indole-3-acetonitrile (PAMDB120247)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120247
Identification
Name: indole-3-acetonitrile
Description:A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (indol-3-yl)acetonitrile
  • (Indol-3-yl)acetonitrile
  • (Indole-3-yl)acetonitrile
  • 3-(cyanomethyl)indole
  • 3-Indoleacetonitrile
  • 3-indolylacetonitrile
  • Indol-3-ylacetonitrile
  • Indole-3-acetonitrile
Chemical Formula: C10H8N2
Average Molecular Weight: 156.187
Monoisotopic Molecular Weight: 156.06874
InChI Key: DMCPFOBLJMLSNX-UHFFFAOYSA-N
InChI:InChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
CAS number: 771-51-7
IUPAC Name:1H-indol-3-ylacetonitrile
Traditional IUPAC Name: indole-3-acetonitrile
SMILES:C2(NC1(C=CC=CC=1C(CC#N)=2))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct Parent 3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 35 - 37 °C
Experimental Properties:
PropertyValueReference
Melting Point35 - 37 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.5 mg/mLALOGPS
logP2.73ALOGPS
logP1.77ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area39.58 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.43 m3·mol-1ChemAxon
Polarizability16.74 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
indole-3-acetonitrile + Water → indole-3-acetamide
Pathways:
  • indole-3-acetate biosynthesis IV (bacteria)PWY-5025
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-2950000000-640d53401ab5b06bad68View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-686ec8d86a82008f6a87View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-0f41c00c3703e04901e8View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-1900000000-144022b6dfec80ddd4a3View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-686ec8d86a82008f6a87View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-0f41c00c3703e04901e8View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-1900000000-144022b6dfec80ddd4a3View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9b52919ba61c73ce0adeView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f8b24a877c386d550c92View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-fc82dffe3b09577e06eeView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9b52919ba61c73ce0adeView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f8b24a877c386d550c92View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-fc82dffe3b09577e06eeView in MoNA
    MSMass Spectrum (Electron Ionization)splash10-0a4i-2900000000-be863c7acf7363ffeedcView in MoNA
    1D NMR1H NMR SpectrumNot Available
    1D NMR13C NMR SpectrumNot Available
    References
    References:
    • Pedras MS, Nycholat CM, Montaut S, Xu Y, Khan AQ (2002)Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Phytochemistry 59, Pubmed: 11867093
    • Michnovicz JJ, Bradlow HL (1990)Induction of estradiol metabolism by dietary indole-3-carbinol in humans. Journal of the National Cancer Institute 82, Pubmed: 2342128
    Synthesis Reference: Ahmad, A.; Spenser, Ian D. 3-Indolepyruvic acid oxime as the precursor of 3-indoleacetonitrile. Canadian Journal of Chemistry (1960), 38 1625-34.
    Material Safety Data Sheet (MSDS) Download (PDF)
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC17566
    HMDBHMDB06524
    CHEMSPIDER312357
    PUBCHEM351795
    KNAPSACKC00000107
    CHEBI17566
    LIGAND-CPDC02938