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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 14:24:16 UTC
Update Date2017-12-07 01:59:12 UTC
HMDB IDHMDB0006524
Secondary Accession Numbers
  • HMDB06524
Metabolite Identification
Common Name3-Indoleacetonitrile
Description3-Indoleacetonitrile is a phytoalexin. Phytoalexins are antibiotics produced by plants that are under attack. Phytoalexins tend to fall into several classes including terpenoids, glycosteroids and alkaloids; however, researchers often find it convenient to extend the definition to include all phytochemicals that are part of the plant's defensive arsenal. Phytoalexins produced in plants act as toxins to the attacking organism. They may puncture the cell wall, delay maturation, disrupt metabolism or prevent reproduction of the pathogen in question. However, phytoalexins are often targeted to specific predators; a plant that has anti-insect phytoalexins may not have the ability to repel a fungal attack. 3-Indoleacetonitrile is common in cruciferous vegetables such as cabbage, cauliflower, broccoli, and Brussels sprouts. Dietary indoles in cruciferous vegetables induce cytochrome P450 enzymes and have prevented tumors in various animal models. Consumption of Brassica vegetables is associated with a reduced risk of cancer of the alimentary tract in animal models and human populations. (PMID: 15612779 , 15884814 , 2342128 , 3014947 , 3880668 , 6334634 , 6419397 , 6426808 , 6584878 , 6725517 , 6838646 , 7123561 ).
Structure
Thumb
Synonyms
ValueSource
(indol-3-yl)AcetonitrileChEBI
(Indole-3-yl)acetonitrileChEBI
3-(Cyanomethyl)indoleChEBI
3-IndolylacetonitrileChEBI
indol-3-YlacetonitrileChEBI
(3-Indolyl)acetonitrileHMDB
1H-indol-3-YlacetonitrileHMDB
1H-Indole-3-acetonitrileHMDB
3-Cyanomethyl-1H-indoleHMDB
3-IndolacetonitrileHMDB
3-Indolyl-acetonitrileHMDB
b-IndoleacetonitrileHMDB
beta-IndoleacetonitrileHMDB
IANHMDB
Indole-3-acetonitrileHMDB
IndoleacetonitrileHMDB
Indolyl-3-acetonitrileHMDB
IndolylacetonitrilHMDB
IndolylacetonitrileHMDB
Usaf CB-29HMDB
Chemical FormulaC10H8N2
Average Molecular Weight156.1839
Monoisotopic Molecular Weight156.068748266
IUPAC Name2-(1H-indol-3-yl)acetonitrile
Traditional Nameindole-3-acetonitrile
CAS Registry Number771-51-7
SMILES
N#CCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
InChI KeyDMCPFOBLJMLSNX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
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 g/LALOGPS
logP2.73ALOGPS
logP1.77ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area39.58 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.43 m³·mol⁻¹ChemAxon
Polarizability16.74 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-2950000000-640d53401ab5b06bad68View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-1930000000-26ddd3b2caf5e0b3a5b6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00fr-9740000000-96b8f06c6fb07ce93a3cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-2950000000-640d53401ab5b06bad68View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0930000000-32debced08db3d4bf8cbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-0900000000-8282b286970c64cd1738View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-458b38914f7ddf5b481aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-4900000000-69f7e3dfc4f01efba464View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9300000000-7e44794a04e8de3d1dafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d454501befd7405d3a7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e95beea8400e01e0632aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-42b4258b99c8588269deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-dba18a56ff6cbe01fe5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-0900000000-cc0c89a2abe2633a9003View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-1d1a4eca72f57a9b927cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-02ai-5900000000-bac26e180028ec3a808fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-016r-7900000000-8ee8a1b5f235ed461d7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-4900000000-3e3f0478af07473aa142View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-1af02646eabe1e90e482View 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 AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Mitochondria
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
FoodDB IDFDB001365
KNApSAcK IDC00000107
Chemspider ID312357
KEGG Compound IDC02938
BioCyc IDINDOLEYL-CPD
BiGG ID1724337
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound351795
PDB IDNot Available
ChEBI ID17566
References
Synthesis ReferenceAhmad, 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)
General References
  1. Michnovicz JJ, Bradlow HL: Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990 Jun 6;82(11):947-9. [PubMed:2342128 ]
  2. Ciska E, Pathak DR: Glucosinolate derivatives in stored fermented cabbage. J Agric Food Chem. 2004 Dec 29;52(26):7938-43. [PubMed:15612779 ]
  3. Smith TK, Lund EK, Clarke RG, Bennett RN, Johnson IT: Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro. J Agric Food Chem. 2005 May 18;53(10):3895-901. [PubMed:15884814 ]
  4. Bradlow HL, Hershcopf R, Martucci C, Fishman J: 16 alpha-hydroxylation of estradiol: a possible risk marker for breast cancer. Ann N Y Acad Sci. 1986;464:138-51. [PubMed:3014947 ]
  5. Degawa M, Kojima M, Hishinuma T, Hashimoto Y: Sex-dependent induction of hepatic enzymes for mutagenic activation of a tryptophan pyrolysate component, 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]-indole, by feeding in mice. Cancer Res. 1985 Jan;45(1):96-102. [PubMed:3880668 ]
  6. Bradfield CA, Bjeldanes LF: Effect of dietary indole-3-carbinol on intestinal and hepatic monooxygenase, glutathione S-transferase and epoxide hydrolase activities in the rat. Food Chem Toxicol. 1984 Dec;22(12):977-82. [PubMed:6334634 ]
  7. Eisele TA, Bailey GS, Nixon JE: The effect of indole-3-carbinol, an aflatoxin B1 hepatocarcinoma inhibitor, and other indole analogs on the rainbow trout hepatic mixed function oxidase system. Toxicol Lett. 1983 Oct-Nov;19(1-2):133-8. [PubMed:6419397 ]
  8. Nixon JE, Hendricks JD, Pawlowski NE, Pereira CB, Sinnhuber RO, Bailey GS: Inhibition of aflatoxin B1 carcinogenesis in rainbow trout by flavone and indole compounds. Carcinogenesis. 1984 May;5(5):615-9. [PubMed:6426808 ]
  9. Kappas A, Anderson KE, Conney AH, Pantuck EJ, Fishman J, Bradlow HL: Nutrition-endocrine interactions: induction of reciprocal changes in the delta 4-5 alpha-reduction of testosterone and the cytochrome P-450-dependent oxidation of estradiol by dietary macronutrients in man. Proc Natl Acad Sci U S A. 1983 Dec;80(24):7646-9. [PubMed:6584878 ]
  10. Anderson KE, Kappas A, Conney AH, Bradlow HL, Fishman J: The influence of dietary protein and carbohydrate on the principal oxidative biotransformations of estradiol in normal subjects. J Clin Endocrinol Metab. 1984 Jul;59(1):103-7. [PubMed:6725517 ]
  11. Bulger WH, Kupfer D: Effect of xenobiotic estrogens and structurally related compounds on 2-hydroxylation of estradiol and on other monooxygenase activities in rat liver. Biochem Pharmacol. 1983 Mar 15;32(6):1005-10. [PubMed:6838646 ]
  12. Shertzer HG: Indole-3-carbinol and indole-3-acetonitrile influence on hepatic microsomal metabolism. Toxicol Appl Pharmacol. 1982 Jun 30;64(2):353-61. [PubMed:7123561 ]