
101
6371
Phosphatidylglycerophosphatase A
P18200
Involved in phosphatidylglycerophosphatase activity. One of the three phospholipid phosphatases, specifically hydrolyzes phosphatidylglycerophosphate.
pgpA
b0418
AP009048
3
3.1.3.27
8847
109
137186
101
9694
cardiolipin synthase c
P75919
ClsC is a third cardiolipin synthase in E. coli. Synthesis of cardiolipin during exponential growth is due to the activity of ClsA, while all three cardiolipin synthases, ClsA, ClsB and ClsC, contribute to cardiolipin synthesis in stationary phase
clsC
25
2.7.8.-
7478
Putative cardiolipin synthase ybhO
P0AA84
Involved in catalytic activity. Catalyzes, in vitro, the phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Can also catalyze phosphatidyl group transfer to water to form phosphatidate. Catalyzes little, if any, cardiolipin synthesis in vivo, even when the expression level is very high.
ybhO
b0789
AP009048
3
2.7.8.-
8849
140
80382
94
137187
101
7329
Cardiolipin synthase
P0A6H8
Involved in phosphotransferase activity, for other substituted phosphate groups. Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Affects resistance to the gyrase inhibitor novobiocin.
cls
b1249
AP009048
3
2.7.8.-
8850
109
80383
94
137188
101
3461
glycerol-3-phosphate dehydrogenase (aerobic)
3
PW_P003461
10234
6009
2
3462
glycerol-3-phosphate acyltransferase
3
PW_P003462
10235
6043
3463
1-acylglycerol-3-phosphate O-acyltransferase
3
PW_P003463
10236
6458
3464
CDP-diglyceride synthetase
3
PW_P003464
10237
6177
3465
phosphatidylserine synthase
3
PW_P003465
10238
7470
3466
phosphatidylserine decarboxylase
3
PW_P003466
10239
6084
3467
phosphatidylglycerophosphate synthase
3
PW_P003467
10240
6176
3468
phosphatidylglycerophosphatase
3
PW_P003468
10241
6098
10242
6371
3486
cardiolipin synthase c
3
PW_P003486
10260
9694
3487
cardiolipin synthase
3
PW_P003487
10261
7478
10262
7329
3113
false
PW_R003113
Right
12372
1134
1
Compound
false
12373
40034
1
Compound
false
12374
146
1
Compound
false
12375
143
1
Compound
false
12376
81
1
Compound
false
3084
3461
1.1.1.94
180632
PW_R180632
Right
682029
2798
1
Compound
false
682030
81
1
Compound
false
682031
1099
1
Compound
false
682032
42972
1
Compound
false
170436
3462
180683
PW_R180683
Right
682230
42972
1
Compound
false
682231
2798
1
Compound
false
682232
1099
1
Compound
false
682233
55580
1
Compound
false
170483
3463
180684
PW_R180684
Right
682234
55580
1
Compound
false
682235
57
1
Compound
false
682236
40034
1
Compound
false
682237
44266
1
Compound
false
682238
170
1
Compound
false
170484
3464
180685
PW_R180685
Right
682239
44266
1
Compound
false
682240
120
1
Compound
false
682241
64
1
Compound
false
682242
40034
1
Compound
false
682243
7895
1
Compound
false
170485
3465
3875
false
PW_R003875
Right
15625
40034
1
Compound
false
15626
7895
1
Compound
false
15627
5005
1
Compound
false
15628
1316
1
Compound
false
3848
3466
181985
PW_R181985
Right
687732
44304
1
Compound
false
687733
81
1
Compound
false
687734
64
1
Compound
false
687735
40034
1
Compound
false
687736
44100
1
Compound
false
171774
3467
2.7.8.5
181986
PW_R181986
Right
687737
44100
1
Compound
false
687738
1420
1
Compound
false
687739
43981
1
Compound
false
687740
1104
1
Compound
false
171775
3468
182832
PW_R182832
Right
691138
43981
1
Compound
false
691139
5005
1
Compound
false
691140
96
1
Compound
false
691141
43608
1
Compound
false
172621
3486
180637
PW_R180637
Right
682051
151
1
ElementCollection
false
682052
81
1
Compound
false
682053
86
1
ElementCollection
false
682054
42972
1
Compound
false
170441
3462
2.3.1.15
180686
PW_R180686
Right
682244
42972
1
Compound
false
682245
151
1
ElementCollection
false
682246
55580
1
Compound
false
682247
86
1
ElementCollection
false
170486
3463
2.3.1.51
182833
PW_R182833
Right
691142
43981
1
Compound
false
691143
6594
1
Compound
false
691144
85
1
Compound
false
691145
43608
1
Compound
false
172622
3487
2.7.8.-
2712236
1134
3
false
546
600
10
regular
100
110
2712237
40034
55
false
666
711
10
regular
78
78
2712238
40034
55
false
2161
716
10
regular
78
78
2712239
40034
55
false
1801
1086
10
regular
78
78
2712240
40034
55
false
1501
1101
10
regular
78
78
2712241
40034
55
false
1781
1691
10
regular
78
78
2712242
146
62
false
684
550
10
regular
50
30
2712243
143
61
false
995
550
10
regular
50
30
2712244
81
3
false
1050
600
10
regular
100
110
2712245
81
3
false
2130
1495
10
regular
100
110
2712246
2798
109
3
false
1080
940
10
regular
100
100
2712247
1099
109
85
false
1420
970
10
regular
50
30
2712248
1099
109
85
false
2025
812
10
regular
50
30
2712249
42972
109
3
false
1550
850
10
regular
100
100
2712250
42972
101
3
false
1550
375
10
regular
100
100
2712251
2798
109
3
false
1690
745
10
regular
100
100
2712252
55580
109
3
false
2060
597
10
regular
100
100
2712253
57
3
false
2366
690
10
regular
100
110
2712254
44266
101
3
false
2257
1169
10
regular
100
110
2712255
170
45
false
2192
983
10
regular
63
43
2712256
120
3
false
2120
1085
10
regular
100
100
2712257
64
3
false
1779
1270
10
regular
100
110
2712258
64
3
false
1794
1495
10
regular
100
110
2712259
7895
101
3
false
1609
1176
10
regular
100
100
2712260
1316
52
false
1175
1101
10
regular
78
78
2712261
5005
101
3
false
1049
1176
10
regular
100
100
2712262
44304
101
3
false
2260
1595
10
regular
100
110
2712263
44100
101
3
false
1615
1600
10
regular
100
100
2712264
1420
49
false
1521
1526
10
regular
78
78
2712265
43981
101
3
false
1053
1598
10
regular
100
100
2712266
1104
46
false
1201
1693
10
regular
44
43
2712267
96
3
false
705
1235
10
regular
100
100
2712268
43608
101
3
false
655
1360
10
regular
100
100
2712269
43608
101
3
false
353
1598
10
regular
100
100
2712270
6594
101
3
false
948
1478
10
regular
100
100
2712271
85
101
3
false
408
1478
10
regular
100
100
18472
151
144
false
1045
295
12
regular
150
70
18473
151
144
false
1640
300
12
regular
150
70
18474
86
144
false
1425
300
12
regular
150
70
18475
86
144
false
2030
300
12
regular
150
70
961878
6009
101
6
false
787
615
8
subunit
regular
160
80
961879
6043
109
2
false
1225
862
8
subunit
regular
150
70
961880
6458
109
2
false
1835
865
8
subunit
regular
150
70
961881
6177
109
2
false
2230
865
8
subunit
regular
150
70
961882
7470
2
false
1925
1190
8
subunit
regular
150
70
961883
6084
140
2
false
1299
1190
8
subunit
regular
150
70
961884
6176
109
2
false
1925
1615
8
subunit
regular
150
70
961885
6098
101
2
false
1301
1563
8
subunit
regular
150
70
961886
6371
101
2
false
1301
1613
8
subunit
regular
150
70
961887
9694
2
false
855
1375
8
subunit
regular
150
70
961888
6043
109
2
false
1225
387
8
subunit
regular
150
70
961889
6458
101
2
false
1832
390
8
subunit
regular
150
70
961890
7478
101
2
false
703
1593
8
subunit
regular
150
70
961891
7329
101
2
false
608
1613
8
subunit
regular
150
70
814476
3461
1305
957643
961878
814477
3462
1305
109
957644
961879
814478
3463
1305
109
957645
961880
814479
3464
1305
957646
961881
814480
3465
1305
957647
961882
814481
3466
1305
957648
961883
814482
3467
1305
957649
961884
814483
3468
1305
101
957650
961885
957651
961886
814484
3486
1305
957652
961887
814485
3462
1305
957653
961888
814486
3463
1305
101
957654
961889
814487
3487
1305
101
957655
961890
957656
961891
3711667
M546 657 C491 657 541 657 451 657
5
false
18
3711668
M646 655 C718 656 711 654 787 655
5
false
18
3711669
M744 750 C745 712 757 655 787 655
5
false
18
3711670
M738 565 C738 608 756 657 787 655
5
false
18
3711671
M995 565 C995 608 981 654 947 655
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3711672
M1050 655 C1003 656 1019 655 947 655
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3711673
M1180 990 C1180 971 1195 897 1225 897
5
false
18
3711674
M1100 710 C1101 736 1099 876 1098 898 C1131 898 1184 899 1225 897
5
false
18
3711675
M1420 985 C1419 971 1405 897 1375 897
5
false
18
true
M 761.9468550441649 270.261556296296 L 747 269 L 753.3808877211858 282.5751343230783
false
3711676
M1550 900 C1520 900 1405 897 1375 897
5
false
18
true
M 761.9468550441649 270.261556296296 L 747 269 L 753.3808877211858 282.5751343230783
false
3711677
M1650 900 C1680 900 1805 900 1835 900
5
false
18
3711678
M1790 795 C1789 826 1805 900 1835 900
5
false
18
3711679
M2025 827 C2023 854 2015 900 1985 900
5
false
18
true
M 761.9468550441649 270.261556296296 L 747 269 L 753.3808877211858 282.5751343230783
false
3711680
M2110 697 C2110 721 2112 876 2112 899 C2086 899 2029 901 1985 900
5
false
18
true
M 761.9468550441649 270.261556296296 L 747 269 L 753.3808877211858 282.5751343230783
false
3711681
M2160 647 C2185 647 2284 646 2306 646 C2306 669 2305 838 2305 865
5
false
18
3711682
M2416 800 C2317 796 2305 835 2305 865
5
false
18
3711683
M2200 794 C2294 792 2305 835 2305 865
5
false
18
3711684
M2307 1169 C2307 1139 2305 965 2305 935
5
false
18
true
M 1418.9468550441647 499.261556296296 L 1404 498 L 1410.380887721186 511.5751343230783
false
3711685
M2223.5 983 C2272.5 984 2305 965 2305 935
5
false
18
true
M 1418.9468550441647 499.261556296296 L 1404 498 L 1410.380887721186 511.5751343230783
false
3711686
M2257 1224 C2227 1224 2105 1225 2075 1225
5
false
18
3711687
M2120 1135 C2120 1197 2105 1225 2075 1225
5
false
18
3711688
M1879 1325 C1880 1243 1895 1225 1925 1225
5
false
18
true
M 1395.9468550441647 866.261556296296 L 1381 865 L 1387.380887721186 878.5751343230784
false
3711689
M1879 1125 C1874 1211 1895 1225 1925 1225
5
false
18
true
M 1395.9468550441647 866.261556296296 L 1381 865 L 1387.380887721186 878.5751343230784
false
3711690
M1709 1226 C1739 1226 1895 1225 1925 1225
5
false
18
true
M 1395.9468550441647 866.261556296296 L 1381 865 L 1387.380887721186 878.5751343230784
false
3711691
M1609 1226 C1579 1226 1479 1225 1449 1225
5
false
18
3711692
M1501 1140 C1503 1205 1479 1225 1449 1225
5
false
18
3711693
M1253 1140 C1252 1206 1269 1225 1299 1225
5
false
18
true
M 967.9468550441649 958.261556296296 L 953 957 L 959.3808877211858 970.5751343230784
false
3711694
M1149 1226 C1179 1226 1269 1225 1299 1225
5
false
18
true
M 967.9468550441649 958.261556296296 L 953 957 L 959.3808877211858 970.5751343230784
false
3711695
M2260 1650 C2230 1650 2105 1650 2075 1650
5
false
18
3711696
M2130 1550 C2133 1625 2105 1650 2075 1650
5
false
18
3711697
M1894 1550 C1896 1623 1895 1650 1925 1650
5
false
18
true
M 1534.9468550441647 1331.261556296296 L 1520 1330 L 1526.380887721186 1343.5751343230784
false
3711698
M1859 1730 C1858 1674 1895 1650 1925 1650
5
false
18
true
M 1534.9468550441647 1331.261556296296 L 1520 1330 L 1526.380887721186 1343.5751343230784
false
3711699
M1715 1650 C1745 1650 1895 1650 1925 1650
5
false
18
true
M 1534.9468550441647 1331.261556296296 L 1520 1330 L 1526.380887721186 1343.5751343230784
false
3711700
M1615 1650 C1585 1650 1481 1648 1451 1648
5
false
18
3711701
M1521 1565 C1520 1630 1481 1648 1451 1648
5
false
18
3711702
M1153 1648 C1183 1648 1271 1648 1301 1648
5
false
18
true
M 977.9468550441649 1320.261556296296 L 963 1319 L 969.3808877211858 1332.5751343230784
false
3711703
M1245 1714.5 C1245 1651.5 1271 1648 1301 1648
5
false
18
true
M 977.9468550441649 1320.261556296296 L 963 1319 L 969.3808877211858 1332.5751343230784
false
3711704
M1103 1598 C1102 1508 1035 1410 1005 1410
5
false
18
3711705
M1099 1276 C1099 1382 1035 1410 1005 1410
5
false
18
3711706
M805 1285 C808 1367 825 1410 855 1410
5
false
18
true
M 568.9468550441649 1160.261556296296 L 554 1159 L 560.3808877211858 1172.5751343230784
false
3711707
M755 1410 C785 1410 825 1410 855 1410
5
false
18
true
M 568.9468550441649 1160.261556296296 L 554 1159 L 560.3808877211858 1172.5751343230784
false
3711708
M1195 330 C1196 382 1195 422 1225 422
5
false
18
3711709
M1100 600 C1099 539 1100 479 1100 421 C1130 421 1196 422 1225 422
5
false
18
3711710
M1425 335 C1428 402 1405 422 1375 422
5
false
18
true
M 853.9468550441649 242.26155629629605 L 839 241 L 845.3808877211858 254.57513432307834
false
3711711
M1550 425 C1520 425 1405 422 1375 422
5
false
18
true
M 853.9468550441649 242.26155629629605 L 839 241 L 845.3808877211858 254.57513432307834
false
3711712
M1650 425 C1680 425 1802 425 1832 425
5
false
18
3711713
M1790 335 C1790 380 1802 425 1832 425
5
false
18
3711714
M2110 597 C2110 564 2109 451 2109 426 C2084 426 2055 425 1985 425
5
false
18
true
M 1238.9468550441647 213.26155629629605 L 1224 212 L 1230.380887721186 225.57513432307834
false
3711715
M2030 335 C2032 412 2012 425 1982 425
5
false
18
true
M 1238.9468550441647 213.26155629629605 L 1224 212 L 1230.380887721186 225.57513432307834
false
3711716
M1053 1648 C1023 1648 788 1648 758 1648
5
false
6
3711717
M948 1528 C951 1638 881 1649 850 1648
5
false
18
3711718
M508 1528 C505 1614 578 1648 608 1648
5
false
18
true
M 25.946855044164835 1385.261556296296 L 11 1384 L 17.380887721185843 1397.5751343230784
false
3711719
M453 1648 C483 1648 578 1648 608 1648
5
false
18
true
M 25.946855044164835 1385.261556296296 L 11 1384 L 17.380887721185843 1397.5751343230784
false
808569
1305
3113
3266404
2712236
3711668
Left
3266405
2712237
3711669
Left
3266406
2712242
3711670
Left
3266407
2712243
3711671
Right
3266408
2712244
3711672
Right
764004
3084
814476
808570
1305
180632
3266409
2712246
3711673
Left
3266410
2712244
3711674
Left
3266411
2712247
3711675
Right
3266412
2712249
3711676
Right
764005
169529
814477
808571
1305
180683
3266413
2712249
3711677
Left
3266414
2712251
3711678
Left
3266415
2712248
3711679
Right
3266416
2712252
3711680
Right
764006
169530
814478
808572
1305
180684
3266417
2712252
3711681
Left
3266418
2712253
3711682
Left
3266419
2712238
3711683
Left
3266420
2712254
3711684
Right
3266421
2712255
3711685
Right
764007
169531
814479
808573
1305
180685
3266422
2712254
3711686
Left
3266423
2712256
3711687
Left
3266424
2712257
3711688
Right
3266425
2712239
3711689
Right
3266426
2712259
3711690
Right
764008
169532
814480
808574
1305
3875
3266427
2712259
3711691
Left
3266428
2712240
3711692
Left
3266429
2712260
3711693
Right
3266430
2712261
3711694
Right
764009
3131
814481
808575
1305
181985
3266431
2712262
3711695
Left
3266432
2712245
3711696
Left
3266433
2712258
3711697
Right
3266434
2712241
3711698
Right
3266435
2712263
3711699
Right
764010
169533
814482
808576
1305
181986
3266436
2712263
3711700
Left
3266437
2712264
3711701
Left
3266438
2712265
3711702
Right
3266439
2712266
3711703
Right
764011
169534
814483
808577
1305
182832
3266440
2712265
3711704
Left
3266441
2712261
3711705
Left
3266442
2712267
3711706
Right
3266443
2712268
3711707
Right
764012
169536
814484
808578
1305
180637
3266444
2712244
3711709
Left
3266445
2712250
3711711
Right
17421
18472
3711708
Left
17422
18474
3711710
Right
764013
170291
814485
808579
1305
180686
3266446
2712250
3711712
Left
3266447
2712252
3711714
Right
17423
18473
3711713
Left
17424
18475
3711715
Right
764014
170292
814486
808580
1305
182833
3266448
2712265
3711716
Left
3266449
2712270
3711717
Left
3266450
2712271
3711718
Right
3266451
2712269
3711719
Right
764015
170297
814487
110719
111017
1305
14
false
301
622
16
regular
107397
2712236
3711667
Right
188008
277
750
1.1
1.1
0
2
92
479
481
371454
M125 225 C125 175 175 125 225 125 C925 125 1836 125 2536 125 C2586 125 2636 175 2636 225 C2636 710 2636 1339 2636 1824 C2636 1874 2586 1924 2536 1924 C1836 1924 925 1924 225 1924 C175 1924 125 1874 125 1824 C125 1339 125 710 125 225
1
true
6
2511.0
1799.0
371455
M227 324 C227 274 277 224 327 224 C967 224 1799 224 2439 224 C2489 224 2539 274 2539 324 C2539 748 2539 1300 2539 1724 C2539 1774 2489 1824 2439 1824 C1799 1824 967 1824 327 1824 C277 1824 227 1774 227 1724 C227 1300 227 748 227 324
1
true
6
2312.0
1600.0