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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:13:06 UTC
NP-MRD IDNP0000134
Secondary Accession NumbersNone
Natural Product Identification
Common NameUridine diphosphate glucuronic acid
DescriptionUridine diphosphate glucuronic acid is a 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. The transfer of glucuronic acid from UDP-alpha-D-glucuronic acid onto a terminal galactose residue is done by beta1,3-glucuronosyltransferases, responsible for the completion of the protein-glycosaminoglycan linkage region of proteoglycans and of the HNK1 epitope of glycoproteins and glycolipids. In humans the enzyme galactose-beta-1,3-glucuronosyltransferase I completes the synthesis of the common linker region of glycosaminoglycans (GAGs) by transferring glucuronic acid (GlcA) onto the terminal galactose of the glycopeptide primer of proteoglycans. The GAG chains of proteoglycans regulate major biological processes such as cell proliferation and recognition, extracellular matrix deposition, and morphogenesis. (PMID: 16815917 ).
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 Mass580.2853 Da
Monoisotopic Mass580.03428 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaPlant
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Beta-hydroxy acid
  • Monoalkyl phosphate
  • Pyrimidone
  • Hydropyrimidine
  • Hydroxy acid
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyran
  • Pyrimidine
  • Alkyl phosphate
  • Tetrahydrofuran
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary alcohol
  • Urea
  • Lactam
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0000935
DrugBank IDDB03041
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. 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. [PubMed:14977865 ]
  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. [PubMed:15729623 ]
  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. [PubMed:11420884 ]
  4. 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. [PubMed:7956743 ]
  5. 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. [PubMed:11334344 ]
  6. 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. [PubMed:11259324 ]
  7. 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. [PubMed:1804651 ]
  8. 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. [PubMed:16815917 ]
  9. (). Clinical Guide to Laboratory Tests, 2nd Ed. Norbert W. Tietz 1990. .