| Common Name |
m-Chlorohippuric acid
| Description |
m-Chlorohippuric acid is an inactive metabolite of Bupropion. The formation of m-chlorobenzoic acid involves side chain cleavage of bupropion to an acidic metabolite in humans (PMID: 3107223 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
3-Chlorohippuric acidChEMBL
3-ChlorohippateGenerator
3-Chlorohippic acidGenerator
m-ChlorohippateGenerator
m-Chlorohippic acidGenerator
(3-chloro-benzoylamino)-Acetic acidHMDB
(3-chlorobenzoylamino)Acetic acidHMDB
m-ChlorohippurateHMDB
N-(3-Chlorobenzoyl)glycineHMDB
| Chemical Formlia |
C9H8ClNO3
| Average Molecliar Weight |
213.618
| Monoisotopic Molecliar Weight |
213.019270834
| IUPAC Name |
2-[(3-chlorophenyl)formamido]acetic acid
| Traditional Name |
m-chlorohippuric acid
| CAS Registry Number |
57728-59-3
| SMILES |
OC(=O)CNC(=O)C1=CC(Cl)=CC=C1
| InChI Identifier |
InChI=1S/C9H8ClNO3/c10-7-3-1-2-6(4-7)9(14)11-5-8(12)13/h1-4H,5H2,(H,11,14)(H,12,13)
| InChI Key |
ICYUIIJXZHPESK-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Benzenoids
| Sub Class |
Benzene and substituted derivatives
| Direct Parent |
Hippuric acids
| Alternative Parents |
N-acyl-alpha amino acids
3-halobenzoic acids and derivatives
Benzoyl derivatives
Chlorobenzenes
Aryl chlorides
Secondary carboxylic acid amides
Monocarboxylic acids and derivatives
Carboxylic acids
Organopnictogen compounds
Organonitrogen compounds
Organochlorides
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Halobenzoic acid or derivatives
3-halobenzoic acid or derivatives
Benzoyl
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Protein synthesis, amino acid biosynthesis
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.33 mg/mLALOGPS
logP0.97ALOGPS
logP1.13ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.92 m3·mol-1ChemAxon
Polarizability19.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022545
| KNApSAcK ID |
Not Available
| Chemspider ID |
435
| KEGG Compound ID |
Not Available
| BioCyc ID |
CPD-3487
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB01309
| Metagene Link |
HMDB01309
| METLIN ID |
6149
| PubChem Compound |
448
| PDB ID |
Not Available
| ChEBI ID |
613377
Product: KS176
References |
| Synthesis Reference |
Taboada, J.; Pavon, A.; Cetina, R. Synthesis of substituted hippuric acids and ir spectra of the intermediate amidoalcohols. Revista de la Sociedad Quimica de Mexico (1975), 19(1), 10-12. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Welch RM, Lai AA, Schroeder DH: Pharmacological significance of the species differences in bupropion metabolism. Xenobiotica. 1987 Mar;17(3):287-98. [PubMed:3107223 ]
|
PMID: 20405049