Record Information
Version1.0
Creation date2010-04-08 22:04:56 UTC
Update date2019-11-27 17:05:02 UTC
Primary IDFDB001365
Secondary Accession Numbers
  • FDB030921
Chemical Information
FooDB Name1H-Indole-3-acetonitrile
DescriptionMyrosinase-induced hydrolysis product of indole glucosinolates, found in cabbage and other crucifers 3-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; 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); 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
CAS Number771-51-7
Structure
Thumb
Synonyms
SynonymSource
(indol-3-yl)AcetonitrileChEBI
(Indole-3-yl)acetonitrileChEBI
3-(Cyanomethyl)indoleChEBI
3-IndolylacetonitrileChEBI
indol-3-YlacetonitrileChEBI
Indole-3-acetonitrileKegg
(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
IndoleacetonitrileHMDB
Indolyl-3-acetonitrileHMDB
IndolylacetonitrilHMDB
IndolylacetonitrileHMDB
Usaf CB-29HMDB
3-IndoleacetonitrileChEBI
(indol-3-yl)acetonitrilebiospider
β-indoleacetonitrilebiospider
1H-indol-3-ylacetonitrilebiospider
3-indolyl-Acetonitrilebiospider
Acetonitrile, 3-indolyl-biospider
B-indoleacetonitrilebiospider
Benzene, pentafluoromethyl-biospider
Beta-indoleacetonitrilebiospider
Beta-indolylacetonitrilebiospider
Indol-3-ylacetonitrilebiospider
Indole-3-acetonitrile (8CI)biospider
indole-3-ylacetonitrilebiospider
Indoleacetonitrile (van)biospider
Indoleyl-CPDbiospider
Usaf cb-29HMDB
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
Chemical FormulaC10H8N2
IUPAC name2-(1H-indol-3-yl)acetonitrile
InChI IdentifierInChI=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
Isomeric SMILESN#CCC1=CNC2=C1C=CC=C2
Average Molecular Weight156.1839
Monoisotopic Molecular Weight156.068748266
Classification
Description belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles 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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 76.90%; H 5.16%; N 17.94%DFC
Melting PointMp 36.5-37°DFC
Boiling PointBp0.2 157°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
ChemSpider ID312357
ChEMBL IDCHEMBL1812654
KEGG Compound IDC02938
Pubchem Compound ID351795
Pubchem Substance IDNot Available
ChEBI ID17566
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06524
CRC / DFC (Dictionary of Food Compounds) IDBNC14-M:BZS43-C
EAFUS IDNot Available
Dr. Duke IDINDOLEACETONITRILE|3-INDOLYLACETONITRILE|INDOLE-3-ACETONITRILE
BIGG ID1724337
KNApSAcK IDC00000107
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
phytohormone26158 A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).