Bovine Metabolome Database: Showing metabocard for ADP-glucose (BMDB0006557)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:23:19 UTC

Update Date

2020-04-22 15:17:50 UTC

BMDB ID

BMDB0006557

Secondary Accession Numbers

BMDB06557

Metabolite Identification

Common Name

ADP-glucose

Description

ADP-glucose, also known as ADPG or ADP-a-D-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 exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on ADP-glucose.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

Chemical Formula

C₁₆H₂₅N₅O₁₅P₂

Average Molecular Weight

589.3417

Monoisotopic Molecular Weight

589.082238179

IUPAC Name

[({[(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

Traditional Name

adp glucose

CAS Registry Number

2140-58-1

SMILES

NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(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

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 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-6.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	3.99	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	311.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.09 m³·mol⁻¹	ChemAxon
Polarizability	48.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05di-5941580000-aa3b11c510a971dd2bae	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05be-8925707000-bdd8b43e72abaa64441b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("ADP-glucose,1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, positive	splash10-0006-0000290000-7f66f6e8af24e4839d36	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-004l-0000950000-739c8280d86a2f6f3b3b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative	splash10-002k-9248080000-875881d0c025c30eb244	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - NA , negative	splash10-003r-3900000000-64717800131918b409d1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1901000000-e41db8583774d0cca66d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0000940000-0f0b4d7b3da79f054155	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000900000-c6a92771658ee7a74bb5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0401900000-e9c970aa89843c279822	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0910520000-894488255e0d2059a6ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0910000000-af7d8977d3d229ea73ee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-39c6318a5ada8cb3ebb4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-1901470000-134113735239a2586876	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1901000000-48fb3c4c1d3e3f084d3d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0563-3900000000-f9f285dafe2da95e8009	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000090000-494b86dfa2b4e6fc0ac1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0570-5421970000-431fd452ea842be1eb27	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2922610000-bc7320a1bf5a6bf0dc76	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000090000-46811e8e339262e18415	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-0841490000-f709931b7e24d70dc4f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2921000000-17d11c3948611bf9ff8b	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

References

Synthesis Reference

Tamura, Kiminori; Morozumi, Manami; Yoshino, Hiroshi; Noda, Yutaka; Suzuki, Morio. Nucleotide anhydrides. Ger. Offen. (1972), 16 pp. CODEN: GWXXBX DE 2038262 19720203 CAN 76:99993 AN 1972:99993

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for ADP-glucose (BMDB0006557)

Structure for BMDB0006557 (ADP-glucose)