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Record Information
Version5.0
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. Hexachlorophene is a drug which is used for use as a surgical scrub and a bacteriostatic skin cleanser. it may also be used to control an outbreak of gram-positive infection where other infection control procedures have been unsuccessful. Based on a literature review a significant number of articles have been published on Hexachlorophene.
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point166.5 °CNot Available
Water Solubility0.00043 g/LNot Available
LogP6.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00043 g/LALOGPS
logP10(6.77) g/LALOGPS
logP10(7.08) g/LChemAxon
logS10(-6) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HexachloropheneOC1=C(CC2=C(O)C(Cl)=CC(Cl)=C2Cl)C(Cl)=C(Cl)C=C1Cl4762.2Standard polar33892256
HexachloropheneOC1=C(CC2=C(O)C(Cl)=CC(Cl)=C2Cl)C(Cl)=C(Cl)C=C1Cl2824.8Standard non polar33892256
HexachloropheneOC1=C(CC2=C(O)C(Cl)=CC(Cl)=C2Cl)C(Cl)=C(Cl)C=C1Cl2797.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hexachlorophene,1TMS,isomer #1C[Si](C)(C)OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl2810.6Semi standard non polar33892256
Hexachlorophene,2TMS,isomer #1C[Si](C)(C)OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(Cl)C(Cl)=CC(Cl)=C1O[Si](C)(C)C2868.0Semi standard non polar33892256
Hexachlorophene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl3179.3Semi standard non polar33892256
Hexachlorophene,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(Cl)C(Cl)=CC(Cl)=C1O[Si](C)(C)C(C)(C)C3468.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hexachlorophene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0600-0129300000-cb3b814466eba79fbe7c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexachlorophene GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9010240000-a29226851efcc2b573352017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexachlorophene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexachlorophene LC-ESI-QFT , negative-QTOFsplash10-0udl-0902800000-eab954bdd46ef95ea0e62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexachlorophene LC-ESI-ITFT , negative-QTOFsplash10-0006-0903000000-af7e51011b8ac55a0b9c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexachlorophene 30V, Negative-QTOFsplash10-0006-0903000000-b5db9f67cdd739d855702021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexachlorophene 15V, Negative-QTOFsplash10-0udi-0102900000-3f1c09b0da5bdeca49862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexachlorophene 45V, Negative-QTOFsplash10-0006-0900000000-2de6711b3225e7d9d1972021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexachlorophene 60V, Negative-QTOFsplash10-052f-0900000000-ede1ae14950bd65d2d7d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexachlorophene 75V, Negative-QTOFsplash10-0a4i-0900000000-2bf64f17df28192e8bbd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexachlorophene 90V, Negative-QTOFsplash10-0a4i-0900000000-9c30a2d14a2059e70b222021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexachlorophene 35V, Negative-QTOFsplash10-0udl-0902800000-fbcab58d9b98e7e36a012021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 10V, Positive-QTOFsplash10-0pb9-0090500000-3520ed20e62597b8f86a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 20V, Positive-QTOFsplash10-0zfr-0061900000-ce0a152491abb1f33f792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 40V, Positive-QTOFsplash10-0a6r-0490000000-a0ce3a9ffe8b9e5d889d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 10V, Negative-QTOFsplash10-0udi-0100900000-e3ab4b6eea7a1952773b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 20V, Negative-QTOFsplash10-0udi-0302900000-25a6b74c90eb83e75b142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 40V, Negative-QTOFsplash10-00l6-0619000000-fbd33033de48509636ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 10V, Positive-QTOFsplash10-0udi-0000900000-cd1e170283951f42dd652021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 20V, Positive-QTOFsplash10-0udi-0000900000-cd1e170283951f42dd652021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 40V, Positive-QTOFsplash10-0zmi-0297300000-f2530c82106732c496702021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 10V, Negative-QTOFsplash10-0udi-0000900000-a8c4b840b6e64e3ef8db2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 20V, Negative-QTOFsplash10-0udi-1102900000-c659b5c5d58a53730f402021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexachlorophene 40V, Negative-QTOFsplash10-001l-9720000000-e35bd296f45503dfe4752021-10-11Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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 ]