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Showing NP-Card for 2-Chlorobenzoic acid (NP0002701)

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Record Information
Version2.0
Created at2020-11-23 19:38:18 UTC
Updated at2021-08-12 19:51:54 UTC
NP-MRD IDNP0002701
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Chlorobenzoic acid
Provided ByBMRBBMRB logo
Description2-Chlorobenzoic acid, also known as O-chlorobenzoate, belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring. 2-Chlorobenzoic acid exists in all living organisms, ranging from bacteria to humans. 2-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. 2-Chlorobenzoic acid was first documented in 1989 (PMID: 2743216). Based on a literature review a small amount of articles have been published on 2-Chlorobenzoic acid (PMID: 18623396) (PMID: 20149490) (PMID: 21312330).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002701 (2-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
   -0.2917   -1.3583    0.0000 C   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
   -2.3392    0.2410    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
    0.0696    1.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9929    2.3967    0.0000 Cl  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
    0.2703   -2.7490    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
   -3.8246    0.4496    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
  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
  8  9  2  0
  9 10  1  0
  9  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
M  END
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3D MOL for NP0002701 (2-Chlorobenzoic acid)

NP0002701
     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.5727   -1.2414    1.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0525   -0.4871    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9315    0.1826   -0.6644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206   -0.2715    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2026   -1.1568   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690   -0.9116   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981    0.2533   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610    1.1538    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0860    0.8847    0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1817    1.9876    1.4975 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4675    0.7837   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588   -2.0493   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -1.6300   -1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1435    0.4481   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6964    2.0539    1.0244 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
  8  9  2  0
  9 10  1  0
  9  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
M  END
Download

3D SDF for NP0002701 (2-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
   -0.2917   -1.3583    0.0000 C   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
   -2.3392    0.2410    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
    0.0696    1.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9929    2.3967    0.0000 Cl  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
    0.2703   -2.7490    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
   -3.8246    0.4496    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
  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
  8  9  2  0
  9 10  1  0
  9  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
M  END
> <DATABASE_ID>
NP0002701

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=CC=C1Cl

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

> <INCHI_KEY>
IKCLCGXPQILATA-UHFFFAOYSA-N

> <FORMULA>
C7H5ClO2

> <MOLECULAR_WEIGHT>
156.57

> <EXACT_MASS>
155.9978071

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
14.050508196265255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-chlorobenzoic acid

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.234873400333333

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.068039035963698

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
38.119

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorobenzoate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002701 (2-Chlorobenzoic acid)

NP0002701
     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.5727   -1.2414    1.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0525   -0.4871    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9315    0.1826   -0.6644 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206   -0.2715    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2026   -1.1568   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690   -0.9116   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0981    0.2533   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610    1.1538    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0860    0.8847    0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1817    1.9876    1.4975 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4675    0.7837   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588   -2.0493   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -1.6300   -1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1435    0.4481   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6964    2.0539    1.0244 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
  8  9  2  0
  9 10  1  0
  9  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
M  END
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PDB for NP0002701 (2-Chlorobenzoic acid)

HEADER    PROTEIN                                 21-JUL-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUL-15         0                                  
HETATM    1  C   UNK     0      30.941 -18.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.281 -18.928   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.621 -18.928   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.010 -16.640   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.281 -20.472   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0      33.601 -18.163   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0      29.621 -20.472   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      32.253 -15.875   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      29.614 -15.882   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      30.941 -21.252   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10                                                       
CONECT    6    2                                                            
CONECT    7    3   10                                                       
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    5    7                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0002701 (2-Chlorobenzoic acid)

COMPND    NP0002701
HETATM    1  O1  UNL     1       2.573  -1.241   1.059  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.052  -0.487   0.230  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.931   0.183  -0.664  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.621  -0.271   0.146  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.203  -1.157  -0.483  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.569  -0.912  -0.585  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.098   0.253  -0.034  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.261   1.154   0.607  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.086   0.885   0.692  1.00  0.00           C  
HETATM   10 CL1  UNL     1       1.182   1.988   1.498  1.00  0.00          CL  
HETATM   11  H1  UNL     1       2.468   0.784  -1.372  1.00  0.00           H  
HETATM   12  H2  UNL     1       0.259  -2.049  -0.897  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.201  -1.630  -1.108  1.00  0.00           H  
HETATM   14  H4  UNL     1      -3.143   0.448  -0.113  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.696   2.054   1.024  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   11
CONECT    4    5    5    9
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8   14
CONECT    8    9    9   15
CONECT    9   10
END
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SMILES for NP0002701 (2-Chlorobenzoic acid)

OC(=O)C1=CC=CC=C1Cl
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INCHI for NP0002701 (2-Chlorobenzoic acid)

InChI=1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
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View in JSmol
Synonyms
ValueSource
O-Chlorobenzoic acidChEBI
O-ChlorobenzoateGenerator
2-ChlorobenzoateGenerator
2-Chlorobenzoic acid, copper (2+) saltHMDB
2-Chlorobenzoic acid, nickel (2+) saltHMDB
2-Chlorobenzoic acid, potassium saltHMDB
Chemical FormulaC7H5ClO2
Average Mass156.5700 Da
Monoisotopic Mass155.99781 Da
IUPAC Name2-chlorobenzoic acid
Traditional Namechlorobenzoate
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
InChI KeyIKCLCGXPQILATA-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 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.39ALOGPS
logP2.23ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.12 m³·mol⁻¹ChemAxon
Polarizability14.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0245065
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8071
KEGG Compound IDC02357
BioCyc IDCPD-256
BiGG IDNot Available
Wikipedia Link2-Chlorobenzoic acid
METLIN IDNot Available
PubChem Compound8374
PDB IDNot Available
ChEBI ID30793
Good Scents IDNot Available
References
General References
  1. Armenante PM, Fava F, Kafkewitz D: Effect of yeast extract on growth kinetics during aerobic biodegradation of chlorobenzoic acids. Biotechnol Bioeng. 1995 Jul 20;47(2):227-33. doi: 10.1002/bit.260470214. [PubMed:18623396 ]
  2. Abu-Hashem AA, Gouda MA, Badria FA: Synthesis of some new pyrimido[2',1':2,3]thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents. Eur J Med Chem. 2010 May;45(5):1976-81. doi: 10.1016/j.ejmech.2010.01.042. Epub 2010 Jan 28. [PubMed:20149490 ]
  3. Fan S, Wang X, Li P, Zhang Q, Zhang W: Simultaneous determination of 13 phytohormones in oilseed rape tissues by liquid chromatography-electrospray tandem mass spectrometry and the evaluation of the matrix effect. J Sep Sci. 2011 Mar;34(6):640-50. doi: 10.1002/jssc.201000541. Epub 2011 Feb 11. [PubMed:21312330 ]
  4. Sylvestre M, Mailhiot K, Ahmad D, Masse R: Isolation and preliminary characterization of a 2-chlorobenzoate degrading Pseudomonas. Can J Microbiol. 1989 Apr;35(4):439-43. doi: 10.1139/m89-067. [PubMed:2743216 ]