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1H-Indole-3-acetonitrile (FDB001365)

Record Information
Version1.0
Creation date2010-04-08 22:04:56 UTC
Update date2020-09-17 15:39:25 UTC
Primary IDFDB001365
Secondary Accession Numbers
  • FDB030921
Chemical Information
FooDB Name1H-Indole-3-acetonitrile
Description3-Indoleacetonitrile, also known as 3-(cyanomethyl)indole or IAN, 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. 3-Indoleacetonitrile is a very weakly acidic compound (based on its pKa). 3-Indoleacetonitrile exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 3-Indoleacetonitrile is found, on average, in the highest concentration within kohlrabis. 3-Indoleacetonitrile has also been detected, but not quantified in, several different foods, such as narrowleaf cattails, kiwis, amaranths, european chestnuts, and olives. This could make 3-indoleacetonitrile a potential biomarker for the consumption of these foods. A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group.
CAS Number771-51-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-2900000000-be863c7acf7363ffeedc2015-03-01View Spectrum
GC-MS1H-Indole-3-acetonitrile, 1 TMS, GC-MS Spectrumsplash10-004i-2950000000-640d53401ab5b06bad68Spectrum
GC-MS1H-Indole-3-acetonitrile, non-derivatized, GC-MS Spectrumsplash10-004i-1930000000-26ddd3b2caf5e0b3a5b6Spectrum
GC-MS1H-Indole-3-acetonitrile, non-derivatized, GC-MS Spectrumsplash10-00fr-9740000000-96b8f06c6fb07ce93a3cSpectrum
GC-MS1H-Indole-3-acetonitrile, non-derivatized, GC-MS Spectrumsplash10-004i-2950000000-640d53401ab5b06bad68Spectrum
GC-MS1H-Indole-3-acetonitrile, non-derivatized, GC-MS Spectrumsplash10-004i-0930000000-32debced08db3d4bf8cbSpectrum
Predicted GC-MS1H-Indole-3-acetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6r-0900000000-8282b286970c64cd1738Spectrum
Predicted GC-MS1H-Indole-3-acetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-458b38914f7ddf5b481a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-4900000000-69f7e3dfc4f01efba4642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9300000000-7e44794a04e8de3d1daf2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d454501befd7405d3a7c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e95beea8400e01e0632a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-42b4258b99c8588269de2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-dba18a56ff6cbe01fe5c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-0900000000-cc0c89a2abe2633a90032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-1d1a4eca72f57a9b927c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-02ai-5900000000-bac26e180028ec3a808f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-016r-7900000000-8ee8a1b5f235ed461d7a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-4900000000-3e3f0478af07473aa1422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-1af02646eabe1e90e4822017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-686ec8d86a82008f6a872015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-0f41c00c3703e04901e82015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-1900000000-144022b6dfec80ddd4a32015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-686ec8d86a82008f6a872015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-0f41c00c3703e04901e82015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-1900000000-144022b6dfec80ddd4a32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9b52919ba61c73ce0ade2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f8b24a877c386d550c922015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-fc82dffe3b09577e06ee2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9b52919ba61c73ce0ade2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f8b24a877c386d550c922015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-fc82dffe3b09577e06ee2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
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).