MiMeDB: Showing metabocard for ADP-Glucose (MMDBc0029838)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:43:44 UTC

Update Date

2024-10-13 07:42:17 UTC

Metabolite ID

MMDBc0029838

Metabolite Identification

Common Name

ADP-Glucose

Description

ADP-glucose serves as the glycosyl donor for formation of bacterial glycogen, amylose in green algae, and amylopectin in higher plants. It is an intermediate in starch and sucrose metabolism and involved in amino sugar and nucleotide sugar metabolism. (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Adenosine diphosphate glucose	ChEBI
Adenosine diphosphoglucose	ChEBI
Adenosine pyrophosphateglucose	ChEBI
ADPG	ChEBI
ADPglucose	ChEBI
ADP-alpha-D-Glucose	Kegg
Adenosine diphosphoric acid glucose	Generator
ADP-a-D-Glucose	Generator
ADP-Α-D-glucose	Generator
Adenosine 5'-(trihydrogen diphosphate) glucopyranosyl ester	HMDB
Adenosine 5'-(trihydrogen diphosphate) p'-alpha-delta-glucopyranosyl ester	HMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-D-glucosyl ester	HMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-delta-glucosyl ester	HMDB
Adenosine 5'-diphosphoglucose	HMDB
Adenosine 5'-pyrophosphate a-delta-glucosyl ester	HMDB
Adenosine 5'-pyrophosphate alpha-D-glucosyl ester	HMDB
Adenosine 5'-pyrophosphate alpha-delta-glucosyl ester	HMDB
Adenosine 5'-pyrophosphate glucosyl ester	HMDB
Adenosine 5'-pyrophosphate mono-D-glucosyl ester	HMDB
Adenosine 5'-pyrophosphate mono-delta-glucosyl ester	HMDB
Adenosine diphosphate D-glucose	HMDB
Adenosine pyrophosphate-glucose	HMDB
Adenosine-5'-diphosphate-glucose	HMDB
ADP-D-Glucose	HMDB
ADP Glucose	HMDB
Diphosphate glucose, adenosine	HMDB
Diphosphoglucose, adenosine	HMDB
Glucose, ADP	HMDB
Glucose, adenosine diphosphate	HMDB
Pyrophosphateglucose, adenosine	HMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-alpha-D-glucosyl ester	HMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-α-D-glucosyl ester	HMDB
Adenosine 5’-(trihydrogen pyrophosphate) mono-D-glucosyl ester	HMDB
Adenosine 5’-(trihydrogen pyrophosphate) mono-α-D-glucosyl ester	HMDB
Adenosine 5’-diphosphoglucose	HMDB
Adenosine 5’-pyrophosphate mono-D-glucosyl ester	HMDB
ADP-Glucose	HMDB

Molecular Formula

C₁₆H₂₅N₅O₁₅P₂

Average Mass

589.3417

Monoisotopic Mass

589.082238179

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

2140-58-1

SMILES

Not Available

InChI Identifier

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

InChI Key

WFPZSXYXPSUOPY-ROYWQJLOSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Imidolactam
Alkyl phosphate
Pyrimidine
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Polyol
Oxacycle
Organic oxide
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Amine
Organonitrogen compound
Primary alcohol
Primary amine
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alpha-D-glucoside (CHEBI:15751 )
ADP-aldose (CHEBI:15751 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000229	ADP-Glucose	Glucose 1-phosphate	nudix (nucleoside diphosphate linked moiety X)-type motif 5	VMH	10567213 10722730 12717453
MMDBr0007831	Glucose 1-phosphate	ADP-Glucose	Not Available	VMH	30371894
MMDBr0010889	ADP-Glucose	Glycogen	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	110	Human feces; Human sputum; Pig ; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	252	Human feces; Human pleural fluid plaque; Pig ; Human ; Human urine; Human mucosa; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	105	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0006557

DrugBank ID

DB01774

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16500

PDB ID

Not Available

ChEBI ID

15751

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wiedemuth K, Muller J, Kahlau A, Amme S, Mock HP, Grzam A, Hell R, Egle K, Beschow H, Humbeck K: Successive maturation and senescence of individual leaves during barley whole plant ontogeny reveals temporal and spatial regulation of photosynthetic function in conjunction with C and N metabolism. J Plant Physiol. 2005 Nov;162(11):1226-36. doi: 10.1016/j.jplph.2005.01.010. [PubMed:16323274 ]
Baroja-Fernandez E, Etxeberria E, Munoz FJ, Moran-Zorzano MT, Alonso-Casajus N, Gonzalez P, Pozueta-Romero J: An important pool of sucrose linked to starch biosynthesis is taken up by endocytosis in heterotrophic cells. Plant Cell Physiol. 2006 Apr;47(4):447-56. doi: 10.1093/pcp/pcj011. Epub 2006 Jan 24. [PubMed:16434435 ]
Bejar CM, Ballicora MA, Iglesias AA, Preiss J: ADPglucose pyrophosphorylase's N-terminus: structural role in allosteric regulation. Biochem Biophys Res Commun. 2006 Apr 28;343(1):216-21. doi: 10.1016/j.bbrc.2006.02.123. Epub 2006 Mar 2. [PubMed:16530732 ]
Lunn JE, Feil R, Hendriks JH, Gibon Y, Morcuende R, Osuna D, Scheible WR, Carillo P, Hajirezaei MR, Stitt M: Sugar-induced increases in trehalose 6-phosphate are correlated with redox activation of ADPglucose pyrophosphorylase and higher rates of starch synthesis in Arabidopsis thaliana. Biochem J. 2006 Jul 1;397(1):139-48. doi: 10.1042/BJ20060083. [PubMed:16551270 ]
Thorneycroft D, Hosein F, Thangavelu M, Clark J, Vizir I, Burrell MM, Ainsworth C: Characterization of a gene from chromosome 1B encoding the large subunit of ADPglucose pyrophosphorylase from wheat: evolutionary divergence and differential expression of Agp2 genes between leaves and developing endosperm. Plant Biotechnol J. 2003 Jul;1(4):259-70. doi: 10.1046/j.1467-7652.2003.00025.x. [PubMed:17163903 ]
Haferkamp I: The diverse members of the mitochondrial carrier family in plants. FEBS Lett. 2007 May 25;581(12):2375-9. doi: 10.1016/j.febslet.2007.02.020. Epub 2007 Feb 26. [PubMed:17321523 ]
Eydallin G, Moran-Zorzano MT, Munoz FJ, Baroja-Fernandez E, Montero M, Alonso-Casajus N, Viale AM, Pozueta-Romero J: An Escherichia coli mutant producing a truncated inactive form of GlgC synthesizes glycogen: further evidences for the occurrence of various important sources of ADPglucose in enterobacteria. FEBS Lett. 2007 Sep 18;581(23):4417-22. doi: 10.1016/j.febslet.2007.08.016. Epub 2007 Aug 15. [PubMed:17719034 ]
Moran-Zorzano MT, Alonso-Casajus N, Munoz FJ, Viale AM, Baroja-Fernandez E, Eydallin G, Pozueta-Romero J: Occurrence of more than one important source of ADPglucose linked to glycogen biosynthesis in Escherichia coli and Salmonella. FEBS Lett. 2007 Sep 18;581(23):4423-9. doi: 10.1016/j.febslet.2007.08.017. Epub 2007 Aug 15. [PubMed:17719035 ]
Smith AM: Prospects for increasing starch and sucrose yields for bioethanol production. Plant J. 2008 May;54(4):546-58. doi: 10.1111/j.1365-313X.2008.03468.x. [PubMed:18476862 ]
Nagai YS, Sakulsingharoj C, Edwards GE, Satoh H, Greene TW, Blakeslee B, Okita TW: Control of starch synthesis in cereals: metabolite analysis of transgenic rice expressing an up-regulated cytoplasmic ADP-glucose pyrophosphorylase in developing seeds. Plant Cell Physiol. 2009 Mar;50(3):635-43. doi: 10.1093/pcp/pcp021. Epub 2009 Feb 10. [PubMed:19208694 ]
Comparot-Moss S, Denyer K: The evolution of the starch biosynthetic pathway in cereals and other grasses. J Exp Bot. 2009;60(9):2481-92. doi: 10.1093/jxb/erp141. [PubMed:19505928 ]
Baroja-Fernandez E, Munoz FJ, Montero M, Etxeberria E, Sesma MT, Ovecka M, Bahaji A, Ezquer I, Li J, Prat S, Pozueta-Romero J: Enhancing sucrose synthase activity in transgenic potato (Solanum tuberosum L.) tubers results in increased levels of starch, ADPglucose and UDPglucose and total yield. Plant Cell Physiol. 2009 Sep;50(9):1651-62. doi: 10.1093/pcp/pcp108. Epub 2009 Jul 16. [PubMed:19608713 ]
Ezquer I, Li J, Ovecka M, Baroja-Fernandez E, Munoz FJ, Montero M, Diaz de Cerio J, Hidalgo M, Sesma MT, Bahaji A, Etxeberria E, Pozueta-Romero J: Microbial volatile emissions promote accumulation of exceptionally high levels of starch in leaves in mono- and dicotyledonous plants. Plant Cell Physiol. 2010 Oct;51(10):1674-93. doi: 10.1093/pcp/pcq126. Epub 2010 Aug 24. [PubMed:20739303 ]
Uhlmann NK, Beckles DM: Storage products and transcriptional analysis of the endosperm of cultivated wheat and two wild wheat species. J Appl Genet. 2010;51(4):431-47. doi: 10.1007/BF03208873. [PubMed:21063061 ]
Fettke J, Malinova I, Albrecht T, Hejazi M, Steup M: Glucose-1-phosphate transport into protoplasts and chloroplasts from leaves of Arabidopsis. Plant Physiol. 2011 Apr;155(4):1723-34. doi: 10.1104/pp.110.168716. Epub 2010 Nov 29. [PubMed:21115809 ]
Ezquer I, Li J, Ovecka M, Baroja-Fernandez E, Munoz FJ, Montero M, Diaz de Cerio J, Hidalgo M, Sesma MT, Bahaji A, Etxeberria E, Pozueta-Romero J: A suggested model for potato MIVOISAP involving functions of central carbohydrate and amino acid metabolism, as well as actin cytoskeleton and endocytosis. Plant Signal Behav. 2010 Dec;5(12):1638-41. doi: 10.4161/psb.5.12.13808. Epub 2010 Dec 1. [PubMed:21150257 ]
Tiessen A, Nerlich A, Faix B, Hummer C, Fox S, Trafford K, Weber H, Weschke W, Geigenberger P: Subcellular analysis of starch metabolism in developing barley seeds using a non-aqueous fractionation method. J Exp Bot. 2012 Mar;63(5):2071-87. doi: 10.1093/jxb/err408. Epub 2011 Dec 26. [PubMed:22200665 ]
Szecowka M, Osorio S, Obata T, Araujo WL, Rohrmann J, Nunes-Nesi A, Fernie AR: Decreasing the mitochondrial synthesis of malate in potato tubers does not affect plastidial starch synthesis, suggesting that the physiological regulation of ADPglucose pyrophosphorylase is context dependent. Plant Physiol. 2012 Dec;160(4):2227-38. doi: 10.1104/pp.112.204826. Epub 2012 Oct 12. [PubMed:23064409 ]
Li J, Baroja-Fernandez E, Bahaji A, Munoz FJ, Ovecka M, Montero M, Sesma MT, Alonso-Casajus N, Almagro G, Sanchez-Lopez AM, Hidalgo M, Zamarbide M, Pozueta-Romero J: Enhancing sucrose synthase activity results in increased levels of starch and ADP-glucose in maize (Zea mays L.) seed endosperms. Plant Cell Physiol. 2013 Feb;54(2):282-94. doi: 10.1093/pcp/pcs180. Epub 2013 Jan 3. [PubMed:23292602 ]
Asencion Diez MD, Aleanzi MC, Iglesias AA, Ballicora MA: A novel dual allosteric activation mechanism of Escherichia coli ADP-glucose pyrophosphorylase: the role of pyruvate. PLoS One. 2014 Aug 7;9(8):e103888. doi: 10.1371/journal.pone.0103888. eCollection 2014. [PubMed:25102309 ]

Showing metabocard for ADP-Glucose (MMDBc0029838)

MOL for #<Metabolite:0x00007fdb2e7a7220>

3D MOL for #<Metabolite:0x00007fdb2e7a7220>

3D SDF for #<Metabolite:0x00007fdb2e7a7220>

3D-SDF for #<Metabolite:0x00007fdb2e7a7220>

PDB for #<Metabolite:0x00007fdb2e7a7220>

3D PDB for #<Metabolite:0x00007fdb2e7a7220>

SMILES for #<Metabolite:0x00007fdb2e7a7220>

INCHI for #<Metabolite:0x00007fdb2e7a7220>

Structure for #<Metabolite:0x00007fdb2e7a7220>

3D Structure for #<Metabolite:0x00007fdb2e7a7220>