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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:45:33 UTC
HMDB IDHMDB0001544
Secondary Accession Numbers
  • HMDB01544
Metabolite Identification
Common Namem-Chlorobenzoic acid
Descriptionm-Chlorobenzoic acid is a metabolic byproduct of the drug bupropion. Bupropion is sold as Wellbutrin, or Zyban and is an atypical antidepressant that acts as a norepinephrine and dopamine reuptake inhibitor, and nicotinic antagonist. In 2007 it was the fourth-most prescribed antidepressant in the United States retail market, with 20.184 million retail prescriptions.
Structure
Thumb
Synonyms
ValueSource
3-cholro-BenzoateHMDB
3-cholro-Benzoic acidHMDB
m-ChlorobenzoateHMDB
3-ChlorobenzoateMeSH
Meta-chlorobenzoateMeSH
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
DescriptionThis compound 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
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.45 mg/mLNot Available
LogP2.68HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP2.24ALOGPS
logP2.23ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.12 m³·mol⁻¹ChemAxon
Polarizability14.21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0bti-3900000000-ff604323020f2ae9a71aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-5900000000-d7df670a2ca1ca0e6e8bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-8930000000-d4bb8e6c4f3c2af4dd81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9000000000-445ad7a7cdf351ff61afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-3a8c49b4b8a48ab54364View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03fr-9000000000-9e820074b36c867c6790View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0bti-3900000000-08061cef88de8dd94741View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-19a9589b2da08d5c712cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-779650a357b717729872View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4900000000-e741e953fcd220ab45e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-e35c168db0e23b06b9b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-0900000000-34b7504f5418ea0a5c65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3900000000-485387f98cf0e9c28408View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>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
FoodDB IDFDB022682
KNApSAcK IDNot Available
Chemspider ID434
KEGG Compound IDNot Available
BioCyc IDCPD-3486
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6311
PubChem Compound447
PDB ID3BZ
ChEBI ID49410
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 ]