UDP-alpha-D-glucuronic acid

Identification

Name
UDP-alpha-D-glucuronic acid
Accession Number
DB03041  (EXPT03177)
Type
Small Molecule
Groups
Experimental
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
  • uridine diphosphate glucuronic acid
  • Uridine-5'-diphosphate-glucuronic acid
Categories
UNII
04SZC4MEFQ
CAS number
2616-64-0
Weight
Average: 580.2853
Monoisotopic: 580.034284934
Chemical Formula
C15H22N2O18P2
InChI Key
HDYANYHVCAPMJV-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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGalactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 3Not AvailableHuman
UUDP-glucose 6-dehydrogenaseNot AvailableStreptococcus pyogenes
UUDP-glucose 4-epimerase
substrate
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00935
KEGG Compound
C00167
PubChem Compound
17473
PubChem Substance
46504863
ChemSpider
16522
BindingDB
50209665
ChEBI
17200
ChEMBL
CHEMBL228057
HET
UGA
Wikipedia
Uridine_diphosphate_glucuronic_acid
PDB Entries
1dlj / 1kws / 1z7e / 2qg4 / 2y0c / 2y0d / 2y0e / 2z86 / 3gg2 / 3pjg
show 1 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0901110000-d434fad6ebdd7797c473
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-3911000000-b27e8f43f987aadd35fd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-4900000000-6c8ee9c73e164f9ccf76
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0imu-4601190000-7a0e82462b874f18b2c4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-9817020000-a72141b1bee762a83bc3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bvl-4901000000-5d52b1b8f03063646a7f
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine nucleotide sugars
Direct Parent
Pyrimidine nucleotide sugars
Alternative Parents
Pyrimidine ribonucleoside diphosphates / Pentose phosphates / Glucuronic acid derivatives / Glycosylamines / Monosaccharide phosphates / Organic pyrophosphates / Beta hydroxy acids and derivatives / Monoalkyl phosphates / Pyrimidones / Hydropyrimidines
show 18 more
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
show 34 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
UDP-sugar (CHEBI:17200)

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-...
Gene Name
B3GAT3
Uniprot ID
O94766
Uniprot Name
Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 3
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
Uniprot Name
UDP-glucose 6-dehydrogenase
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Udp-n-acetylglucosamine 4-epimerase activity
Specific Function
Catalyzes two distinct but analogous reactions: the reversible epimerization of UDP-glucose to UDP-galactose and the reversible epimerization of UDP-N-acetylglucosamine to UDP-N-acetylgalactosamine...
Gene Name
GALE
Uniprot ID
Q14376
Uniprot Name
UDP-glucose 4-epimerase
Molecular Weight
38281.435 Da
References
  1. Bhatia C, Oerum S, Bray J, Kavanagh KL, Shafqat N, Yue W, Oppermann U: Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships. Chem Biol Interact. 2015 Jun 5;234:114-25. doi: 10.1016/j.cbi.2014.12.013. Epub 2014 Dec 16. [PubMed:25526675]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:22