1870
Pathway
2-O-alpha-Mannosyl-D-glycerate Degradation
2-O-α-Mannosyl-D-glycerate (MG; also named as Alpha-Mannosylglycerate) is an organic compound that will affect the osmosis in hyperthermophilic archaea and bacteria. In E.coli, 2-O-α-mannosyl-D-glycerate PTS permease (mngA) import MG into cell, and then phosphorylate MG to 2-O-(6-phospho-α-mannosyl)-D-glycerate by phosphocarrier protein HPr. 2-O-(6-phospho-α-mannosyl)-D-glycerate is converted to glyceric acid as well as mannose 6-phosphate by alpha-mannosidase mngB. Finally, glyceric acid is catalyzed to 2-Phospho-D-glyceric acid with ATP as energy source by Glycerate kinase 2. E.coli can't use MG as osmotic stress protection, but it can use MG as a carbon source.
Metabolic
PW002096
Center
PathwayVisualizationContext2383
1748
1945
#000099
PathwayVisualization1854
1870
2-O-alpha-Mannosyl-D-glycerate Degradation
2-O-α-Mannosyl-D-glycerate (MG; also named as Alpha-Mannosylglycerate) is an organic compound that will affect the osmosis in hyperthermophilic archaea and bacteria. In E.coli, 2-O-α-mannosyl-D-glycerate PTS permease (mngA) import MG into cell, and then phosphorylate MG to 2-O-(6-phospho-α-mannosyl)-D-glycerate by phosphocarrier protein HPr. 2-O-(6-phospho-α-mannosyl)-D-glycerate is converted to glyceric acid as well as mannose 6-phosphate by alpha-mannosidase mngB. Finally, glyceric acid is catalyzed to 2-Phospho-D-glyceric acid with ATP as energy source by Glycerate kinase 2. E.coli can't use MG as osmotic stress protection, but it can use MG as a carbon source.
Metabolic
3
109883
583
InhibitorySubPathway
109414
1870
Compound
3939
14645248
Sampaio MM, Chevance F, Dippel R, Eppler T, Schlegel A, Boos W, Lu YJ, Rock CO: Phosphotransferase-mediated transport of the osmolyte 2-O-alpha-mannosyl-D-glycerate in Escherichia coli occurs by the product of the mngA (hrsA) gene and is regulated by the mngR (farR) gene product acting as repressor. J Biol Chem. 2004 Feb 13;279(7):5537-48. doi: 10.1074/jbc.M310980200. Epub 2003 Nov 25.
1870
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
1
Homo sapiens
9606
Eukaryote
Human
2
Bacteria
2
Prokaryote
Bacteria
3
Escherichia coli
562
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
110
Bacillus velezensis MRC5958
492670
Prokaryote
Velezensis
5
Cytoplasm
GO:0005737
6
Lysosome
GO:0005764
4
Peroxisome
GO:0005777
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
10
Cell Membrane
GO:0005886
11
Extracellular Space
GO:0005615
16
Lysosomal Lumen
GO:0043202
7
Endoplasmic Reticulum Membrane
GO:0005789
1
Cytosol
GO:0005829
18
Melanosome Membrane
GO:0033162
13
Endoplasmic Reticulum
GO:0005783
25
Golgi apparatus
GO:0005794
14
Mitochondrial Outer Membrane
GO:0005741
12
Mitochondrial Inner Membrane
GO:0005743
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
27
Peroxisome Membrane
GO:0005778
32
Inner Membrane
GO:0070258
19
sarcoplasmic reticulum
GO:0016529
24
Mitochondrial Intermembrane Space
GO:0005758
1
Liver
BTO:0000759
72
9
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
28
Stomach
BTO:0001307
155
26
7
Nervous System
BTO:0001484
8
Blood Vessel
BTO:0001102
74
11
11
Heart
BTO:0000562
73
10
2
Endothelium
BTO:0000393
18
Pancreas
BTO:0000988
8
5
1
1
PW_BS000008
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6
1
1
PW_BS000009
5
4
1
1
PW_BS000005
4
3
1
1
PW_BS000004
3
2
1
1
PW_BS000003
14
10
1
PW_BS000014
13
1
2
1
PW_BS000013
15
11
1
PW_BS000015
28
1
16
1
1
PW_BS000028
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1
7
1
1
PW_BS000010
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4
1
1
1
PW_BS000020
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18
1
1
PW_BS000033
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13
1
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PW_BS000036
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PW_BS000093
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PW_BS000007
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PW_BS000100
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PW_BS000113
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PW_BS000110
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PW_BS000125
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PW_BS000126
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PW_BS000127
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PW_BS000130
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PW_BS000114
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PW_BS000129
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PW_BS000135
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PW_BS000118
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PW_BS000006
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PW_BS000140
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PW_BS000101
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PW_BS000143
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PW_BS000146
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PW_BS000107
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PW_BS000147
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PW_BS000151
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PW_BS000157
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PW_BS000163
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PW_BS000159
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PW_BS000001
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PW_BS000166
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PW_BS000178
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PW_BS000180
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PW_BS000152
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1
3
1
PW_BS000117
188
1
18
PW_BS000024
160
1
18
1
PW_BS000160
205
5
6
1
PW_BS000024
207
6
6
1
PW_BS000024
206
2
6
1
PW_BS000024
211
10
18
PW_BS000024
213
7
18
1
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
198
5
18
1
PW_BS000024
216
4
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
222
3
4
1
PW_BS000024
224
2
4
1
PW_BS000024
190
11
18
PW_BS000024
170
18
PW_BS000170
225
35
4
1
PW_BS000024
226
4
4
1
PW_BS000024
162
12
18
1
PW_BS000162
26
1
1
1
5
PW_BS000026
277
1
2
18
PW_BS000024
164
4
PW_BS000164
281
1
25
1
PW_BS000024
285
10
4
1
PW_BS000024
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
249
13
4
1
PW_BS000024
227
34
4
1
PW_BS000024
65
11
1
PW_BS000065
290
5
49
1
PW_BS000024
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
298
1
7
10
1
PW_BS000024
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13
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PW_BS000024
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PW_BS000024
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16
10
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1
23
PW_BS000024
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31
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PW_BS000024
322
1
23
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PW_BS000024
293
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PW_BS000024
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132
1
12
1
PW_BS000132
133
3
12
1
PW_BS000133
134
12
12
1
PW_BS000134
331
7
12
1
PW_BS000028
332
1
7
12
1
PW_BS000028
333
1
2
12
PW_BS000028
115
10
12
PW_BS000115
334
4
12
1
PW_BS000028
336
1
12
1
PW_BS000028
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
347
1
3
12
5
PW_BS000028
329
14
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
356
25
12
1
PW_BS000028
360
4
10
12
1
PW_BS000028
368
3
60
1
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
119
2
17
1
PW_BS000119
383
7
5
1
PW_BS000100
384
12
5
1
PW_BS000100
390
7
6
1
PW_BS000112
391
12
6
1
PW_BS000112
398
7
17
1
PW_BS000113
232
40
3
PW_BS000024
122
5
5
1
PW_BS000122
406
3
5
1
PW_BS000115
407
2
5
1
PW_BS000115
408
4
5
1
PW_BS000115
124
1
5
1
PW_BS000124
412
1
2
5
PW_BS000115
405
10
5
PW_BS000115
409
11
5
PW_BS000115
415
18
5
1
PW_BS000115
414
1
5
5
1
PW_BS000115
425
1
3
5
5
PW_BS000115
429
1
5
1
PW_BS000115
121
12
17
1
PW_BS000121
419
25
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
382
14
5
1
PW_BS000100
436
25
5
PW_BS000115
120
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17
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PW_BS000120
374
4
17
1
PW_BS000053
443
6
17
1
PW_BS000115
446
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2
17
PW_BS000115
376
10
17
PW_BS000053
137
11
17
PW_BS000137
447
1
7
17
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PW_BS000115
136
13
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PW_BS000136
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1
16
17
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PW_BS000115
451
18
17
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PW_BS000115
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1
5
17
1
PW_BS000115
460
1
3
17
5
PW_BS000115
464
1
17
1
PW_BS000115
455
25
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
399
14
17
1
PW_BS000113
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
297
5
10
1
PW_BS000024
479
3
10
1
PW_BS000115
481
2
10
1
PW_BS000115
482
4
10
1
PW_BS000115
299
1
10
1
PW_BS000024
483
11
10
PW_BS000115
478
10
10
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
495
7
10
1
PW_BS000115
484
14
10
1
PW_BS000115
480
12
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1
PW_BS000115
501
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6
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515
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10
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1
PW_BS000115
389
14
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1
PW_BS000112
395
13
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1
PW_BS000113
513
1
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6
1
PW_BS000115
16
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1
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PW_BS000016
32
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39
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1
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7709
2-O-(6-Phospho-α-mannosyl)-D-glycerate
HMDB0012152
2-O-(6-Phospho-alpha-mannosyl)-D-glycerate is an alpha-D-mannosylglycerate (MG) that is an intermediate in 2-O-alpha-mannosyl-D-glycerate degradation. It can be generated from 2-O-alpha-mannosyl-D-glycerate via the enzyme 2-O-alpha-mannosyl-D-glycerate transporting phosphotransferase system (mngA). 2-O-Alpha-mannosyl-D-glycerate is a natural extremolyte identified in microorganisms growing under extremely high temperatures up to 100 oC, and had been shown to protect proteins against various stress conditions such as heat, freezing, thawing, and drying. MG that is naturally occurring hyperthermophilic osmolytes, could be potential drug candidates or lead compounds against alpha,beta aggregation associated with Alzheimer's disease(PMID: 18304694). In most organisms MG is produced from guanosine pyrophosphate mannose (GDP-alpha-D-mannose) via mannosyl-3-phosphoglycerate in two steps, catalyzed by the enzymes mannosyl-3-phosphoglycerate synthase and mannosyl-3-phosphoglycerate phosphatase.
C16699
24892815
61001
CPD0-1063
26332075
OC[C@@H](O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O)C(O)=O
C9H17O12P
InChI=1S/C9H17O12P/c10-1-3(8(14)15)20-9-7(13)6(12)5(11)4(21-9)2-19-22(16,17)18/h3-7,9-13H,1-2H2,(H,14,15)(H2,16,17,18)/t3-,4-,5-,6+,7+,9+/m1/s1
BOLXAGHGKNGVBE-MTXRGOKVSA-N
(2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}propanoic acid
348.1978
348.04576252
-1.09
7
(2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}propanoic acid
0
-3
C16699
2-o-(6-phospho-a-mannosyl)-d-glycerate;2-o-(6-phospho-a-mannosyl)-d-glyceric acid;2-o-(6-phospho-alpha-mannosyl)-d-glyceric acid;2-o-(6-phospho-alpha-mannosyl)-delta-glycerate;2-o-(6-phospho-alpha-mannosyl)-delta-glyceric acid;2-o-(6-phospho-alpha-d-mannosyl)-d-glycerate;2-o-(6-phospho-a-d-mannosyl)-d-glycerate;2-o-(6-phospho-a-d-mannosyl)-d-glyceric acid;2-o-(6-phospho-alpha-d-mannosyl)-d-glyceric acid;2-o-(6-phospho-α-d-mannosyl)-d-glycerate;2-o-(6-phospho-α-d-mannosyl)-d-glyceric acid;2-o-(6-phospho-α-mannosyl)-d-glycerate;2-o-(6-phospho-α-mannosyl)-d-glyceric acid
PW_C007709
2O6pDg
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
848
Mannose 6-phosphate
HMDB0001078
Mannose 6-phosphate, also known as alpha-D-mannose-6-p or man-6-p, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Mannose 6-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Mannose 6-phosphate has been found throughout most human tissues. Within the cell, mannose 6-phosphate is primarily located in the cytoplasm. In humans, mannose 6-phosphate is involved in the fructose and mannose degradation pathway and the fructose intolerance, hereditary pathway. Mannose 6-phosphate is also involved in the metabolic disorder called the fructosuria pathway. Mannose-6-phosphate is a potent competitive inhibitor of pinocytosis of human platelet beta-glucuronidase and it is a necessary component of the recognition marker on the enzyme for pinocytosis by human fibroblasts as well (PMID 908752).
3672-15-9
C00275
439198
49728
MANNOSE-6P
388338
O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O
C6H13O9P
InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1
NBSCHQHZLSJFNQ-RWOPYEJCSA-N
{[(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
260.1358
260.029718526
-0.92
6
mannose 6 phosphate
0
-2
FDB022411
D-mannose 6-phosphate;Man-6-p;Mannose 6-phosphate;Mannose-6-phosphate;Alpha-d-mannose-6-p;Alpha-d-mannose-6-phosphate;Alpha-delta-mannose-6-p;Alpha-delta-mannose-6-phosphate;Delta-mannose 6-phosphate
PW_C000848
Man-6P
1016
8
13320
151
77921
111
120718
122
123323
135
90
Glyceric acid
HMDB0000139
Glyceric acid is a colourless syrupy acid, obtained from oxidation of glycerol. It is a compound that is secreted excessively in the urine by patients suffering from D-glyceric aciduria, an inborn error of metabolism, and D-glycerate anemia. Deficiency of human glycerate kinase leads to D-glycerate acidemia/D-glyceric aciduria. Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive, and metabolic acidosis. At sufficiently high levels, glyceric acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Glyceric acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic 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 abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated glyceric aciduria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.
473-81-4
C00258
439194
32398
2-PG
388334
OC[C@@H](O)C(O)=O
C3H6O4
InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1
RBNPOMFGQQGHHO-UWTATZPHSA-N
(2R)-2,3-dihydroxypropanoic acid
106.0773
106.02660868
0.78
3
glycerate
0
-1
FDB012242
(r)-glycerate;D-glycerate;D-glyceric acid;Glycerate;Glyceric acid;A,b-hydroxypropionate;A,b-hydroxypropionic acid;Alpha,beta-hydroxypropionic acid;R-glyceric acid;Alpha,beta-hydroxypropionate;α,β-hydroxypropionate;α,β-hydroxypropionic acid;R-glycerate
PW_C000090
Glycera
2052
8
3476
2
5739
108
6014
147
42620
315
78034
111
78107
132
121387
122
122155
124
123946
135
124707
118
126313
299
127874
388
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
1870
2-Phospho-D-glyceric acid
HMDB0003391
2-Phospho-D-glycerate or 2PG is an intermediate in gluconeogenesis. It is a glyceric acid which serves as the substrate in the ninth step of glycolysis. 2PG is converted by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. More specifically, 2PG can be generated from Glycerate-3-phosphate via phosphoglycerate mutase or from phosphoenolpyrvate via alpha enolase.
C00631
439278
17835
2-PG
388411
DB01709
OC[C@@H](OP(O)(O)=O)C(O)=O
C3H7O7P
InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1
GXIURPTVHJPJLF-UWTATZPHSA-N
(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid
186.0572
185.99293909
-0.96
4
(+-)-2-phosphoglycerate
0
-3
FDB001407
(2r)-3-hydroxy-2-(phosphonooxy)propanoate;(2r)-3-hydroxy-2-(phosphonooxy)propanoic acid;2-phospho-d-glycerate;2-phospho-d-glyceric acid;3-d-hydroxy-2-phosphonooxy-propanoate;3-d-hydroxy-2-phosphonooxy-propanoic acid;D-glycerate 2-phosphate;2-phospho-(r)-glycerate;D-glyceric acid 2-phosphoric acid;2-phospho-(r)-glyceric acid
PW_C001870
2PDG
2263
2
5918
147
5949
151
6899
160
77113
132
121194
124
123765
118
125962
299
127418
388
1034
Adenosine diphosphate
HMDB0001341
Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.
58-64-0
C00008
6022
16761
ADP
5800
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
XTWYTFMLZFPYCI-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
427.2011
427.029414749
-2.12
6
adenosine-diphosphate
0
-2
FDB021817
Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid
PW_C001034
ADP
23
4
134
8
415
22
482
13
801
5
963
15
978
3
1061
14
1518
2
1901
49
2104
18
2113
10
2161
58
2408
59
2435
27
2728
47
2736
46
2855
29
3165
72
3635
61
4400
23
4476
31
4770
91
5036
26
5157
7
5208
97
5217
100
5315
111
5349
112
5392
103
5446
120
5544
129
5572
133
5624
108
5741
117
5764
101
5849
143
5856
146
5878
107
5899
147
5926
151
6050
155
6111
161
6231
166
6495
178
6700
94
6841
188
6872
160
7159
205
7187
206
7208
210
7226
213
7231
211
7300
198
7303
216
7391
217
7410
218
7433
163
7483
222
8187
225
11851
277
11905
170
12013
281
12180
285
13262
223
15329
308
42328
315
42398
313
42622
322
42696
318
77029
253
77087
132
77216
134
77306
329
77472
333
77663
336
78039
332
78043
350
78170
128
78215
351
78244
353
78414
335
78495
115
78705
331
78849
130
78920
334
80030
368
80622
118
80651
135
80676
119
94827
124
113283
388
116204
109
119944
122
119994
406
120156
407
120318
382
120366
412
121248
429
121394
123
121399
433
121472
408
121899
383
121976
410
122064
125
122085
405
122405
422
122445
435
122973
399
123013
446
123818
464
123953
447
123958
468
124030
374
124452
398
124529
444
124615
136
124636
376
124947
472
124975
375
125012
470
125334
297
125373
479
125492
299
125517
481
125645
484
126125
485
126219
300
126235
495
126242
478
126550
491
126597
499
126915
501
127733
516
127780
395
127797
390
127803
209
128122
508
128168
517
128313
389
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
41176
2(α-D-Mannosyl)-D-glycerate
2(α-D-mannosyl)-D-glycerate; 2(alpha-D-Mannosyl)-D-glycerate; 2(alpha-D-Mannosyl)-D-glyceric acid; 2-(α-D-mannopyranosyl)-D-glycerate; 2-(alpha-D-Mannopyranosyl)-D-glycerate; 2-(alpha-D-Mannopyranosyl)-D-glyceric acid; 2-O-alpha-Mannosyl-D-glycerate; 2-O-alpha-Mannosyl-D-glyceric acid; Alpha-Mannosylglycerate; Alpha-Mannosylglyceric acid; Mannosylglycerate; Mannosylglyceric acid
443262
15847
[H][C@](CO)(O[C@@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])O)C(O)=O
C9H16O9
InChI=1S/C9H16O9/c10-1-3-5(12)6(13)7(14)9(17-3)18-4(2-11)8(15)16/h3-7,9-14H,1-2H2,(H,15,16)/t3-,4-,5-,6+,7+,9-/m1/s1
DDXCFDOPXBPUJC-SAYMMRJXSA-N
(2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid
268.2179
268.07943211
0.06
6
(2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid
0
-1
PW_C041176
2αDMDG
6656
107
42390
318
7259
Alpha-mannosidase mngB
P54746
Involved in catalytic activity. May hydrolyze mannosyl-D-glycerate to mannose-6- phosphate and glycerate.
mngB
b0732
AP009048
3
3.2.1.170
6417
Glycerate kinase 2
P23524
Involved in glycerate kinase activity. ATP + (R)-glycerate = ADP + 3-phospho-(R)- glycerate.
garK
b3124
AP009048
3
2.7.1.165
5744
117
7464
Phosphocarrier protein HPr
P0AA04
Involved in sugar:hydrogen symporter activity. General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III).
ptsH
b2415
AP009048
3
2.7.11.-
5702
108
6673
107
6674
117
8930
101
135644
610
10354
2-O-α-mannosyl-D-glycerate PTS permease
P13669
Represses mngA and mngB. Regulates its own expression.
mngR
25
6658
109
4088
α-mannosidase
25
PW_P004088
11104
7259
1
6806
117
1422
glycerate kinase
3
PW_P001422
1654
6417
1549
HPr - phosphorylated
3
PW_P001549
1828
7464
1550
HPr
3
PW_P001550
1829
7464
3938
2-O-α-mannosyl-D-glycerate PTS permease
3
PW_P003938
10917
10354
6116
false
PW_R006116
Right
25028
7709
1
Compound
false
25029
1420
1
Compound
false
25030
848
1
Compound
false
25031
90
1
Compound
false
6077
4088
3.2.1.170
6117
false
PW_R006117
Right
25032
90
1
Compound
false
25033
414
1
Compound
false
25034
1870
1
Compound
false
25035
1034
1
Compound
false
25036
40034
1
Compound
false
6078
1422
192
PW_RCT000192
Right
1146
192
41176
Compound
1
107
1147
192
1549
ProteinComplex
1
117
1148
192
7709
Compound
1
117
1149
192
1550
ProteinComplex
1
117
192
71619
7709
3
false
647
626
10
regular
100
130
71620
1420
49
false
557
767
10
regular
78
78
71621
848
3
false
542
966
10
regular
100
110
71622
90
3
false
647
1086
10
regular
100
100
71623
414
42
false
852
1066
10
regular
50
30
71624
1870
3
false
1310
1081
10
regular
100
110
71625
1034
43
false
1165
1061
10
regular
50
30
71626
40034
55
false
1170
1192
10
regular
78
78
71628
41176
107
3
false
647
211
10
regular
100
120
32809
7259
2
false
622
876
8
subunit
regular
150
70
32810
6417
2
false
944
1103
8
subunit
regular
150
70
32814
7464
117
2
false
492
511
8
subunit
regular
150
70
32815
7464
117
2
false
762
526
8
subunit
regular
150
70
32816
10354
109
76
false
624
386
8
subunit
regular
150
70
27548
4088
1854
32490
32809
27549
1422
1854
32491
32810
27553
1549
1854
117
32495
32814
27554
1550
1854
117
32496
32815
27555
3938
1854
109
32497
32816
101655
M697 756 C697 786 697 846 697 876
5
false
18
101656
M635 806 C698 809 696 839 697 876
5
false
18
101657
M642 1021 C702 1018 697 976 697 946
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101658
M697 1086 C697 1056 697 976 697 946
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
101659
M747 1136 C785 1137 893 1138 944 1138
5
false
18
101660
M877 1096 C878 1135 896 1138 944 1138
5
false
18
101661
M1310 1136 C1280 1138 1132 1136 1094 1138
5
false
18
true
M 153.58949584850177 227.99128306538606 L 138.64264080433693 226.72972676909 L 145.02352852552278 240.30486109216835
false
101662
M1190 1091 C1188 1136 1150 1138 1094 1138
5
false
18
true
M 153.58949584850177 227.99128306538606 L 138.64264080433693 226.72972676909 L 145.02352852552278 240.30486109216835
false
101663
M1209 1192 C1209 1162 1151 1136 1094 1138
5
false
18
true
M 153.58949584850177 227.99128306538606 L 138.64264080433693 226.72972676909 L 145.02352852552278 240.30486109216835
false
101669
M697 331 C697 361 699 356 699 386
5
false
18
101670
M697 626 C697 596 699 486 699 456
5
false
18
true
M 153.58949584850177 13.26155629629604 L 138.64264080433693 12 L 145.02352852552278 25.575134323078345
false
101671
M642 546 C699 544 699 500 700 461
5
false
18
101672
M762 561 C724 566 698 526 699 456
5
false
18
true
M 153.58949584850177 13.26155629629604 L 138.64264080433693 12 L 145.02352852552278 25.575134323078345
false
3660979
M1360 1081 C1360 1051 1362 928 1362 898
5
false
18
true
M 1704.5 869.9903810567666 L 1697 857 L 1689.5 869.9903810567666
false
20771
1854
6116
80708
71619
101655
Left
80709
71620
101656
Left
80710
71621
101657
Right
80711
71622
101658
Right
20947
6077
27548
20772
1854
6117
80712
71622
101659
Left
80713
71623
101660
Left
80714
71624
101661
Right
80715
71625
101662
Right
80716
71626
101663
Right
20948
6078
27549
451
192
1854
2511
71628
101669
Left
2512
71619
101670
Right
123
27553
101671
Left
124
27554
101672
Right
451
27555
226
109555
109883
1854
14
false
1287
828
16
regular
106248
71624
3660979
Left
186491
799
583
1.0
1.0
0
2
92
479
481
3612
M125 225 C125 175 175 125 225 125 C680 125 1272 125 1727 125 C1777 125 1827 175 1827 225 C1827 618 1827 1130 1827 1523 C1827 1573 1777 1623 1727 1623 C1272 1623 680 1623 225 1623 C175 1623 125 1573 125 1523 C125 1130 125 618 125 225
1
true
6
1702.0
1498.0
3613
M419 527.7027000903736 C419 477.7027000903736 469 427.7027000903736 519 427.7027000903736 C793 427.7027000903736 1150 427.7027000903736 1424 427.7027000903736 C1474 427.7027000903736 1524 477.7027000903736 1524 527.7027000903736 C1524 739.7027000903736 1524 1015.7027000903736 1524 1227.7027000903736 C1524 1277.7027000903736 1474 1327.7027000903736 1424 1327.7027000903736 C1150 1327.7027000903736 793 1327.7027000903736 519 1327.7027000903736 C469 1327.7027000903736 419 1277.7027000903736 419 1227.7027000903736 C419 1015.7027000903736 419 739.7027000903736 419 527.7027000903736
1
true
6
0.0
0.0