Record Information
Version1.0
Creation date2011-09-21 01:25:43 UTC
Update date2015-07-21 06:59:08 UTC
Primary IDFDB027514
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6-Hydroxy-5-methoxyindole glucuronide
Description6-Hydroxy-5-methoxyindole glucuronide is a natural human metabolite of 6-hydroxy-5-methoxyindole 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. [HMDB]
CAS Number77463-72-0
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP-0.14ALOGPS
logP-0.34ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.6 m³·mol⁻¹ChemAxon
Polarizability32.12 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H17NO8
IUPAC name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-methoxy-1H-indol-6-yl)oxy]oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C15H17NO8/c1-22-8-4-6-2-3-16-7(6)5-9(8)23-15-12(19)10(17)11(18)13(24-15)14(20)21/h2-5,10-13,15-19H,1H3,(H,20,21)/t10-,11-,12+,13-,15+/m0/s1
InChI KeyNECCHCPFFUXUOB-DKBOKBLXSA-N
Isomeric SMILESCOC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C2NC=CC2=C1
Average Molecular Weight339.2974
Monoisotopic Molecular Weight339.095416525
Classification
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Indole
  • Indole or derivatives
  • Anisole
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Pyran
  • Pyrrole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Polyol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Ether
  • Carboxylic acid
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS6-Hydroxy-5-methoxyindole glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0abc-9342000000-3b7608e6112d03939eeeSpectrum
Predicted GC-MS6-Hydroxy-5-methoxyindole glucuronide, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-5252149000-e830bf1b3fd29ed745e7Spectrum
Predicted GC-MS6-Hydroxy-5-methoxyindole glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0905000000-ca082ed83a5b427342ab2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-15d17db7edda9dfc757c2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1900000000-bf986b93479da03f8ce12016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pc-2937000000-a9c524fa5d8e98996df92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-1911000000-8becbdc4ee8f68b034eb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01pk-2900000000-20da055a41f44ecbed9f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0109000000-baa3136eee7eb13731152021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01wk-2913000000-6677f1aa7366381f26bd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0012-2912000000-4f1598452d9eda61ec282021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03kc-0519000000-59f4a469bc825b03517b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0893000000-0c9aeb64e73777f198792021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2910000000-7495b1f74b5a0ae53d202021-09-22View Spectrum
NMRNot Available
ChemSpider ID170260
ChEMBL IDNot Available
KEGG Compound IDC03033
Pubchem Compound ID196513
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10362
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference