ChemFOnt: Showing chemical card for GDP-alpha-D-glucose (CFc000283883)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:37:34 UTC

Chemfont ID

CFc000283883

Molecule Identification

Common Name

GDP-alpha-D-glucose

Definition

Gdp-alpha-d-glucose is soluble (in water) and a moderately acidic compound (based on its pKa). Gdp-alpha-d-glucose can be found in a number of food items such as watercress, french plantain, tartary buckwheat, and cherimoya, which makes gdp-alpha-d-glucose a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
9-[3,4-Dihydroxy-5-({[hydroxy({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olic acid	Generator

Chemical Formula

C₁₆H₂₃N₅O₁₆P₂

Average Molecular Weight

603.328

Monoisotopic Molecular Weight

603.062600836

IUPAC Name

[5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxy}phosphonate

Traditional Name

[5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxyphosphonate

CAS Registry Number

5750-57-2

SMILES

NC1=NC2=C(N=CN2C2OC(COP([O-])(=O)OP([O-])(=O)OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(=O)N1

InChI Identifier

InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/p-2

InChI Key

MVMSCBBUIHUTGJ-UHFFFAOYSA-L

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-oxopurine
Hypoxanthine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Pyrimidone
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Vinylogous amide
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Polyol
Organoheterocyclic compound
Azacycle
Oxacycle
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Primary amine
Organooxygen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a GDP-sugar (GDP-MANNOSE )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	10.6 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-5.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	333.09 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	116.27 m³·mol⁻¹	ChemAxon
Polarizability	50.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0304367

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030880

KNApSAcK ID

Not Available

Chemspider ID

19501249

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20705993

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for GDP-alpha-D-glucose (CFc000283883)

MOL for CFc000283883 (GDP-alpha-D-glucose)

3D MOL for CFc000283883 (GDP-alpha-D-glucose)

3D SDF for CFc000283883 (GDP-alpha-D-glucose)

3D-SDF for CFc000283883 (GDP-alpha-D-glucose)

PDB for CFc000283883 (GDP-alpha-D-glucose)

3D PDB for CFc000283883 (GDP-alpha-D-glucose)

SMILES for CFc000283883 (GDP-alpha-D-glucose)

INCHI for CFc000283883 (GDP-alpha-D-glucose)

Structure for CFc000283883 (GDP-alpha-D-glucose)

3D Structure for CFc000283883 (GDP-alpha-D-glucose)