methyl (indol-3-yl)acetate (PAMDB120037)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120037
Identification
Name: methyl (indol-3-yl)acetate
Description:The methyl ester of indole-3-acetic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • β-indolylacetic acid methyl ester
  • Indole-3-acetic acid, methyl ester
  • methyl (indol-3-yl)acetate
  • methyl 3-indolylacetate
  • methyl β-indoleacetate
  • methyl β-indolylacetate
  • Methyl indol-3-ylacetate
Chemical Formula: C11H11NO2
Average Molecular Weight: 189.213
Monoisotopic Molecular Weight: 189.07898
InChI Key: KTHADMDGDNYQRX-UHFFFAOYSA-N
InChI: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
CAS number: 1912-33-0
IUPAC Name:methyl 1H-indol-3-ylacetate
Traditional IUPAC Name: methyl 2-(1H-indol-3-yl)acetate
SMILES:C1(NC2(=C(C=1CC(=O)OC)C=CC=C2))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as indole-3-acetic acid derivatives. These are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Indoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct Parent Indole-3-acetic acid derivatives
Alternative Parents
Substituents
  • Indole-3-acetic acid derivative
  • Indole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Methyl ester
  • Pyrrole
  • Carboxylic acid ester
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: 125 °C
Experimental Properties:
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.15 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.22 m3·mol-1ChemAxon
Polarizability19.78 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
methyl (indol-3-yl)acetate + Water → Hydrogen ion + indole-3-acetate + Methanol
Pathways:
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0900000000-7d3a77321747e2d401acView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067l-0900000000-62938325fd422dd6deb0View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-28357c158878b23b8d7dView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-16a552d5cbd68ae58f19View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1900000000-bcfc9d1086e698bcc38aView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-2900000000-c2f4d4b1ed40e99b468fView in MoNA
    MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-836e9d12c7099556a53eView in MoNA
    References
    References:
    • Zubieta C, Ross JR, Koscheski P, Yang Y, Pichersky E, Noel JP (2003)Structural basis for substrate recognition in the salicylic acid carboxyl methyltransferase family. The Plant cell 15, Pubmed: 12897246
    • Zhang S, Li Z, Wu X, Huang Q, Shen HM, Ong CN (2006)Methyl-3-indolylacetate inhibits cancer cell invasion by targeting the MEK1/2-ERK1/2 signaling pathway. Molecular cancer therapeutics 5, Pubmed: 17172432
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC72782
    HMDBHMDB29738
    CHEBI72782
    CHEMSPIDER67279
    PUBCHEM74706
    KNAPSACKC00000101