Record Information
Version1.0
Creation date2010-04-08 22:04:56 UTC
Update date2019-11-26 02:56:22 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
BioavailabilityYesChemAxon
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 KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-2950000000-640d53401ab5b06bad68JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-1930000000-26ddd3b2caf5e0b3a5b6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00fr-9740000000-96b8f06c6fb07ce93a3cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-2950000000-640d53401ab5b06bad68JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0930000000-32debced08db3d4bf8cbJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-0900000000-8282b286970c64cd1738JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-458b38914f7ddf5b481aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-4900000000-69f7e3dfc4f01efba464JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9300000000-7e44794a04e8de3d1dafJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d454501befd7405d3a7cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e95beea8400e01e0632aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-42b4258b99c8588269deJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-dba18a56ff6cbe01fe5cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-0900000000-cc0c89a2abe2633a9003JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-1d1a4eca72f57a9b927cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-02ai-5900000000-bac26e180028ec3a808fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-016r-7900000000-8ee8a1b5f235ed461d7aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-4900000000-3e3f0478af07473aa142JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-1af02646eabe1e90e482JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-686ec8d86a82008f6a87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-0f41c00c3703e04901e8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-1900000000-144022b6dfec80ddd4a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-686ec8d86a82008f6a87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-0f41c00c3703e04901e8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-1900000000-144022b6dfec80ddd4a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9b52919ba61c73ce0adeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f8b24a877c386d550c92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-fc82dffe3b09577e06eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9b52919ba61c73ce0adeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f8b24a877c386d550c92JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-fc82dffe3b09577e06eeJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0a4i-2900000000-be863c7acf7363ffeedcJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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).