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Showing metabocard for m-Chlorobenzoic acid (HMDB0001544)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:47 UTC
HMDB IDHMDB0001544
Secondary Accession Numbers
  • HMDB01544
Metabolite Identification
Common Namem-Chlorobenzoic acid
Descriptionm-Chlorobenzoic acid, also known as m-chlorobenzoate, belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring. m-Chlorobenzoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on m-Chlorobenzoic acid.
Structure
Data?1676999747
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001544 (m-Chlorobenzoic acid)

  Mrv1652303102016452D          

 10 10  0  0  0  0            999 V2000
   10.8791   -7.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1698   -7.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4561   -7.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7297   -7.4949    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.8791   -8.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1698   -9.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4561   -8.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5924   -7.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5900   -6.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3081   -7.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  7  3  2  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
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3D MOL for HMDB0001544 (m-Chlorobenzoic acid)

HMDB0001544
     RDKit          3D
m-Chlorobenzoic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.4356   -1.5372   -0.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -0.3783   -0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.7103   -0.7797 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255   -0.1583   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064    1.1202   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    1.3100    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461    0.2339    0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5636   -1.0512    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043   -2.4582    0.5278 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496   -1.2212   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476    1.0253    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070    1.9399   -0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5813    2.3117    0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0834    0.3662    0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634   -2.2131   -0.1858 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  1  0
  8 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
 10 15  1  0
M  END
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3D SDF for HMDB0001544 (m-Chlorobenzoic acid)

  Mrv1652303102016452D          

 10 10  0  0  0  0            999 V2000
   10.8791   -7.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1698   -7.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4561   -7.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7297   -7.4949    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.8791   -8.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1698   -9.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4561   -8.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5924   -7.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5900   -6.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3081   -7.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  7  3  2  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001544

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
LULAYUGMBFYYEX-UHFFFAOYSA-N

> <FORMULA>
C7H5ClO2

> <MOLECULAR_WEIGHT>
156.566

> <EXACT_MASS>
155.997807111

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
14.208950939865442

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-chlorobenzoic acid

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.234873400333333

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8966841409420327

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
38.119

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-chlorobenzoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0001544 (m-Chlorobenzoic acid)

HMDB0001544
     RDKit          3D
m-Chlorobenzoic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.4356   -1.5372   -0.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -0.3783   -0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.7103   -0.7797 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255   -0.1583   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064    1.1202   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    1.3100    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461    0.2339    0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5636   -1.0512    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043   -2.4582    0.5278 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496   -1.2212   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3476    1.0253    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070    1.9399   -0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5813    2.3117    0.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0834    0.3662    0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634   -2.2131   -0.1858 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  1  0
  8 10  2  0
 10  4  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
 10 15  1  0
M  END
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PDB for HMDB0001544 (m-Chlorobenzoic acid)

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      20.308 -14.745   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.984 -13.990   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.651 -14.745   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      16.295 -13.990   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0      20.308 -16.293   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.984 -17.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.651 -16.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.639 -13.971   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      21.635 -12.431   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.975 -14.737   0.000  0.00  0.00           O+0
CONECT    1    2    5    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    3    6                                                       
CONECT    8    9   10    1                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0001544 (m-Chlorobenzoic acid)

COMPND    HMDB0001544
HETATM    1  O1  UNL     1       2.436  -1.537  -0.755  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.012  -0.378  -0.603  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.839   0.710  -0.780  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.625  -0.158  -0.233  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.106   1.120  -0.052  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.208   1.310   0.298  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.046   0.234   0.478  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.564  -1.051   0.306  1.00  0.00           C  
HETATM    9 CL1  UNL     1      -2.604  -2.458   0.528  1.00  0.00          CL  
HETATM   10  C7  UNL     1      -0.250  -1.221  -0.043  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.348   1.025   0.060  1.00  0.00           H  
HETATM   12  H2  UNL     1       0.807   1.940  -0.205  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.581   2.312   0.431  1.00  0.00           H  
HETATM   14  H4  UNL     1      -3.083   0.366   0.754  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.163  -2.213  -0.186  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   14
CONECT    8    9   10   10
CONECT   10   15
END
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SMILES for HMDB0001544 (m-Chlorobenzoic acid)

OC(=O)C1=CC(Cl)=CC=C1
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INCHI for HMDB0001544 (m-Chlorobenzoic acid)

InChI=1S/C7H5ClO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H,9,10)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
m-ChlorobenzoateGenerator
3-cholro-BenzoateHMDB
3-cholro-Benzoic acidHMDB
3-ChlorobenzoateMeSH, Generator, HMDB
Meta-chlorobenzoateMeSH, HMDB
m-Chlorobenzoic acidChEBI
Chemical FormulaC7H5ClO2
Average Molecular Weight156.566
Monoisotopic Molecular Weight155.997807111
IUPAC Name3-chlorobenzoic acid
Traditional Name3-chlorobenzoic acid
CAS Registry Number535-80-8
SMILES
OC(=O)C1=CC(Cl)=CC=C1
InChI Identifier
InChI=1S/C7H5ClO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H,9,10)
InChI KeyLULAYUGMBFYYEX-UHFFFAOYSA-N
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 Parents
Substituents
  • 3-halobenzoic acid or derivatives
  • 3-halobenzoic acid
  • Halobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.45 mg/mLNot Available
LogP2.68HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.68 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022682
KNApSAcK IDC00052343
Chemspider ID434
KEGG Compound IDNot Available
BioCyc IDCPD-3486
BiGG IDNot Available
Wikipedia LinkChlorobenzoic acid
METLIN ID6311
PubChem Compound447
PDB IDNot Available
ChEBI ID49410
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWu, Wenliang; Zhu, Xurong; Zhu, Ningdong; Chen, Mingde. Methods for preparation of m-chlorobenzoic acid. Nanjing Huagong Daxue Xuebao (1997), 19(4), 117-124.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Welch RM, Lai AA, Schroeder DH: Pharmacological significance of the species differences in bupropion metabolism. Xenobiotica. 1987 Mar;17(3):287-98. [PubMed:3107223 ]