Showing metabocard for 4-chlorophenylacetic acid (MMDBc0055474)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 19:53:44 UTC
Update Date2025-10-07 16:04:20 UTC
Metabolite IDMMDBc0055474
Metabolite Identification
Common Name4-chlorophenylacetic acid
Description4-chlorophenylacetic acid is a chlorinated aromatic compound belonging to the class of carboxylic acids. Its chemical structure features a phenyl group substituted with a chlorine atom at the para position and a carboxylic acid group, making it a derivative of phenylacetic acid. This compound is involved in various biochemical pathways, including olfactory signaling, where it interacts with specific olfactory receptors, such as ORA1 in zebrafish, highlighting its potential role in the perception of pheromones (PMID:38092113 ). Additionally, it has been identified as a metabolite associated with functional motor scales and potential typing biomarkers, indicating its relevance in metabolic profiling (PMID:38615366 ). Research has also shown that 4-chlorophenylacetic acid can be produced through the microbial transformation of 4-chlorostyrene in Pseudomonas fluorescens, suggesting its involvement in biotransformation processes (PMID:29892568 ). Furthermore, it has been noted for its potential toxicity in relation to certain bacteria, linking it to environmental and health-related studies (PMID:37468867 ). Overall, 4-chlorophenylacetic acid serves as an important compound in both chemical and biological contexts.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f2df5826598>


  Mrv1652306172221532D          

 11 11  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
    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
   -0.0000   -1.6500    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
   -0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  5  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  1  2  0  0  0  0
  6  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
M  CHG  1  11  -1
M  END
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3D MOL for #<Metabolite:0x00007f2df5826598>

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3D SDF for #<Metabolite:0x00007f2df5826598>

  Mrv1652306172221532D          

 11 11  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
    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
   -0.0000   -1.6500    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
   -0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  5  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  1  2  0  0  0  0
  6  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
MMDBc0055474

> <DATABASE_NAME>
MIME

> <SMILES>
[O-]C(=O)CC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H7ClO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)/p-1

> <INCHI_KEY>
CDPKJZJVTHSESZ-UHFFFAOYSA-M

> <FORMULA>
C8H6ClO2

> <MOLECULAR_WEIGHT>
169.58

> <EXACT_MASS>
169.0061807

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
15.705422355071137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.2150387816666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7656943697793954

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
53.0075

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4-chlorophenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f2df5826598>
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PDB for #<Metabolite:0x00007f2df5826598>
HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000  -3.080   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  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O-1
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    7                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    4    9                                                  
CONECT    8    5   10   11                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for #<Metabolite:0x00007f2df5826598>
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SMILES for #<Metabolite:0x00007f2df5826598>
[O-]C(=O)CC1=CC=C(Cl)C=C1
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INCHI for #<Metabolite:0x00007f2df5826598>
InChI=1S/C8H7ClO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)/p-1
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Synonyms
ValueSource
4-CHLOROPHENYLACETic acidGenerator
4-Chlorophenylacetic acid, sodium saltMeSH
4-Chlorophenylacetic acid, potassium saltMeSH
Molecular FormulaC8H6ClO2
Average Mass169.58
Monoisotopic Mass169.0061807
IUPAC Name2-(4-chlorophenyl)acetate
Traditional Name(4-chlorophenyl)acetate
CAS Registry NumberNot Available
SMILES
[O-]C(=O)CC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C8H7ClO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)/p-1
InChI KeyCDPKJZJVTHSESZ-UHFFFAOYSA-M