Showing Compound Udp-glucose (FDB005660)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:47 UTC

Update date

2020-09-17 15:38:32 UTC

Primary ID

FDB005660

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Udp-glucose

Description

Uridine diphosphate glucose, also known as udpglucose or UDP-alpha-D-glucose, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphate glucose is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphate glucose exists in all living species, ranging from bacteria to humans. Within humans, uridine diphosphate glucose participates in a number of enzymatic reactions. In particular, galactose 1-phosphate and uridine diphosphate glucose can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is catalyzed by the enzyme galactose-1-phosphate uridylyltransferase. In addition, uridine diphosphate glucose can be biosynthesized from uridine diphosphategalactose through its interaction with the enzyme UDP-glucose 4-epimerase. In humans, uridine diphosphate glucose is involved in galactose metabolism. Outside of the human body, Uridine diphosphate glucose has been detected, but not quantified in, several different foods, such as tea, ostrich ferns, chickpea, cinnamons, and sourdoughs. This could make uridine diphosphate glucose a potential biomarker for the consumption of these foods.

CAS Number

133-89-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
GLUCOSE-uridine-C1,5'-diphosphATE	ChEBI
UDP-D-Glucose	ChEBI
UDPglucose	ChEBI
URIDINE-5'-diphosphATE-glucose	ChEBI
UDP-alpha-D-Glucose	Kegg
GLUCOSE-uridine-C1,5'-diphosphoric acid	Generator
URIDINE-5'-diphosphoric acid-glucose	Generator
UDP-a-D-Glucose	Generator
UDP-Α-D-glucose	Generator
Uridine diphosphoric acid glucose	Generator
Diphosphate glucose, uridine	HMDB
Diphosphoglucose, uridine	HMDB
Glucose, UDP	HMDB
Glucose, uridine diphosphate	HMDB
UDP Glucose	HMDB
UDPG	HMDB
Uridine diphosphoglucose	HMDB
UDP-GLC	HMDB
UDP-Glucose	HMDB
Uridine 5'-(alpha-D-glucopyranosyl pyrophosphate)	HMDB
Uridine 5'-(α-D-glucopyranosyl pyrophosphate)	HMDB
Uridine 5'-diphosphate glucose	HMDB
Uridine 5'-diphospho-alpha-D-glucose	HMDB
Uridine 5'-diphospho-α-D-glucose	HMDB
Uridine 5'-diphosphoglucose	HMDB
Uridine 5’-(α-D-glucopyranosyl pyrophosphate)	HMDB
Uridine 5’-diphosphate glucose	HMDB
Uridine 5’-diphospho-α-D-glucose	HMDB
Uridine 5’-diphosphoglucose	HMDB
Uridine diphospho-D-glucose	HMDB
Uridine pyrophosphate-glucose	HMDB
Uridine diphosphate glucose	ChEBI
Udp glucose	biospider
Udp-d-glucose	biospider
Udp-delta-glucose	biospider
Udp-GLC	biospider
UPG	biospider
Uridine 5'-diphospho-a-D-glucose	biospider
Uridine 5'-diphospho-alpha-delta-glucose	biospider
Uridine 5'-pyrophosphate a-D-glucopyranosyl ester	biospider
Uridine 5'-pyrophosphate a-delta-glucopyranosyl ester	biospider
Uridine diphospho-d-glucose	biospider
Uridine diphospho-delta-glucose	biospider

Predicted Properties

Property	Value	Source
Water Solubility	15 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	291.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	106.46 m³·mol⁻¹	ChemAxon
Polarizability	45.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C15H24N2O17P2

IUPAC name

[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-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

InChI Identifier

InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1

InChI Key

HSCJRCZFDFQWRP-JZMIEXBBSA-N

Isomeric SMILES

OC[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)[C@@H]1O

Average Molecular Weight

566.3018

Monoisotopic Molecular Weight

566.055020376

Classification

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Urea
Secondary alcohol
Lactam
Polyol
Oxacycle
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-D-glucose (CHEBI:46229 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Tissue and substructures:

Skeletal muscle

Organ and components:

Liver

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Udp-glucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-054k-3933570000-89f658b2d26ff158d84c	Spectrum
Predicted GC-MS	Udp-glucose, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-4942706000-3a83736296429f83adee	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-014i-0000090000-1692ab5f5dad1cf7e436	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-015a-0439510000-69e7cd4c2c365a24706b	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0109-5753970000-03f34041208ba93ef87a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0901110000-4b81825405869909992e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3911000000-6fd09254750e77963110	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5900000000-03a2a98eb0aa84737530	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4901260000-8396a090c14de7f2d708	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-8907020000-94410556a0288cb8167b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-5901000000-10132c85ad33464d4eef	Spectrum