You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameD-Glucuronic Acid
Accession NumberDB03156  (EXPT01175)
TypeSmall Molecule
GroupsExperimental
DescriptionNot 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
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
Categories
UNII8A5D83Q4RW
CAS number6556-12-3
WeightAverage: 194.1394
Monoisotopic: 194.042652674
Chemical FormulaC6H10O7
InChI KeyInChIKey=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
O[C@@H]1O[C@@H]([C@@H](O)[[email protected]](O)[[email protected]]1O)C(O)=O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentGlucuronic acid derivatives
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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-0.578
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point165 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 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
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
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
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
Molecular Weight:
78485.96 Da
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23