585
Pathway
Galactose Metabolism
Galactose can be synthesized through two pathways: melibiose degradation involving an alpha galactosidase and lactose degradation involving a beta galactosidase. Melibiose is first transported inside the cell through the melibiose:Li+/Na+/H+ symporter. Once inside the cell, melibiose is degraded through alpha galactosidase into an alpha-D-galactose and a beta-D-glucose. The beta-D-glucose is phosphorylated by a glucokinase to produce a beta-D-glucose-6-phosphate which can spontaneously be turned into a alpha D glucose 6 phosphate. This alpha D-glucose-6-phosphate is metabolized into a glucose -1-phosphate through a phosphoglucomutase-1. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase.
Galactose can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose.
Beta-D-galactose can also be uptaken from the environment through a galactose proton symporter.
Galactose is degraded through the following process:
Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell
Metabolic
PW000821
Center
PathwayVisualizationContext1108
2825
4050
#000099
PathwayVisualization569
585
Galactose Metabolism
Galactose can be synthesized through two pathways: melibiose degradation involving an alpha galactosidase and lactose degradation involving a beta galactosidase. Melibiose is first transported inside the cell through the melibiose:Li+/Na+/H+ symporter. Once inside the cell, melibiose is degraded through alpha galactosidase into an alpha-D-galactose and a beta-D-glucose. The beta-D-glucose is phosphorylated by a glucokinase to produce a beta-D-glucose-6-phosphate which can spontaneously be turned into a alpha D glucose 6 phosphate. This alpha D-glucose-6-phosphate is metabolized into a glucose -1-phosphate through a phosphoglucomutase-1. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase.
Galactose can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose.
Beta-D-galactose can also be uptaken from the environment through a galactose proton symporter.
Galactose is degraded through the following process:
Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell
Metabolic
3
109705
583
SubPathway
109205
1906
Compound
117
2210
4284510
Kamogawa A, Kurahashi K: Purification and properties of uridinediphosphate glucose pyrophosphorylase from Escherichia coli K12. J Biochem. 1965 Jun;57(6):758-65.
585
Pathway
2211
12695547
Lazarowski ER, Shea DA, Boucher RC, Harden TK: Release of cellular UDP-glucose as a potential extracellular signaling molecule. Mol Pharmacol. 2003 May;63(5):1190-7.
585
Pathway
2212
12007641
Lerouge I, Vanderleyden J: O-antigen structural variation: mechanisms and possible roles in animal/plant-microbe interactions. FEMS Microbiol Rev. 2002 Mar;26(1):17-47.
585
Pathway
2213
8647345
Frey PA: The Leloir pathway: a mechanistic imperative for three enzymes to change the stereochemical configuration of a single carbon in galactose. FASEB J. 1996 Mar;10(4):461-70.
585
Pathway
2215
12893935
Abramson J, Smirnova I, Kasho V, Verner G, Kaback HR, Iwata S: Structure and mechanism of the lactose permease of Escherichia coli. Science. 2003 Aug 1;301(5633):610-5. doi: 10.1126/science.1088196.
585
Pathway
2216
6767683
Huber RE, Lytton J, Fung EB: Efflux of beta-galactosidase products from Escherichia coli. J Bacteriol. 1980 Feb;141(2):528-33.
585
Pathway
2217
6426769
Huber RE, Hurlburt KL: Escherichia coli growth on lactose requires cycling of beta-galactosidase products into the medium. Can J Microbiol. 1984 Mar;30(3):411-5.
585
Pathway
2218
13718526
JACOB F, MONOD J: Genetic regulatory mechanisms in the synthesis of proteins. J Mol Biol. 1961 Jun;3:318-56.
585
Pathway
2219
10438463
Liu JY, Miller PF, Willard J, Olson ER: Functional and biochemical characterization of Escherichia coli sugar efflux transporters. J Biol Chem. 1999 Aug 13;274(33):22977-84.
585
Pathway
2220
10209755
Liu JY, Miller PF, Gosink M, Olson ER: The identification of a new family of sugar efflux pumps in Escherichia coli. Mol Microbiol. 1999 Mar;31(6):1845-51.
585
Pathway
2221
11937062
Wang XG, Olsen LR, Roderick SL: Structure of the lac operon galactoside acetyltransferase. Structure. 2002 Apr;10(4):581-8.
585
Pathway
2277
5543331
Burstein C, Kepes A: The alpha-galactosidase from Escherichia coli K12. Biochim Biophys Acta. 1971 Jan 26;230(1):52-63.
585
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
7
Epithelial Cell
CL:0000066
2
Platelet
CL:0000233
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
1
Homo sapiens
9606
Eukaryote
Human
24
Solanum lycopersicum
4081
Eukaryote
Tomato
3
Escherichia coli
562
Prokaryote
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
23
Pseudomonas aeruginosa
287
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
21
Xenopus laevis
8355
Eukaryote
African clawed frog
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
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
110
Bacillus velezensis MRC5958
492670
Prokaryote
Velezensis
5
Cytoplasm
GO:0005737
1
Cytosol
GO:0005829
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
24
Mitochondrial Intermembrane Space
GO:0005758
13
Endoplasmic Reticulum
GO:0005783
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
4
Peroxisome
GO:0005777
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
15
Nucleus
GO:0005634
27
Peroxisome Membrane
GO:0005778
25
Golgi apparatus
GO:0005794
6
Lysosome
GO:0005764
19
sarcoplasmic reticulum
GO:0016529
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
25
Intestine
BTO:0000648
2
Endothelium
BTO:0000393
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
4
Adrenal Medulla
BTO:0000049
71
8
11
Heart
BTO:0000562
73
10
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1
PW_BS000115
502
4
6
1
PW_BS000115
504
18
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
513
1
7
6
1
PW_BS000115
167
31
1
PW_BS000167
707
1
25
PW_BS000512
280
31
25
PW_BS000024
71
11
1
3
PW_BS000071
74
1
3
PW_BS000074
158
34
24
1
PW_BS000158
609
5
110
1
PW_BS000503
610
1
110
PW_BS000503
613
32
110
PW_BS000503
192
Uridine triphosphate
HMDB0000285
Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety. Uridine triphosphate has the role of a source of energy or an activator of substrates in metabolic reactions, like that of adenosine triphosphate, but more specific. When Uridine triphosphate activates a substrate, UDP-substrate is usually formed and inorganic phosphate is released. (Wikipedia).
63-39-8
C00075
6133
15713
UTP
5903
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
C9H15N2O15P3
InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)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)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
PGAVKCOVUIYSFO-XVFCMESISA-N
({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
484.1411
483.968527356
-1.76
7
uridine 5'-triphosphoric acid
0
-3
FDB021929
5'-utp;Utp;Uridine 5'-triphosphate;Uridine mono(tetrahydrogen triphosphate);Uridine triphosphate;Uteplex;H4utp;Uridine 5'-triphosphoric acid
PW_C000192
UTP
393
8
1514
2
3123
29
5979
147
6175
108
7270
160
42712
315
77299
111
77932
336
78252
132
120310
122
121262
429
121362
124
122965
135
123832
464
123921
118
125639
297
126035
299
127271
205
127487
388
40034
Hydrogen Ion
HMDB0059597
Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])
C00080
1038
15378
1010
[H+]
H
InChI=1S/p+1
GPRLSGONYQIRFK-UHFFFAOYSA-N
hydron
1.0079
1.007825032
0
hydron
1
0
H+;H(+);Hydrogen cation;Hydron;Proton
PW_C040034
H+
215
4
670
8
753
15
788
31
848
3
1116
2
1463
26
1464
54
2231
49
2780
17
4250
22
4254
42
4547
10
4576
18
4694
70
5241
103
5327
111
5353
112
5626
108
5639
107
5699
100
5720
105
5742
117
5963
147
6037
155
6070
157
6093
161
6130
159
6232
166
6483
178
6601
152
6692
101
6843
188
6910
187
7100
163
7168
205
7191
206
7453
219
7454
220
7472
222
7525
213
7532
210
7558
212
7572
160
7590
170
8195
225
8218
151
8243
226
8413
162
8420
224
9139
195
9155
249
11915
164
12015
281
12181
285
12246
286
12266
287
12521
227
13257
223
13325
294
15330
308
42329
315
42354
318
42401
322
42405
312
42454
320
76912
293
77136
133
77210
134
77372
331
77804
114
77955
132
77990
327
77991
347
78379
345
79929
130
80019
368
80387
310
80388
304
80722
119
93823
124
94823
383
110550
388
112855
94
113280
390
115537
398
115539
118
115856
336
116205
109
119973
406
120193
407
120549
122
120593
409
121170
424
121171
425
122569
418
122615
384
122687
125
122758
120
123183
135
123218
137
123742
459
123743
460
125141
454
125188
121
125273
136
125359
479
125550
481
125730
483
125736
297
125809
299
126517
495
126717
489
126766
480
126823
300
126902
501
127213
208
128308
506
128361
391
128430
395
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
504
Galactose 1-phosphate
HMDB0000645
Galactose 1-phosphate is a member of the class of compounds known as monosaccharide phosphates. Monosaccharide phosphates are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Galactose 1-phosphate is an intermediate in the galactose metabolism and nucleotide sugars metabolism pathways (KEGG). It is formed from galactose by galactokinase (Wikipedia). Galactose 1-phosphate is considered to be soluble (in water) and acidic.
2255-14-3
C00446
123912
17973
GALACTOSE-1P
110443
DB02317
OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@H]1O
C6H13O9P
InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3+,4+,5-,6-/m1/s1
HXXFSFRBOHSIMQ-FPRJBGLDSA-N
{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
260.1358
260.029718526
-0.91
6
galactose 1 phosphate
0
-2
FDB001159
1-(dihydrogen phosphate) galactitol;1-phosphate a-d-galactopyranose;D-galactose 1-phosphate;Galactopyranose 1-phosphate;Galactose 1-phosphate;A-d-1-(dihydrogen phosphate) galactopyranose;A-d-galactopyranosyl phosphate;A-d-galactose 1-phosphate;A-d-galactosyl phosphate;Alpha-d-1-(dihydrogen phosphate) galactopyranose;Alpha-d-galactopyranosyl phosphate;Alpha-d-galactose 1-phosphate;Alpha-d-galactosyl phosphate;Alpha-d-galactopyranose 1-phosphate;A-d-galactopyranose 1-phosphate;A-d-galactopyranose 1-phosphoric acid;Alpha-d-galactopyranose 1-phosphoric acid;α-d-galactopyranose 1-phosphate;α-d-galactopyranose 1-phosphoric acid;Galactose 1-phosphoric acid
PW_C000504
G1P
1137
8
1532
2
3111
29
12572
151
77920
336
78260
132
78408
111
120837
122
121247
429
121370
124
123422
135
123817
464
123929
118
125828
297
126043
299
127281
205
127495
388
193
Uridine diphosphate glucose
HMDB0000286
Uridine diphosphate glucose is a key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.
133-89-1
C00029
53477679
UDP-GLUCOSE
DB01861
OC[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)N2C=CC(=O)NC2=O)[C@@H](O)[C@H](O)[C@H]1O
C15H24N2O17P2
InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14?/m0/s1
HSCJRCZFDFQWRP-LPTOLDDLSA-N
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
566.3018
566.055020376
-1.58
9
udp-α-D-glucose
0
-2
FDB005660
(udp)glucose;(upd)-glucose;Udp glucose;Udp-d-glucose;Udp-glc;Udp-glucose;Udp-a-d-glucose;Udp-alpha-d-glucose;Udp-alpha-delta-glucose;Udp-delta-glucose;Udpg;Udpglucose;Uridine 5'-diphosphate glucose;Uridine 5'-diphospho-a-d-glucose;Uridine 5'-diphospho-alpha-d-glucose;Uridine 5'-diphospho-alpha-delta-glucose;Uridine 5'-diphosphoglucose;Uridine 5'-pyrophosphate a-d-glucopyranosyl ester;Uridine 5'-pyrophosphate a-delta-glucopyranosyl ester;Uridine diphosphate-glucose;Uridine diphospho-d-glucose;Uridine diphospho-delta-glucose;Uridine diphosphoglucose;Uridine pyrophosphate-glucose
PW_C000193
UDPG
1127
8
1515
2
2196
49
2203
43
3118
29
5980
147
7245
213
7249
214
7271
160
8432
151
11911
164
77927
336
78253
132
78402
111
78882
331
78885
356
120828
122
121255
429
121363
124
122100
383
122104
419
123413
135
123825
464
123922
118
124651
398
124655
455
125819
297
126036
299
126256
495
126260
490
127272
205
127488
388
127819
390
127823
507
93
D-Galactose
HMDB0000143
D-Galactose is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. D-Galactose is an energy-providing nutrient and also a necessary basic substrate for the biosynthesis of many macromolecules in the body. Metabolic pathways for D-Galactose are important not only for the provision of these pathways but also for the prevention of D-Galactose and D-Galactose metabolite accumulation. The main source of D-Galactose is lactose in the milk of mammals, but it can also be found in some fruits and vegetables. Utilization of D-Galactose in all living cells is initiated by the phosphorylation of the hexose by the enzyme galactokinase (E.C. 2.7.1.6) (GALK) to form D-Galactose-1-phosphate. In the presence of D-Galactose-1-phosphate uridyltransferase (E.C. 2.7.7.12) (GALT) D-Galactose-1-phosphate is exchanged with glucose-1-phosphate in UDP-glucose to form UDP-galactose. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. Deficiency of the enzyme GALT in galactosemic patients leads to the accumulation of D-Galactose-1-phosphate. Classic galactosemia-a term that denotes the presence of D-Galactose in the blood is the rare inborn error of D-Galactose metabolism, diagnosed by the deficiency of the second enzyme of the D-Galactose assimilation pathway, GALT, which, in turn, is caused by mutations at the GALT gene. (PMID: 15256214, 11020650, 10408771).
59-23-4
C00984
439357
28061
GALACTOSE
388480
OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O
C6H12O6
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6+/m1/s1
WQZGKKKJIJFFOK-PHYPRBDBSA-N
(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
180.1559
180.063388116
0.64
5
galactose
0
0
FDB012703
(+)-galactose;5abp;8abp;D-(+)-galactose;D-galactose;D-hexose;Gal;Gla;Glc;Galactose;Galactose (nf);Hexose;Alpha d-galactose;Alpha-d-galactopyranose;Alpha-d-galactose;Alpha-d-gal;Gal-alpha;A d-galactose;α d-galactose;A-d-gal;α-d-gal;Gal-a;Gal-α
PW_C000093
D-Gal
1142
8
2212
9
2680
60
2731
61
3133
29
3937
51
7255
215
12571
151
77896
113
77943
336
78237
352
78250
353
78251
326
78410
111
120840
122
121221
126
121271
429
122386
436
122392
437
122393
416
123425
135
123791
443
123842
464
124940
471
124962
472
124963
452
125831
297
126266
301
127284
205
127830
207
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
1034
Adenosine diphosphate
HMDB0001341
Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.
58-64-0
C00008
6022
16761
ADP
5800
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
XTWYTFMLZFPYCI-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
427.2011
427.029414749
-2.12
6
adenosine-diphosphate
0
-2
FDB021817
Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid
PW_C001034
ADP
23
4
134
8
415
22
482
13
801
5
963
15
978
3
1061
14
1518
2
1901
49
2104
18
2113
10
2161
58
2408
59
2435
27
2728
47
2736
46
2855
29
3165
72
3635
61
4400
23
4476
31
4770
91
5036
26
5157
7
5208
97
5217
100
5315
111
5349
112
5392
103
5446
120
5544
129
5572
133
5624
108
5741
117
5764
101
5849
143
5856
146
5878
107
5899
147
5926
151
6050
155
6111
161
6231
166
6495
178
6700
94
6841
188
6872
160
7159
205
7187
206
7208
210
7226
213
7231
211
7300
198
7303
216
7391
217
7410
218
7433
163
7483
222
8187
225
11851
277
11905
170
12013
281
12180
285
13262
223
15329
308
42328
315
42398
313
42622
322
42696
318
77029
253
77087
132
77216
134
77306
329
77472
333
77663
336
78039
332
78043
350
78170
128
78215
351
78244
353
78414
335
78495
115
78705
331
78849
130
78920
334
80030
368
80622
118
80651
135
80676
119
94827
124
113283
388
116204
109
119944
122
119994
406
120156
407
120318
382
120366
412
121248
429
121394
123
121399
433
121472
408
121899
383
121976
410
122064
125
122085
405
122405
422
122445
435
122973
399
123013
446
123818
464
123953
447
123958
468
124030
374
124452
398
124529
444
124615
136
124636
376
124947
472
124975
375
125012
470
125334
297
125373
479
125492
299
125517
481
125645
484
126125
485
126219
300
126235
495
126242
478
126550
491
126597
499
126915
501
127733
516
127780
395
127797
390
127803
209
128122
508
128168
517
128313
389
1894
β-D-Galactose
HMDB0003449
Galactose is an optical isomer of glucose. An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Deficiency of galactosyl-1-phosphate uridyltransferase (Galactose-1-phosphate uridyl-transferase deficiency disease) causes an error in galactose metabolism called galactosemia, resulting in elevations of galactose in the blood. Galactose (Gal) (also called brain sugar) is a type of sugar found in dairy products, in sugar beets and other gums and mucilages. It is also synthesized by the body, where it forms part of glycolipids and glycoproteins in several tissues. It is considered a nutritive sweetener because it has food energy. Galactose is less sweet than glucose and not very water-soluble. Galactose is a monosaccharide constituent, together with glucose, of the disaccharide lactose. The hydrolysis of lactose to glucose and galactose is catalyzed by the enzyme beta-galactosidase, a lactase. In the human body, glucose is changed into galactose in order to enable the mammary glands to secrete lactose. Galactan is a polymer of the sugar galactose. It is found in hemicellulose and can be converted to galactose by hydrolysis.
7296-64-2
C00962
439353
27667
ALPHA-N-DIACETYLNEURAMINYL-23-BETA-D-ETC
388476
OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O
C6H12O6
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6-/m1/s1
WQZGKKKJIJFFOK-FPRJBGLDSA-N
(2R,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
180.1559
180.063388116
0.64
5
β D-galactose
0
0
FDB021788
B-d-galactose;B-galactose;Beta d-galactose;Beta-d-galactopyranose;Beta-d-galactose;Beta-d-galactoside;Beta-d-galactosides;Beta-galactose;Beta-delta-galactoside;Beta-delta-galactosides;Delta-galactose;Beta-d-gal;Gal-beta;B-d-gal;β-d-gal;β-d-galactose;Gal-b;Gal-β
PW_C001894
BD-Gal
6141
107
6142
108
6143
105
12570
151
42433
318
42434
315
119
α-Lactose
HMDB0000186
alpha-Lactose is the major sugar present in milk and the main source of energy supplied to the newborn mammalian in its mother's milk. Lactose is also an important osmotic regulator of lactation. It is digested by the intestinal lactase (EC 3.2.1.108), an enzyme expressed in newborns. Its activity declines following weaning. As a result, adult mammals are normally lactose-intolerant and more than 75% of the human adult population suffers from lactase deficiency. Lactase deficiency is present in up to 80 percent of blacks and Latinos, and up to 100 percent of American Indians and Asians. Persons with lactose intolerance are unable to digest significant amounts of lactose. Common symptoms include abdominal pain and bloating, excessive flatus, and watery stool following the ingestion of foods containing lactose. A sizable number of adults believe they are lactose intolerant but do not actually have impaired lactose digestion, and some persons with lactase deficiency can tolerate moderate amounts of ingested lactose. A diagnosis of lactose intolerance can usually be made with a careful history supported by dietary manipulation. If necessary, diagnosis can be confirmed by using a breath hydrogen or lactose tolerance test. These mostly uncomfortable symptoms of lactose maldigestion are blamed for a variably dairy consumption. There is, however, emerging evidence that certain lactic acid-producing bacteria, which selectively consume prebiotics, may be beneficial against some lower intestinal diseases. Lactose maldigestion and lactose should perhaps be re-evaluated as a potential provider of such a prebiotic. Treatment consists primarily of avoiding lactose-containing foods. Lactase enzyme supplements may be helpful. The degree of lactose malabsorption varies greatly among patients with lactose intolerance, but most of them can ingest up to 350 mL of milk daily without symptoms. Lactose-intolerant patients must ensure adequate calcium intake. (PMID: 13130292, 12216958, 12197838, 12018807).
63-42-3
C00243
84571
36219
LACTOSE
76293
DB04465
OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O
C12H22O11
InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5+,6+,7-,8-,9-,10-,11+,12+/m1/s1
GUBGYTABKSRVRQ-XLOQQCSPSA-N
(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
342.2965
342.116211546
0.23
8
α-lactose
0
0
FDB001145
(+)-lactose;1-beta-d-galactopyranosyl-4-alpha-d-glucopyranose;1-beta-delta-galactopyranosyl-4-alpha-delta-glucopyranose;4-o-hexopyranosylhexose;Aletobiose;Anhydrous lactose;Dilactose;Fast-flo lactose;Flowlac 100;Galactinum;Glc-(4-1)gal;Granulac 140m;Lactin;Lactin (carbohydrate);Lactobiose;Lactohale 300;Lactose;Lactose fast-flo;Lactose anhydride;Milk sugar;Osmolactan;Pharmatosa dcl 21;Pharmatose 21;Pharmatose 325m;Pharmatose dcl 15;Prismalac;Respitose ml 003;Respitose sv 003;Saccharum lactin;Sachelac;Sorbalac 400;Sorbolac 400;Spherolac;Super-tab;Tablettose;Tablettose 70;Tablettose 80;Zeparox ep;A-lactose;Alpha-lactose;4-o-beta-d-galactopyranosyl-alpha-d-glucopyranose;Beta-d-galp-(1->4)-alpha-d-glcp;1-b-d-galactopyranosyl-4-a-d-glucopyranose;1-β-d-galactopyranosyl-4-α-d-glucopyranose;α-lactose;4-o-b-d-galactopyranosyl-a-d-glucopyranose;4-o-β-d-galactopyranosyl-α-d-glucopyranose;B-d-galp-(1->4)-a-d-glcp;β-d-galp-(1->4)-α-d-glcp
PW_C000119
Lactin
1546
43
2677
60
3099
9
5706
108
6062
105
6063
107
42425
318
42426
315
77908
113
78234
352
78265
356
121234
126
121376
419
122383
436
123804
443
123935
455
124937
471
126049
490
127501
507
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
395
β-D-Glucose
HMDB0000516
Beta-D-Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement. A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. This group contains a benzene and also an ethylene group, being derived from styrolene. Coniferin, C16H22O8, occurs in the cambium of conifer wood. Emulsin converts it into glucose and coniferyl alcohol, while oxidation gives glycovanillin, which yields with emulsin glucose and vanillin. Syringin, which occurs in the bark of Syringe vulgaris, is a methoxyconiferin. Phloridzus occurs in the root-bark of various fruit trees; it hydrolyses to glucose and phloretin, which is the phloroglucin ester of paraoxyhydratropic acid. It is related to the pentosides naringin, C21HEOi1, which hydrolyses to rhamnose and naringenin, the phioroglucin ester of para-oxycinnamic acid, and hesperidin, which hydrolyses to rhamnose and hesperetin, the phloroglucin ester of meta-oxy-para-methoxycinnamic acid or isoferulic acid, C10H10O4. Classification of the glucosides is a matter of some difficulty. One based on the chemical constitution of the non-glucose part of the molecules has been proposed that frames four groups: (I) ethylene derivatives, (2) benzene derivatives, (3) styrolene derivatives, (4) anthracene derivatives. A group may also be made to include the cyanogenetic glucosides, i.e. those containing prussic acid. Other classifications follow a botanical classification, which has several advantages; in particular, plants of allied genera contain similar compounds. In this article the chemical classification will be followed, and only the more important compounds will be discussed here.
492-61-5
C00221
64689
15903
58238
OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
C6H12O6
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6-/m1/s1
WQZGKKKJIJFFOK-VFUOTHLCSA-N
(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
180.1559
180.063388116
0.64
5
glucoside
0
0
FDB011824
B-d-glucopyranose;B-dextrose;B-glucose;Beta-d-glucopyranose;Beta-d-glucose;Beta-dextrose;Beta-glucose;Beta-delta-glucopyranose;Glucose
PW_C000395
Glu
2222
2
3605
60
3608
61
3646
51
3647
29
5902
147
5929
151
6366
107
6875
160
9044
226
12988
167
42606
318
77090
132
79059
352
79061
353
79062
336
79064
326
121175
124
122582
436
122585
437
122586
429
122588
416
123747
118
125154
471
125157
472
125158
464
125160
452
125941
299
127401
388
206
Uridine diphosphategalactose
HMDB0000302
Uridine diphosphategalactose (UDPgal) is a nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. UDPgal is a pivotal compound in the metabolism of galactose. UDPgal is a product of the galactose-l-phosphate uridyl transferase (EC 2.7.7.10) reaction but may also be made from Glucose-l-P, involving uridine diphosphate galactose-4-epimerase (EC 5.1.3.2). UDPgal is the necessary galactosyl donor of galactose in the metabolism to incorporate it into complex oligosaccharides, glycoproteins and glycolipids (galactosides). Defective galactosylation of complex glycoconjugates exists in tissues from galactosemic patients. There is a tendency for galactosemic red cell UDPgal to be in the low normal range with a high uridine diphosphate glucose to UDP-gal ratio. This may reflect an inability of red cell UDPgal-4'-epimerase to maintain a normal ratio and consequently higher levels of UDPgal. In the more complex white blood cells and cultured fibroblasts, the UDPgal content and the uridine diphosphate glucose to UDPgal ratio of galactosemics are normal. Therefore, defective galactosylation observed in galactosemic fibroblasts must result from a defect in the transfer of galactose from UDPgal to these moieties. (PMID: 2122114, 7671968).
2956-16-3
C00052
18068
67119
UDP-GLACTOSE
17069
OC[C@H]1O[C@H](O[P@@](O)(=O)O[P@@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@H]1O
C15H24N2O17P2
InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8+,9-,10+,11-,12-,13-,14-/m1/s1
HSCJRCZFDFQWRP-ABVWGUQPSA-N
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
566.3018
566.055020376
-1.58
9
{[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid
0
-2
FDB021811
Gdu;Udp galactose;Udp-d-galactopyranose;Udp-d-galactose;Udp-gal;Udp-galactopyranose;Udp-galactose;Udp-a-d-galactose;Udp-alpha-d-galactose;Udp-alpha-delta-galactose;Udp-delta-galactopyranose;Udp-delta-galactose;Udpgalactose;Upg;Udpgal;Uridine 5'-(alpha-d-galactopyranosyl pyrophosphate);Uridine 5'-(alpha-delta-galactopyranosyl pyrophosphate);Uridine 5'-[3-(d-galactopyranosyl) dihydrogen diphosphate];Uridine 5'-diphosphate galactose;Uridine 5'-diphosphogalactose;Uridine 5'-pyrophosphate d-galactosyl ester;Uridine 5'-pyrophosphate a-d-galactopyranosyl ester;Uridine 5'-pyrophosphate a-d-galactosyl ester;Uridine 5'-pyrophosphate a-delta-galactopyranosyl ester;Uridine 5'-pyrophosphate a-delta-galactosyl ester;Uridine 5'-pyrophosphate alpha-d-galactosyl ester;Uridine 5'-pyrophosphate alpha-delta-galactosyl ester;Uridine diphosphate galactose;Uridine diphosphate-d-galactose;Uridine diphosphate-delta-galactose;Uridine diphosphate-galactose;Uridine diphosphogalactose;Uridine pyrophosphate a-d-galactopyranosyl ester;Uridine pyrophosphate a-delta-galactopyranosyl ester;Uridine pyrophosphate alpha-d-galactopyranosyl ester;Uridine pyrophosphate alpha-delta-galactopyranosyl ester;Uridine pyrophosphogalactose;Uridinediphosphate galactose;Uridinediphosphogalactose;Udp-alpha-d-galactopyranose;Udp-α-d-galactose;Udp-a-d-galactopyranose;Udp-α-d-galactopyranose;Uridine diphosphoric acid galactose
PW_C000206
UDPPG
1136
8
1531
2
1544
43
3113
29
77922
336
78259
132
78263
356
78407
111
120836
122
121250
429
121369
124
121374
419
123421
135
123820
464
123928
118
123933
455
125827
297
126042
299
126047
490
127280
205
127494
388
127499
507
41026
Hydrogen ion
Hydrogen ion, also known as proton or H+, belongs to the class of inorganic compounds known as other non-metal hydrides. These are inorganic compounds in which the heaviest atom bonded to a hydrogen atom is belongs to the class of 'other non-metals'. In humans, hydrogen ion is involved in cardiolipin biosynthesis CL(a-13:0/i-20:0/i-19:0/i-18:0) pathway, cardiolipin biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) pathway, cardiolipin biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway, and cardiolipin biosynthesis CL(i-13:0/i-12:0/i-17:0/i-20:0) pathway. Hydrogen ion is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)) pathway, de novo triacylglycerol biosynthesis TG(22:1(13Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, de novo triacylglycerol biosynthesis TG(14:0/24:1(15Z)/24:0) pathway, and de novo triacylglycerol biosynthesis TG(20:0/24:1(15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway. Outside of the human body, hydrogen ion can be found in a number of food items such as wax gourd, swede, black huckleberry, and banana. This makes hydrogen ion a potential biomarker for the consumption of these food products.
[H+]
H
InChI=1S/p+1
GPRLSGONYQIRFK-UHFFFAOYSA-N
hydron
1.0079
1.007825032
0
hydron
1
0
PW_C041026
HI
6020
105
6021
107
6182
108
9148
249
42718
315
1906
β-D-Glucose 6-phosphate
HMDB0003498
Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen, especially if blood glucose levels are high.
C01172
439427
17719
388538
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-VFUOTHLCSA-N
{[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
260.1358
260.029718526
-0.92
6
β-D-glucose 6-phosphate
0
-2
FDB023183
Beta-d-glucose 6-(dihydrogen phosphate);Beta-d-glucose 6-phosphate;6-h2po3glcbeta;6-o-phosphono-beta-d-glucopyranose;Beta-d-glucose 6-phosphic acid;Beta-d-glucose-6-phosphate;B-d-glucose 6-phosphate;B-d-glucose 6-phosphoric acid;Beta-d-glucose 6-phosphoric acid;β-d-glucose 6-phosphate;β-d-glucose 6-phosphoric acid;6-o-phosphono-b-d-glucopyranose;6-o-phosphono-β-d-glucopyranose;B-d-glucose 6-(dihydrogen phosphate);B-d-glucose 6-(dihydrogen phosphoric acid);Beta-d-glucose 6-(dihydrogen phosphoric acid);β-d-glucose 6-(dihydrogen phosphate);β-d-glucose 6-(dihydrogen phosphoric acid);B-d-glucose-6-phosphate;B-d-glucose-6-phosphoric acid;Beta-d-glucose-6-phosphoric acid;β-d-glucose-6-phosphate;β-d-glucose-6-phosphoric acid
PW_C001906
BDGlu6P
1728
2
3649
29
5903
147
5931
151
6211
108
6288
107
6877
160
12982
166
13290
225
42381
318
42382
315
77092
132
79063
336
121177
124
122587
429
123749
118
125159
464
125943
299
127403
388
137064
707
137065
280
33
Melibiose
HMDB0000048
Melibiose is disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes. It is not an endogenous metabolite but may be obtained from the consumption of partially fermented molasses, brown sugar or honey. Antibodies to melibiose will appear in individuals affected by Chagas' disease (Trypanosoma cruzi infection). Melibiose is not metabolized by humans, but can be broken down by gut microflora, such as E. coli. In fact, E. coli is able to utilize melibiose as a sole source of carbon. Melibiose is first imported by the melibiose permease, MelB and then converted to β-D-glucose and β-D-galactose by the α-galactosidase encoded by melA. Because of its poor digestability Melibiose (along with rhamnose) can be used together for noninvasive intestinal mucosa barrier testing. This test can be used to assess malabsorption or impairment of intestinal permeability. Recent studies with dietary melibiose have shown that can strongly affected the Th cell responses to an ingested antigen. It has been suggested that melibiose could be used to enhance the induction of oral tolerance. (PMID 17986780).
585-99-9
C05402
440658
28053
MELIBIOSE
389538
OC[C@H]1O[C@H](OC[C@H]2OC(O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O
C12H22O11
InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11?,12+/m1/s1
DLRVVLDZNNYCBX-ABXHMFFYSA-N
(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
342.2965
342.116211546
0.17
8
(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
0
0
FDB001204
6-(d-galactosido)-d-glucose;6-(d-galactosido)-delta-glucose;6-(a-d-galactosido)-d-glucose;6-(a-delta-galactosido)-delta-glucose;6-o-hexopyranosylhexose;6-o-a-d-galactopyranosyl-d-glucose;6-o-alpha-d-galactopyranosyl-d-glucose;6-o-alpha-delta-galactopyranosyl-delta-glucose;D-(+)-melibiose;D-melibiose;Melibiose;Mellibiose;Alpha-d-melibiose;Alpha-melibiose;Alpha-delta-melibiose;Delta-(+)-melibiose;Delta-melibiose;(gal)1 (glc)1;6-o-(alpha-d-galactopyranosyl)-d-glucopyranose;6-o-alpha-d-galactopyranosyl-d-glucopyranose;Alpha-d-gal-(1->6)-d-glc;Alpha-d-galactosyl-(1->6)-d-glucose;Alpha-d-galp-(1->6)-d-glcp;Gal-alpha(1,6)glc
PW_C000033
MeliB
3100
9
6144
107
6145
108
6148
105
42462
318
42463
315
77909
113
121235
126
123805
443
458
Sodium
HMDB0000588
Sodium ions are necessary for regulation of blood and body fluids, transmission of nerve impulses, heart activity, and certain metabolic functions. Physiologically, it exists as an ion in the body. Sodium is needed by animals, which maintain high concentrations in their blood and extracellular fluids, but the ion is not needed by plants. The human requirement for sodium in the diet is less than 500 mg per day, which is typically less than a tenth as much as many diets "seasoned to taste." Most people consume far more sodium than is physiologically needed. For certain people with salt-sensitive blood pressure, this extra intake may cause a negative effect on health.
17341-25-2
C01330
923
29101
899
[Na+]
Na
InChI=1S/Na/q+1
FKNQFGJONOIPTF-UHFFFAOYSA-N
sodium(1+) ion
22.9898
22.989769675
0
sodium(1+) ion
1
1
FDB003523
Sodium;Sodium ion;Na(+);Na+
PW_C000458
Na+
2093
15
2094
2
2724
60
2725
61
3157
71
3158
72
3185
74
3615
51
4607
8
5860
105
5861
107
5862
108
7149
187
7150
188
42337
318
42338
315
78239
353
78243
326
78249
352
79047
132
122389
436
122390
437
122635
416
122636
124
124942
472
124946
452
124960
471
125209
118
2607
Lithium
HMDB0005949
Lithium (Li) is an alkali metal. First described as a mood stabilizer in 1949, it remains an efficacious treatment for bipolar disorders. Recent emerging evidence of its neuroprotective and neurogenic effects alludes to lithium's potential therapeutic use in stroke and neurodegenerative diseases. One intriguing clinical application is in the treatment of Alzheimer's disease. Ongoing clinical trials are evaluating lithium's abilities to lower tau and beta-amyloid levels in cerebrospinal fluid in Alzheimer's patients. Lithium reduces brain inositol levels by inhibiting the enzyme inositol monophosphatase. This suggests that inositol monophosphatase inhibition is a key mechanism of Li's therapeutic action and that design of new inositol monophosphatase inhibitors may be a practical strategy to create new compounds with Li-like therapeutic effects. Lithium reduces the severity of some behavioral complications of Alzheimer's disease (AD). And there are growing indications that Li may be of benefit to the underlying pathology of AD, as well as an array of other common CNS disorders, including stroke, Parkinson's disease, and Huntington's disease. Physiologically, it exists as an ion in the body. Despite these demonstrated and prospective therapeutic benefits, Li's mechanism of action remains elusive, and opinions differ regarding the most relevant molecular targets. Lithium inhibits several enzymes; significant among these are inositol monophosphatase (IMPase), glycogen synthase kinase-3 (GSK-3), and the proteasome. Lithium has a narrow therapeutic range, and several well characterised adverse effects limit the potential usefulness of higher doses. Acute ingestion in Li-naive patients is generally associated with only short-lived exposure to high concentrations, due to extensive distribution of Li throughout the total body water compartment. Conversely, chronic toxicity and acute-on-therapeutic ingestion are associated with prolonged exposure to higher tissue concentrations and, therefore, greater toxicity. Lithium toxicity may be life threatening, or result in persistent cognitive and neurological impairment. Therefore, enhanced Li clearance has been explored as a means of minimizing exposure to high tissue concentrations. Although haemodialysis is highly effective in removing circulating Li, serum concentrations often rebound so repeated or prolonged treatment may be required. Continuous arteriovenous haemodiafiltration and continuous venovenous haemodiafiltration increase Li clearance, albeit to a lesser extent than haemodialysis, and are more widely accessible. Lithium reduces brain inositol levels by inhibiting IMPase, suggesting that IMPase's inhibition is a key mechanism of Li's therapeutic action and that design of new IMPase inhibitors may be a practical strategy to create new compounds with Li-like therapeutic effects. (PMID: 17688381, 17316163, 8110911, 17288494).
17341-24-1
C15473
28486
49713
LI%2b
26502
DB01356
[Li+]
Li
InChI=1S/Li/q+1
HBBGRARXTFLTSG-UHFFFAOYSA-N
lithium(1+) ion
6.941
7.016004049
0
lithium(1+) ion
1
1
FDB004181
Li;Li(+) cation;Li(+) ion;Lithium atom;Lithium element;Li(+);Lithium cation;Lithium ion;Lithium, ion;Lithium, ion (li1+)
PW_C002607
Lithium
6146
107
6147
108
6149
105
42464
318
42465
315
1851
α-D-Glucose
HMDB0003345
Alpha-D-Glucose, also known as alpha-dextrose or alpha-D-GLC, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Alpha-D-Glucose exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Alpha-D-Glucose has been found in human epidermis and intestine tissues, and has also been detected in multiple biofluids, such as feces and saliva. Within the cell, Alpha-D-glucose is primarily located in the cytoplasm. Alpha-D-Glucose exists in all living organisms, ranging from bacteria to humans. Alpha-D-Glucose participates in a number of enzymatic reactions. In particular, Alpha-D-Glucose and Beta-D-glucose can be biosynthesized from α,α-trehalose; which is mediated by the enzyme cytoplasmic trehalase. Furthermore, Beta-D-Glucose and Alpha-D-glucose can be biosynthesized from α,α-trehalose; which is catalyzed by the enzyme periplasmic trehalase. Furthermore, Alpha-D-Glucose can be converted into α-D-glucose 6-phosphate through its interaction with the enzyme glucose PTS permease. Finally, Alpha-D-Glucose can be converted into α-D-glucose 6-phosphate; which is catalyzed by the enzyme glucose PTS permease. In humans, Alpha-D-glucose is involved in the nucleotide sugars metabolism pathway, the starch and sucrose metabolism pathway, the fructose intolerance, hereditary pathway, and the fructose and mannose degradation pathway. Alpha-D-Glucose is also involved in several metabolic disorders, some of which include the glycogenosis, type ia. von gierke disease pathway, sucrase-isomaltase deficiency, fructose-1,6-diphosphatase deficiency, and the mucopolysaccharidosis vi. sly syndrome pathway. Outside of the human body, Alpha-D-glucose can be found in a number of food items such as naranjilla, shallot, apple, and peach (var.). This makes Alpha-D-glucose a potential biomarker for the consumption of these food products. Alpha-D-Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement.
492-62-6
C00267
79025
17925
ALPHA-GLUCOSE-16-BISPHOSPHATE
71358
OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O
C6H12O6
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6+/m1/s1
WQZGKKKJIJFFOK-DVKNGEFBSA-N
(2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
180.1559
180.063388116
0.64
5
α-glucose
0
0
FDB011829
Hexopyranose;A-d-glucopyranose;A-d-glucose;A-dextrose;A-glucose;Alpha-d-glucopyranose;Alpha-d-glucose;Alpha-dextrose;Alpha-glucose;Alpha-delta-glucopyranose;Alpha-delta-glucose;Alpha-d-glc;A-d-glc;α-d-glc;α-d-glucose;α-dextrose
PW_C001851
a-D-Glc
1006
8
2218
2
2297
15
3128
29
3606
60
5901
147
5928
151
6205
105
6874
160
7264
190
42605
320
77089
132
77912
111
77938
336
78900
114
79060
352
120710
122
121174
124
121267
429
122356
409
122583
436
123315
135
123746
118
123837
464
124910
137
125155
471
125814
297
125940
299
127266
205
127400
388
1083
Glucose 6-phosphate
HMDB0001401
Glucose 6 phosphate (alpha-D-glucose 6 phosphate or G6P) is the alpha-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Glucose 6 phosphate is an ester of glucose with phosphoric acid, made in the course of glucose metabolism by mammalian and other cells. It is a normal constituent of resting muscle and probably is in constant equilibrium with fructose-6-phosphate. (Stedman, 26th ed). Glucose-6-phosphate is a phosphorylated glucose molecule on carbon 6. When glucose enters a cell, it is immediately phosphorylated to G6P. This is catalyzed with hexokinase enzymes, thus consuming one ATP. A major reason for immediate phosphorylation of the glucose is so that it cannot diffuse out of the cell. The phosphorylation adds a charged group so the G6P cannot easily cross cell membranes. G6P can travel down two metabolic pathways, glycolysis and the pentose phosphate pathway. In addition to the metabolic pathways, G6P can also be stored as glycogen in the liver if blood glucose levels are high. If the body needs energy or carbon skeletons for syntheses, G6P can be isomerized to Fructose-6-phosphate and then phosphorylated to Fructose-1,6-bisphosphate. Note, the molecule now has 2 phosphoryl groups attached. The addition of the 2nd phosphoryl group is an irreversible step, so once this happens G6P will enter glycolysis and be turned into pyruvate (ATP production occurs). If blood glucose levels are high, the body needs a way to store the excess glucose. After being converted to G6P, phosphoglucose mutase (isomerase) can turn the molecule into glucose-1-phosphate. Glucose-1-phosphate can then be combined with uridine triphosphate (UTP) to form UDP-glucose. This reaction is driven by the hydrolysis of pyrophosphate that is released in the reaction. Now, the activated UDP-glucose can add to a growing glycogen molecule with the help of glycogen synthase. This is a very efficient storage mechanism for glucose since it costs the body only 1 ATP to store the 1 glucose molecule and virtually no energy to remove it from storage. It is important to note that glucose-6-phosphate is an allosteric activator of glycogen synthase, which makes sense because when the level of glucose is high the body should store the excess glucose as glycogen. On the other hand, glycogen synthase is inhibited when it is phosphorylated by protein kinase a during times of high stress or low blood glucose levels. -- Wikipedia.
56-73-5
C00092
5958
4170
GLC-6-P
5743
OC1O[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-GASJEMHNSA-N
{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
260.1358
260.029718526
-0.92
6
glucose 6-phosphate
0
-2
FDB021818
D(+)-glucopyranose 6-phosphate;D-glucose 6-phosphate;D-glucose-6-dihydrogen phosphate;D-hexose 6-phosphate;Glucose 6-phosphate;Glucose-6-phosphate;Robison ester;A-d-glucose 6- phosphate;Alpha-d-glucose 6- phosphate;Alpha-d-glucose 6-phosphate;Alpha-d-hexose 6-phosphate;6-o-phosphono-d-glucopyranose;Glc6p;D-glucopyranose 6-phosphoric acid;D-glucose 6-phosphoric acid
PW_C001083
Gluc-6P
1118
8
1804
2
2381
18
3125
29
5898
147
5925
151
6065
158
6871
160
7403
198
11912
164
12577
225
77086
132
77936
336
77949
130
78164
111
120824
122
121172
124
121200
125
121264
429
123409
135
123744
118
123770
136
123834
464
125815
297
125938
299
127267
205
127398
388
42898
β-D-glucose 1-phosphate
(2R,3S,4R,5R,6S)-3,4,5,6-Tetrahydroxyoxan-2-yl phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). β-D-glucose 1-phosphate has the chemical formula C5H9O9P, and an average molecular weight of 244.093. β-D-glucose 1-phosphate is involved in few pathways, which are Amino Sugar and Nucleotide Sugar Metabolism III Pathway, Starch and Sucrose Metabolism Pathway, Galactose Metabolism Pathway, and Galactose Degradation/Leloir Pathway.
57684
O[C@H]1O[C@H](OP([O-])([O-])=O)[C@@H](O)[C@H](O)[C@H]1O
C5H9O9P
InChI=1S/C5H11O9P/c6-1-2(7)4(9)13-5(3(1)8)14-15(10,11)12/h1-9H,(H2,10,11,12)/p-2/t1-,2-,3+,4+,5-/m1/s1
VPFDELVVUOEHIT-OGZQUKKDSA-L
(2R,3S,4R,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl phosphate
244.093
243.999516028
-0.45
4
(2R,3S,4R,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl phosphate
-2
-2
β-d-glucopyranose 1-phosphate
PW_C042898
βDG1P
6369
108
42850
315
41033
α-D-glucose-1-phosphate
Alpha-D-Glucose-1-phosphate, also known as D-glucose 1-phosphoric acid or alpha-D-glucopyranosyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Alpha-D-Glucose-1-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Alpha-D-Glucose-1-phosphate can be converted into alpha-D-glucose..
OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
C6H13O9P
InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1
HXXFSFRBOHSIMQ-VFUOTHLCSA-N
{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
260.1358
260.029718526
-0.91
6
α-D-glucose 1-phosphate
0
-2
PW_C041033
aD-g1P
5977
147
1041
Phosphoglucomutase-1
P36871
This enzyme participates in both the breakdown and synthesis of glucose.
HMDBP01107
PGM1
1p31
BC090856
1
5.4.2.2
1121
8
1771
2
2302
14
3127
29
6208
108
135640
609
6246
UTP--glucose-1-phosphate uridylyltransferase_
P0AEP3
Involved in UTP:glucose-1-phosphate uridylyltransferase activity. May play a role in stationary phase survival.
galU
b1236
AP009048
3
2.7.7.9
6011
Galactokinase
P0A6T3
Involved in galactokinase activity. ATP + D-galactose = ADP + alpha-D-galactose 1- phosphate.
galK
b0757
AP009048
3
2.7.1.6
8710
101
6112
Aldose 1-epimerase
P0A9C3
Involved in aldose 1-epimerase activity. Mutarotase converts alpha-aldose to the beta-anomer. It is active on D-glucose, L-arabinose, D-xylose, D-galactose, maltose and lactose.
galM
b0756
AP009048
3
5.1.3.3
8711
101
5831
Beta-galactosidase
P00722
Involved in beta-galactosidase activity. Hydrolysis of terminal non-reducing beta-D- galactose residues in beta-D-galactosides.
lacZ
b0344
AP009048
3
3.2.1.23
136932
117
136933
101
7007
Lactose permease
P02920
Involved in transport. Responsible for transport of beta-galactosides into the cell, with the concomitant import of a proton (symport system).
lacY
b0343
AP009048
3
8606
109
136935
117
5964
Galactose-1-phosphate uridylyltransferase
P09148
Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity. UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose.
galT
b0758
AP009048
3
2.7.7.12
6016
Glucokinase
P0A6V8
Involved in glucokinase activity. Not highly important in E.coli as glucose is transported into the cell by the PTS system already as glucose 6-phosphate.
glk
b2388
AP009048
3
2.7.1.2
8712
101
135638
609
6873
Galactose-proton symporter
P0AEP1
Involved in transmembrane transporter activity. Uptake of galactose across the boundary membrane with the concomitant transport of protons into the cell (symport system).
galP
b2943
AP009048
3
8610
109
6887
Melibiose carrier protein
P02921
Involved in transporter activity. Responsible for melibiose transport. It is capable of using hydrogen, sodium, and lithium cations as coupling cations for cotransport, depending on the particular sugar transported (symport system).
melB
b4120
AP009048
3
8622
109
5900
Alpha-galactosidase
P06720
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds. Hydrolysis of terminal, non-reducing alpha-D- galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids.
melA
b4119
AP009048
3
3.2.1.22
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
6694
PTS system glucose-specific EIICB component
P69786
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity. The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration.
ptsG
b1101
AP009048
3
2.7.1.69
6203
109
135648
613
6693
Glucose-specific phosphotransferase enzyme IIA component
P69783
Involved in sugar:hydrogen symporter activity. The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport.
crr
b2417
AP009048
3
2.7.1.-
6152
109
8932
101
135649
613
6769
Putative beta-phosphoglucomutase
P77366
Involved in beta-phosphoglucomutase activity. Reversible transformation of glucose 6-phosphate and beta-glucose 1-phosphate.
ycjU
b1317
AP009048
3
5.4.2.6
8713
101
135639
609
5963
UDP-glucose 4-epimerase
P09147
Involved in catalytic activity. UDP-glucose = UDP-galactose.
galE
b0759
AP009048
3
5.1.3.2
135819
117
135834
101
6010
Glucose-6-phosphate isomerase
P0A6T1
Involved in glucose-6-phosphate isomerase activity. D-glucose 6-phosphate = D-fructose 6- phosphate.
pgi
b4025
AP009048
3
5.3.1.9
6212
108
8592
101
135637
609
135826
117
7538
putative aldose 1-epimerase
P39173
yeaD
b1780
3
5.1.3.15
135827
117
1551
phosphoglucomutase
3
PW_P001551
1830
1041
1552
UTP--glucose-1-phosphate uridylyltransferase
3
PW_P001552
1831
6246
1555
galactokinase
3
PW_P001555
1834
6011
1556
galactose-1-epimerase
3
PW_P001556
1835
6112
1557
β-galactosidase
3
PW_P001557
1836
5831
4
1558
lactose / melibiose:H+ symporter LacY
3
PW_P001558
1837
7007
1553
galactose-1-phosphate uridylyltransferase
3
PW_P001553
1832
5964
2
3535
glucokinase
3
PW_P003535
10372
6016
3536
galactose H+ symporter
3
PW_P003536
10373
6873
3537
melibiose: H+/Li+/Na+
3
PW_P003537
10374
6887
3538
alpha-galactosidase
3
PW_P003538
10375
5900
2
1549
HPr - phosphorylated
3
PW_P001549
1828
7464
1550
HPr
3
PW_P001550
1829
7464
3575
glucose PTS permease
3
PW_P003575
10413
6694
2
10414
6693
3580
β-phosphoglucomutase
3
PW_P003580
10419
6769
1554
UDP-glucose 4-epimerase
3
PW_P001554
1833
5963
2
12871
glucose-6-phosphate isomerase
3
PW_P012871
22631
6010
135824
117
12872
putative aldose 1-epimerase
3
PW_P012872
22632
7538
1
135825
117
2952
false
PW_R002952
Right
11721
93
1
Compound
false
11722
414
1
Compound
false
11723
1034
1
Compound
false
11724
40034
1
Compound
false
11725
504
1
Compound
false
2919
1555
2.7.1.6
2956
false
PW_R002956
Right
11734
119
1
Compound
false
11735
1420
1
Compound
false
11736
1894
1
Compound
false
11737
395
1
Compound
false
2923
1557
3.2.1.23
3352
false
PW_R003352
Right
13373
1906
1
Compound
false
13374
42898
1
Compound
false
3321
3580
5.4.2.6
3556
false
PW_R003556
Right
14285
1083
1
Compound
false
14286
41033
1
Compound
false
3546
1551
2954
false
PW_R002954
Right
11728
1894
1
Compound
false
11729
93
1
Compound
false
2921
1556
3298
false
PW_R003298
Right
13161
33
1
Compound
false
13162
1420
1
Compound
false
13163
93
1
Compound
false
13164
395
1
Compound
false
3260
3538
3.2.1.22
3297
false
PW_R003297
Right
13156
395
1
Compound
false
13157
414
1
Compound
false
13158
41026
1
Compound
false
13159
1034
1
Compound
false
13160
1906
1
Compound
false
3259
3535
2.7.1.2
2951
false
PW_R002951
Both
11719
193
1
Compound
false
11720
206
1
Compound
false
2918
1554
5.1.3.2
179354
PW_R179354
Right
676718
504
1
Compound
false
676719
193
1
Compound
false
676720
206
1
Compound
false
676721
41033
1
Compound
false
169256
1553
3566
false
PW_R003566
Right
14332
41033
1
Compound
false
14333
192
1
Compound
false
14334
40034
1
Compound
false
14335
170
1
Compound
false
14336
193
1
Compound
false
3555
1552
179357
PW_R179357
Right
676730
1906
1
Compound
false
676731
1083
1
Compound
false
169259
12871
169260
12872
5.1.3.15
133
PW_RCT000133
Right
792
133
1851
Compound
1
105
793
133
1549
ProteinComplex
1
108
795
133
1550
ProteinComplex
1
108
133
138
PW_RCT000138
Right
814
138
395
Compound
1
107
815
138
1549
ProteinComplex
1
108
816
138
1906
Compound
1
108
817
138
1550
ProteinComplex
1
108
138
361
PW_T000361
Active
420
119
1
Compound
107
108
Right
421
40034
1
Compound
107
108
Right
307
1558
2015-03-24T18:27:30-06:00
2015-03-24T18:27:30-06:00
109
399
PW_T000399
480
1894
1
Compound
107
108
Right
481
40034
1
Compound
107
108
Right
343
3536
2015-05-01T11:24:30-06:00
2015-05-01T11:24:30-06:00
109
403
PW_T000403
488
33
1
Compound
107
108
Right
489
2607
1
Compound
107
108
Right
347
3537
2015-05-01T15:10:31-06:00
2015-05-01T15:10:31-06:00
109
402
PW_T000402
486
33
1
Compound
107
108
Right
487
458
1
Compound
107
108
Right
346
3537
2015-05-01T13:57:42-06:00
2015-05-01T13:57:42-06:00
109
401
PW_T000401
484
33
1
Compound
107
108
Right
485
40034
1
Compound
107
108
Right
345
3537
2015-05-01T13:53:05-06:00
2015-05-01T13:53:05-06:00
109
15795
192
117
3
false
2359
2166
10
regular
100
110
15796
40034
55
false
2385
1961
10
regular
78
78
15797
170
45
false
2621
1950
10
regular
63
43
15799
504
3
false
1899
1496
10
regular
100
110
15802
193
117
3
false
2514
1671
10
regular
100
120
15804
192
3
false
2863
1791
10
regular
100
110
15805
40034
55
false
2868
1607
10
regular
78
78
15806
170
45
false
2631
1794
10
regular
63
43
15807
93
3
false
1354
1499
10
regular
100
100
15808
414
42
false
1484
1609
10
regular
50
30
15809
1034
43
false
1769
1613
10
regular
50
30
15810
40034
55
false
1755
1383
10
regular
78
78
15811
1894
3
false
1354
1059
10
regular
100
100
15812
119
3
false
1354
659
10
regular
100
100
15813
1420
49
false
1264
785
10
regular
78
78
15814
395
3
false
1479
954
10
regular
100
100
15815
119
108
3
false
1354
249
10
regular
100
100
15816
40034
107
55
false
1246
550
10
regular
78
78
15817
40034
108
55
false
1236
330
10
regular
78
78
18649
206
3
false
2114
1676
10
regular
100
110
18652
414
42
false
1231
1778
10
regular
50
30
18653
41026
3
false
989
1933
10
regular
100
100
18654
1034
43
false
1239
1958
10
regular
50
30
18655
1906
117
3
false
1124
2038
10
regular
100
110
18703
1894
107
3
false
201
1061
10
regular
100
100
18707
40034
107
55
false
318
977
10
regular
78
78
18708
40034
108
55
false
607
982
10
regular
78
78
18709
33
107
3
false
201
1316
10
regular
100
100
18710
33
108
3
false
866
1501
10
regular
100
100
18711
40034
107
55
false
317
1226
10
regular
78
78
18712
40034
108
55
false
612
1226
10
regular
78
78
18713
33
107
3
false
201
1502
10
regular
100
100
18714
458
107
58
false
312
1427
10
regular
78
78
18715
458
108
58
false
607
1428
10
regular
78
78
18716
33
107
3
false
201
1681
10
regular
100
100
18717
2607
107
3
false
301
1796
10
regular
100
100
18718
2607
108
3
false
571
1796
10
regular
100
100
18728
1420
49
false
977
1378
10
regular
78
78
18730
395
3
false
1126
1656
10
regular
100
100
22172
1851
105
3
false
3749
1682
10
regular
100
100
22173
1083
108
3
false
3344
1677
10
regular
100
110
22174
395
107
3
false
1957
252
10
regular
100
100
22175
1906
108
3
false
1962
677
10
regular
100
110
22177
42898
3
false
1962
1062
10
regular
100
110
22183
41033
3
false
2969
1677
10
regular
100
110
2678381
41033
117
3
false
1899
2036
10
regular
100
110
2678388
1083
117
3
false
1524
2036
10
regular
100
110
7900
1041
8
2
false
1689
2056
8
subunit
regular
150
70
7901
6246
2
false
2489
2058
8
subunit
regular
150
70
7904
6246
2
false
2713
1698
8
subunit
regular
150
70
7905
6011
101
2
false
1574
1517
8
subunit
regular
150
70
7906
6112
101
2
false
1329
1286
8
subunit
regular
150
70
7907
5831
8
false
1334
866
8
subunit
regular
140
85
7908
7007
109
76
false
1329
449
8
subunit
regular
150
70
9009
5964
6
false
1869
1693
8
subunit
regular
160
80
9010
6016
101
2
false
1099
1838
8
subunit
regular
150
70
9025
6873
109
76
false
401
1076
8
subunit
regular
150
70
9026
6887
109
76
false
401
1330
8
subunit
regular
150
70
9027
6887
109
76
false
401
1516
8
subunit
regular
150
70
9028
6887
109
76
false
401
1696
8
subunit
regular
150
70
9032
5900
6
false
1096
1511
8
subunit
regular
160
80
10644
7464
108
2
false
3374
1492
8
subunit
regular
150
70
10645
7464
108
2
false
3379
1872
8
subunit
regular
150
70
10646
6694
109
77
false
3496
1632
8
subunit
regular
160
80
10647
6693
109
76
false
3501
1697
8
subunit
regular
150
70
10648
7464
108
2
false
1647
527
8
subunit
regular
150
70
10649
7464
108
2
false
2107
527
8
subunit
regular
150
70
10650
6694
109
77
false
1799
437
8
subunit
regular
160
80
10651
6693
109
76
false
1934
447
8
subunit
regular
150
70
10653
6769
101
2
false
1937
862
8
subunit
regular
150
70
10656
1041
8
2
false
3129
1697
8
subunit
regular
150
70
947990
5963
117
6
false
2286
1691
8
subunit
regular
160
80
947994
6010
117
2
false
1321
2008
8
subunit
regular
150
70
947995
7538
117
2
false
1291
2058
8
subunit
regular
150
70
6348
1551
569
7801
7900
6349
1552
569
7802
7901
6352
1552
569
7805
7904
6353
1555
569
7806
7905
6354
1556
569
7807
7906
6355
1557
569
7808
7907
6356
1558
569
7809
7908
7200
1553
569
8880
9009
7201
3535
569
8881
9010
7216
3536
569
8896
9025
7217
3537
569
8897
9026
7218
3537
569
8898
9027
7219
3537
569
8899
9028
7223
3538
569
8903
9032
8331
1549
569
108
10466
10644
8332
1550
569
108
10467
10645
8333
3575
569
109
10468
10646
10469
10647
8334
1549
569
108
10470
10648
8335
1550
569
108
10471
10649
8336
3575
569
109
10472
10650
10473
10651
8338
3580
569
10475
10653
8341
1551
569
10478
10656
802865
1554
569
117
943870
947990
802869
12871
569
117
943874
947994
802870
12872
569
117
943875
947995
24066
M1454 1549 C1484 1549 1544 1552 1574 1552
5
false
18
24067
M1509 1609 C1516 1546 1551 1564 1574 1552
5
false
18
24068
M1794 1613 C1797 1575 1754 1552 1724 1552
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24069
M1794 1461 C1794 1519 1754 1552 1724 1552
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24070
M1899 1551 C1869 1551 1754 1552 1724 1552
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24073
M1404 759 C1404 789 1404 836 1404 866
5
false
18
24074
M1342 824 C1371 822 1404 836 1404 866
5
false
18
24075
M1404 1059 C1404 1029 1404 981 1404 951
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24076
M1479 1004 C1431 1012 1404 981 1404 951
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
24077
M1404 659 C1404 629 1404 549 1404 519
83
false
18
true
M 1027.5 375.0096189432334 L 1035 388 L 1042.5 375.0096189432334
false
24078
M1404 349 C1404 379 1404 419 1404 449
83
false
18
false
false
24079
M1324 589 C1390 592 1404 549 1404 519
83
false
18
true
M 888.5 416.0096189432334 L 896 429 L 903.5 416.0096189432334
false
24080
M1314 369 C1370 371 1397 411 1404 449
83
false
18
false
false
32909
M3749 1732 C3723 1732 3667 1731 3651 1732
5
false
18
32910
M3444 1732 C3484 1732 3472 1733 3501 1732
5
false
18
true
M 1729.83578946806 529.3726814770471 L 1714.8889344238953 528.1111251807511 L 1721.2698221450812 541.6862595038294
false
32911
M3524 1527 C3551 1530 3568 1577 3576 1632
5
false
18
32912
M3529 1907 C3585 1903 3573 1809 3576 1767
5
false
18
true
M 1729.83578946806 529.3726814770471 L 1714.8889344238953 528.1111251807511 L 1721.2698221450812 541.6862595038294
false
32913
M2007 352 C2007 368 2008 423 2009 447
5
false
18
32914
M2012 677 C2012 647 2009 547 2009 517
5
false
18
true
M 1697.6135663922405 84.92822525884537 L 1682.6667113480758 83.66666896254934 L 1689.0475990692617 97.24180328562768
false
32915
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3657664
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false
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