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Showing NP-Card for 4-Chlorobenzoic acid (NP0002740)

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Record Information
Version2.0
Created at2020-11-23 19:39:16 UTC
Updated at2021-08-19 23:59:18 UTC
NP-MRD IDNP0002740
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Chlorobenzoic acid
Provided ByBMRBBMRB logo
Description4-Chlorobenzoic acid, also known as 4-chloro-benzoate, belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring. 4-Chlorobenzoic acid exists in all living organisms, ranging from bacteria to humans. 4-Chlorobenzoic 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-Chlorobenzoic acid was first documented in 2011 (PMID: 21184141). Based on a literature review a small amount of articles have been published on 4-Chlorobenzoic acid (PMID: 21595458) (PMID: 22142728) (PMID: 23529656).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002740 (4-Chlorobenzoic acid)


     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.6791   -1.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1171   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404    0.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6316   -0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    1.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4158    1.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3392    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246    0.4496    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7771   -1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5259    0.5888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929    2.3967    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9779    2.8139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005   -2.3318    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2703   -2.7490    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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  9 14  1  0
 10 15  1  0
M  END
Download

3D MOL for NP0002740 (4-Chlorobenzoic acid)

NP0002740
     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.5591   -1.6205   -0.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -0.4659   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093    0.5861   -0.4232 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6930   -0.2401   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1736    1.0233    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731    1.2450    0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0603    0.1912    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806    0.4298    0.5395 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5635   -1.0790    0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064   -1.2861   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9918    1.2417    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    1.8777    0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5321    2.2532    0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2672   -1.8870    0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783   -2.2695   -0.3018 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  9 14  1  0
 10 15  1  0
M  END
Download

3D SDF for NP0002740 (4-Chlorobenzoic acid)


     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.6791   -1.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1171   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0404    0.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6316   -0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0696    1.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4158    1.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3392    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246    0.4496    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7771   -1.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5259    0.5888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929    2.3967    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9779    2.8139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005   -2.3318    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2703   -2.7490    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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  9 14  1  0
 10 15  1  0
M  END
> <DATABASE_ID>
NP0002740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H5ClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)

> <INCHI_KEY>
XRHGYUZYPHTUJZ-UHFFFAOYSA-N

> <FORMULA>
C7H5ClO2

> <MOLECULAR_WEIGHT>
156.566

> <EXACT_MASS>
155.997807111

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
14.257667558846693

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-chlorobenzoic acid

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.234873400333333

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.068247388493656

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
38.119

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-chlorobenzoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002740 (4-Chlorobenzoic acid)

NP0002740
     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.5591   -1.6205   -0.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -0.4659   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093    0.5861   -0.4232 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6930   -0.2401   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1736    1.0233    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1731    1.2450    0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0603    0.1912    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806    0.4298    0.5395 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5635   -1.0790    0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064   -1.2861   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9918    1.2417    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    1.8777    0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5321    2.2532    0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2672   -1.8870    0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783   -2.2695   -0.3018 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  9 14  1  0
 10 15  1  0
M  END
Download

PDB for NP0002740 (4-Chlorobenzoic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   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   1.540   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 Cl   UNK     0       1.334   3.850   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0002740 (4-Chlorobenzoic acid)

COMPND    NP0002740
HETATM    1  O1  UNL     1       2.559  -1.621  -0.580  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.112  -0.466  -0.399  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.009   0.586  -0.423  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.693  -0.240  -0.172  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.174   1.023   0.029  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.173   1.245   0.246  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.060   0.191   0.268  1.00  0.00           C  
HETATM    8 CL1  UNL     1      -3.781   0.430   0.540  1.00  0.00          CL  
HETATM    9  C6  UNL     1      -1.564  -1.079   0.069  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.206  -1.286  -0.148  1.00  0.00           C  
HETATM   11  H1  UNL     1       2.992   1.242   0.371  1.00  0.00           H  
HETATM   12  H2  UNL     1       0.866   1.878   0.015  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.532   2.253   0.398  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.267  -1.887   0.089  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.178  -2.270  -0.302  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5   10
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8    9
CONECT    9   10   10   14
CONECT   10   15
END
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SMILES for NP0002740 (4-Chlorobenzoic acid)

OC(=O)C1=CC=C(Cl)C=C1
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INCHI for NP0002740 (4-Chlorobenzoic acid)

InChI=1S/C7H5ClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)
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View in JSmol
Synonyms
ValueSource
4-CHLORO-benzoIC ACIDChEBI
p-Chlorbenzoic acidChEBI
p-Chlorobenzoic acidChEBI
4-CHLORO-benzoateGenerator
p-ChlorbenzoateGenerator
p-ChlorobenzoateGenerator
4-ChlorobenzoateGenerator
4-Chlorobenzoic acid, mercury(+2)(2:1) saltHMDB
Para-chlorobenzoic acidHMDB
4-Chlorobenzoic acid, sodium salt, 11C-labeledHMDB
4-Chlorobenzoic acid, sodium saltHMDB
4-Chlorobenzoic acid, calcium(2:1) saltHMDB
4-Chlorobenzoic acid, mercury(+1) saltHMDB
4-Chlorobenzoic acidKEGG
Chemical FormulaC7H5ClO2
Average Mass156.5660 Da
Monoisotopic Mass155.99781 Da
IUPAC Name4-chlorobenzoic acid
Traditional Name4-chlorobenzoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C7H5ClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)
InChI KeyXRHGYUZYPHTUJZ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHalobenzoic acids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point243.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point287.25 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility72 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP2.650The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP2.22ALOGPS
logP2.23ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.07ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.12 m³·mol⁻¹ChemAxon
Polarizability14.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0246393
DrugBank IDDB03728
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6079
KEGG Compound IDC02370
BioCyc IDCPD-615
BiGG IDNot Available
Wikipedia Link4-Chlorobenzoic acid
METLIN IDNot Available
PubChem Compound6318
PDB IDNot Available
ChEBI ID30747
Good Scents IDrw1098391
References
General References
  1. Xiao P, Mori T, Kamei I, Kondo R: A novel metabolic pathway for biodegradation of DDT by the white rot fungi, Phlebia lindtneri and Phlebia brevispora. Biodegradation. 2011 Sep;22(5):859-67. doi: 10.1007/s10532-010-9443-z. Epub 2010 Dec 24. [PubMed:21184141 ]
  2. He Y, Grieser F, Ashokkumar M: Kinetics and mechanism for the sonophotocatalytic degradation of p-chlorobenzoic acid. J Phys Chem A. 2011 Jun 23;115(24):6582-8. doi: 10.1021/jp203518s. Epub 2011 May 31. [PubMed:21595458 ]
  3. Nguyen AT, Sato Y, Iwasaki T, Miyauchi K, Tokuda M, Kasai D, Masai E, Fukuda M: Characterization of the 1,1-dichloro-2,2-bis(4-chlorophenyl)ethylene (DDE) degradation system in Janibacter sp. TYM3221. Enzyme Microb Technol. 2011 Dec 10;49(6-7):532-9. doi: 10.1016/j.enzmictec.2011.06.017. Epub 2011 Jun 30. [PubMed:22142728 ]
  4. Chang YC, Takada K, Choi D, Toyama T, Sawada K, Kikuchi S: Isolation of biphenyl and polychlorinated biphenyl-degrading bacteria and their degradation pathway. Appl Biochem Biotechnol. 2013 May;170(2):381-98. doi: 10.1007/s12010-013-0191-5. Epub 2013 Mar 27. [PubMed:23529656 ]