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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:31:28 UTC
Update Date2019-07-23 06:18:52 UTC
HMDB IDHMDB0035514
Secondary Accession Numbers
  • HMDB35514
Metabolite Identification
Common Namexi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid
Descriptionxi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid, also known as oxindole-3-acetic acid or 2-oxindol-3-yl-acetate, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, xi-2,3-Dihydro-2-oxo-1H-indole-3-acetic acid has been detected, but not quantified in, several different foods, such as brassicas, cereals and cereal products, fats and oils, and fruits. This could make XI-2,3-dihydro-2-oxo-1H-indole-3-acetic acid a potential biomarker for the consumption of these foods.
Structure
Data?1563862732
Synonyms
ValueSource
2-Oxindol-3-yl-acetic acidChEBI
Oxindole-3-acetic acidChEBI
2-Oxindol-3-yl-acetateGenerator
Oxindole-3-acetateGenerator
XI-2,3-dihydro-2-oxo-1H-indole-3-acetateGenerator
2-(2-oxo-3-Indolinyl)acetic acidHMDB
2-Hydroxy-1H-indole-3-acetic acidHMDB
2-Oxindole-3-acetateGenerator
2-Oxindole-3-acetic acidMeSH
Chemical FormulaC10H9NO3
Average Molecular Weight191.1834
Monoisotopic Molecular Weight191.058243159
IUPAC Name2-(2-hydroxy-3H-indol-3-yl)acetic acid
Traditional Name(2-hydroxy-3H-indol-3-yl)acetic acid
CAS Registry Number2971-31-5
SMILES
OC(=O)CC1C(O)=NC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H9NO3/c12-9(13)5-7-6-3-1-2-4-8(6)11-10(7)14/h1-4,7H,5H2,(H,11,14)(H,12,13)
InChI KeyILGMGHZPXRDCCS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • Indole
  • Dihydroindole
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point146 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.66 g/LALOGPS
logP0.43ALOGPS
logP1.47ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)0.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.18 m³·mol⁻¹ChemAxon
Polarizability18.77 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-000w-1900000000-e5a212fef915b5bbb8afSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-7091000000-9a678e4207c2b4a64178Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-61b1ae7ba4cc295dfebcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-2900000000-df96872eeeeda61461a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6y-4900000000-cfdd72592cdd31791a7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-64cbb94b04cb529faf96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-1900000000-a9a300173b2b5995f6d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-8900000000-26716a18ea0f2ee82b56Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014206
KNApSAcK IDNot Available
Chemspider ID2338343
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3080590
PDB IDNot Available
ChEBI ID133221
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .