2171
Pathway
Leloir Pathway
The pathway starts with the isomerization of Beta-D-galactose into Alpha-D-galactose through a galactose mutarotase. Alpha-D-galactose is then phosphorylated through an ATP dependent galactokinase resulting in the release of ADP, a hydrogen ion and alpha-D-galactose 1-phosphate. The latter compound reacts with UDP glucose which is the result of UTP reacting with alpha-D-glucose through a uridinephosphoglucose pyrophosphorylase. The reaction between alpha-D-galactose 1-phosphate and UDP glucose results in the release of glucose 1-phosphate and UDP-alpha-D-galactose.
Glucose 1-phosphate can be further isomerized into glucose 6-phosphate, while UDP-alpha-D-galactose can be reverted into UDP glucose through a UDP-epimerase.
Metabolic
PW002397
Center
PathwayVisualizationContext2683
1250
2499
#000099
PathwayVisualization2154
2171
Leloir Pathway
The pathway starts with the isomerization of Beta-D-galactose into Alpha-D-galactose through a galactose mutarotase. Alpha-D-galactose is then phosphorylated through an ATP dependent galactokinase resulting in the release of ADP, a hydrogen ion and alpha-D-galactose 1-phosphate. The latter compound reacts with UDP glucose which is the result of UTP reacting with alpha-D-glucose through a uridinephosphoglucose pyrophosphorylase. The reaction between alpha-D-galactose 1-phosphate and UDP glucose results in the release of glucose 1-phosphate and UDP-alpha-D-galactose.
Glucose 1-phosphate can be further isomerized into glucose 6-phosphate, while UDP-alpha-D-galactose can be reverted into UDP glucose through a UDP-epimerase.
Metabolic
18
111282
Endocytosis
SubPathway
5008
14764091
Majumdar S, Ghatak J, Mukherji S, Bhattacharjee H, Bhaduri A: UDPgalactose 4-epimerase from Saccharomyces cerevisiae. A bifunctional enzyme with aldose 1-epimerase activity. Eur J Biochem. 2004 Feb;271(4):753-9.
2171
Pathway
5009
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.
2171
Pathway
1
Cell
CL:0000000
7
Epithelial Cell
CL:0000066
2
Platelet
CL:0000233
5
Hepatocyte
CL:0000182
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
3
Escherichia coli
562
Prokaryote
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
23
Pseudomonas aeruginosa
287
Prokaryote
1
Homo sapiens
9606
Eukaryote
Human
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
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
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
7
Chlamydomonas reinhardtii
3055
Eukaryote
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
31
Periplasmic Space
GO:0005620
1
Cytosol
GO:0005829
11
Extracellular Space
GO:0005615
5
Cytoplasm
GO:0005737
6
Lysosome
GO:0005764
3
Mitochondrial Matrix
GO:0005759
14
Mitochondrial Outer Membrane
GO:0005741
2
Mitochondrion
GO:0005739
15
Nucleus
GO:0005634
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
7
Endoplasmic Reticulum Membrane
GO:0005789
10
Cell Membrane
GO:0005886
27
Peroxisome Membrane
GO:0005778
35
Chloroplast
GO:0009507
12
Mitochondrial Inner Membrane
GO:0005743
32
Inner Membrane
GO:0070258
19
sarcoplasmic reticulum
GO:0016529
24
Mitochondrial Intermembrane Space
GO:0005758
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
25
Golgi apparatus
GO:0005794
25
Intestine
BTO:0000648
1
Liver
BTO:0000759
72
9
8
Blood Vessel
BTO:0001102
74
11
2
Endothelium
BTO:0000393
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
28
Stomach
BTO:0001307
155
26
107
31
3
PW_BS000107
108
1
3
PW_BS000108
105
11
3
PW_BS000105
151
1
4
1
PW_BS000151
318
31
23
PW_BS000024
315
1
23
PW_BS000024
8
5
1
1
PW_BS000008
9
6
1
1
PW_BS000009
60
25
1
PW_BS000060
61
25
1
7
PW_BS000061
29
1
1
1
PW_BS000029
51
8
1
PW_BS000051
215
6
18
1
PW_BS000024
113
6
12
1
PW_BS000113
336
1
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
326
8
12
PW_BS000028
111
5
12
1
PW_BS000111
122
5
5
1
PW_BS000122
126
6
5
1
PW_BS000126
429
1
5
1
PW_BS000115
436
25
5
PW_BS000115
437
25
5
7
PW_BS000115
416
8
5
PW_BS000115
135
5
17
1
PW_BS000135
443
6
17
1
PW_BS000115
464
1
17
1
PW_BS000115
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
452
8
17
PW_BS000115
297
5
10
1
PW_BS000024
301
6
10
1
PW_BS000024
205
5
6
1
PW_BS000024
207
6
6
1
PW_BS000024
2
1
1
1
PW_BS000002
4
3
1
1
PW_BS000004
16
2
1
2
PW_BS000016
22
14
1
1
PW_BS000022
13
1
2
1
PW_BS000013
32
1
15
1
5
PW_BS000032
5
4
1
1
PW_BS000005
39
7
1
1
3
PW_BS000039
3
2
1
1
PW_BS000003
18
13
1
1
PW_BS000018
10
1
7
1
1
PW_BS000010
49
7
1
1
PW_BS000049
14
10
1
PW_BS000014
58
1
14
1
1
PW_BS000058
59
27
1
1
PW_BS000059
27
15
1
PW_BS000027
46
1
1
4
PW_BS000046
66
18
5
1
8
PW_BS000066
72
5
1
3
PW_BS000072
23
15
1
1
PW_BS000023
31
1
5
1
1
PW_BS000031
91
8
5
1
1
PW_BS000091
54
1
3
1
5
PW_BS000054
89
2
PW_BS000089
26
1
1
1
5
PW_BS000026
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
100
5
2
1
PW_BS000100
104
14
3
1
PW_BS000104
101
5
3
1
PW_BS000101
112
2
12
1
PW_BS000112
103
3
3
1
PW_BS000103
117
1
3
1
PW_BS000117
118
1
17
1
PW_BS000118
120
3
17
1
PW_BS000120
129
1
5
12
1
PW_BS000129
132
1
12
1
PW_BS000132
133
3
12
1
PW_BS000133
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
147
1
24
1
PW_BS000147
155
3
24
1
PW_BS000155
161
3
18
1
PW_BS000161
166
1
1
PW_BS000166
178
3
21
1
PW_BS000178
188
1
18
PW_BS000024
160
1
18
1
PW_BS000160
199
14
18
1
PW_BS000024
206
2
6
1
PW_BS000024
210
13
18
1
PW_BS000024
213
7
18
1
PW_BS000024
211
10
18
PW_BS000024
198
5
18
1
PW_BS000024
216
4
18
1
PW_BS000024
217
15
18
PW_BS000024
218
15
18
1
PW_BS000024
163
2
18
1
PW_BS000163
222
3
4
1
PW_BS000024
190
11
18
PW_BS000024
225
35
4
1
PW_BS000024
277
1
2
18
PW_BS000024
170
18
PW_BS000170
281
1
25
1
PW_BS000024
164
4
PW_BS000164
285
10
4
1
PW_BS000024
226
4
4
1
PW_BS000024
290
5
49
1
PW_BS000024
223
12
4
1
PW_BS000024
308
10
1
1
PW_BS000024
322
1
23
1
PW_BS000024
253
5
4
1
PW_BS000024
134
12
12
1
PW_BS000134
329
14
12
1
PW_BS000028
333
1
2
12
PW_BS000028
332
1
7
12
1
PW_BS000028
350
1
14
12
1
PW_BS000028
128
15
12
1
PW_BS000128
351
15
12
PW_BS000028
335
27
12
1
PW_BS000028
115
10
12
PW_BS000115
130
13
12
1
PW_BS000130
331
7
12
1
PW_BS000028
334
4
12
1
PW_BS000028
368
3
60
1
PW_BS000028
184
1
2
1
PW_BS000024
119
2
17
1
PW_BS000119
1
1
PW_BS000001
124
1
5
1
PW_BS000124
94
3
PW_BS000094
388
1
6
1
PW_BS000112
109
32
3
PW_BS000109
406
3
5
1
PW_BS000115
407
2
5
1
PW_BS000115
382
14
5
1
PW_BS000100
412
1
2
5
PW_BS000115
123
1
7
5
1
PW_BS000123
433
1
14
5
1
PW_BS000115
408
4
5
1
PW_BS000115
410
15
5
1
PW_BS000115
125
13
5
1
PW_BS000125
383
7
5
1
PW_BS000100
405
10
5
PW_BS000115
422
27
5
1
PW_BS000115
435
15
5
PW_BS000115
399
14
17
1
PW_BS000113
446
1
2
17
PW_BS000115
447
1
7
17
1
PW_BS000115
468
1
14
17
1
PW_BS000115
374
4
17
1
PW_BS000053
444
15
17
1
PW_BS000115
136
13
17
1
PW_BS000136
398
7
17
1
PW_BS000113
376
10
17
PW_BS000053
375
27
17
1
PW_BS000053
470
15
17
PW_BS000115
479
3
10
1
PW_BS000115
299
1
10
1
PW_BS000024
481
2
10
1
PW_BS000115
484
14
10
1
PW_BS000115
485
15
10
1
PW_BS000115
300
13
10
1
PW_BS000024
495
7
10
1
PW_BS000115
478
10
10
PW_BS000115
491
27
10
1
PW_BS000115
499
15
10
PW_BS000115
501
3
6
1
PW_BS000115
389
14
6
1
PW_BS000112
516
15
6
1
PW_BS000115
395
13
6
1
PW_BS000113
390
7
6
1
PW_BS000112
209
10
6
PW_BS000024
508
27
6
1
PW_BS000115
517
15
6
PW_BS000115
15
11
1
PW_BS000015
47
19
1
4
PW_BS000047
313
23
PW_BS000024
17
12
1
1
PW_BS000017
42
24
1
1
PW_BS000042
70
28
5
1
1
PW_BS000070
157
2
24
1
PW_BS000157
159
24
PW_BS000159
152
8
4
PW_BS000152
187
31
18
PW_BS000024
219
31
4
PW_BS000024
220
1
4
PW_BS000024
212
1
7
18
1
PW_BS000024
162
12
18
1
PW_BS000162
224
2
4
1
PW_BS000024
195
13
18
PW_BS000024
249
13
4
1
PW_BS000024
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
227
34
4
1
PW_BS000024
294
11
4
1
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
293
4
1
PW_BS000024
114
11
12
PW_BS000114
327
1
1
12
5
PW_BS000028
347
1
3
12
5
PW_BS000028
345
24
12
1
PW_BS000028
310
31
2
PW_BS000024
304
1
2
PW_BS000024
409
11
5
PW_BS000115
424
1
1
5
5
PW_BS000115
425
1
3
5
5
PW_BS000115
418
24
5
1
PW_BS000115
384
12
5
1
PW_BS000100
137
11
17
PW_BS000137
459
1
1
17
5
PW_BS000115
460
1
3
17
5
PW_BS000115
454
24
17
1
PW_BS000115
121
12
17
1
PW_BS000121
483
11
10
PW_BS000115
489
24
10
1
PW_BS000115
480
12
10
1
PW_BS000115
208
11
6
PW_BS000024
506
24
6
1
PW_BS000115
391
12
6
1
PW_BS000112
6
1
3
1
PW_BS000006
43
25
1
1
PW_BS000043
356
25
12
1
PW_BS000028
419
25
5
1
PW_BS000115
455
25
17
1
PW_BS000115
490
25
10
1
PW_BS000115
507
25
6
1
PW_BS000115
214
25
18
1
PW_BS000024
158
34
24
1
PW_BS000158
189
32
18
PW_BS000024
254
5
18
PW_BS000024
644
1
7
1
PW_BS000508
646
2
7
1
PW_BS000508
693
7
4
1
PW_BS000512
708
1
29
1
PW_BS000512
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
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
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
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
1207
Glucose 1-phosphate
HMDB0001586
The direct product of the reaction in which glycogen phosphorylase cleaves off a molecule of glucose from a greater glycogen structure. It cannot travel down many metabolic pathways and must be interconverted by the enzyme phosphoglucomutase in order to become glucose 6-phosphate. Free glucose 1-phosphate can also react with UTP to form UDP-glucose. It can then return to the greater glycogen structure via glycogen synthase.
59-56-3
C00103
439165
16077
GLC-1-P
388311
OC[C@H]1OC(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-GASJEMHNSA-N
{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
260.1358
260.029718526
-0.91
6
glucose 1-phosphate
0
-2
FDB021830
Cori ester;D-glucopyranose 1-phosphate;D-glucose 1-phosphate;D-glucose-1-p;D-glucose-1-phosphate;Glucose 1-phosphate;Glucose monophosphate;Glucose-1-phosphate;Glucose-1p;A-d-glucopyranosyl phosphate;A-d-glucose 1-phosphate;Alpha-d-glucopyranosyl phosphate;Alpha-d-glucose 1-phosphate;Alpha-d-glucose-1-phosphate;Alpha-delta-glucopyranosyl phosphate;Alpha-delta-glucose 1-phosphate;Alpha-delta-glucose-1-phosphate;Delta-glucopyranose 1-phosphate;Delta-glucose 1-phosphate;Delta-glucose-1-p;Delta-glucose-1-phosphate;1-o-phosphono-d-glucopyranose;Glc-1-p;D-glucopyranose 1-phosphoric acid;D-glucose 1-phosphoric acid
PW_C001207
Gluc1P
1120
8
1505
2
3117
29
5690
6
5909
147
5939
151
6887
160
12576
225
77101
132
77926
336
78401
111
120826
122
121186
124
121254
429
123411
135
123757
118
123824
464
125817
297
125953
299
127269
205
127412
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
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
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
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
40980
UDP
Also known uridine 5'-diphosphate or uridine diphosphoric acid, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. Uridine 5'-diphosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Uridine 5'-diphosphate has been found in human prostate, endocrine gland and placenta tissues, and has also been primarily detected in blood. Uridine 5'-diphosphate can be found anywhere throughout the human cell, such as in endoplasmic reticulum, nucleus, mitochondria, and lysosome. Uridine 5'-diphosphate exists in all living organisms, ranging from bacteria to humans. Uridine 5'-diphosphate participates in a number of enzymatic reactions. In particular, Uridine 5'-diphosphate can be biosynthesized from uridine 5'-monophosphate; which is catalyzed by the enzyme UMP kinase. Furthermore, Uridine 5'-diphosphate can be converted into uridine triphosphate through the action of the enzyme nucleoside diphosphate kinase. Finally, Uridine 5'-diphosphate and trehalose 6-phosphate can be biosynthesized from uridine diphosphate glucose and alpha-D-glucose 6-phosphate through the action of the enzyme trehalose-6-phosphate synthase. In humans, uridine 5'-diphosphate is involved in the morphine metabolism pathway, the androstenedione metabolism pathway, the mycophenolic Acid metabolism pathway, and the tramadol metabolism pathway. Uridine 5'-diphosphate is also involved in several metabolic disorders, some of which include 17-Beta hydroxysteroid dehydrogenase III deficiency, the mucopolysaccharidosis vi. sly syndrome pathway, glycogen synthetase deficiency, and UMP synthase deficiency (orotic aciduria). Outside of the human body, uridine 5'-diphosphate can be found in a number of food items such as hickory nut, cocoa bean, sunburst squash (pattypan squash), and sorghum. This makes uridine 5'-diphosphate a potential biomarker for the consumption of these food products.
58223
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
C9H14N2O12P2
InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
XCCTYIAWTASOJW-XVFCMESISA-N
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
404.1612
404.002196946
-1.66
6
UDP
0
-2
Uridine-diphosphate, uridine-5'-diphosphate
PW_C040980
UDP
5984
147
9969
Unknown
Unknown
18
1.3.1.71
6083
161
6121
162
6845
189
6885
160
7036
163
7063
188
7210
210
7213
211
7217
212
7223
213
7237
214
7241
215
7283
190
7301
198
7305
216
7392
217
7412
218
9275
254
11854
277
136087
644
136098
646
136985
253
136986
226
136987
693
136988
249
137079
708
10594
Protein GAL3
P13045
The GAL3 regulatory function is required for rapid induction of the galactose system. At normal induction, galactose in the presence of the GAL3 protein may lead to the induction of the GAL genes, including GAL1. Then the galactokinase protein (GAL1) in the presence of galactose may reinforce the induction leading to a higher expression level. Upon depletion of galactose, the inducing activity of the galactokinase protein may decrease, after which transcription of the GAL genes, including GAL1, may decrease.
GAL3
29
7844
160
10595
Phosphoglucomutase 2
P37012
Major phosphoglucomutase isozyme that catalyzes the reversible interconversion of glucose 1-phosphate and glucose 6-phosphate (PubMed:5784209). Constitutes about 80-90% of the phosphoglucomutase activity in the cell (PubMed:14264884, PubMed:5231755). Key enzyme in hexose metabolism. The forward reaction is an essential step in the energy metabolism of galactose since the product of the galactose pathway enzymes in yeast is glucose 1-phosphate. The reverse reaction is an essential step for biosynthesis when carbon sources other than galactose are the energy source because glucose 1-phosphate is the starting point for the synthesis of UDP-glucose, which acts as a precursor for the synthesis of oligosaccharides and trehalose (PubMed:14264884).
PGM2
29
5.4.2.2
7847
160
10596
Phosphoglucomutase 1
P33401
Minor phosphoglucomutase isozyme that catalyzes the interconversion of glucose 1-phosphate and glucose 6-phosphate (PubMed:5784209). Constitutes about 10-20% of the phosphoglucomutase activity in the cell (PubMed:14264884, PubMed:5231755). Key enzyme in hexose metabolism. The forward reaction is an essential step in the energy metabolism of galactose since the product of the galactose pathway enzymes in yeast is glucose 1-phosphate. The reverse reaction is an essential step for biosynthesis when carbon sources other than galactose are the energy source because glucose 1-phosphate is the starting point for the synthesis of UDP-glucose, which acts as a precursor for the synthesis of oligosaccharides and trehalose (PubMed:14264884).
PGM1
29
5.4.2.2
7846
160
10597
Probable UTP--glucose-1-phosphate uridylyltransferase
P38709
Plays a central role as a glucosyl donor in cellular metabolic pathways.
YHL012W
29
2.7.7.9
7845
160
10582
Bifunctional protein GAL10
P04397
Mutarotase converts alpha-aldose to the beta-anomer. It is active on D-glucose, L-arabinose, D-xylose, D-galactose, maltose and lactose (By similarity).
GAL10
29
5.1.3.2; 5.1.3.3
10589
galactokinase
P04385
GAL1
29
2.7.1.6
10583
Galactose-1-phosphate uridylyltransferase
P08431
GAL7
29
2.7.7.12
10590
phosphoglucomutase 1
P33401
Minor phosphoglucomutase isozyme that catalyzes the interconversion of glucose 1-phosphate and glucose 6-phosphate (PubMed:5784209). Constitutes about 10-20% of the phosphoglucomutase activity in the cell (PubMed:14264884, PubMed:5231755). Key enzyme in hexose metabolism. The forward reaction is an essential step in the energy metabolism of galactose since the product of the galactose pathway enzymes in yeast is glucose 1-phosphate. The reverse reaction is an essential step for biosynthesis when carbon sources other than galactose are the energy source because glucose 1-phosphate is the starting point for the synthesis of UDP-glucose, which acts as a precursor for the synthesis of oligosaccharides and trehalose (PubMed:14264884).
PGM1
29
5.4.2.2
8994
241
10591
phosphoglucomutase 2
P37012
Major phosphoglucomutase isozyme that catalyzes the reversible interconversion of glucose 1-phosphate and glucose 6-phosphate (PubMed:5784209). Constitutes about 80-90% of the phosphoglucomutase activity in the cell (PubMed:14264884, PubMed:5231755). Key enzyme in hexose metabolism. The forward reaction is an essential step in the energy metabolism of galactose since the product of the galactose pathway enzymes in yeast is glucose 1-phosphate. The reverse reaction is an essential step for biosynthesis when carbon sources other than galactose are the energy source because glucose 1-phosphate is the starting point for the synthesis of UDP-glucose, which acts as a precursor for the synthesis of oligosaccharides and trehalose (PubMed:14264884).
PGM2
29
5.4.2.2
8995
241
10592
uridinephosphoglucose pyrophosphorylase
P32861
Plays a central role as a glucosyl donor in cellular metabolic pathways.
UGP1
29
2.7.7.9
4299
galactose mutarotase
18
PW_P004299
11353
10582
4300
galactokinase
18
PW_P004300
11354
10589
4301
Gal7
18
PW_P004301
11355
10583
4302
phosphoglucomutase
18
PW_P004302
11356
10590
11357
10591
4303
uridinephosphoglucose pyrophosphorylase
18
PW_P004303
11358
10592
6358
false
PW_R006358
Right
26039
1894
1
Compound
false
26040
93
1
Compound
false
6284
4299
5.1.3.2,5.1.3.3
6359
false
PW_R006359
Right
26041
414
1
Compound
false
26042
93
1
Compound
false
26043
1034
1
Compound
false
26044
40034
1
Compound
false
26045
504
1
Compound
false
6285
4300
2.7.1.6
6361
false
PW_R006361
Both
26050
206
1
Compound
false
26051
193
1
Compound
false
6287
4299
6362
false
PW_R006362
Right
26052
1207
1
Compound
false
26053
1083
1
Compound
false
6288
4302
5.4.2.2
6363
false
PW_R006363
Right
26054
1207
1
Compound
false
26055
192
1
Compound
false
26056
40034
1
Compound
false
26057
193
1
Compound
false
26058
40980
1
Compound
false
6289
4303
2.7.7.9
6360
false
PW_R006360
Right
26046
504
1
Compound
false
26047
193
1
Compound
false
26048
1207
1
Compound
false
26049
206
1
Compound
false
6286
4301
2.7.7.12
77848
1894
3
false
281
328
10
regular
100
100
77849
93
3
false
721
328
10
regular
100
100
77850
414
42
false
861
423
10
regular
50
30
77851
1034
43
false
1141
301
10
regular
50
30
77852
40034
55
false
1112
436
10
regular
78
78
77853
504
3
false
1211
324
10
regular
100
110
77855
1207
3
false
1696
324
10
regular
100
110
77856
206
3
false
1476
709
10
regular
100
110
77857
193
3
false
1081
704
10
regular
100
120
77858
1083
3
false
2096
324
10
regular
100
110
77859
1207
3
false
486
707
10
regular
100
110
77860
192
3
false
631
612
10
regular
100
110
77861
40034
55
false
647
827
10
regular
78
78
77862
40980
3
false
956
819
10
regular
100
100
37414
9969
160
2
false
461
343
8
subunit
regular
150
70
37415
10594
160
2
false
936
345
8
subunit
regular
150
70
37416
9969
160
2
false
1451
346
8
subunit
regular
150
70
37417
9969
160
2
false
1261
731
8
subunit
regular
150
70
37418
10595
160
2
false
1881
299
8
subunit
regular
150
70
37419
10596
160
2
false
1881
344
8
subunit
regular
150
70
37420
10597
160
2
false
771
729
8
subunit
regular
150
70
30506
4299
2154
36751
37414
30507
4300
2154
36752
37415
30508
4301
2154
36753
37416
30509
4299
2154
36754
37417
30510
4302
2154
36755
37418
36756
37419
30511
4303
2154
36757
37420
112138
M381 378 C407 378 418 378 461 378
5
false
18
112139
M721 378 C661 379 660 378 611 378
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
112140
M886 423 C886 395 906 380 936 380
5
false
18
112141
M821 378 C851 378 906 378 936 378
5
false
18
112142
M1166 331 C1166 376 1116 380 1086 380
5
false
18
true
M 25.946855044164835 253.26155629629605 L 11 252 L 17.380887721185843 265.5751343230783
false
112143
M1151 436 C1150 377 1116 380 1086 380
5
false
18
true
M 25.946855044164835 253.26155629629605 L 11 252 L 17.380887721185843 265.5751343230783
false
112144
M1211 379 C1181 379 1116 380 1086 380
5
false
18
true
M 25.946855044164835 253.26155629629605 L 11 252 L 17.380887721185843 265.5751343230783
false
112149
M1476 764 C1455 764 1436 764 1412 763
5
false
18
true
M 869.9468550441649 570.261556296296 L 855 569 L 861.3808877211858 582.5751343230784
false
112150
M1181 764 C1201 764 1224 764 1259 765
5
false
18
true
M 869.9468550441649 570.261556296296 L 855 569 L 861.3808877211858 582.5751343230784
false
112151
M1796 379 C1815 379 1859 378 1881 379
5
false
18
112152
M2096 379 C2055 379 2051 378 2031 379
5
false
18
true
M 745.9468550441649 811.261556296296 L 731 810 L 737.3808877211858 823.5751343230784
false
112153
M586 762 C639 763 743 763 771 764
5
false
18
112154
M681 722 C681 770 736 765 771 764
5
false
18
112155
M686 827 C687 767 732 764 771 764
5
false
18
112156
M1081 764 C1010 764 968 764 921 764
5
false
18
true
M 1366.9468550441647 149.26155629629605 L 1352 148 L 1358.380887721186 161.57513432307834
false
112157
M1006 819 C1005 772 974 765 921 764
5
false
18
true
M 1366.9468550441647 149.26155629629605 L 1352 148 L 1358.380887721186 161.57513432307834
false
3665629
M1311 379 C1345 379 1402 379 1451 378
5
false
18
3665630
M1131 704 C1299 704 1367 702 1451 702 C1451 620 1451 481 1451 381
5
false
18
3665631
M1696 379 C1679 379 1620 379 1601 379
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3665632
M1526 709 C1526 679 1526 446 1526 416
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3722197
M331 428 C329 514 331 467 330 515
5
false
18
true
M 338.19595247413 441.1612411265071 L 331 428 L 323.20000707617737 440.81249821027563
false
23014
2154
6358
88377
77848
112138
Left
88378
77849
112139
Right
22835
6284
30506
23015
2154
6359
88379
77850
112140
Left
88380
77849
112141
Left
88381
77851
112142
Right
88382
77852
112143
Right
88383
77853
112144
Right
22836
6285
30507
23017
2154
6361
88388
77856
112149
Left
88389
77857
112150
Right
22838
6287
30509
23018
2154
6362
88390
77855
112151
Left
88391
77858
112152
Right
22839
6288
30510
23019
2154
6363
88392
77859
112153
Left
88393
77860
112154
Left
88394
77861
112155
Left
88395
77857
112156
Right
88396
77862
112157
Right
22840
6289
30511
798463
2154
6360
3227083
77853
3665629
Left
3227084
77857
3665630
Left
3227085
77855
3665631
Right
3227086
77856
3665632
Right
754042
6286
30508
110981
111282
2154
217
false
255
515
16
regular
68765
3722197
186735
1639
440
1.0
1.0
0
2
90
484
497
4235
M223 325 C223 275 273 225 323 225 C884 225 1613 225 2174 225 C2224 225 2274 275 2274 325 C2274 507 2274 742 2274 924 C2274 974 2224 1024 2174 1024 C1613 1024 884 1024 323 1024 C273 1024 223 974 223 924 C223 742 223 507 223 325
1
true
6
2051.0
799.0
4236
M125 225 C125 175 175 125 225 125 C846 125 1653 125 2274 125 C2324 125 2374 175 2374 225 C2374 467 2374 783 2374 1025 C2374 1075 2324 1125 2274 1125 C1653 1125 846 1125 225 1125 C175 1125 125 1075 125 1025 C125 783 125 467 125 225
1
true
6
2249.0
1000.0