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
Synonyms
SynonymSource
(3-Indolyl)acetonitrilebiospider
(indol-3-yl)acetonitrilebiospider
(Indole-3-yl)acetonitrilebiospider
β-indoleacetonitrilebiospider
1H-indol-3-ylacetonitrilebiospider
1H-Indole-3-acetonitriledb_source
3-(Cyanomethyl)indolebiospider
3-Cyanomethyl-1H-indoledb_source
3-Indolacetonitrilebiospider
3-Indoleacetonitrilebiospider
3-indolyl-Acetonitrilebiospider
3-Indolylacetonitrilebiospider
Acetonitrile, 3-indolyl-biospider
B-indoleacetonitrilebiospider
Benzene, pentafluoromethyl-biospider
Beta-indoleacetonitrilebiospider
Beta-indolylacetonitrilebiospider
IANbiospider
Indol-3-ylacetonitrilebiospider
Indole-3-acetonitrilebiospider
Indole-3-acetonitrile (8CI)biospider
indole-3-ylacetonitrilebiospider
Indoleacetonitrilebiospider
Indoleacetonitrile (van)biospider
Indoleyl-CPDbiospider
Indolyl-3-acetonitrilebiospider
Indolylacetonitrilbiospider
Indolylacetonitrilebiospider
Usaf cb-29HMDB
Predicted PropertiesNot Available
Chemical FormulaC10H8N2
IUPAC name
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
ClassificationNot classified
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
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
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).