Bovine Metabolome Database: Showing metabocard for Uridine diphosphate glucose (BMDB0000286)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:50 UTC

Update Date

2020-06-04 20:19:13 UTC

BMDB ID

BMDB0000286

Secondary Accession Numbers

BMDB00286

Metabolite Identification

Common Name

Uridine diphosphate 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₁₅H₂₄N₂O₁₇P₂

Average Molecular Weight

566.3018

Monoisotopic Molecular Weight

566.055020376

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

Traditional Name

udp-α-D-glucose

CAS Registry Number

133-89-1

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

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

Chemical Taxonomy

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

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Endoplasmic reticulum
Golgi

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	-1.4	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	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	splash10-054k-3933570000-89f658b2d26ff158d84c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-4942706000-3a83736296429f83adee	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Uridine diphosphate glucose,1TMS,#1" TMS) - 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-014i-0000090000-1692ab5f5dad1cf7e436	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-015a-0439510000-69e7cd4c2c365a24706b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0109-5753970000-03f34041208ba93ef87a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00fr-9257000000-73b85a465d99ce92467d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00ba-9333000000-b57dc1340555f1a997b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00fr-9257000000-ba1e6c754b8f04d5b659	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9000000000-9bd63595c19dbe18d143	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-4b94aa10fd96d2d9c505	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0009000000-996cd4acdaa34c877460	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0901110000-4b81825405869909992e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3911000000-6fd09254750e77963110	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5900000000-03a2a98eb0aa84737530	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4901260000-8396a090c14de7f2d708	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-8907020000-94410556a0288cb8167b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-5901000000-10132c85ad33464d4eef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0000960000-6404d8d944e1ae6f30e2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-07e1-2322960000-6af539ce21752f9023ba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fr-9732000000-b0c81adc41b1d799e1e8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-8cab8f2bc0fb9e9e8ba9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057j-9203870000-d60681ff91f741bdb867	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-3519000000-67ca2f9355ef7f94a47d	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
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, 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
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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Endoplasmic reticulum
Golgi

Biospecimen Locations

Liver
Skeletal Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Nucleotide Sugars Metabolism		Not Available
Galactose Metabolism		Not Available
Lactose Synthesis		Not Available
Starch and Sucrose Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Detected and Quantified	126 +/- 32 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000286

DrugBank ID

DB01861

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005660

KNApSAcK ID

C00001514

Chemspider ID

Not Available

KEGG Compound ID

C00029

BioCyc ID

CPD-12575

BiGG ID

Not Available

Wikipedia Link

Uridine_diphosphate_glucose

METLIN ID

Not Available

PubChem Compound

8629

PDB ID

Not Available

ChEBI ID

46229

References

Synthesis Reference

Burma, D. P.; Mortimer, D. C. Biosynthesis of uridine diphosphate glucose and sucrose in sugar-beet leaf. Archives of Biochemistry and Biophysics (1956), 62 16-28.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Phosphoglucomutase-1

General function:: Carbohydrate transport and metabolism
Specific function:: This enzyme participates in both the breakdown and synthesis of glucose.
Gene Name:: PGM1
Uniprot ID:: Q08DP0
Molecular weight:: 61589.0

Reactions

Uridine diphosphate glucose → Glucose 1-phosphate	details

Enzyme Details

2. UDP-glucose 6-dehydrogenase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Catalyzes the formation of UDP-alpha-D-glucuronate, a constituent of complex glycosaminoglycans (By similarity). Required for the biosynthesis of chondroitin sulfate and heparan sulfate. Required for embryonic development via its role in the biosynthesis of glycosaminoglycans (By similarity).
Gene Name:: UGDH
Uniprot ID:: P12378
Molecular weight:: 55136.0

Reactions

Uridine diphosphate glucose + 2 NAD + Water → Uridine diphosphate glucuronic acid +2 NADH	details

Enzyme Details

3. Galactose-1-phosphate uridylyltransferase

General function:: Energy production and conversion
Specific function:: Not Available
Gene Name:: GALT
Uniprot ID:: Q0V7N7
Molecular weight:: 37812.0

Enzyme Details

4. Glycogen [starch] synthase, muscle

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Transfers the glycosyl residue from UDP-Glc to the non-reducing end of alpha-1,4-glucan.
Gene Name:: GYS1
Uniprot ID:: A7MB78
Molecular weight:: 83814.0

Reactions

Uridine diphosphate glucose → Amylose + Uridine 5'-diphosphate	details

Enzyme Details

5. Galactose-1-phosphate uridylyltransferase

General function:: Energy production and conversion
Specific function:: Not Available
Gene Name:: GALT
Uniprot ID:: Q58CX1
Molecular weight:: 41288.0

Reactions

Uridine diphosphategalactose + Glucose 1-phosphate → Uridine diphosphate glucose + Galactose 1-phosphate	details
Uridine diphosphate glucose + Galactose 1-phosphate → Uridine diphosphategalactose + Glucose 1-phosphate	details
Uridine diphosphategalactose + Glucose 1-phosphate → Galactose 1-phosphate + Uridine diphosphate glucose	details

Enzyme Details

6. UTP--glucose-1-phosphate uridylyltransferase

General function:: Involved in UTP:glucose-1-phosphate uridylyltransferase
Specific function:: Plays a central role as a glucosyl donor in cellular metabolic pathways.
Gene Name:: UGP2
Uniprot ID:: Q07130
Molecular weight:: 56903.0

Reactions

Glucose 1-phosphate + Uridine triphosphate → Uridine diphosphate glucose + Pyrophosphate	details
Uridine diphosphate glucose + Pyrophosphate → Glucose 1-phosphate + Uridine triphosphate	details

Enzyme Details

7. P2Y purinoceptor 14

General function:: Involved in purinergic nucleotide receptor activity, G-
Specific function:: Receptor for UDP-glucose and other UDP-sugar coupled to G-proteins. Not activated by ATP, ADP, UTP or ATP (By similarity).
Gene Name:: P2RY14
Uniprot ID:: Q3SX17
Molecular weight:: 38697.0

Enzyme Details

8. UDP-glucose 4-epimerase

General function:: Not Available
Specific function:: Catalyzes two distinct but analogous reactions: the reversible epimerization of UDP-glucose to UDP-galactose and the reversible epimerization of UDP-N-acetylglucosamine to UDP-N-acetylgalactosamine. The reaction with UDP-Gal plays a critical role in the Leloir pathway of galactose catabolism in which galactose is converted to the glycolytic intermediate glucose 6-phosphate. It contributes to the catabolism of dietary galactose and enables the endogenous biosynthesis of both UDP-Gal and UDP-GalNAc when exogenous sources are limited. Both UDP-sugar interconversions are important in the synthesis of glycoproteins and glycolipids.
Gene Name:: GALE
Uniprot ID:: Q3T105
Molecular weight:: 38254.0

Reactions

Uridine diphosphate glucose + Galactose 1-phosphate → Uridine diphosphategalactose + Glucose 1-phosphate	details
Uridine diphosphategalactose → Uridine diphosphate glucose	details

Showing metabocard for Uridine diphosphate glucose (BMDB0000286)

Structure for BMDB0000286 (Uridine diphosphate glucose)

Enzymes

Reactions

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