Uridine diphosphate glucuronic acid (CHEM035001)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:24:32 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM035001
Identification
Common NameUridine diphosphate glucuronic acid
ClassSmall Molecule
DescriptionA nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP iduronic acid, which donates iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass580.285 g/mol
Monoisotopic Mass580.034 g/mol
CAS Registry Number2616-64-0
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
SMILESO[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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.1 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w29-3322930000-0ce18416678ea80bec67Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004r-4862914000-b91973e084ab99d92364Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Uridine diphosphate glucuronic acid,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0135690000-0ff1e6a4900ecdc6a915Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0000090000-1cdeb28950f03fda28eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0r29-5934300000-e5fcfe66852c383b82d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-bc00d530c5ce60dfe672Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3922200000-353e174f91c8b182064cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-d434fad6ebdd7797c473Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-b27e8f43f987aadd35fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4900000000-6c8ee9c73e164f9ccf76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imu-4601190000-7a0e82462b874f18b2c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9817020000-a72141b1bee762a83bc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvl-4901000000-5d52b1b8f03063646a7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001090000-c773521e9e340d5e6564Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-055e-9424840000-deea5ee6888efff36f31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5a-3936510000-b41af0ea55c95b9da1e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1700490000-7f9159b24d34e9358740Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4921760000-cd1fe2a62f343b8eb5baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0209-6940100000-aa916ad8a0ed15e6eb2aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03041
HMDB IDHMDB0000935
FooDB IDFDB031240
Phenol Explorer IDNot Available
KNApSAcK IDC00007238
BiGG ID34117
BioCyc IDUDP-GLUCURONATE
METLIN ID5884
PDB IDNot Available
Wikipedia LinkUridine_diphosphate_glucuronic_acid
Chemspider ID16522
ChEBI ID17200
PubChem Compound ID17473
Kegg Compound IDC00167
YMDB IDYMDB16123
ECMDB IDECMDB01384
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simon, 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
2. Quintus J, Kovar KA, Link P, Hamacher H: Urinary excretion of arbutin metabolites after oral administration of bearberry leaf extracts. Planta Med. 2005 Feb;71(2):147-52.
3. Cappiello M, Giuliani L, Rane A, Pacifici GM: Uridine 5'-diphosphoglucuronic acid (UDPGLcUA) in the human fetal liver, kidney and placenta. Eur J Drug Metab Pharmacokinet. 2000 Jul-Dec;25(3-4):161-3.
4. Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of ezetimibe (Zetia). Drug Metab Dispos. 2004 Mar;32(3):314-20.
5. Huskey SW, Doss GA, Miller RR, Schoen WR, Chiu SH: N-glucuronidation reactions. II. Relative N-glucuronidation reactivity of methylbiphenyl tetrazole, methylbiphenyl triazole, and methylbiphenyl imidazole in rat, monkey, and human hepatic microsomes. Drug Metab Dispos. 1994 Jul-Aug;22(4):651-8.
6. Alkharfy KM, Frye RF: High-performance liquid chromatographic assay for acetaminophen glucuronide in human liver microsomes. J Chromatogr B Biomed Sci Appl. 2001 Apr 5;753(2):303-8.
7. Hagenauer B, Salamon A, Thalhammer T, Kunert O, Haslinger E, Klingler P, Senderowicz AM, Sausville EA, Jager W: In vitro glucuronidation of the cyclin-dependent kinase inhibitor flavopiridol by rat and human liver microsomes: involvement of UDP-glucuronosyltransferases 1A1 and 1A9. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):407-14.
8. Cappiello M, Giuliani L, Pacifici GM: Distribution of UDP-glucuronosyltransferase and its endogenous substrate uridine 5'-diphosphoglucuronic acid in human tissues. Eur J Clin Pharmacol. 1991;41(4):345-50.
9. Fondeur-Gelinotte M, Lattard V, Oriol R, Mollicone R, Jacquinet JC, Mulliert G, Gulberti S, Netter P, Magdalou J, Ouzzine M, Fournel-Gigleux S: Phylogenetic and mutational analyses reveal key residues for UDP-glucuronic acid binding and activity of beta1,3-glucuronosyltransferase I (GlcAT-I). Protein Sci. 2006 Jul;15(7):1667-78.
10. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
11. Clinical Guide to Laboratory Tests, 2nd Ed. Norbert W. Tietz 1990
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=11420884
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=13984680
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=14351193