Record Information
Version1.0
Creation date2011-09-21 00:12:10 UTC
Update date2015-07-21 06:57:09 UTC
Primary IDFDB022325
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number2616-64-0
Structure
Thumb
Synonyms
SynonymSource
a-D-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyroate)HMDB
a-D-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)hmdb
a-D-Glucopyranuronic acid ester with uridine 5'-pyroateHMDB
a-D-Glucopyranuronic acid ester with uridine 5'-pyrophosphatehmdb
alpha-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diate)HMDB
alpha-D-Glucopyranuronic acid 1-P'-ester with uridine 5'-(trihydrogen diphosphate)hmdb
alpha-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyroate)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 diate)HMDB
alpha-delta-Glucopyranuronic acid 1-P'-ester with uridine 5'-(trihydrogen diphosphate)hmdb
alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyroateHMDB
alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphatehmdb
Glucopyranuronic acid 1-ester with uridine 5'-pyroateHMDB
Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphatehmdb
UDP glucuronatehmdb
Udp glucuronic acidhmdb
UDP-a-D-GlucuronateGenerator
UDP-a-D-Glucuronic acidGenerator
UDP-alpha-D-glucuronatehmdb
UDP-alpha-D-Glucuronic acidGenerator
UDP-alpha-delta-glucuronatehmdb
UDP-D-glucuronatehmdb
UDP-D-glucuronic acidhmdb
UDP-delta-glucuronatehmdb
UDP-delta-glucuronic acidhmdb
UDP-GlcUAhmdb
UDP-glucuronatehmdb
UDP-Glucuronic acidGenerator
UDP-α-D-glucuronateGenerator
UDP-α-D-glucuronic acidGenerator
UDPGAhmdb
UDPglucuronatehmdb
UDPglucuronic acidGenerator
UGAhmdb
Uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diate]HMDB
uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diphosphate]hmdb
Uridine 5'-dio-a-D-glucuronateHMDB
Uridine 5'-dio-a-D-glucuronic acidHMDB
Uridine 5'-dio-alpha-delta-glucuronateHMDB
Uridine 5'-dio-alpha-delta-glucuronic acidHMDB
Uridine 5'-dio-glucuronic acidHMDB
Uridine 5'-dioglucuronateHMDB
Uridine 5'-dioglucuronic acidHMDB
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 diate glucuronateGenerator
Uridine diate glucuronic acidChEBI
Uridine diate-glucuronateHMDB
Uridine diic acid glucuronic acidGenerator
Uridine dio-D-glucuronateHMDB
Uridine dio-D-glucuronic acidHMDB
Uridine dio-delta-glucuronateHMDB
Uridine dio-delta-glucuronic acidHMDB
Uridine dioglucuronateHMDB
Uridine dioglucuronic acidHMDB
Uridine diphosphate glucuronatehmdb
Uridine diphosphate glucuronic acidhmdb
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 pyrooglucuronateHMDB
Uridine pyrooglucuronic acidHMDB
Uridine pyrophosphoglucuronatehmdb
Uridine pyrophosphoglucuronic acidhmdb
URIDINE-5'-diate-glucuronateGenerator
URIDINE-5'-diATE-glucuronIC ACIDChEBI
URIDINE-5'-diic acid-glucuronic acidGenerator
Uridinedioglucuronic acidHMDB
Uridinediphosphoglucuronic acidhmdb
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
Polarizability45.26 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H22N2O18P2
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
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 KeyInChIKey=HDYANYHVCAPMJV-LXQIFKJMSA-N
Isomeric SMILES[H]OC(=O)[C@@]1([H])O[C@]([H])(OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]2([H])O[C@@]([H])(N3C([H])=C([H])C(=O)N([H])C3=O)[C@]([H])(O[H])[C@]2([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Average Molecular Weight580
Monoisotopic Molecular Weight580
Classification
DescriptionThis compound belongs to the class of chemical entities known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
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
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydroxy acid
  • Hydropyrimidine
  • Monosaccharide
  • Pyrimidine
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Pyran
  • Oxane
  • Phosphoric acid ester
  • Vinylogous amide
  • Oxolane
  • Heteroaromatic compound
  • Urea
  • Secondary alcohol
  • Lactam
  • Polyol
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
ChemSpider ID16522
ChEMBL IDCHEMBL228057
KEGG Compound IDC00167
Pubchem Compound ID17473
Pubchem Substance IDNot Available
ChEBI ID17200
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00935
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34117
KNApSAcK IDNot Available
HET IDUGA
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDUridine diphosphate glucuronic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B10UGT2B10P36537
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-8UGT1A8Q9HAW9
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 1-10UGT1A10Q9HAW8
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 1-7UGT1A7Q9HAW7
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
Exostosin-1EXT1Q16394
Exostosin-2EXT2Q93063
Chondroitin sulfate glucuronyltransferaseCHPF2Q9P2E5
Pathways
NameSMPDB LinkKEGG Link
Nucleotide Sugars MetabolismSMP00010 map00520
Starch and Sucrose MetabolismSMP00058 map00500
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference