Record Information
Version1.0
Creation date2011-09-21 01:54:00 UTC
Update date2017-04-03 04:56:45 UTC
Primary IDFDB029324
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Indole carboxylic acid glucuronide
Description3-Indole carboxylic acid glucuronide is a natural human metabolites of Indole-3-carboxylic acid. Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite (PMID 4844607) and has been found elevated in patients with liver diseases (PMID 13905029). 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 Number120-72-9
Structure
Thumb
Synonyms
SynonymSource
3-Indole carboxylate glucuronideGenerator
Indole-3-carboxylate glucuronideHMDB
1H-Indole-3-carboxylate glucuronideHMDB
1H-Indole-3-carboxylic acid glucuronideHMDB
3-Indole carboxylic acid glucuronosideHMDB
3-Indolecarboxylate glucuronideHMDB
3-Indolecarboxylic acid glucuronideHMDB
3-Indoleformate glucuronideHMDB
3-Indoleformic acid glucuronideHMDB
3-Indolylcarboxylate glucuronideHMDB
3-Indolylcarboxylic acid glucuronideHMDB
Indole-3 carboxylate glucuronideHMDB
Indole-3-carboxilic acid-O-glucuronideHMDB
Indole-3-carboxylic acid glucuronideHMDB
Indole-3-carboxylic acid glucuronosideHMDB
Indole-3-carboxylicacid glucuronideHMDB
(3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylateGenerator
3-Indole Carboxylic acid glucuronidehmdb
Indole - 3 Carboxylate glucuronidehmdb
Predicted Properties
PropertyValueSource
Water Solubility8.93 g/LALOGPS
logP-0.14ALOGPS
logP-0.018ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.31 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.7 m³·mol⁻¹ChemAxon
Polarizability32.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H15NO8
IUPAC name(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C15H15NO8/c17-9-10(18)12(13(20)21)23-15(11(9)19)24-14(22)7-5-16-8-4-2-1-3-6(7)8/h1-5,9-12,15-19H,(H,20,21)/t9-,10-,11+,12?,15-/m0/s1
InChI KeyBDNWJTRKUBXAGH-DOVARBIBSA-N
Isomeric SMILESO[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CNC3=CC=CC=C23)OC([C@H]1O)C(O)=O
Average Molecular Weight337.2815
Monoisotopic Molecular Weight337.079766461
Classification
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
  • Indolecarboxylic acid derivative
  • Indole
  • Indole or derivatives
  • Pyrrole-3-carboxylic acid or derivatives
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Substituted pyrrole
  • Benzenoid
  • Vinylogous amide
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Azacycle
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Indole carboxylic acid glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4l-9221000000-e405acbb88ebd4f37923Spectrum
Predicted GC-MS3-Indole carboxylic acid glucuronide, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-4941047000-f01e76abc2e863b6a421Spectrum
Predicted GC-MS3-Indole carboxylic acid glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0902000000-e8fb84e81fcefb88928b2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-c6aa02214865ae939df32016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-1900000000-7c819f04717299b3f7432016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y3-1913000000-4ae8bab45fad6c393e9f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-1900000000-18e5eb04fe891824393f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xu-5900000000-af080777a9b1c93909a72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0609000000-9768d5748961306bdf082021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0902000000-fe9a3cf27ec94e3aaf832021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-1900000000-15a5ec877ba7065f42c62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0509000000-642d74c686a5391c75342021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-2932000000-0fefa625351cecfa36e02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-088ab2e521f234147fe42021-09-24View Spectrum
NMRNot Available
ChemSpider ID28533205
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481645
Pubchem Substance IDNot Available
ChEBI ID68486
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13189
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mothball
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
burnt
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference