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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-10-01 18:05:29 UTC
Update Date2021-10-01 18:05:29 UTC
HMDB IDHMDB0304946
Secondary Accession NumbersNone
Metabolite Identification
Common NameIndole-3-acetic acid ethyl ester
Descriptionethyl 2-(1H-indol-3-yl)acetate 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. ethyl 2-(1H-indol-3-yl)acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
Ethyl 2-(1H-indol-3-yl)acetic acidGenerator
Indole-3-acetic acid ethyl esterMeSH
Ethyl 3-indoleacetic acidGenerator
Chemical FormulaC12H13NO2
Average Molecular Weight203.2371
Monoisotopic Molecular Weight203.094628665
IUPAC Nameethyl 2-(1H-indol-3-yl)acetate
Traditional Nameethyl 2-(1H-indol-3-yl)acetate
CAS Registry NumberNot Available
SMILES
CCOC(=O)CC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C12H13NO2/c1-2-15-12(14)7-9-8-13-11-6-4-3-5-10(9)11/h3-6,8,13H,2,7H2,1H3
InChI KeyHUDBDWIQSIGUDI-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
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.04ALOGPS
logP2.21ChemAxon
logS-2.6ALOGPS
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 Count4ChemAxon
Refractivity57.97 m³·mol⁻¹ChemAxon
Polarizability21.91 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
AllCCS[M+H]+144.83132859911
AllCCS[M+H-H2O]+140.69132859911
AllCCS[M+Na]+149.79532859911
AllCCS[M+NH4]+148.68532859911
AllCCS[M-H]-148.71432859911
AllCCS[M+Na-2H]-148.83532859911
AllCCS[M+HCOO]-149.06332859911
DeepCCS[M-2H]-177.18830932474
DeepCCS[M+Na]+152.72630932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indole-3-acetic acid ethyl ester,1TMS,isomer #1CCOC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C121919.7Semi standard non polar33892256
Indole-3-acetic acid ethyl ester,1TMS,isomer #1CCOC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C121876.5Standard non polar33892256
Indole-3-acetic acid ethyl ester,1TMS,isomer #1CCOC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C122303.7Standard polar33892256
Indole-3-acetic acid ethyl ester,1TBDMS,isomer #1CCOC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122148.2Semi standard non polar33892256
Indole-3-acetic acid ethyl ester,1TBDMS,isomer #1CCOC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122087.5Standard non polar33892256
Indole-3-acetic acid ethyl ester,1TBDMS,isomer #1CCOC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122413.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Indole-3-acetic acid ethyl ester GC-MS (1 TMS)splash10-0udi-0190000000-9ff7f511234eecd992ad2014-06-16HMDB team, MONA, MassBankView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 10V, Positive-QTOFsplash10-001i-0910000000-13351c26b7a034511c822021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 20V, Positive-QTOFsplash10-053r-0910000000-a888639e608fd01985c02021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 40V, Positive-QTOFsplash10-001i-4900000000-51fc457668a013d5f1452021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 10V, Negative-QTOFsplash10-0a4i-1920000000-05ad9a381447428a0a592021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 20V, Negative-QTOFsplash10-0560-0900000000-e4b5c541ac380f91db352021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 40V, Negative-QTOFsplash10-004i-0900000000-d795bf47b023cf7eb8fc2021-10-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13067
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. National Institute of Environmental Health Science (NIEHS) [Link]