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Record Information
Version1.0
Creation Date2016-09-30 22:38:49 UTC
Update Date2020-05-21 16:26:58 UTC
BMDB IDBMDB0000935
Secondary Accession Numbers
  • BMDB00935
Metabolite Identification
Common NameUridine diphosphate glucuronic acid
DescriptionUridine diphosphate glucuronic acid, also known as udpglucuronate or UDP-a-D-glucuronic acid, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Uridine diphosphate glucuronic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphate glucuronic acid exists in all living species, ranging from bacteria to humans. Within cattle, uridine diphosphate glucuronic acid participates in a number of enzymatic reactions. In particular, 2-methoxyestrone and uridine diphosphate glucuronic acid can be converted into 2-methoxyestrone 3-glucuronide and uridine 5'-diphosphate through the action of the enzyme UDP-glucuronosyltransferase 1-1. In addition, estrone and uridine diphosphate glucuronic acid can be converted into estrone glucuronide and uridine 5'-diphosphate; which is mediated by the enzyme UDP-glucuronosyltransferase 1-1. In cattle, uridine diphosphate glucuronic acid is involved in the metabolic pathway called the estrone metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
UDP-alpha-D-GlucuronateChEBI
UDP-D-GlucuronateChEBI
UDP-GlucuronateChEBI
UDPglucuronateChEBI
URIDINE-5'-diphosphATE-glucuronIC ACIDChEBI
UDP-a-D-GlucuronateGenerator
UDP-a-D-Glucuronic acidGenerator
UDP-alpha-D-Glucuronic acidGenerator
UDP-Α-D-glucuronateGenerator
UDP-Α-D-glucuronic acidGenerator
UDP-D-Glucuronic acidGenerator
UDP-Glucuronic acidGenerator
UDPglucuronic acidGenerator
URIDINE-5'-diphosphate-glucuronateGenerator
URIDINE-5'-diphosphoric acid-glucuronic acidGenerator
Uridine diphosphate glucuronateGenerator
Uridine diphosphoric acid glucuronic acidGenerator
a-D-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)HMDB
a-D-Glucopyranuronic acid ester with uridine 5'-pyrophosphateHMDB
alpha-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate)HMDB
alpha-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)HMDB
alpha-delta-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate)HMDB
alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphateHMDB
Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphateHMDB
UDP GlucuronateHMDB
UDP Glucuronic acidHMDB
UDP-alpha-delta-GlucuronateHMDB
UDP-delta-GlucuronateHMDB
UDP-delta-Glucuronic acidHMDB
UDP-GlcUAHMDB
UDPGAHMDB
UGAHMDB
Uridine 5'-diphospho-a-D-glucuronateHMDB
Uridine 5'-diphospho-a-D-glucuronic acidHMDB
Uridine 5'-diphospho-alpha-delta-glucuronateHMDB
Uridine 5'-diphospho-alpha-delta-glucuronic acidHMDB
Uridine 5'-diphospho-glucuronic acidHMDB
Uridine 5'-diphosphoglucuronateHMDB
Uridine 5'-diphosphoglucuronic acidHMDB
Uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diphosphate]HMDB
Uridine diphosphate-glucuronateHMDB
Uridine diphospho-D-glucuronateHMDB
Uridine diphospho-D-glucuronic acidHMDB
Uridine diphospho-delta-glucuronateHMDB
Uridine diphospho-delta-glucuronic acidHMDB
Uridine diphosphoglucuronateHMDB
Uridine diphosphoglucuronic acidHMDB
Uridine pyrophosphoglucuronateHMDB
Uridine pyrophosphoglucuronic acidHMDB
Uridinediphosphoglucuronic acidHMDB
Acid, UDP glucuronicHMDB
Acid, uridine diphosphoglucuronicHMDB
Glucuronic acid, UDPHMDB
Diphosphoglucuronic acid, uridineHMDB
Uridine 5'-diphospho-alpha-D-glucuronic acidHMDB
Uridine 5'-diphospho-α-D-glucuronic acidHMDB
Uridine 5’-diphospho-α-D-glucuronic acidHMDB
Uridine 5’-diphosphoglucuronic acidHMDB
Uridine diphosphate glucuronic acidHMDB
Chemical FormulaC15H22N2O18P2
Average Molecular Weight580.2853
Monoisotopic Molecular Weight580.034284934
IUPAC Name(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Nameudp-α-D-glucuronic acid
CAS Registry Number2616-64-0
SMILES
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O
InChI Identifier
InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1
InChI KeyHDYANYHVCAPMJV-LXQIFKJMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.2ALOGPS
logP-4.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area308.61 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.32 m³·mol⁻¹ChemAxon
Polarizability45.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w29-3322930000-0ce18416678ea80bec67View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004r-4862914000-b91973e084ab99d92364View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-d434fad6ebdd7797c473View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-b27e8f43f987aadd35fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4900000000-6c8ee9c73e164f9ccf76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imu-4601190000-7a0e82462b874f18b2c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9817020000-a72141b1bee762a83bc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvl-4901000000-5d52b1b8f03063646a7fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Mitochondria
Biospecimen Locations
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000935
DrugBank IDDB03041
Phenol Explorer Compound IDNot Available
FooDB IDFDB031240
KNApSAcK IDC00007238
Chemspider ID16522
KEGG Compound IDC00167
BioCyc IDUDP-GLUCURONATE
BiGG ID34117
Wikipedia LinkUridine_diphosphate_glucuronic_acid
METLIN ID5884
PubChem Compound17473
PDB IDNot Available
ChEBI ID17200
References
Synthesis ReferenceSimon, Ethan S.; Grabowski, Sven; Whitesides, George M. Convenient syntheses of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate and their use in the preparation of UDP-glucose, UDP-glucuronic acid, and GDP-mannose. J. Org. Chem., 1990, 55 (6), pp 1834–1841 DOI: 10.1021/jo00293a030
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Not Available
Gene Name:
TGDS
Uniprot ID:
A6QLW2
Molecular weight:
40666.0
Reactions
Uridine diphosphate glucuronic acid → UDP-D-Xylose + Carbon dioxidedetails
General function:
Involved in glucuronosyl-N-acetylglucosaminyl-proteogly
Specific function:
Glycosyltransferase required for the biosynthesis of heparan-sulfate. The EXT1/EXT2 complex possesses substantially higher glycosyltransferase activity than EXT1 or EXT2 alone. Appears to be a tumor suppressor. Required for the exosomal release of SDCBP, CD63 and syndecan.
Gene Name:
EXT2
Uniprot ID:
O77783
Molecular weight:
81887.0
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the addition of GlcNAc or GlcUA monosaccharides to the nascent hyaluronan polymer. Therefore, it is essential to hyaluronan synthesis a major component of most extracellular matrices that has a structural role in tissues architectures and regulates cell adhesion, migration and differentiation. This is one of the isozymes catalyzing that reaction and it is particularly responsible for the synthesis of high molecular mass hyaluronan. Required for the transition of endocardial cushion cells into mesenchymal cells, a process crucial for heart development. May also play a role in vasculogenesis. High molecular mass hyaluronan also play a role in early contact inhibition a process which stops cell growth when cells come into contact with each other or the extracellular matrix (By similarity).
Gene Name:
HAS2
Uniprot ID:
O97711
Molecular weight:
63459.0
General function:
Involved in glucuronosyl-N-acetylglucosaminyl-proteogly
Specific function:
Glycosyltransferase required for the biosynthesis of heparan-sulfate. The EXT1/EXT2 complex possesses substantially higher glycosyltransferase activity than EXT1 or EXT2 alone. Required for the exosomal release of SDCBP, CD63 and syndecan (By similarity).
Gene Name:
EXT1
Uniprot ID:
A5D7I4
Molecular weight:
86299.0
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 NADHdetails
General function:
Carbohydrate transport and metabolism
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds (By similarity).
Gene Name:
UGT3A1
Uniprot ID:
Q1LZI1
Molecular weight:
59682.0
Reactions
Uridine diphosphate glucuronic acid → Isovalerylglucuronide + Uridine 5'-diphosphatedetails