indole-3-acetamide (PAMDB120131)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120131
Identification
Name: indole-3-acetamide
Description:A member of the class of indoles that is acetamide substituted by a 1H-indol-3-yl group at position 2. It is an intermediate in the production of plant hormone indole acetic acid (IAA).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1H-indole-3-acetamide
  • 3-indoleacetamide
  • Indole-3-acetamide
  • indole-3-acetamide
  • Indole-3-acetamide
  • indoleacetamide
Chemical Formula: C10H10N2O
Average Molecular Weight: 174.202
Monoisotopic Molecular Weight: 174.07932
InChI Key: ZOAMBXDOGPRZLP-UHFFFAOYSA-N
InChI:InChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)
CAS number: 879-37-8
IUPAC Name:2-(1H-indol-3-yl)acetamide
Traditional IUPAC Name: indole-3-acetamide
SMILES:C1(=C(CC(N)=O)C2(=CC=CC=C(N1)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
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:0
Melting point: 150 - 151 °C
Experimental Properties:
PropertyValueReference
Melting Point150 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 mg/mLALOGPS
logP1.17ALOGPS
logP0.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)15.94ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.88 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.27 m3·mol-1ChemAxon
Polarizability18.23 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-acetamide + Water → indole-3-acetate + Ammonium
indole-3-acetonitrile + Water → indole-3-acetamide
Oxygen + L-Tryptophan → indole-3-acetamide + Water + Carbon dioxide
Pathways:
  • indole-3-acetate biosynthesis IV (bacteria)PWY-5025
  • indole-3-acetate biosynthesis III (bacteria)PWY-3161
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-000i-1940000000-2e0b818a401b68b37cb0View in MoNA
    GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1690000000-bd0b44e69af5595426d5View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0900000000-1f155ed0ed5f83f86725View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0900000000-07eabe3745639209f133View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-b726329bdc2f6e86c331View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-a3d953ff50b9cf857473View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ec-2900000000-945fb87e55e153b51160View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-8838f76ce5faa9a04337View in MoNA
    MSMass Spectrum (Electron Ionization)splash10-001i-4900000000-6404e04bc67c64bf01feView in MoNA
    1D NMR1H NMR SpectrumNot Available
    1D NMR13C NMR SpectrumNot Available
    References
    References:
    • Yin C, Park JJ, Gang DR, Hulbert SH (2014)Characterization of a tryptophan 2-monooxygenase gene from Puccinia graminis f. sp. tritici involved in auxin biosynthesis and rust pathogenicity. Molecular plant-microbe interactions : MPMI 27, Pubmed: 24350783
    • Gaweska HM, Taylor AB, Hart PJ, Fitzpatrick PF (2013)Structure of the flavoprotein tryptophan 2-monooxygenase, a key enzyme in the formation of galls in plants. Biochemistry 52, Pubmed: 23521653
    • Dimkpa CO, Zeng J, McLean JE, Britt DW, Zhan J, Anderson AJ (2012)Production of indole-3-acetic acid via the indole-3-acetamide pathway in the plant-beneficial bacterium Pseudomonas chlororaphis O6 is inhibited by ZnO nanoparticles but enhanced by CuO nanoparticles. Applied and environmental microbiology 78, Pubmed: 22210218
    • Kulkarni GB, Sanjeevkumar S, Kirankumar B, Santoshkumar M, Karegoudar TB (2013)Indole-3-acetic acid biosynthesis in Fusarium delphinoides strain GPK, a causal agent of Wilt in Chickpea. Applied biochemistry and biotechnology 169, Pubmed: 23306880
    • Tsavkelova E, Oeser B, Oren-Young L, Israeli M, Sasson Y, Tudzynski B, Sharon A (2012)Identification and functional characterization of indole-3-acetamide-mediated IAA biosynthesis in plant-associated Fusarium species. Fungal genetics and biology : FG & B 49, Pubmed: 22079545
    • Mano Y, Nemoto K (2012)The pathway of auxin biosynthesis in plants. Journal of experimental botany 63, Pubmed: 22447967
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC16031
    HMDBHMDB29739
    CHEMSPIDER386
    PUBCHEM397
    CHEBI16031
    LIGAND-CPDC02693
    CAS879-37-8