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Showing metabocard for Pentachlorophenol (HMDB0041974)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-13 11:51:03 UTC
Update Date2019-07-23 06:35:19 UTC
HMDB IDHMDB0041974
Secondary Accession Numbers
  • HMDB41974
Metabolite Identification
Common NamePentachlorophenol
DescriptionPentachlorophenol, also known as PCP or chlorophen, belongs to the class of organic compounds known as p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring. Pentachlorophenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Pentachlorophenol exists in all living organisms, ranging from bacteria to humans. It can be found in two forms: Pentachlorophenol itself or as the sodium salt of PCP, which dissolves easily in water. Pentachlorophenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. Prenatal exposure has been linked to impaired fetal growth and development.
Structure
Data?1563863719
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3,4,5,6-PentachlorophenolChEBI
PCPChEBI
1-Hydroxy-2,3,4,5,6-pentachlorobenzeneHMDB
2, 3,4,5,6-PentachlorophenolHMDB
2,3,4,5,6-Pentachlorophenol (acd/name 4.0)HMDB
Chem-tolHMDB
ChlorophenHMDB
Dowicide 7HMDB
Dowicide gHMDB
DurotoxHMDB
FungifenHMDB
Glazd pentaHMDB
Grundier arbezolHMDB
LauxtolHMDB
Lauxtol aHMDB
LiropremHMDB
PCP (Pesticide)HMDB
PenchlorolHMDB
PentaHMDB
Penta-kilHMDB
Pentachloro-phenolHMDB
PentachlorophenateHMDB
Pentachlorophenol pureHMDB
PentaconHMDB
PentasolHMDB
PenwarHMDB
PeratoxHMDB
PermacideHMDB
PermagardHMDB
PermasanHMDB
PermatoxHMDB
PermiteHMDB
Phenol, pentachloro-, pureHMDB
Preventol pHMDB
SantobriteHMDB
SantophenHMDB
Santophen 20HMDB
SinituhoHMDB
Term-i-trolHMDB
Thompson'S wood fixHMDB
WeedoneHMDB
Sodium pentachlorophenateHMDB
Pentachlorophenate, sodiumHMDB
Chemical FormulaC6HCl5O
Average Molecular Weight266.337
Monoisotopic Molecular Weight263.847003189
IUPAC Namepentachlorophenol
Traditional Namepermite
CAS Registry Number87-86-5
SMILES
OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl
InChI Identifier
InChI=1S/C6HCl5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
InChI KeyIZUPBVBPLAPZRR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassHalophenols
Direct ParentP-chlorophenols
Alternative Parents
Substituents
  • 4-chlorophenol
  • 2-chlorophenol
  • 3-chlorophenol
  • Halobenzene
  • Chlorobenzene
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Process

Industrial process:

Role

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point174 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 mg/mL at 25 °CNot Available
LogP5.12Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP4.99ALOGPS
logP4.69ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.98ChemAxon
pKa (Strongest Basic)-8.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.06 m³·mol⁻¹ChemAxon
Polarizability20.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-3590000000-e28db0931c3a64c5acdcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006x-8219000000-8910acf1ed3be43cd77bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006x-9313000000-9b0f7071c23978d3b163Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-3590000000-e28db0931c3a64c5acdcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006x-8219000000-8910acf1ed3be43cd77bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006x-9313000000-9b0f7071c23978d3b163Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0090000000-372477d228a07e38fb8cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9037000000-c0568714ed7ae0793386Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0090000000-c07304b5de53109ffe95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0090000000-c07304b5de53109ffe95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0090000000-a2ac24a2b8c95d48eaa9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0090000000-f11dce9638967fa2edd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0090000000-444986831b0f32a73b6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0090000000-5e8d19e4bc541c1b66e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0090000000-60df94932344c9ac45caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-fe16cb367a3097b46dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-fe16cb367a3097b46dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0090000000-a2ad498e1418227155d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-5ba49a7b3703eabe8481Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-3d5f8e3c5b92e6bffb78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0090000000-3d5f8e3c5b92e6bffb78Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-3590000000-1be327edcf96b221d568Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.000505 (0.000424-0.000637) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
 details
UrineDetected and Quantified0.000743 (0.000586-0.00114) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007496
Chemspider ID967
KEGG Compound IDC02575
BioCyc IDPENTACHLOROPHENOL
BiGG IDNot Available
Wikipedia LinkPentachlorophenol
METLIN IDNot Available
PubChem Compound992
PDB IDPCI
ChEBI ID17642
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Baker PB, Carriere Y: Effectiveness of commercial and experimental termite monitors for the desert subterranean termite Heterotermes aureus (Isoptera: Rhinotermitidae) in southern Arizona. J Econ Entomol. 2011 Aug;104(4):1339-42. [PubMed:21882701 ]
  2. Pan J, Yang Y, Geng C, Yeung LW, Cao X, Dai T: Polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins and dibenzofurans in marine and lacustrine sediments from the Shandong Peninsula, China. J Hazard Mater. 2010 Apr 15;176(1-3):274-9. doi: 10.1016/j.jhazmat.2009.11.024. Epub 2009 Nov 11. [PubMed:19959279 ]
  3. Zhou L, Li H, Yu Z, Ren M, Zeng X, Peng P, Sheng G, Fu J: Chlorinated and brominated dibenzo-p-dioxins and dibenzofurans in surface sediment from Taihu Lake, China. J Environ Monit. 2012 Jul;14(7):1935-42. doi: 10.1039/c2em10818f. Epub 2012 May 29. [PubMed:22641387 ]
  4. Xu MX, Yan JH, Lu SY, Li XD, Chen T, Ni MJ, Dai HF, Cen KF: Source identification of PCDD/Fs in agricultural soils near to a Chinese MSWI plant through isomer-specific data analysis. Chemosphere. 2008 Apr;71(6):1144-55. doi: 10.1016/j.chemosphere.2007.10.032. Epub 2008 Feb 14. [PubMed:18279911 ]
  5. Nidasio G, Broglia L, Sozze T: [Quantification of pentachlorophenol in urine by gas chromatography/mass spectrometry with a fragmentographic technic]. G Ital Med Lav. 1985 Jul;7(4):157-61. [PubMed:3836922 ]
  6. Tisch M, Lohmeier A, Schmezer P, Bartsch H, Maier H: [Genotoxic effect of the insecticides pentachlorophenol and lindane on human nasal mucosal epithelium]. Dtsch Med Wochenschr. 2001 Jul 27;126(30):840-4. [PubMed:11512281 ]
  7. Gonczi C, Hollo A, Komaromi S, Molnar J: [Elevated pentachlorphenol in urine following Fungifen therapy]. Orv Hetil. 1991 Feb 17;132(7):361-3. [PubMed:2057200 ]
  8. Kalman DA, Horstman SW: Persistence of tetrachlorophenol and pentachlorophenol in exposed woodworkers. J Toxicol Clin Toxicol. 1983 Jun;20(4):343-52. [PubMed:6655774 ]
  9. Persson Y, Lundstedt S, Oberg L, Tysklind M: Levels of chlorinated compounds (CPs, PCPPs, PCDEs, PCDFs and PCDDs) in soils at contaminated sawmill sites in Sweden. Chemosphere. 2007 Jan;66(2):234-42. Epub 2006 Jul 24. [PubMed:16860850 ]