732
Pathway
Secondary Metabolites: Trehalose Biosynthesis and Metabolism
Threhalose biosynthesis begins with an Alpha-D-glucose-1-phosphate interacting with an ATP through a glucose-1-phosphate adenylyltransferase resulting in the release of a pyrophosphate and an ADP-glucose. The latter compound interacts in a reversible reaction with an amylose through a glycogen synthase resulting in the release of an ADP and an amylose. Amylose then interacts in a reversible reaction with 1,4-α-glucan branching enzyme resulting in a glycogen
Glycogen can also be produced by a reversible reaction with Amylose through a maltodextrin phosphorylase, releasing a phosphate and a glycogen.
Glycogen is then transformed into trehalose through a glycogen debranching enzyme. Alpha Alpha Trehalose can be degraded by reacting with with a water molecule through a cytoplasmic trehalase resulting in the release of a Beta-D-glucose and an Alpha-D-glucose.phosphorylated resulting in a Beta-D-glucose 6-phosphate. This compound is phosphorylated and can then join glycolysis
Alpha Alpha Trehalose can be degraded in the periplasmic space by reacting with with a water molecule through a periplasmic trehalase resulting in the release of a Beta-D-glucose and an Alpha-D-glucose.
The beta-D-glucose can be transported into the cytosol through a PTS permease where it is phosphorylated resulting in a Beta-D-glucose 6-phosphate. This compound can then join glycolysis
Metabolic
PW000968
Center
PathwayVisualizationContext1255
2300
2454
#000099
PathwayVisualization716
732
Secondary Metabolites: Trehalose Biosynthesis and Metabolism
Threhalose biosynthesis begins with an Alpha-D-glucose-1-phosphate interacting with an ATP through a glucose-1-phosphate adenylyltransferase resulting in the release of a pyrophosphate and an ADP-glucose. The latter compound interacts in a reversible reaction with an amylose through a glycogen synthase resulting in the release of an ADP and an amylose. Amylose then interacts in a reversible reaction with 1,4-α-glucan branching enzyme resulting in a glycogen
Glycogen can also be produced by a reversible reaction with Amylose through a maltodextrin phosphorylase, releasing a phosphate and a glycogen.
Glycogen is then transformed into trehalose through a glycogen debranching enzyme. Alpha Alpha Trehalose can be degraded by reacting with with a water molecule through a cytoplasmic trehalase resulting in the release of a Beta-D-glucose and an Alpha-D-glucose.phosphorylated resulting in a Beta-D-glucose 6-phosphate. This compound is phosphorylated and can then join glycolysis
Alpha Alpha Trehalose can be degraded in the periplasmic space by reacting with with a water molecule through a periplasmic trehalase resulting in the release of a Beta-D-glucose and an Alpha-D-glucose.
The beta-D-glucose can be transported into the cytosol through a PTS permease where it is phosphorylated resulting in a Beta-D-glucose 6-phosphate. This compound can then join glycolysis
Metabolic
3
112383
Endocytosis
SubPathway
111973
42934
Compound
2442
11081789
Arguelles JC: Physiological roles of trehalose in bacteria and yeasts: a comparative analysis. Arch Microbiol. 2000 Oct;174(4):217-24.
732
Pathway
2443
12626396
Elbein AD, Pan YT, Pastuszak I, Carroll D: New insights on trehalose: a multifunctional molecule. Glycobiology. 2003 Apr;13(4):17R-27R. doi: 10.1093/glycob/cwg047. Epub 2003 Jan 22.
732
Pathway
2444
3131312
Giaever HM, Styrvold OB, Kaasen I, Strom AR: Biochemical and genetic characterization of osmoregulatory trehalose synthesis in Escherichia coli. J Bacteriol. 1988 Jun;170(6):2841-9.
732
Pathway
2445
1744047
Hengge-Aronis R, Klein W, Lange R, Rimmele M, Boos W: Trehalose synthesis genes are controlled by the putative sigma factor encoded by rpoS and are involved in stationary-phase thermotolerance in Escherichia coli. J Bacteriol. 1991 Dec;173(24):7918-24.
732
Pathway
2446
8837441
Horlacher R, Peist R, Boos W: Improved method for the preparative synthesis of labeled trehalose of high specific activity by Escherichia coli. Appl Environ Microbiol. 1996 Oct;62(10):3861-3.
732
Pathway
2447
12105274
Kandror O, DeLeon A, Goldberg AL: Trehalose synthesis is induced upon exposure of Escherichia coli to cold and is essential for viability at low temperatures. Proc Natl Acad Sci U S A. 2002 Jul 23;99(15):9727-32. doi: 10.1073/pnas.142314099. Epub 2002 Jul 8.
732
Pathway
2448
2883950
Larsen PI, Sydnes LK, Landfald B, Strom AR: Osmoregulation in Escherichia coli by accumulation of organic osmolytes: betaines, glutamic acid, and trehalose. Arch Microbiol. 1987 Feb;147(1):1-7.
732
Pathway
2449
12065209
Richards AB, Krakowka S, Dexter LB, Schmid H, Wolterbeek AP, Waalkens-Berendsen DH, Shigoyuki A, Kurimoto M: Trehalose: a review of properties, history of use and human tolerance, and results of multiple safety studies. Food Chem Toxicol. 2002 Jul;40(7):871-98.
732
Pathway
2450
23302511
Ruhal R, Kataria R, Choudhury B: Trends in bacterial trehalose metabolism and significant nodes of metabolic pathway in the direction of trehalose accumulation. Microb Biotechnol. 2013 Sep;6(5):493-502. doi: 10.1111/1751-7915.12029. Epub 2013 Jan 10.
732
Pathway
2451
1825082
Styrvold OB, Strom AR: Synthesis, accumulation, and excretion of trehalose in osmotically stressed Escherichia coli K-12 strains: influence of amber suppressors and function of the periplasmic trehalase. J Bacteriol. 1991 Feb;173(3):1187-92.
732
Pathway
2452
8391102
Strom AR, Kaasen I: Trehalose metabolism in Escherichia coli: stress protection and stress regulation of gene expression. Mol Microbiol. 1993 Apr;8(2):205-10.
732
Pathway
2453
8892826
Horlacher R, Uhland K, Klein W, Ehrmann M, Boos W: Characterization of a cytoplasmic trehalase of Escherichia coli. J Bacteriol. 1996 Nov;178(21):6250-7.
732
Pathway
1
Cell
CL:0000000
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
5
Hepatocyte
CL:0000182
6
Myocyte
CL:0000187
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
3
Escherichia coli
562
Prokaryote
1
Homo sapiens
9606
Eukaryote
Human
23
Pseudomonas aeruginosa
287
Prokaryote
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
2
Bacteria
2
Prokaryote
Bacteria
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
25
Escherichia coli (strain K12)
83333
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
110
Bacillus velezensis MRC5958
492670
Prokaryote
Velezensis
1
Cytosol
GO:0005829
3
Mitochondrial Matrix
GO:0005759
5
Cytoplasm
GO:0005737
14
Mitochondrial Outer Membrane
GO:0005741
2
Mitochondrion
GO:0005739
4
Peroxisome
GO:0005777
11
Extracellular Space
GO:0005615
10
Cell Membrane
GO:0005886
7
Endoplasmic Reticulum Membrane
GO:0005789
13
Endoplasmic Reticulum
GO:0005783
27
Peroxisome Membrane
GO:0005778
15
Nucleus
GO:0005634
19
sarcoplasmic reticulum
GO:0016529
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
12
Mitochondrial Inner Membrane
GO:0005743
32
Inner Membrane
GO:0070258
34
Plant-Type Vacuole
GO:0000325
24
Mitochondrial Intermembrane Space
GO:0005758
25
Golgi apparatus
GO:0005794
26
Golgi apparatus membrane
GO:0000139
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
40
Periplasm
GO:0042597
1
Liver
BTO:0000759
72
9
25
Intestine
BTO:0000648
8
Blood Vessel
BTO:0001102
74
11
3
Sympathetic Nervous System
BTO:0001832
4
Adrenal Medulla
BTO:0000049
71
8
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
2
Endothelium
BTO:0000393
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
5
cardiocyte
BTO:0001539
28
Stomach
BTO:0001307
155
26
11
Heart
BTO:0000562
73
10
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PW_BS000024
609
5
110
1
PW_BS000503
612
40
110
PW_BS000503
613
32
110
PW_BS000503
2809
ADP-glucose
HMDB0006557
ADP-Glucose, also known as adpg or ADP glucose, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. ADP-Glucose is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, ADP-glucose is primarily located in the cytoplasm. ADP-Glucose exists in all living organisms, ranging from bacteria to humans. ADP-Glucose participates in a number of enzymatic reactions. In particular, ADP-Glucose can be biosynthesized from alpha-D-glucose-1-phosphate through the action of the enzyme glucose-1-phosphate adenylyltransferase. In addition, ADP-Glucose and amylose can be converted into amylose through the action of the enzyme glycogen synthase. Outside of the human body, ADP-glucose can be found in cereals and cereal products. This makes ADP-glucose a potential biomarker for the consumption of this food product. Serves as the glycosyl donor for formation of bacterial glycogen, amylose in green algae, and amylopectin in higher plants.
2140-58-1
C00498
16500
15751
ADP-D-GLUCOSE
15642
DB01774
NC1=C2N=CN([C@@H]3O[C@H](CO[P@](O)(=O)O[P@](O)(=O)O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H]3O)C2=NC=N1
C16H25N5O15P2
InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/t5-,6-,8-,9-,10+,11-,12-,15-,16-/m1/s1
WFPZSXYXPSUOPY-ROYWQJLOSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-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
589.3417
589.082238179
-2.09
9
adp glucose
0
-2
FDB001211
Adp-d-glucose;Adp-glucose;Adenosine 5'-(trihydrogen diphosphate) p'-alpha-delta-glucopyranosyl ester;Adenosine 5'-(trihydrogen diphosphate) glucopyranosyl ester;Adenosine 5'-(trihydrogen pyrophosphate) mono-d-glucosyl ester;Adenosine 5'-(trihydrogen pyrophosphate) mono-delta-glucosyl ester;Adenosine 5'-diphosphoglucose;Adenosine 5'-pyrophosphate a-delta-glucosyl ester;Adenosine 5'-pyrophosphate alpha-d-glucosyl ester;Adenosine 5'-pyrophosphate alpha-delta-glucosyl ester;Adenosine 5'-pyrophosphate glucosyl ester;Adenosine 5'-pyrophosphate mono-d-glucosyl ester;Adenosine 5'-pyrophosphate mono-delta-glucosyl ester;Adenosine diphosphate d-glucose;Adenosine diphosphate glucose;Adenosine diphosphoglucose;Adenosine pyrophosphate-glucose;Adenosine-5'-diphosphate-glucose;Adenosine pyrophosphateglucose;Adpg;Adpglucose;Adenosine diphosphoric acid glucose
PW_C002809
ADP-Glu
6209
108
6238
166
42723
315
1872
Amylose
HMDB0003403
Amylose is defined as a linear molecule of (1→4) linked alpha-D-glucopyranosyl units, but it is today well established that some molecules are slightly branched by (1→6)-alpha-linkages. The oldest criteria for linearity consisted in the susceptibility of the molecule to complete hydrolysis by beta-amylase. This enzyme splits the (1→4) bonds from the non-reducing end of a chain releasing beta-maltosyl units, but cannot cleave the (1→6) bonds. When degraded by pure beta-amylase, linear macromolecules are completely converted into maltose, whereas branched chains give also one beta-limit dextrin consisting of the remaining inner core polysaccharide structure with its outer chains recessed. Starches of different botanical origins possess different granular sizes, morphology, polymorphism and enzyme digestibility. These characteristics are related to the chemical structures of the amylopectin and amylose and how they are arranged in the starch granule. (PMID 9730163).
9005-82-7
C00718
53477771
28102
COC1OC(CO)C(OC2OC(CO)C(OC)C(O)C2O)C(O)C1O
C14H26O11
InChI=1S/C14H26O11/c1-21-11-5(3-15)24-14(10(20)7(11)17)25-12-6(4-16)23-13(22-2)9(19)8(12)18/h5-20H,3-4H2,1-2H3
PTHCMJGKKRQCBF-UHFFFAOYSA-N
370.3496
370.147511674
-0.04
0
FDB001130
(1,4-alpha-d-glucosyl)n;(1,4-alpha-d-glucosyl)n+1;(1,4-alpha-d-glucosyl)n-1;(1,4-alpha-delta-glucosyl)n;(1,4-alpha-delta-glucosyl)n+1;(1,4-alpha-delta-glucosyl)n-1;1,4-alpha-d-glucan;1,4-alpha-delta-glucan;4-{(1,4)-alpha-d-glucosyl}(n-1)-d-glucose;4-{(1,4)-alpha-delta-glucosyl}(n-1)-delta-glucose;Amylose;Amylose chain
PW_C001872
Amylose
2305
2
7274
160
78904
132
122363
124
124917
118
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
605
Glycogen
HMDB0000757
Glycogen is a highly-branched polymer of about 30,000 glucose residues and has a molecular weight between 106 and 107 daltons (4.8 million approx.). Most of Glc units are linked by alpha-1,4 glycosidic bonds, approximately 1 in 12 Glc residues also makes -1,6 glycosidic bond with a second Glc which results in the creation of a branch. Glycogen only has one reducing end and a large number of non-reducing ends with a free hydroxyl group at carbon 4. The glycogen granules contain both glycogen and the enzymes of glycogen synthesis (glycogenesis) and degradation (glycogenolysis). The enzymes are nested between the outer branches of the glycogen molecules and act on the non-reducing ends. Therefore, the many non-reducing end-branches of glycogen facilitate its rapid synthesis and breakdown. In hypoglycemia caused by excessive insulin, liver glycogen levels are high, but the high insulin level prevents the glycogenolysis necessary to maintain normal blood sugar levels. Glucagon is a common treatment for this type of hypoglycemia. Glycogen is a polysaccharide that is the principal storage form of glucose (Glc) in animal and human cells. Glycogen is found in the form of granules in the cytosol in many cell types. Hepatocytes (liver cells) have the highest concentration of it - up to 8% of the fresh weight in well fed state, or 100 to 120 g in an adult - giving liver a distinctive, 'starchy taste'. In the muscles, glycogen is found in a much lower concentration (1% of the muscle mass), but the total amount exceeds that in liver. Small amounts of glycogen are found in the kidneys, and even smaller amounts in certain glial cells in the brain and white blood cells.
9005-79-2
C00182
439177
28087
CPD0-971
388322
OC[C@H]1O[C@H](OC[C@H]2O[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]3CO)[C@H](O)[C@@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
C24H42O21
InChI=1S/C24H42O21/c25-1-5-9(28)11(30)16(35)22(41-5)39-4-8-20(45-23-17(36)12(31)10(29)6(2-26)42-23)14(33)18(37)24(43-8)44-19-7(3-27)40-21(38)15(34)13(19)32/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15-,16-,17-,18-,19-,20-,21+,22+,23-,24-/m1/s1
BYSGBSNPRWKUQH-UJDJLXLFSA-N
(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
666.5777
666.221858406
-0.29
14
(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
0
0
DBMET00509
FDB022227
Animal starch;Glycogen;Liver starch;Lyoglycogen;Phytoglycogen
PW_C000605
Glycogn
2309
2
2324
15
7276
160
7278
190
78905
132
78906
114
122365
124
122367
409
124919
118
124921
137
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
1104
Phosphate
HMDB0001429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
[O-]P([O-])([O-])=O
O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3
NBIIXXVUZAFLBC-UHFFFAOYSA-K
phosphoric acid
94.9714
94.95342
3
phosphoric acid
0
-2
DBMET00532
FDB022617
Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ion
PW_C001104
Pi
24
4
84
8
814
5
818
18
831
2
980
3
1763
14
1767
49
2500
10
2729
47
2737
46
3129
29
3166
72
3636
61
3851
23
4249
22
4475
31
5031
27
5158
7
5207
97
5216
100
5317
111
5351
112
5381
103
5447
120
5543
129
5573
133
5605
135
5625
108
5693
6
5848
143
5855
146
5911
147
5941
151
6040
155
6100
161
6294
107
6487
178
6691
101
6714
117
6842
188
6889
160
7161
205
7189
206
7212
211
7306
198
7389
210
7402
212
7436
163
7475
222
8196
225
8258
227
10118
241
10134
257
11748
132
11761
115
11773
213
11904
170
11927
164
12014
281
12728
290
13263
223
34819
17
42255
304
42350
315
42435
318
43692
322
77018
253
77194
293
77217
134
77940
336
77966
130
78048
332
78057
329
78245
353
78669
331
80022
368
89279
308
93831
383
94796
384
110558
390
110640
391
113235
94
115845
398
116206
109
119982
406
120069
122
120699
407
121057
124
121216
125
121268
429
121352
121
121409
123
121423
382
121852
405
123304
119
123621
118
123786
136
123838
464
123968
447
123981
399
124405
376
124948
472
125362
479
125446
297
125774
481
125954
299
126221
478
126594
300
126604
298
126723
484
126904
501
127413
388
127783
209
128166
395
128177
513
128315
389
1148
Pyridoxal 5'-phosphate
HMDB0001491
This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). -- Pubchem; Pyridoxal-phosphate (PLP, pyridoxal-5'-phosphate) is a cofactor of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. -- Wikipedia.
54-47-7
C00018
1051
18405
PYRIDOXAL_PHOSPHATE
1022
DB00114
CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O
C8H10NO6P
InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
NGVDGCNFYWLIFO-UHFFFAOYSA-N
[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
247.1419
247.024573569
-1.64
3
pyridoxal phosphate
0
-2
FDB021820
Apolon b6;Biosechs;Codecarboxylase;Coenzyme b6;Hairoxal;Hexermin-p;Hi-pyridoxin;Hiadelon;Himitan;Pal-p;Plp;Phosphopyridoxal;Phosphopyridoxal coenzyme;Pidopidon;Piodel;Pydoxal;Pyridoxal 5'-phosphate;Pyridoxal 5-phosphate;Pyridoxal p;Pyridoxal phosphate;Pyridoxal-p;Pyridoxyl phosphate;Pyromijin;Sechvitan;Vitahexin-p;Vitazechs;3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate;Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphoric acid ester;Pyridoxal 5'-(dihydrogen phosphate);Pyridoxal-5'-phosphate;Pyridoxal 5'-phosphoric acid;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid;Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphate ester;Pyridoxal 5'-(dihydrogen phosphoric acid);Pyridoxal 5-phosphoric acid;Pyridoxal phosphoric acid;Pyridoxal-5'-phosphoric acid
PW_C001148
Pyr-5'P
18
2
32
4
45
3
51
8
122
1
401
19
696
20
1110
42
1450
50
1458
26
2120
10
2150
49
5325
111
5416
117
5421
103
5441
118
5455
120
5567
132
5581
133
6533
85
7018
160
7167
205
7216
212
7222
213
11858
161
12175
151
12623
31
12628
18
12684
289
12689
290
77017
253
77037
225
77041
293
77052
224
77526
112
77764
341
77973
346
77979
327
78292
345
78855
332
78862
331
80696
135
98630
7
119912
122
120024
124
120029
406
120087
407
120817
418
121149
423
121155
424
122069
123
122076
383
122834
119
123402
454
123721
458
123727
459
124620
447
124627
398
125302
297
125402
299
125407
479
125458
481
125803
489
126224
298
126231
495
126942
388
126947
501
126996
206
127258
506
127786
513
127793
390
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
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
423
Magnesium
HMDB0000547
Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.
22537-22-0
C00305
888
18420
13-HYDROXY-MAGNESIUM-PROTOPORP
865
DB01378
[Mg++]
Mg
InChI=1S/Mg/q+2
JLVVSXFLKOJNIY-UHFFFAOYSA-N
magnesium(2+) ion
24.305
23.985041898
0
magnesium(2+) ion
2
2
FDB003518
Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+
PW_C000423
Mg2+
86
8
227
4
268
16
476
2
727
26
811
5
819
18
883
22
936
39
983
3
992
21
1167
46
1483
49
1529
43
1764
14
2124
10
2411
59
2942
23
3126
29
3373
7
4540
31
4774
91
4869
54
4974
56
5253
104
5329
111
5356
112
5376
103
5906
147
5934
151
6038
155
6094
161
6250
166
6484
178
6594
164
6881
160
6979
199
7170
205
7194
206
7227
213
7233
211
7250
214
7310
216
7313
198
7473
222
11763
132
11843
210
12312
225
12324
249
12513
288
12581
226
12729
290
15275
285
15337
308
77137
133
77236
329
77937
336
78393
334
78417
335
78489
115
78522
331
78536
356
78574
130
80020
368
80045
184
80048
372
80623
118
80654
135
80865
15
80965
253
81841
51
93832
383
94900
27
108596
223
110559
390
115687
398
119974
406
120070
122
120247
382
120702
407
120981
408
121181
124
121265
429
121319
419
121924
125
122086
405
122408
422
122759
120
122921
399
123307
119
123546
374
123835
464
123889
455
124477
136
124637
376
124978
375
125447
297
125598
484
125669
479
125777
481
125921
482
125947
299
125973
495
126000
490
126243
478
126553
491
126753
300
127125
389
127164
501
127380
502
127407
388
127451
507
127804
209
128125
508
128347
395
833
Fructose 1,6-bisphosphate
HMDB0001058
Fructose 1,6-bisphosphate is fructose sugar or fructosephosphate that has been phosphorylated on carbons 1 and 6. The beta-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell is converted to fructose 1,6-bisphosphate at some point. Fructose 1,6-bisphosphate is a key component in the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate The enzyme phosphofructokinase uses ATP to transfer a phosphate group to fructose 6-phosphate to form fructose 1, 6-bisphosphate. fructose The enzyme aldolase splits fructose 1, 6-bisphosphate into two sugars that are isomers of each other. These two sugars are dihydroxyacetone phosphate and glyceraldehyde phosphate. Fructose 1,6-bisphosphate is an allosteric activator of pyruvate kinase.
488-69-7
C00354
445557
16905
FRUCTOSE-16-DIPHOSPHATE
393165
O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O
C6H14O12P2
InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1
RNBGYGVWRKECFJ-ZXXMMSQZSA-N
{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
340.1157
339.996048936
-1.33
7
[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid
0
-4
FDB022397
D-fructose 1,6-biphosphate;D-fructose 1,6-bis(dihydrogen phosphate);D-fructose 1,6-bisphosphate;D-fructose 1,6-diphosphate;D-fructose-1,6-bisphosphate;D-fructose-1,6-diphosphate;Diphosphofructose;Esafosfan;Esafosfina;Fdp;Fosfructose;Fructose 1,6-bis;Fructose 1,6-bisphosphate;Fructose 1,6-diphosphate;Harden-young ester;1,6-di-o-phosphono-alpha-d-fructofuranose;Alpha fructose 1,6-diphosphate;1,6-di-o-phosphono-a-d-fructofuranose;1,6-di-o-phosphono-α-d-fructofuranose
PW_C000833
Fru1,6P
1021
8
1790
2
5905
147
5933
151
6880
160
13358
225
77095
132
77931
111
120727
122
121180
124
123328
135
123752
118
125946
299
127406
388
42934
α,α-trehalose
Neotrehalose belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Neotrehalose exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa).
7427
16551
OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[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(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
HDTRYLNUVZCQOY-LIZSDCNHSA-N
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol
342.2965
342.116211546
0.24
8
α,α'-trehalose
0
0
α-d-glucopyranosyl α-d-glucopyranoside, α-d-glcp-(1↔1)-α-d-glcp, d-(+)-trehalose
PW_C042934
ααT
6370
107
42852
318
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
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
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
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
6013
Glycogen synthase
P0A6U8
Involved in biosynthetic process. Synthesizes alpha-1,4-glucan chains using ADP-glucose.
glgA
b3429
AP009048
3
2.4.1.21
5823
Maltodextrin phosphorylase
P00490
Involved in phosphorylase activity. Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
malP
b3417
AP009048
3
2.4.1.1
10002
Glucose-1-phosphate adenylyltransferase
P0A6V1
Catalyzes the synthesis of ADP-glucose, a sugar donor used in elongation reactions on alpha-glucans.
glgC
25
2.7.7.27
6210
108
7301
Glycogen debranching enzyme
P15067
Involved in catalytic activity. Hydrolyzes the alpha-1,6-glucosidic linkages in glycogen which has first been partially depolymerized by phosphorylase. Shows only very little activity with native glycogen.
glgX
b3431
AP009048
3
3.2.1.-
6672
Cytoplasmic trehalase
P62601
Involved in catalytic activity. Hydrolyzes trehalose to glucose. Could be involved, in cells returning to low osmolarity conditions, in the utilization of the accumulated cytoplasmic trehalose, which was synthesized in response to high osmolarity.
treF
b3519
AP009048
3
3.2.1.28
8817
101
135641
609
6332
Periplasmic trehalase
P13482
Involved in catalytic activity. Provides the cells with the ability to utilize trehalose at high osmolarity by splitting it into glucose molecules that can subsequently be taken up by the phosphotransferase-mediated uptake system.
treA
b1197
AP009048
3
3.2.1.28
8818
232
135642
612
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
5932
1,4-alpha-glucan-branching enzyme
P07762
Involved in 1,4-alpha-glucan branching enzyme activity. Catalyzes the formation of the alpha-1,6-glucosidic linkages in glycogen by scission of a 1,4-alpha-linked oligosaccharide from growing alpha-1,4-glucan chains and the subsequent attachment of the oligosaccharide to the alpha-1,6 position. Has a preference for transferring chains of 5 to 16 glucose units.
glgB
b3432
AP009048
3
2.4.1.18
135933
304
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
137934
117
3732
glycogen synthase
3
PW_P003732
10628
6013
3730
maltodextrin phosphorylase
3
PW_P003730
10626
5823
2
537
1148
3578
glucose-1-phosphate adenylyltransferase
3
PW_P003578
10417
10002
4
538
423
539
833
3736
glycogen debranching enzyme
3
PW_P003736
10633
7301
3737
cytoplasmic trehalase
3
PW_P003737
10634
6672
3738
periplasmic trehalase
3
PW_P003738
10635
6332
3535
glucokinase
3
PW_P003535
10372
6016
3731
1,4-α-glucan branching enzyme
3
PW_P003731
10627
5932
3575
glucose PTS permease
3
PW_P003575
10413
6694
2
10414
6693
3512
false
PW_R003512
Both
14103
2809
1
Compound
false
14104
1872
1
Compound
false
14105
1872
1
Compound
false
14106
1034
1
Compound
false
3492
3732
2.4.1.21
3515
false
PW_R003515
Both
14116
605
1
Compound
false
14117
42934
1
Compound
false
3495
3736
3.2.1.-
3516
false
PW_R003516
Right
14118
42934
1
Compound
false
14119
1420
1
Compound
false
14120
1851
1
Compound
false
14121
395
1
Compound
false
3496
3737
3.2.1.28
3297
false
PW_R003297
Right
13156
395
1
Compound
false
13157
414
1
Compound
false
13158
40034
1
Compound
false
13159
1034
1
Compound
false
13160
1906
1
Compound
false
3259
3535
2.7.1.2
3508
false
PW_R003508
Both
14092
1872
1
Compound
false
14093
605
1
Compound
false
3489
3731
2.4.1.18
3517
false
PW_R003517
Right
14122
42934
1
Compound
false
14123
1420
1
Compound
false
14124
395
1
Compound
false
14125
1851
1
Compound
false
3497
3738
3.2.1.28
3711
true
PW_R003711
Both
14928
1851
1
Compound
false
14929
395
1
Compound
false
3507
false
PW_R003507
Both
14088
41033
1
Compound
false
14089
1872
1
Compound
false
14090
1104
1
Compound
false
14091
605
1
Compound
false
3488
3730
2.4.1.1
3349
false
PW_R003349
Right
13363
41033
1
Compound
false
13364
414
1
Compound
false
13365
2809
1
Compound
false
13366
170
1
Compound
false
3318
3578
2.7.7.27
10420
PW_T010419
10792
395
1
Compound
107
101
Right
1589
3575
2019-08-12T15:04:34-06:00
2019-08-12T15:04:34-06:00
109
23888
2809
3
false
701
697
10
regular
100
100
23892
1872
3
false
811
602
10
regular
100
100
23893
1872
3
false
1146
694
10
regular
100
100
23894
1034
43
false
1086
669
10
regular
50
30
23895
605
3
false
1706
1103
10
regular
100
100
23896
41033
3
false
701
1097
10
regular
100
110
23898
1104
46
false
1582
1065
10
regular
44
43
23899
1148
9
false
1381
1110
10
regular
100
35
23901
414
42
false
641
1038
10
regular
50
30
23902
170
45
false
639
829
10
regular
63
43
23903
423
9
false
731
931
10
regular
100
25
23904
833
9
false
706
926
10
regular
100
35
23906
42934
3
false
1706
1593
10
regular
100
100
70255
1851
3
false
987
2013
10
regular
100
100
70258
1420
49
false
1593
1529
10
regular
78
78
70259
1851
3
false
1291
1508
10
regular
100
100
70260
395
3
false
1153
1595
10
regular
100
100
70262
42934
3
false
512
1905
10
regular
100
100
70263
1420
49
false
658
1835
10
regular
78
78
70265
414
42
false
1068
1580
10
regular
50
30
70266
40034
3
false
728
1500
10
regular
100
100
70267
1034
43
false
768
1690
10
regular
50
30
70268
1906
3
false
618
1590
10
regular
100
110
2718502
395
101
3
false
1153
1905
1
regular
100
100
11577
6013
2
false
911
712
8
subunit
regular
150
70
11579
5823
6
false
1351
1115
8
subunit
regular
160
80
11580
10002
8
false
681
916
8
subunit
regular
140
85
11582
7301
2
false
1681
1368
8
subunit
regular
150
70
32272
6672
101
2
false
1406
1608
8
subunit
regular
150
70
32273
6332
232
2
false
767
1920
8
subunit
regular
150
70
32274
6016
101
2
false
871
1610
8
subunit
regular
150
70
948262
5932
304
2
false
1681
934
8
subunit
regular
150
70
964382
6694
77
false
978
1735
8
subunit
regular
160
80
964383
6693
76
false
1128
1740
20
subunit
regular
150
70
8982
3732
716
11369
11577
8984
3730
716
11371
11579
3306
23899
35970
Cofactor
8985
3578
716
11372
11580
3307
23903
35977
Cofactor
3308
23904
35978
Cofactor
8987
3736
716
11374
11582
27140
3737
716
31954
32272
27141
3738
716
31955
32273
27142
3535
716
31956
32274
803091
3731
716
304
944134
948262
816567
3575
716
960147
964382
960148
964383
35960
M801 747 C831 747 881 747 911 747
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
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