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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:02:25 UTC

Update Date

2023-02-21 17:24:04 UTC

HMDB ID

HMDB0034236

Secondary Accession Numbers

HMDB34236

Metabolite Identification

Common Name

Benzenepropanenitrile

Description

Benzenepropanenitrile, also known as 2-phenylethyl cyanide or (2-cyanoethyl)benzene, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzenepropanenitrile has been detected, but not quantified in, several different foods, such as herbs and spices, cauliflowers (Brassica oleracea var. botrytis), cabbages (Brassica oleracea var. capitata), broccolis (Brassica oleracea var. italica), and brassicas. This could make benzenepropanenitrile a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Benzenepropanenitrile.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2-Cyanoethyl)benzene	ChEBI
1-Phenyl-2-cyanoethane	ChEBI
2-Phenylethyl cyanide	ChEBI
3-Phenylpropiononitrile	ChEBI
Benzenepropionitrile	ChEBI
beta-Phenyl propionitrile	ChEBI
beta-Phenylethyl cyanide	ChEBI
Hydrocinnamique nitrile	ChEBI
Hydrocinnamonitrile	ChEBI
Phenylpropanonitrile	ChEBI
Phenylpropionitrile	ChEBI
b-Phenyl propionitrile	Generator
Β-phenyl propionitrile	Generator
b-Phenylethyl cyanide	Generator
Β-phenylethyl cyanide	Generator
3-Phenylpropanonitril	MetaCyc, HMDB
1-cyano-2-Phenylethane	HMDB
3-Phenylpropanenitrile	HMDB
3-Phenylpropionitrile	HMDB
Benzenepropanitrile	HMDB
beta-Phenylpropionitrile	HMDB
Phenethyl cyanide	HMDB
Benzenepropanenitrile	ChEBI

Chemical Formula

C₉H₉N

Average Molecular Weight

131.1745

Monoisotopic Molecular Weight

131.073499293

IUPAC Name

3-phenylpropanenitrile

Traditional Name

benzylacetonitrile

CAS Registry Number

645-59-0

SMILES

N#CCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C9H9N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7H2

InChI Key

ACRWYXSKEHUQDB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

nitrile (CHEBI:85426 )
benzenes (CHEBI:85426 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034236)
Cytoplasm (HMDB: HMDB0034236)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034236)

Source

Exogenous

Food

Food (HMDB: HMDB0034236)

Vegetable

Cabbage

Brassica

Brassicas (FooDB: FOOD00857)

Herb and spice

Spice

White mustard (FooDB: FOOD00413)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034236)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034236)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-1 °C	Not Available
Boiling Point	261.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1679 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.72	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.15 g/L	ALOGPS
logP	1.94	ALOGPS
logP	2.11	ChemAxon
logS	-1.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.79 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.95 m³·mol⁻¹	ChemAxon
Polarizability	14.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	127.91	31661259
DarkChem	[M-H]-	124.258	31661259
DeepCCS	[M+H]+	126.014	30932474
DeepCCS	[M-H]-	123.067	30932474
DeepCCS	[M-2H]-	159.821	30932474
DeepCCS	[M+Na]+	134.895	30932474
AllCCS	[M+H]+	126.8	32859911
AllCCS	[M+H-H2O]+	122.2	32859911
AllCCS	[M+NH4]+	131.2	32859911
AllCCS	[M+Na]+	132.5	32859911
AllCCS	[M-H]-	127.5	32859911
AllCCS	[M+Na-2H]-	129.1	32859911
AllCCS	[M+HCOO]-	130.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzenepropanenitrile	N#CCCC1=CC=CC=C1	2058.5	Standard polar	33892256
Benzenepropanenitrile	N#CCCC1=CC=CC=C1	1190.2	Standard non polar	33892256
Benzenepropanenitrile	N#CCCC1=CC=CC=C1	1239.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Benzenepropanenitrile EI-B (Non-derivatized)	splash10-0006-9200000000-c15196ced049b8e3681a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzenepropanenitrile EI-B (Non-derivatized)	splash10-0006-9200000000-c15196ced049b8e3681a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzenepropanenitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-3f8b538083f03e684b1c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzenepropanenitrile GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 10V, Positive-QTOF	splash10-001i-0900000000-422476e232336cb1bc3b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 20V, Positive-QTOF	splash10-014i-1900000000-f25456149c249dad541c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 40V, Positive-QTOF	splash10-0uxu-9300000000-e6661cd33a9f8f3bed59	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 10V, Negative-QTOF	splash10-001i-0900000000-4076b2a2555b65c14bc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 20V, Negative-QTOF	splash10-001i-1900000000-317c2d4de54973a867e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 40V, Negative-QTOF	splash10-0w4l-9700000000-45f7d73f62355efe4384	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 10V, Positive-QTOF	splash10-001l-3900000000-f580aa6d0d3cb66199a2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 20V, Positive-QTOF	splash10-0a6r-9800000000-96778021816794d9dec3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 40V, Positive-QTOF	splash10-016u-9000000000-8e8a4a1f79e82cd94f85	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 10V, Negative-QTOF	splash10-001i-0900000000-244a9c7ac26f19950926	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 20V, Negative-QTOF	splash10-001i-0900000000-ead876da804cd98552cd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzenepropanenitrile 40V, Negative-QTOF	splash10-004i-9200000000-30b5e7202812ed8f217a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012548

KNApSAcK ID

C00029809

Chemspider ID

12061

KEGG Compound ID

Not Available

BioCyc ID

CPD-14673

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12581

PDB ID

Not Available

ChEBI ID

85426

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1058521

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Benzenepropanenitrile (HMDB0034236)

MOL for HMDB0034236 (Benzenepropanenitrile)

3D MOL for HMDB0034236 (Benzenepropanenitrile)

3D SDF for HMDB0034236 (Benzenepropanenitrile)

3D-SDF for HMDB0034236 (Benzenepropanenitrile)

PDB for HMDB0034236 (Benzenepropanenitrile)

3D PDB for HMDB0034236 (Benzenepropanenitrile)

SMILES for HMDB0034236 (Benzenepropanenitrile)

INCHI for HMDB0034236 (Benzenepropanenitrile)

Structure for HMDB0034236 (Benzenepropanenitrile)

3D Structure for HMDB0034236 (Benzenepropanenitrile)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra