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Showing NP-Card for Benzenepropanenitrile (NP0047905)

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Record Information
Version2.0
Created at2022-03-17 20:47:52 UTC
Updated at2022-03-17 20:47:52 UTC
NP-MRD IDNP0047905
Secondary Accession NumbersNone
Natural Product Identification
Common NameBenzenepropanenitrile
DescriptionBenzenepropanenitrile, also known as 2-phenylethyl cyanide or 3-phenylpropiononitrile, 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 is possibly neutral. Outside of the human body, Benzenepropanenitrile has been detected, but not quantified in, several different foods, such as broccoli, cabbages, cauliflowers, brassicas, and herbs and spices. This could make benzenepropanenitrile a potential biomarker for the consumption of these foods. Benzenepropanenitrile is found in Brassica napus , Brassica oleracea, Descurainia sophia and Nasturtium officinale . Benzenepropanenitrile was first documented in 1990 (PMID: 24264910). A nitrile that is propionitrile in which one of the methyl hydrogens has been replaced by a phenyl group (PMID: 11826962) (PMID: 19637256) (PMID: 22698371).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047905 (Benzenepropanenitrile)


  Mrv1652304272018582D          

 10 10  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6  9  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  3  0  0  0  0
M  END
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3D MOL for NP0047905 (Benzenepropanenitrile)

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3D SDF for NP0047905 (Benzenepropanenitrile)

  Mrv1652304272018582D          

 10 10  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6  9  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0047905

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C9H9N

> <MOLECULAR_WEIGHT>
131.1745

> <EXACT_MASS>
131.073499293

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.844501916604175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-phenylpropanenitrile

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
2.1135116369999998

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
23.79

> <JCHEM_REFRACTIVITY>
40.9459

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzylacetonitrile

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047905 (Benzenepropanenitrile)
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PDB for NP0047905 (Benzenepropanenitrile)
HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -6.930   1.334   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    7    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3    9                                                       
CONECT    7    4    9                                                       
CONECT    8    4   10                                                       
CONECT    9    5    6    7                                                  
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0047905 (Benzenepropanenitrile)
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SMILES for NP0047905 (Benzenepropanenitrile)
N#CCCC1=CC=CC=C1
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INCHI for NP0047905 (Benzenepropanenitrile)
InChI=1S/C9H9N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7H2
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View in JSmol
Synonyms
ValueSource
(2-Cyanoethyl)benzeneChEBI
1-Phenyl-2-cyanoethaneChEBI
2-Phenylethyl cyanideChEBI
3-PhenylpropiononitrileChEBI
BenzenepropionitrileChEBI
beta-Phenyl propionitrileChEBI
beta-Phenylethyl cyanideChEBI
Hydrocinnamique nitrileChEBI
HydrocinnamonitrileChEBI
PhenylpropanonitrileChEBI
PhenylpropionitrileChEBI
b-Phenyl propionitrileGenerator
Β-phenyl propionitrileGenerator
b-Phenylethyl cyanideGenerator
Β-phenylethyl cyanideGenerator
3-PhenylpropanonitrilHMDB
1-Cyano-2-phenylethaneHMDB
3-PhenylpropanenitrileHMDB
3-PhenylpropionitrileHMDB
BenzenepropanitrileHMDB
beta-PhenylpropionitrileHMDB
Phenethyl cyanideHMDB
BenzenepropanenitrileChEBI
Chemical FormulaC9H9N
Average Mass131.1745 Da
Monoisotopic Mass131.07350 Da
IUPAC Name3-phenylpropanenitrile
Traditional Namebenzylacetonitrile
CAS Registry Number645-59-0
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 KeyACRWYXSKEHUQDB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Brassica napusPlant
Brassica oleraceaLOTUS Database
Brassica oleracea var. botrytisFooDB
    • L. Valettea X. Fernandez, S. Poulain, A.-M. Loiseau, L. Lizzani-Cuvelier, R. Levieil, L. Restier....
Descurainia SophiaLOTUS Database
Nasturtium officinalePlant
Sinapis albaFooDB
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.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives  
Alternative Parents
Substituents
  • Monocyclic benzene moiety
    • 

  • Nitrile
    • 

  • Carbonitrile
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.94ALOGPS
logP2.11ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.95 m³·mol⁻¹ChemAxon
Polarizability14.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034236  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012548  
KNApSAcK IDC00029809  
Chemspider ID12061  
KEGG Compound IDNot Available
BioCyc IDCPD-14673  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12581  
PDB IDNot Available
ChEBI ID85426  
Good Scents IDNot Available
References
General References
  1. Xie SX, Kato Y, Asano Y: High yield synthesis of nitriles by a new enzyme, phenylacetaldoxime dehydratase, from Bacillus sp. strain OxB-1. Biosci Biotechnol Biochem. 2001 Dec;65(12):2666-72. doi: 10.1271/bbb.65.2666. [PubMed:11826962  ] 
  2. Bini L, Pidko EA, Muller C, van Santen RA, Vogt D: Lewis acid controlled regioselectivity in styrene hydrocyanation. Chemistry. 2009 Sep 7;15(35):8768-78. doi: 10.1002/chem.200802611. [PubMed:19637256  ] 
  3. van Ommen Kloeke AE, Jager T, van Gestel CA, Ellers J, van Pomeren M, Krommenhoek T, Styrishave B, Hansen M, Roelofs D: Time-related survival effects of two gluconasturtiin hydrolysis products on the terrestrial isopod Porcellio scaber. Chemosphere. 2012 Nov;89(9):1084-90. doi: 10.1016/j.chemosphere.2012.05.074. Epub 2012 Jun 12. [PubMed:22698371  ] 
  4. Newman RM, Kerfoot WC, Hanscom Z 3rd: Watercress and amphipods Potential chemical defense in a spring stream macrophyte. J Chem Ecol. 1990 Jan;16(1):245-59. doi: 10.1007/BF01021282. [PubMed:24264910  ]