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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:32 UTC
HMDB IDHMDB0014894
Secondary Accession Numbers
  • HMDB14894
Metabolite Identification
Common NameHexachlorophene
DescriptionHexachlorophene, also known as gamophen or acigena, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. It is also used in agriculture as an acaricide and fungicide, but is not approved for such use within the European Union. Hexachlorophene is a drug. Hexachlorophene is an extremely weak basic (essentially neutral) compound (based on its pKa). An organochlorine compound that is diphenylmethane in which each of the phenyl groups is substituted by chlorines at positions 2, 3, and 5, and by a hydroxy group at position 6. An antiseptic that is effective against Gram-positive organisms, it is used in soaps and creams for the treatment of various skin disorders.
Structure
Data?1582753232
Synonyms
ValueSource
2,2',3,3',5,5'-Hexachloro-6,6'-dihydroxydiphenylmethaneChEBI
2,2'-Dihydroxy-3,3',5,5',6,6'-hexachlorodiphenylmethaneChEBI
2,2'-Dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethaneChEBI
2,2'-Methanediylbis(3,4,6-trichlorophenol)ChEBI
AcigenaChEBI
AlmedermChEBI
ArmohexChEBI
Bis(2-hydroxy-3,5,6-trichlorophenyl)methaneChEBI
Bis(3,5,6-trichloro-2-hydroxyphenyl)methaneChEBI
DistodinChEBI
EsaclorofeneChEBI
ExofeneChEBI
GamophenChEBI
GamopheneChEBI
Germa-medicaChEBI
Hexa-germChEBI
HexabalmChEBI
HexachlorophenumChEBI
HexaclorofenoChEBI
HexafenChEBI
HexascrubChEBI
HexideChEBI
NabacChEBI
Phiso-scrubChEBI
PhisodanChEBI
Septi-softChEBI
SeptisolChEBI
SeptofenChEBI
Solu-heksChEBI
Soy-domeChEBI
Staphene OChEBI
Ster-zacChEBI
SteralChEBI
SteraskinChEBI
Surgi-cenChEBI
Surgi-cinChEBI
SurofeneChEBI
TersasepticChEBI
TurgexChEBI
PhisohexKegg
HexachlorophaneHMDB
Chemical FormulaC13H6Cl6O2
Average Molecular Weight406.904
Monoisotopic Molecular Weight403.849895678
IUPAC Name3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
Traditional Namepre-op
CAS Registry Number70-30-4
SMILES
OC1=C(CC2=C(O)C(Cl)=CC(Cl)=C2Cl)C(Cl)=C(Cl)C=C1Cl
InChI Identifier
InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21/h2-3,20-21H,1H2
InChI KeyACGUYXCXAPNIKK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • 4-halophenol
  • 3-halophenol
  • 2-halophenol
  • 3-chlorophenol
  • 2-chlorophenol
  • 4-chlorophenol
  • Chlorobenzene
  • Halobenzene
  • Phenol
  • Aryl halide
  • Aryl chloride
  • Organic oxygen compound
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • 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 PointNot AvailableNot Available
Boiling Point166.5 °CNot Available
Water Solubility0.00043 g/LNot Available
LogP6.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00043 g/LALOGPS
logP6.77ALOGPS
logP7.08ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)5.15ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.59 m³·mol⁻¹ChemAxon
Polarizability34.07 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0600-0129300000-cb3b814466eba79fbe7cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9010240000-a29226851efcc2b57335Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udl-0902800000-eab954bdd46ef95ea0e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0903000000-af7e51011b8ac55a0b9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0090500000-3520ed20e62597b8f86aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0061900000-ce0a152491abb1f33f79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-0490000000-a0ce3a9ffe8b9e5d889dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0100900000-e3ab4b6eea7a1952773bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0302900000-25a6b74c90eb83e75b14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00l6-0619000000-fbd33033de48509636efSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00756 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00756 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00756
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3472
KEGG Compound IDC08039
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHexachlorophene
METLIN IDNot Available
PubChem Compound3598
PDB IDNot Available
ChEBI ID5693
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in iron ion binding
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q) (By similarity).
Gene Name:
SDHD
Uniprot ID:
O14521
Molecular weight:
17042.82
References
  1. Lokanatha V, Sailaja P, Rajendra W: In vitro kinetics of the rat brain succinate dehydrogenase inhibition by hexachlorophene. J Biochem Mol Toxicol. 1999;13(6):303-6. [PubMed:10487417 ]
General function:
Involved in oxidoreductase activity
Specific function:
May be involved in learning and memory reactions by increasing the turnover of the excitatory neurotransmitter glutamate (By similarity).
Gene Name:
GLUD1
Uniprot ID:
P00367
Molecular weight:
61397.315
References
  1. Li M, Smith CJ, Walker MT, Smith TJ: Novel inhibitors complexed with glutamate dehydrogenase: allosteric regulation by control of protein dynamics. J Biol Chem. 2009 Aug 21;284(34):22988-3000. doi: 10.1074/jbc.M109.020222. Epub 2009 Jun 15. [PubMed:19531491 ]
  2. Wang JL, Buhler DR: Inhibition of dehydrogenase enzymes by hexachlorophene. Biochem Pharmacol. 1978;27(24):2947-53. [PubMed:570044 ]