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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2019-01-11 19:34:46 UTC
HMDB IDHMDB0014994
Secondary Accession Numbers
  • HMDB14994
Metabolite Identification
Common NameChlorphenesin
DescriptionChlorphenesin is only found in individuals that have used or taken this drug. It is a centrally acting muscle relaxant. Its mode of action is unknown. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1203)The mechanism of action of chlorphenesin is not well defined, and its effects are measured mainly by subjective responses. It is known that chlorphenesin acts in the central nervous system (CNS) rather than directly on skeletal muscle.
Structure
Data?1547235285
Synonyms
ValueSource
3-(4-Chlorophenoxy)-1,2-propanediolChEBI
3-(P-Chlorophenoxy)-1,2-propanediolChEBI
3-(P-Chlorophenoxy)propane-1,2-diolChEBI
ChlorphenesineChEBI
ChlorphenesinumChEBI
ClorfenesinaChEBI
Glycerol alpha-P-chlorophenyl etherChEBI
P-Chlorophenyl-alpha-glyceryl etherChEBI
Glycerol a-P-chlorophenyl etherGenerator
Glycerol α-P-chlorophenyl etherGenerator
P-Chlorophenyl-a-glyceryl etherGenerator
P-Chlorophenyl-α-glyceryl etherGenerator
alpha-Glyceryl etherHMDB
ChlorophenesinHMDB
P-ChlorophenylHMDB
P-Chlorophenyl glyceryl etherHMDB
Chemical FormulaC9H11ClO3
Average Molecular Weight202.635
Monoisotopic Molecular Weight202.039671925
IUPAC Name3-(4-chlorophenoxy)propane-1,2-diol
Traditional Namechlorphenesin
CAS Registry Number104-29-0
SMILES
OCC(O)COC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C9H11ClO3/c10-7-1-3-9(4-2-7)13-6-8(12)5-11/h1-4,8,11-12H,5-6H2
InChI KeyMXOAEAUPQDYUQM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • 1,2-diol
  • Secondary alcohol
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point78 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.4 g/LNot Available
LogP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP1.46ALOGPS
logP1.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.58 m³·mol⁻¹ChemAxon
Polarizability20.1 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9800000000-88df1753febdfff7153dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bi-9541000000-ce281ad2dccaf18ccfd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1590000000-3d797e166b8494affb9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbi-5920000000-e0d1c894f4515cc74e67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9800000000-445bd6978c1b0076259dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-1980000000-f91642767ca76bc37c7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-35ca9b080c52fdd635daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3900000000-fc0f6af590cf1a1f4b02View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00856 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00856 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00856
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7411
KEGG Compound IDC07928
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorphenesin
METLIN IDNot Available
PubChem Compound7697
PDB IDNot Available
ChEBI ID3642
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dalessio DJ: Medical treatment of the major neuralgias. Semin Neurol. 1988 Dec;8(4):286-90. [PubMed:3074423 ]
  2. Malley A, Baecher L: Inhibition of histamine and SRS-A from monkey lung tissue by chlorophenesin. J Immunol. 1971 Aug;107(2):586-8. [PubMed:4105542 ]
  3. Kurachi M, Aihara H: Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats. Jpn J Pharmacol. 1984 Sep;36(1):7-13. [PubMed:6503049 ]
  4. GASSER R: [Two new acaricides of the bi-(pchlorophenyl)-carbinol group]. Experientia. 1952 Feb 15;8(2):65-7. [PubMed:14945408 ]
  5. Modha J, Datta N, Parekh H: Synthesis and biological evaluation of some new 3 ,4-dihydropyrimidin-4-ones. Farmaco. 2001 Sep;56(9):641-6. [PubMed:11680807 ]
  6. Burnett R: DDT residues: distribution of concentrations in Emerita analoga (stimpson) along coastal California. Science. 1971 Nov 5;174(4009):606-8. [PubMed:5114825 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
References
  1. Springer RH, Dimmitt MK, Novinson T, O'Brien DE, Robins RK, Simon LN, Miller JP: Synthesis and enzymic activity of some novel xanthine oxidase inhibitors. 3-Substituted 5,7-dihydroxypyrazolo(1,5-alpha)pyrimidines. J Med Chem. 1976 Feb;19(2):291-6. [PubMed:2778 ]
General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Westlake GE, Bunyan PJ, Stanley PI, Walker CH: The effects of 1,1-di(p-chlorophenyl)-2-chloroethylene on plasma enzymes and blood constituents in the Japanese quail. Chem Biol Interact. 1979 May;25(2-3):197-210. [PubMed:466732 ]
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Fernandez P, Guillen MI, Gomar F, Aller E, Molina P, Alcaraz MJ: A novel cyclo-oxygenase-2 inhibitor modulates catabolic and antiinflammatory mediators in osteoarthritis. Biochem Pharmacol. 2004 Aug 1;68(3):417-21. [PubMed:15242808 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Medina-Diaz IM, Arteaga-Illan G, de Leon MB, Cisneros B, Sierra-Santoyo A, Vega L, Gonzalez FJ, Elizondo G: Pregnane X receptor-dependent induction of the CYP3A4 gene by o,p'-1,1,1,-trichloro-2,2-bis (p-chlorophenyl)ethane. Drug Metab Dispos. 2007 Jan;35(1):95-102. Epub 2006 Oct 11. [PubMed:17035600 ]
  2. Petersen MS, Halling J, Damkier P, Nielsen F, Grandjean P, Weihe P, Brosen K: Polychlorinated biphenyl (PCB) induction of CYP3A4 enzyme activity in healthy Faroese adults. Toxicol Appl Pharmacol. 2007 Oct 15;224(2):202-6. Epub 2007 Jul 14. [PubMed:17692354 ]
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
References
  1. Holloway AC, Stys KA, Foster WG: DDE-induced changes in aromatase activity in endometrial stromal cells in culture. Endocrine. 2005 Jun;27(1):45-50. [PubMed:16077170 ]
  2. Younglai EV, Holloway AC, Lim GE, Foster WG: Synergistic effects between FSH and 1,1-dichloro-2,2-bis(P-chlorophenyl)ethylene (P,P'-DDE) on human granulosa cell aromatase activity. Hum Reprod. 2004 May;19(5):1089-93. Epub 2004 Apr 7. [PubMed:15070871 ]