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Identification
NameUDP-alpha-D-glucuronic acid
Accession NumberDB03041  (EXPT03177)
TypeSmall Molecule
GroupsExperimental
Description

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. [PubChem]

Structure
Thumb
Synonyms
UDP-alpha-D-glucuronate
UDP-D-glucuronate
UDP-glucuronate
UDP-Glucuronic Acid
UDPglucuronate
UDPglucuronate
uridine diphosphate glucuronic acid
Uridine-5'-diphosphate-glucuronic acid
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII04SZC4MEFQ
CAS number2616-64-0
WeightAverage: 580.2853
Monoisotopic: 580.034284934
Chemical FormulaC15H22N2O18P2
InChI KeyHDYANYHVCAPMJV-LXQIFKJMSA-N
InChI
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
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
SMILES
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[[email protected]]2O[C@@H]([C@@H](O)[[email protected]](O)[[email protected]]2O)C(O)=O)O[[email protected]]([C@@H]1O)N1C=CC(=O)NC1=O
Taxonomy
DescriptionThis compound 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
  • Glucuronic acid or derivatives
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Monoalkyl phosphate
  • Pyrimidone
  • Beta-hydroxy acid
  • Alkyl phosphate
  • Pyrimidine
  • Pyran
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydroxy acid
  • Hydropyrimidine
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Secondary alcohol
  • Polyol
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9675
Blood Brain Barrier+0.522
Caco-2 permeable-0.8251
P-glycoprotein substrateNon-substrate0.7638
P-glycoprotein inhibitor INon-inhibitor0.8023
P-glycoprotein inhibitor IINon-inhibitor0.9441
Renal organic cation transporterNon-inhibitor0.9396
CYP450 2C9 substrateNon-substrate0.6646
CYP450 2D6 substrateNon-substrate0.8589
CYP450 3A4 substrateNon-substrate0.5312
CYP450 1A2 substrateNon-inhibitor0.867
CYP450 2C9 inhibitorNon-inhibitor0.8764
CYP450 2D6 inhibitorNon-inhibitor0.8742
CYP450 2C19 inhibitorNon-inhibitor0.8316
CYP450 3A4 inhibitorNon-inhibitor0.7204
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8237
Ames testNon AMES toxic0.8575
CarcinogenicityNon-carcinogens0.9131
BiodegradationNot ready biodegradable0.5835
Rat acute toxicity2.3361 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9732
hERG inhibition (predictor II)Non-inhibitor0.6161
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.32 m3·mol-1ChemAxon
Polarizability45.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
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
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein phosphatase activator activity
Specific Function:
Glycosaminoglycans biosynthesis. Involved in forming the linkage tetrasaccharide present in heparan sulfate and chondroitin sulfate. Transfers a glucuronic acid moiety from the uridine diphosphate-glucuronic acid (UDP-GlcUA) to the common linkage region trisaccharide Gal-beta-1,3-Gal-beta-1,4-Xyl covalently bound to a Ser residue at the glycosaminylglycan attachment site of proteoglycans. Can a...
Gene Name:
B3GAT3
Uniprot ID:
O94766
Molecular Weight:
37121.52 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Streptococcus pyogenes
Pharmacological action
unknown
General Function:
Udp-glucose 6-dehydrogenase activity
Specific Function:
Catalyzes the formation of UDP-glucuronic acid which is required for capsular hyaluronic acid synthesis.
Gene Name:
hasB
Uniprot ID:
P0C0F4
Molecular Weight:
45482.795 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 06, 2016 15:18