Human Metabolome Database Version 3.5

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Showing metabocard for UDP-4-dehydro-6-deoxy-D-glucose (HMDB12300)

Blood
Urine

Record Information

Version

3.5

Creation Date

2009-04-06 10:22:35 -0600

Update Date

2013-02-08 17:28:45 -0700

HMDB ID

HMDB12300

Secondary Accession Numbers

None

Metabolite Identification

Common Name

UDP-4-dehydro-6-deoxy-D-glucose

Description

UDP-4-dehydro-6-deoxy-D-glucose is synthesized from UDP-glucose through the enzyme UDP-glucose 4,6-dehydratase.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

UDP-4-Keto-6-deoxy-D-glucose
UDP-4-Oxo-6-deoxy-D-glucose

Chemical Formula

C₁₅H₂₂N₂O₁₆P₂

Average Molecular Weight

548.2865

Monoisotopic Molecular Weight

548.04445569

IUPAC Name

{[(2S,3R,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid

Traditional IUPAC Name

[(2S,3R,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy({[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)C1=O

InChI Identifier

InChI=1S/C15H22N2O16P2/c1-5-8(19)10(21)12(23)14(30-5)32-35(27,28)33-34(25,26)29-4-6-9(20)11(22)13(31-6)17-3-2-7(18)16-15(17)24/h2-3,5-6,9-14,20-23H,4H2,1H3,(H,25,26)(H,27,28)(H,16,18,24)/t5-,6-,9-,10+,11-,12-,13-,14+/m1/s1

InChI Key

DDWGQQADOIMFOI-XRTQJECLSA-N

Chemical Taxonomy

Kingdom

Organic Compounds

Super Class

Nucleosides, Nucleotides, and Analogues

Class

Pyrimidine Nucleotides

Sub Class

Pyrimidine Nucleotide Sugars

Other Descriptors

Aromatic Heteropolycyclic Compounds
Pyrimidine Ribonucleoside Diphosphates

Substituents

1,2 Diol
Disaccharide Phosphate
Glycosyl Compound
Hydropyrimidine
Ketone
Mixed Pentose/Hexose Disaccharide
N Glycosyl Compound
Organic Hypophosphite
Organic Phosphite
Organic Pyrophosphate
Oxane
Oxolane
Phosphoric Acid Ester
Pyrimidine
Pyrimidone
Saccharide
Secondary Alcohol

Direct Parent

Pyrimidine Nucleotide Sugars

Ontology

Status

Expected and Not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

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
Water Solubility	15.3 g/L	ALOGPS
LogP	-0.85	ALOGPS
LogP	-3.3	ChemAxon
LogS	-1.55	ALOGPS
pKa (strongest acidic)	1.73	ChemAxon
pKa (strongest basic)	-3.7	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	268.15 A²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	104.15	ChemAxon
Polarizability	44.12	ChemAxon
Formal Charge	0	ChemAxon
Physiological Charge	-2	ChemAxon