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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:32:20 UTC
Update Date2022-03-07 02:52:16 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

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available138.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00002172
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.20531661259
DarkChem[M-H]-142.74331661259
DeepCCS[M+H]+139.76430932474
DeepCCS[M-H]-136.88830932474
DeepCCS[M-2H]-173.18230932474
DeepCCS[M+Na]+148.7230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Indole-3-methyl acetateCOC(=O)CC1=CNC2=C1C=CC=C22824.9Standard polar33892256
Indole-3-methyl acetateCOC(=O)CC1=CNC2=C1C=CC=C21551.9Standard non polar33892256
Indole-3-methyl acetateCOC(=O)CC1=CNC2=C1C=CC=C21871.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indole-3-methyl acetate,1TMS,isomer #1COC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C121851.7Semi standard non polar33892256
Indole-3-methyl acetate,1TMS,isomer #1COC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C121826.0Standard non polar33892256
Indole-3-methyl acetate,1TBDMS,isomer #1COC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122073.5Semi standard non polar33892256
Indole-3-methyl acetate,1TBDMS,isomer #1COC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122036.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-methyl acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-12f9f10dded04cfa55bb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indole-3-methyl acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-836e9d12c7099556a53e2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate , negative-QTOFsplash10-000b-9100000000-dccaeed4872b37996ae02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate 10V, Negative-QTOFsplash10-002r-0900000000-93ad72de0a2df050f91e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate 20V, Negative-QTOFsplash10-004i-0900000000-fa208ad1d037870ce3812021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate 40V, Negative-QTOFsplash10-003r-1900000000-71ddefb18c494b0b88ce2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate 20V, Positive-QTOFsplash10-001i-0900000000-7782a1ff5183bbcf0b072021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate 40V, Positive-QTOFsplash10-001i-3900000000-88cdd87758cddbe91c402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate 20V, Positive-QTOFsplash10-001i-0900000000-0bc333a2a19ec5358af92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate 10V, Positive-QTOFsplash10-001i-0900000000-330f6712f52543e28edf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate 40V, Positive-QTOFsplash10-0fai-3900000000-eae34f80cf307a8667182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Indole-3-methyl acetate 10V, Positive-QTOFsplash10-001i-0900000000-e8f4f5611dceb348f3992021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 10V, Positive-QTOFsplash10-052f-0900000000-7d3a77321747e2d401ac2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 20V, Positive-QTOFsplash10-067l-0900000000-62938325fd422dd6deb02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 40V, Positive-QTOFsplash10-001i-1900000000-28357c158878b23b8d7d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 10V, Negative-QTOFsplash10-000i-0900000000-16a552d5cbd68ae58f192015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 20V, Negative-QTOFsplash10-052r-1900000000-bcfc9d1086e698bcc38a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 40V, Negative-QTOFsplash10-0a4l-2900000000-c2f4d4b1ed40e99b468f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 10V, Negative-QTOFsplash10-052r-0900000000-dc056e18eb6d65f8971d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 20V, Negative-QTOFsplash10-0a4i-0900000000-b89c24a506e11c57df0d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 40V, Negative-QTOFsplash10-014i-0900000000-97eedbbda576017d285d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 10V, Positive-QTOFsplash10-001i-0900000000-132e476c89cb227616c92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 20V, Positive-QTOFsplash10-001i-0900000000-4304da11019da4e6b8952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-methyl acetate 40V, Positive-QTOFsplash10-0fc0-3900000000-ae7137b0676ddc9dfdc72021-09-24Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .