Showing metabocard for 4-chlorophenylacetonitrile (MMDBc0054267)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 23:02:38 UTC
Update Date2025-10-07 16:08:26 UTC
Metabolite IDMMDBc0054267
Metabolite Identification
Common Name4-chlorophenylacetonitrile
Description4-chlorophenylacetonitrile is a nitrile compound that belongs to the class of aromatic acetonitriles. Its chemical structure features a chlorinated phenyl group attached to an acetonitrile moiety, which contributes to its biological activity. In studies involving HepG2 cells, 4-chlorophenylacetonitrile has been shown to exhibit cytotoxic effects, with an IC50 value of 812.83 µM, indicating its potential influence on cellular pathways related to proliferation and apoptosis (PMID:39852761 ). The presence of the chlorine substituent on the phenyl ring may enhance its reactivity and interaction with biological targets, potentially affecting metabolic pathways. While the specific biological significance of 4-chlorophenylacetonitrile requires further exploration, its involvement in cellular toxicity suggests it may participate in mechanisms related to oxidative stress or signal transduction, warranting additional research into its pharmacological properties and potential therapeutic applications.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9a886de2a8>


  Mrv1572004221606482D          

 10 10  0  0  0  0            999 V2000
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  1  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  3  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9a886de2a8>

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3D SDF for #<Metabolite:0x00007f9a886de2a8>

  Mrv1572004221606482D          

 10 10  0  0  0  0            999 V2000
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  1  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  3  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054267

> <DATABASE_NAME>
MIME

> <SMILES>
ClC1=CC=C(CC#N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H6ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2

> <INCHI_KEY>
IVYMIRMKXZAHRV-UHFFFAOYSA-N

> <FORMULA>
C8H6ClN

> <MOLECULAR_WEIGHT>
151.59

> <EXACT_MASS>
151.0188769

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
15.022467438387133

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-chlorophenyl)acetonitrile

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.2729876483333333

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.025201850684045

> <JCHEM_POLAR_SURFACE_AREA>
23.79

> <JCHEM_REFRACTIVITY>
41.1497

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-chlorobenzyl cyanide

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for #<Metabolite:0x00007f9a886de2a8>
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PDB for #<Metabolite:0x00007f9a886de2a8>
HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM   10  N   UNK     0       4.001  -3.850   0.000  0.00  0.00           N+0
CONECT    1    3    7                                                       
CONECT    2    4    7                                                       
CONECT    3    1    8                                                       
CONECT    4    2    8                                                       
CONECT    5    6    7                                                       
CONECT    6    5   10                                                       
CONECT    7    1    2    5                                                  
CONECT    8    3    4    9                                                  
CONECT    9    8                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for #<Metabolite:0x00007f9a886de2a8>
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SMILES for #<Metabolite:0x00007f9a886de2a8>
ClC1=CC=C(CC#N)C=C1
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INCHI for #<Metabolite:0x00007f9a886de2a8>
InChI=1S/C8H6ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2
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Synonyms
ValueSource
(p-Chlorophenyl)acetonitrileChEBI
4-ChlorobenzeneacetonitrileChEBI
4-Chlorobenzyl cyanideChEBI
p-Chlorobenzyl cyanideChEBI
Molecular FormulaC8H6ClN
Average Mass151.59
Monoisotopic Mass151.0188769
IUPAC Name2-(4-chlorophenyl)acetonitrile
Traditional Name4-chlorobenzyl cyanide
CAS Registry NumberNot Available
SMILES
ClC1=CC=C(CC#N)C=C1
InChI Identifier
InChI=1S/C8H6ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2
InChI KeyIVYMIRMKXZAHRV-UHFFFAOYSA-N