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Showing NP-Card for 4-Chlorophenylacetate (NP0002722)

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Record Information
Version2.0
Created at2020-11-23 19:38:47 UTC
Updated at2021-08-12 19:51:57 UTC
NP-MRD IDNP0002722
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Chlorophenylacetate
Provided ByBMRBBMRB logo
Description4-Chlorophenylacetic acid, also known as (p-chlorophenyl)acetate or 4-chlorobenzeneacetate, belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. 4-Chlorophenylacetic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 4-Chlorophenylacetate is found in Apis cerana. It was first documented in 1978 (PMID: 637537). Based on a literature review a significant number of articles have been published on 4-Chlorophenylacetic acid (PMID: 17984079) (PMID: 3994362) (PMID: 6240395) (PMID: 7076135).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002722 (4-Chlorophenylacetate)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    3.5912   -1.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9439   -0.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7921    0.9364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4484   -0.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0471   -0.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954   -1.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381    0.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5336    0.2793    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944    1.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876    0.8203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644    1.3108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -1.6803    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -2.6590    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -2.4270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372    2.7536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1538    2.5216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  3 12  1  0
  4 13  1  1
  4 14  1  0
  6 15  1  0
  7 16  1  0
 10 17  1  0
 11 18  1  0
M  END
Download

3D MOL for NP0002722 (4-Chlorophenylacetate)

NP0002722
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    3.6760   -0.7334   -0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -0.2094    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188    0.3250    1.2760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5156   -0.2148   -1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1495   -0.0051   -0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.0870   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458   -0.9558    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.2782    0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943    0.4698    1.1719 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7319    1.3555    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4561    1.2377   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.2842    2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7036    0.5256   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5911   -1.2117   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -2.0949   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075   -1.8174    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452    2.3210    0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0780    2.1007   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
 10 17  1  0
 11 18  1  0
M  END
Download

3D SDF for NP0002722 (4-Chlorophenylacetate)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    3.5912   -1.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9439   -0.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7921    0.9364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4484   -0.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0471   -0.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954   -1.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381    0.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5336    0.2793    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944    1.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876    0.8203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644    1.3108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -1.6803    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -2.6590    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -2.4270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372    2.7536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1538    2.5216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  3 12  1  0
  4 13  1  1
  4 14  1  0
  6 15  1  0
  7 16  1  0
 10 17  1  0
 11 18  1  0
M  END
> <DATABASE_ID>
NP0002722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=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)

> <INCHI_KEY>
CDPKJZJVTHSESZ-UHFFFAOYSA-N

> <FORMULA>
C8H7ClO2

> <MOLECULAR_WEIGHT>
170.593

> <EXACT_MASS>
170.013457175

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.136061477436797

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-chlorophenyl)acetic acid

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.2150387816666663

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7656943697793954

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
42.1704

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4-chlorophenyl)acetic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002722 (4-Chlorophenylacetate)

NP0002722
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    3.6760   -0.7334   -0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -0.2094    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188    0.3250    1.2760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5156   -0.2148   -1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1495   -0.0051   -0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.0870   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458   -0.9558    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.2782    0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0943    0.4698    1.1719 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7319    1.3555    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4561    1.2377   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.2842    2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7036    0.5256   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5911   -1.2117   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -2.0949   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075   -1.8174    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452    2.3210    0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0780    2.1007   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
 10 17  1  0
 11 18  1  0
M  END
Download

PDB for NP0002722 (4-Chlorophenylacetate)

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
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
Download

3D PDB for NP0002722 (4-Chlorophenylacetate)

COMPND    NP0002722
HETATM    1  O1  UNL     1       3.676  -0.733  -0.279  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.563  -0.209   0.004  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.419   0.325   1.276  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.516  -0.215  -1.039  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.150  -0.005  -0.498  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.568  -1.087  -0.024  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.846  -0.956   0.481  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.458   0.278   0.529  1.00  0.00           C  
HETATM    9 CL1  UNL     1      -4.094   0.470   1.172  1.00  0.00          CL  
HETATM   10  C7  UNL     1      -1.732   1.355   0.053  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.456   1.238  -0.453  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.254  -0.284   2.086  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.704   0.526  -1.859  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.591  -1.212  -1.554  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.142  -2.095  -0.033  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.407  -1.817   0.854  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.245   2.321   0.102  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.078   2.101  -0.820  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6    6   11
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   10
CONECT   10   11   11   17
CONECT   11   18
END
Download

SMILES for NP0002722 (4-Chlorophenylacetate)

OC(=O)CC1=CC=C(Cl)C=C1
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INCHI for NP0002722 (4-Chlorophenylacetate)

InChI=1S/C8H7ClO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)
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View in JSmol
Synonyms
ValueSource
(p-Chlorophenyl)acetic acidChEBI
4-Chlorobenzeneacetic acidChEBI
p-Chlorophenylacetic acidChEBI
(p-Chlorophenyl)acetateGenerator
4-ChlorobenzeneacetateGenerator
p-ChlorophenylacetateGenerator
4-ChlorophenylacetateGenerator
4-Chlorophenylacetic acid, potassium saltHMDB
4-Chlorophenylacetic acid, sodium saltHMDB
Chemical FormulaC8H7ClO2
Average Mass170.5930 Da
Monoisotopic Mass170.01346 Da
IUPAC Name2-(4-chlorophenyl)acetic acid
Traditional Name(4-chlorophenyl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=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)
InChI KeyCDPKJZJVTHSESZ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP2.34ALOGPS
logP2.22ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.17 m³·mol⁻¹ChemAxon
Polarizability16.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0246401
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID15093
KEGG Compound IDC03077
BioCyc IDCPD-1786
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15880
PDB IDNot Available
ChEBI ID30749
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Subba-Rao RV, Alexander M: Bacterial and fungal cometabolism of 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT) and its breakdown products. Appl Environ Microbiol. 1985 Mar;49(3):509-16. doi: 10.1128/aem.49.3.509-516.1985. [PubMed:3994362 ]
  3. Loo YH, Rabe A, Potempska A, Wang P, Fersko R, Wisniewski HM: Experimental maternal phenylketonuria: an examination of two animal models. Dev Neurosci. 1983-1984;6(4-5):227-34. doi: 10.1159/000112349. [PubMed:6240395 ]
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