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Human Metabolome Database Version 3.5

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Showing metabocard for m-Chlorobenzoic acid (HMDB01544)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:44 -0700
HMDB ID HMDB01544
Secondary Accession Numbers None
Metabolite Identification
Common Name m-Chlorobenzoic acid
Description m-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Cholro-benzoate
  2. 3-Cholro-benzoic acid
  3. m-Chlorobenzoate
  4. m-Chlorobenzoic acid
Chemical Formula C7H5ClO2
Average Molecular Weight 156.566
Monoisotopic Molecular Weight 155.997807111
IUPAC Name 3-chlorobenzoic acid
Traditional IUPAC Name 3-chlorobenzoic acid
CAS Registry Number 535-80-8
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 Key LULAYUGMBFYYEX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • monochlorobenzoic acid(ChEBI)
Substituents
  • Aryl Chloride
  • Benzoyl
  • Carboxylic Acid
  • Chlorobenzene
  • Organochloride
Direct Parent Benzoic Acid and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 158 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.45 mg/mL Not Available
LogP 2.68 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.82 g/L ALOGPS
LogP 2.24 ALOGPS
LogP 2.23 ChemAxon
LogS -2.28 ALOGPS
pKa (strongest acidic) 3.9 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 38.12 ChemAxon
Polarizability 14.21 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-7M)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Urine Detected and Quantified
0.68 umol/mmol creatinine Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022682
KNApSAcK ID Not Available
Chemspider ID 434 Link_out
KEGG Compound ID Not Available
BioCyc ID CPD-3486 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01544 Link_out
Metagene Link HMDB01544 Link_out
METLIN ID 6311 Link_out
PubChem Compound 447 Link_out
PDB ID 3BZ Link_out
ChEBI ID 19985 Link_out
References
Synthesis Reference Wu, 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 Link_out