D-Glucuronic Acid

Identification

Name
D-Glucuronic Acid
Accession Number
DB03156  (EXPT01175)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • alpha-D-glucopyranuronic acid
  • alpha-D-glucuronic acid
  • alpha-delta-glucopyranuronic acid
  • alpha-delta-glucuronic acid
  • D-(+)-glucuronate
  • D-(+)-glucuronic acid
  • D-glucuronate
  • delta-(+)-glucuronate
  • delta-(+)-glucuronic acid
  • delta-glucuronate
  • GCU
  • Glucosiduronate
  • Glucosiduronic acid
  • Glucuronate
  • Glucuronic acid
Categories
UNII
00A9JB14O6
CAS number
6556-12-3
Weight
Average: 194.1394
Monoisotopic: 194.042652674
Chemical Formula
C6H10O7
InChI Key
AEMOLEFTQBMNLQ-QIUUJYRFSA-N
InChI
InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6+/m0/s1
IUPAC Name
(2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHyaluronate lyaseNot AvailableStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
UChondroitinase-ACNot AvailablePedobacter heparinus (strain ATCC 13125 / DSM 2366 / NCIB 9290)
UAlpha-glucuronidaseNot AvailableGeobacillus stearothermophilus
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

Synthesis Reference

Gerhard Weber, Karlheinz Schrader, "D-glucuronic acid-urea condensate preparation for smoothing human skin." U.S. Patent US4703041, issued October 27, 1987.

US4703041
General References
Not Available
External Links
KEGG Compound
C08350
PubChem Compound
441478
PubChem Substance
46504768
ChemSpider
390202
ChEBI
28860
ChEMBL
CHEMBL1159524
HET
BDP
Wikipedia
Glucuronic_acid
PDB Entries
1cap / 1gqk / 1gql / 1hm3 / 1hmw / 1hua / 1loh / 1lxk / 1lxm / 1n7q
show 40 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
PropertyValueSource
melting point (°C)165 °CPhysProp
water solubility485 mg/mLHMP experimental
logP-2.57HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility295.0 mg/mLALOGPS
logP-2.3ALOGPS
logP-2.6ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.79 m3·mol-1ChemAxon
Polarizability16.37 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.578
Blood Brain Barrier+0.5892
Caco-2 permeable-0.7
P-glycoprotein substrateNon-substrate0.6735
P-glycoprotein inhibitor INon-inhibitor0.9619
P-glycoprotein inhibitor IINon-inhibitor0.9857
Renal organic cation transporterNon-inhibitor0.9366
CYP450 2C9 substrateNon-substrate0.8459
CYP450 2D6 substrateNon-substrate0.9061
CYP450 3A4 substrateNon-substrate0.7387
CYP450 1A2 substrateNon-inhibitor0.9586
CYP450 2C9 inhibitorNon-inhibitor0.977
CYP450 2D6 inhibitorNon-inhibitor0.9713
CYP450 2C19 inhibitorNon-inhibitor0.9793
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.97
Ames testNon AMES toxic0.9426
CarcinogenicityNon-carcinogens0.9428
BiodegradationReady biodegradable0.7998
Rat acute toxicity1.6092 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9828
hERG inhibition (predictor II)Non-inhibitor0.9744
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as glucuronic acid derivatives. These are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Glucuronic acid derivatives
Alternative Parents
Beta hydroxy acids and derivatives / Pyrans / Oxanes / Monosaccharides / Secondary alcohols / Hemiacetals / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids
show 3 more
Substituents
Glucuronic acid or derivatives / Beta-hydroxy acid / Hydroxy acid / Pyran / Monosaccharide / Oxane / Hemiacetal / Secondary alcohol / Carboxylic acid derivative / Carboxylic acid
show 9 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
D-glucopyranuronic acid (CHEBI:28860)

Targets

Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
General Function
Hyaluronate lyase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q54873
Uniprot Name
Hyaluronate lyase
Molecular Weight
120770.645 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
Pedobacter heparinus (strain ATCC 13125 / DSM 2366 / NCIB 9290)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
cslA
Uniprot ID
Q59288
Uniprot Name
Chondroitinase-AC
Molecular Weight
79693.285 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
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Xylan alpha-1,2-glucuronosidase activity
Specific Function
Not Available
Gene Name
aguA
Uniprot ID
Q8VVD2
Uniprot Name
Xylan alpha-1,2-glucuronidase
Molecular Weight
78485.96 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:09