Showing Compound 1H-Indole-3-acetonitrile (FDB001365)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:56 UTC

Update date

2020-09-17 15:39:25 UTC

Primary ID

FDB001365

Secondary Accession Numbers

FDB030921

Chemical Information

FooDB Name

1H-Indole-3-acetonitrile

Description

3-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 Number

771-51-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
(1H-Indol-3-yl)acetonitrile	HMDB
(3-Indolyl)acetonitrile	HMDB
(indol-3-yl)Acetonitrile	ChEBI
(indol-3-yl)acetonitrile	biospider
(Indole-3-yl)acetonitrile	ChEBI
1H-indol-3-Ylacetonitrile	HMDB
1H-indol-3-ylacetonitrile	biospider
1H-Indole-3-acetonitrile	HMDB
3-(Cyanomethyl)indole	ChEBI
3-Cyanomethyl-1H-indole	HMDB

Showing 1 to 10 of 37 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.5 g/L	ALOGPS
logP	2.73	ALOGPS
logP	1.77	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.58 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.43 m³·mol⁻¹	ChemAxon
Polarizability	16.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H8N2

IUPAC name

2-(1H-indol-3-yl)acetonitrile

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 Key

DMCPFOBLJMLSNX-UHFFFAOYSA-N

Isomeric SMILES

N#CCC1=CNC2=C1C=CC=C2

Average Molecular Weight

156.1839

Monoisotopic Molecular Weight

156.068748266

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:17566 )
nitrile (CHEBI:17566 )
a small molecule (INDOLEYL-CPD )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Mitochondria

Source:

Biological:

Plant:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp0.2 157°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 76.90%; H 5.16%; N 17.94%	DFC
Melting Point	Mp 36.5-37°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-2900000000-be863c7acf7363ffeedc	2015-03-01	View Spectrum
GC-MS	1H-Indole-3-acetonitrile, 1 TMS, GC-MS Spectrum	splash10-004i-2950000000-640d53401ab5b06bad68	Spectrum
GC-MS	1H-Indole-3-acetonitrile, non-derivatized, GC-MS Spectrum	splash10-004i-1930000000-26ddd3b2caf5e0b3a5b6	Spectrum
GC-MS	1H-Indole-3-acetonitrile, non-derivatized, GC-MS Spectrum	splash10-00fr-9740000000-96b8f06c6fb07ce93a3c	Spectrum
GC-MS	1H-Indole-3-acetonitrile, non-derivatized, GC-MS Spectrum	splash10-004i-2950000000-640d53401ab5b06bad68	Spectrum
GC-MS	1H-Indole-3-acetonitrile, non-derivatized, GC-MS Spectrum	splash10-004i-0930000000-32debced08db3d4bf8cb	Spectrum
Predicted GC-MS	1H-Indole-3-acetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6r-0900000000-8282b286970c64cd1738	Spectrum
Predicted GC-MS	1H-Indole-3-acetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-458b38914f7ddf5b481a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-4900000000-69f7e3dfc4f01efba464	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-056r-9300000000-7e44794a04e8de3d1daf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-d454501befd7405d3a7c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-e95beea8400e01e0632a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-42b4258b99c8588269de	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-dba18a56ff6cbe01fe5c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00lr-0900000000-cc0c89a2abe2633a9003	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0900000000-1d1a4eca72f57a9b927c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-02ai-5900000000-bac26e180028ec3a808f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-016r-7900000000-8ee8a1b5f235ed461d7a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-4900000000-3e3f0478af07473aa142	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9000000000-1af02646eabe1e90e482	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-686ec8d86a82008f6a87	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-0f41c00c3703e04901e8	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-1900000000-144022b6dfec80ddd4a3	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-686ec8d86a82008f6a87	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-0f41c00c3703e04901e8	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-1900000000-144022b6dfec80ddd4a3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-9b52919ba61c73ce0ade	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-f8b24a877c386d550c92	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1900000000-fc82dffe3b09577e06ee	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-9b52919ba61c73ce0ade	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-f8b24a877c386d550c92	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1900000000-fc82dffe3b09577e06ee	2015-05-27	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17566

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06524

CRC / DFC (Dictionary of Food Compounds) ID

BNC14-M:BZS43-C

EAFUS ID

Not Available

Dr. Duke ID

INDOLEACETONITRILE|3-INDOLYLACETONITRILE|INDOLE-3-ACETONITRILE

BIGG ID

1724337

KNApSAcK ID

C00000107

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Broccoli	Expected but not quantified	Not Available	DUKE, HMDB
Brussel sprouts	Expected but not quantified	Not Available	DUKE, HMDB
Cabbage	Expected but not quantified	Not Available	DUKE, HMDB
Cauliflower	Expected but not quantified	Not Available	KNAPSACK, HMDB
Chinese cabbage	Expected but not quantified	Not Available	KNAPSACK, HMDB
Garden tomato (var.)	Expected but not quantified	Not Available	KNAPSACK, HMDB
Gram bean	Expected but not quantified	Not Available	KNAPSACK, HMDB
Grape	Expected but not quantified	Not Available	KNAPSACK, HMDB
Horseradish tree	Expected but not quantified	Not Available	DUKE, HMDB
Japanese persimmon	Expected but not quantified	Not Available	KNAPSACK, HMDB

Showing 1 to 10 of 564 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
phytohormone	26158	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