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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:30:29 UTC
HMDB IDHMDB14894
Secondary Accession NumbersNone
Metabolite Identification
Common NameHexachlorophene
DescriptionA chlorinated bisphenol antiseptic with a bacteriostatic action against Gram-positive organisms, but much less effective against Gram-negative organisms. It is mainly used in soaps and creams and is an ingredient of various preparations used for skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p797)
Structure
Thumb
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
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 KeyInChIKey=ACGUYXCXAPNIKK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These 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-chlorophenol
  • 2-chlorophenol
  • 3-chlorophenol
  • 2-halophenol
  • 3-halophenol
  • 4-halophenol
  • Phenol
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents, Local
  • Anti-Infectives
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point166.5 °CNot Available
Water Solubility4.33e-04 g/LNot Available
LogP6.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000433 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.59 m3·mol-1ChemAxon
Polarizability34.07 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00756
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00756
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00756
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3472
KEGG Compound IDC08039
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHexachlorophene
NuGOwiki LinkHMDB14894
Metagene LinkHMDB14894
METLIN IDNot Available
PubChem Compound3598
PDB IDH3P
ChEBI ID108167
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. [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. Epub 2009 Jun 15. [19531491 ]
  2. Wang JL, Buhler DR: Inhibition of dehydrogenase enzymes by hexachlorophene. Biochem Pharmacol. 1978;27(24):2947-53. [570044 ]