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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:32:20 UTC
Update Date2020-02-26 21:44:17 UTC
HMDB IDHMDB0029738
Secondary Accession Numbers
  • HMDB29738
Metabolite Identification
Common NameIndole-3-methyl acetate
DescriptionIndole-3-methyl acetate, also known as methyl indole-3-acetate (methyl-IAA), is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 30120222 ). Pediatric enthesitis-related arthritis (ERA) patients (i.e. spondyloarthropathy associated with inflammatory bowel disease) have intestinal inflammation and decreased gut microbial diversity. Such alterations in the gut microbiota resulted in the reduction of tryptophan metabolism and several tryptophan metabolites in pediatric ERA fecal samples, including indole-3-methyl acetate (PMID: 27786174 ). Indole-3-methyl acetate is found in apple, and has been isolated from immature seeds of beach pea (Lathyrus maritimus), Vicia amurensis, wild soybean (Glycine soja), lobiya (Vigna catiang var. sinensis) and hyacinth bean (Dolichos lablab).
Structure
Data?1582753457
Synonyms
ValueSource
beta-Indolylacetic acid methyl esterChEBI
Indole-3-acetic acid, methyl esterChEBI
Methyl 3-indolylacetateChEBI
Methyl beta-indoleacetateChEBI
Methyl beta-indolylacetateChEBI
Methyl indol-3-ylacetateChEBI
b-Indolylacetate methyl esterGenerator
b-Indolylacetic acid methyl esterGenerator
beta-Indolylacetate methyl esterGenerator
Β-indolylacetate methyl esterGenerator
Β-indolylacetic acid methyl esterGenerator
Indole-3-acetate, methyl esterGenerator
Methyl 3-indolylacetic acidGenerator
Methyl b-indoleacetateGenerator
Methyl b-indoleacetic acidGenerator
Methyl beta-indoleacetic acidGenerator
Methyl β-indoleacetateGenerator
Methyl β-indoleacetic acidGenerator
Methyl b-indolylacetateGenerator
Methyl b-indolylacetic acidGenerator
Methyl beta-indolylacetic acidGenerator
Methyl β-indolylacetateGenerator
Methyl β-indolylacetic acidGenerator
Methyl indol-3-ylacetic acidGenerator
Indole-3-methyl acetic acidGenerator
1H-Indole-3-acetic acid, methyl esterHMDB
beta -Indolylacetic acid methyl esterHMDB
IAA methyl esterHMDB
Indole-3-acetic acid methyl esterHMDB
INDOLE-3-acetIC ACID methylesterHMDB
MeiaaHMDB
Methyl 1H-indol-3-ylacetateHMDB
Methyl 2-(1H-indol-3-yl)acetateHMDB
Methyl beta -indoleacetateHMDB
Methyl beta -indolylacetateHMDB
Methyl iaaHMDB
Methyl indole-3-acetateHMDB
Methylester OF 3-indoleacetic acidHMDB
Methyl (indol-3-yl)acetic acidGenerator
(1H-Indol-3-yl)acetic acid methyl esterHMDB
Indolyl-3-acetic acid methyl esterHMDB
Methyl 1H-indole-3-acetateHMDB
Methyl-IAAHMDB
Chemical FormulaC11H11NO2
Average Molecular Weight189.2105
Monoisotopic Molecular Weight189.078978601
IUPAC Namemethyl 2-(1H-indol-3-yl)acetate
Traditional Namemethyl 1H-indol-3-ylacetate
CAS Registry Number1912-33-0
SMILES
COC(=O)CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C11H11NO2/c1-14-11(13)6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,12H,6H2,1H3
InChI KeyKTHADMDGDNYQRX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndole-3-acetic acid derivatives
Alternative Parents
Substituents
  • Indole-3-acetic acid derivative
  • 3-alkylindole
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Methyl ester
  • Pyrrole
  • Carboxylic acid ester
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP2.61ALOGPS
logP1.86ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)15.04ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area42.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.22 m³·mol⁻¹ChemAxon
Polarizability19.78 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, Positivesplash10-001i-1900000000-12f9f10dded04cfa55bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000b-9100000000-dccaeed4872b37996ae0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0900000000-7d3a77321747e2d401acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067l-0900000000-62938325fd422dd6deb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-28357c158878b23b8d7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-16a552d5cbd68ae58f19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1900000000-bcfc9d1086e698bcc38aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-2900000000-c2f4d4b1ed40e99b468fSpectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-836e9d12c7099556a53eSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
UrineDetected and Quantified0.768 umol/mmol creatinineAdult (>18 years old)Female
Pregnancy
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000936
KNApSAcK IDC00000101
Chemspider ID67279
KEGG Compound IDNot Available
BioCyc IDCPD-10546
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74706
PDB IDNot Available
ChEBI ID72782
Food Biomarker OntologyNot Available
VMH IDCE2122
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]
  2. Stoll ML, Kumar R, Lefkowitz EJ, Cron RQ, Morrow CD, Barnes S: Fecal metabolomics in pediatric spondyloarthritis implicate decreased metabolic diversity and altered tryptophan metabolism as pathogenic factors. Genes Immun. 2016 Dec;17(7):400-405. doi: 10.1038/gene.2016.38. Epub 2016 Oct 27. [PubMed:27786174 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .