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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2008-09-15 16:02:27 UTC
Update Date2019-07-23 05:54:21 UTC
HMDB IDHMDB0010314
Secondary Accession Numbers
  • HMDB10314
Metabolite Identification
Common NameBeta-D-Glucopyranuronic acid
DescriptionSalicylacyl 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
Data?1563861261
Synonyms
ValueSource
b-D-GlucopyranuronateGenerator
b-D-Glucopyranuronic acidGenerator
beta-D-GlucopyranuronateGenerator
Β-D-glucopyranuronateGenerator
Β-D-glucopyranuronic acidGenerator
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(2-hydroxybenzoyl)oxyoxane-2-carboxylic acidHMDB
1-(2-HydroxybenzoateHMDB
1-(2-Hydroxybenzoate) beta-D-glucopyranuronic acidHMDB
1-(2-Hydroxybenzoate) beta-delta-glucopyranuronic acidHMDB
1-(2-Hydroxybenzoic acidHMDB
Acyl sa glucuronideHMDB
Salicyl acyl glucuronideHMDB
Salicylacyl glucuronideHMDB
Chemical FormulaC13H14O9
Average Molecular Weight314.2449
Monoisotopic Molecular Weight314.063782046
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxybenzoyloxy)oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxybenzoyloxy)oxane-2-carboxylic acid
CAS Registry Number29315-53-5
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 KeyIXVVXKRKCLJCKA-UNLLLRGISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • O-hydroxybenzoic acid ester
  • Salicylic acid or derivatives
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Beta-hydroxy acid
  • Pyran
  • Hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Oxane
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility20.8 g/LALOGPS
logP-0.62ALOGPS
logP0.23ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.95ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.59 m³·mol⁻¹ChemAxon
Polarizability28.11 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9430000000-2a4f0c4deaff6c4abb73JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-06r6-2511119000-59f9672d4beab9a8844fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007a-0921000000-deba0e5c59d184c9d5e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0900000000-bbf3cfca43ba05860073JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-6900000000-0c1d8f8007fa6b2a3c2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-029i-2933000000-5b35c7a1e0ad8e165c2fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-7920000000-b2e496121f275b5584ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-0e8d009e9ee72ff94b65JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027466
KNApSAcK IDNot Available
Chemspider ID147725
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound168876
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot 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 ]
  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 ]
  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 ]
  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 ]
  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 ]

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Plays an important role in the degradation of dermatan and keratan sulfates.
Gene Name:
GUSB
Uniprot ID:
P08236
Molecular weight:
74731.46