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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-04-09 21:18:57 UTC
Update Date2019-07-23 07:13:23 UTC
HMDB IDHMDB0060001
Secondary Accession Numbers
  • HMDB60001
Metabolite Identification
Common NameIndole-3-acetic-acid-O-glucuronide
DescriptionIndole-3-acetic-acid-O-glucuronide is a conjugate of Indole-3-acetic-acid and glucuronide. A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides. (Wikipedia)
Structure
Data?1563866003
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[2-(1H-indol-3-yl)acetyl]oxy}oxane-2-carboxylateGenerator
Chemical FormulaC16H17NO8
Average Molecular Weight351.3081
Monoisotopic Molecular Weight351.095416525
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(1H-indol-3-yl)acetyl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(1H-indol-3-yl)acetyl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=CNC3=C2C=CC=C3)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C16H17NO8/c18-10(5-7-6-17-9-4-2-1-3-8(7)9)24-16-13(21)11(19)12(20)14(25-16)15(22)23/h1-4,6,11-14,16-17,19-21H,5H2,(H,22,23)/t11-,12-,13+,14-,16+/m0/s1
InChI KeyBPTLUNCVRGWZSW-JHZZJYKESA-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
  • Indole-3-acetic acid derivative
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.26 g/LALOGPS
logP-0.11ALOGPS
logP-0.24ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.75 m³·mol⁻¹ChemAxon
Polarizability33.5 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6912000000-966fe33f20413c2cf0b6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-1911022000-db6d3d519dfbdce478a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-057i-0903000000-af77dc75dc3504a6106aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-0900000000-e8f7a98e0d79d19e48b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0560-1900000000-1d39e6133188cfc327fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0902000000-e44c053e9952cb27b3ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05gi-1900000000-3a0dc031516b57da09c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-4900000000-1e87aa9b67aa9ab6b05eSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDNot Available
    KNApSAcK IDNot Available
    Chemspider IDNot Available
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound124202110
    PDB IDNot Available
    ChEBI ID89622
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565 ]