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Human Metabolome Database Version 3.5

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Showing metabocard for Beta-D-Glucopyranuronic acid (HMDB10314)

Record Information
Version 3.5
Creation Date 2008-09-15 10:02:27 -0600
Update Date 2013-02-08 17:24:32 -0700
HMDB ID HMDB10314
Secondary Accession Numbers None
Metabolite Identification
Common Name Beta-D-Glucopyranuronic acid
Description Salicylacyl glucuronide is a natural human metabolite of acetylsilacylic acid generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxybenzoyl)oxyoxane-2-carboxylic acid
  2. 1-(2-Hydroxybenzoate
  3. 1-(2-Hydroxybenzoate) beta-D-Glucopyranuronic acid
  4. 1-(2-Hydroxybenzoate) beta-delta-Glucopyranuronic acid
  5. 1-(2-Hydroxybenzoic acid
  6. Acyl SA glucuronide
  7. Salicyl acyl glucuronide
Chemical Formula C13H14O9
Average Molecular Weight 314.2449
Monoisotopic Molecular Weight 314.063782046
IUPAC Name (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxyphenyl)carbonyloxy]oxane-2-carboxylic acid
Traditional IUPAC Name (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxyphenyl)carbonyloxy]oxane-2-carboxylic acid
CAS Registry Number 29315-53-5
SMILES O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CC=CC=C2O)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier InChI=1S/C13H14O9/c14-6-4-2-1-3-5(6)12(20)22-13-9(17)7(15)8(16)10(21-13)11(18)19/h1-4,7-10,13-17H,(H,18,19)/t7-,8-,9+,10-,13-/m0/s1
InChI Key IXVVXKRKCLJCKA-UNLLLRGISA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Sugar Acids and Derivatives
Sub Class Glucuronic Acid Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • Hexoses
  • O-glycosyl Compounds
Substituents
  • 1,2 Diol
  • Benzoate
  • Benzoyl
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
  • Hydroxybenzoic Acid
  • Oxane
  • Phenol
  • Phenol Derivative
  • Salicylate
  • Secondary Alcohol
Direct Parent Glucuronic Acid Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Waste products
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 20.8 g/L ALOGPS
LogP -0.62 ALOGPS
LogP 0.23 ChemAxon
LogS -1.18 ALOGPS
pKa (strongest acidic) 2.95 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 153.75 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 67.59 ChemAxon
Polarizability 28.11 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027466
KNApSAcK ID Not Available
Chemspider ID 147725 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB10314 Link_out
Metagene Link HMDB10314 Link_out
METLIN ID Not Available
PubChem Compound 168876 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Liu JH, Smith PC: Direct analysis of salicylic acid, salicyl acyl glucuronide, salicyluric acid and gentisic acid in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):61-70. Pubmed: 8634769 Link_out
  2. Dickinson RG, Baker PV, King AR: Studies on the reactivity of acyl glucuronides--VII. Salicyl acyl glucuronide reactivity in vitro and covalent binding of salicylic acid to plasma protein of humans taking aspirin. Biochem Pharmacol. 1994 Feb 9;47(3):469-76. Pubmed: 8117314 Link_out
  3. Shen JJ, Wanwimolruk S, Roberts MS: Novel direct high-performance liquid chromatographic method for determination of salicylate glucuronide conjugates in human urine. J Chromatogr. 1991 Apr 19;565(1-2):309-20. Pubmed: 1874875 Link_out
  4. Patel DK, Notarianni LJ, Bennett PN: Comparative metabolism of high doses of aspirin in man and rat. Xenobiotica. 1990 Aug;20(8):847-54. Pubmed: 2219967 Link_out
  5. Day RO, Furst DE, Dromgoole SH, Paulus HE: Changes in salicylate serum concentration and metabolism during chronic dosing in normal volunteers. Biopharm Drug Dispos. 1988 May-Jun;9(3):273-83. Pubmed: 3395669 Link_out
Enzymes
Name: Beta-glucuronidase
Reactions:
    Gene Name: GUSB
    Uniprot ID: P08236 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA