Pentachlorophenol (CED0000031)

Record Information
Version1.0
Creation Date2009-03-06 18:57:58 UTC
Update Date2026-08-23 16:32:14 UTC
Accession NumberCHEM000041
Identification
Common NamePentachlorophenol
ClassSmall Molecule
Description
Pentachlorophenol (C6HCl5O) is a solid organic compound with an average molecular weight of 266.34 g/mol. Pentachlorophenol belongs to the halophenols, a subclass of phenols within the organic compounds. This exogenous compound is classified as a benzenoid and is utilized industrially as a pesticide (PMC11411717), biocide, fungicide (PMC7009407), and degradant/impurity. Environmentally, it is recognized as a persistent organic pollutant (PMC11049475), and biologically it serves as an inhibitor (PMC3985935) and human xenobiotic metabolite. Exposure occurs via oral, inhalation, and touch routes, with recorded sources including drinking water, building and construction materials such as floors and roofs, food processing, household cleaning products, electrical and electronic equipment, and various household items. It is present in polyethylene terephthalate but not detected in polycarbonate. The compound acts on numerous protein targets. It inhibits phenol-sulfotransferases, including SULT1A1 and SULT1A3, and inhibits acetylcholinesterase in erythrocyte membranes. Pentachlorophenol disrupts thyroid homeostasis by competing for thyroxine binding sites on SERPINA7 and competing with thyroxine for uptake into cerebrospinal fluid at the T4 binding site of transthyretin. It further inhibits O-acetyltransferases, such as CRAT and CHAT. As an organochloride, it inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase (including ATP1A1, ATP1A2, ATP1A3, and FXYD2), leading to intracellular free calcium ion accumulation and subsequent central nervous system stimuli propagation. It also inhibits mitochondrial ATP-ase activity via ATP4A and ATP4B, preventing ATP formation. Additionally, it antagonizes GABA-A receptors (including GABRA1, GABRA2, GABRA3, and GABRA4), blocking chloride ion uptake and causing central nervous system hyperexcitability. Health effects associated with pentachlorophenol include lymphoma (PMC5453502, PMC6625894) and an increase in non-Hodgkin lymphoma (PMC10598475).
Contaminant Type
  • Aromatic Hydrocarbon
  • Human Neurotoxin
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
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 Mass266.337 g/mol
Monoisotopic Mass263.847 g/mol
CAS Registry Number87-86-5
IUPAC Namepentachlorophenol
Traditional Namepermite
SMILESOC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceColorless (pure) or dark gray to brown (inpure) solid.
Experimental Properties
PropertyValue
Melting Point174°C
Boiling Point309-310°C
Solubility0.014 mg/mL at 25°C
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
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-014i-3590000000-e28db0931c3a64c5acdcNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-006x-8219000000-8910acf1ed3be43cd77bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-006x-9313000000-9b0f7071c23978d3b163Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-014i-3590000000-e28db0931c3a64c5acdcNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-006x-8219000000-8910acf1ed3be43cd77bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-006x-9313000000-9b0f7071c23978d3b163Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-014i-0090000000-372477d228a07e38fb8cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-9037000000-c0568714ed7ae0793386Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-c07304b5de53109ffe95Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-c07304b5de53109ffe95Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-a2ac24a2b8c95d48eaa9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-f11dce9638967fa2edd6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-444986831b0f32a73b6cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-5e8d19e4bc541c1b66e6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-60df94932344c9ac45caNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-5205c07a823be8027dcbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-5e8d19e4bc541c1b66e6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-a2ac24a2b8c95d48eaa9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-41111bd228347e1b53acNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-c07304b5de53109ffe95Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-65f2bd9ec1d84906a46aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-444986831b0f32a73b6cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-fe16cb367a3097b46dceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-fe16cb367a3097b46dceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-0090000000-a2ad498e1418227155d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-5ba49a7b3703eabe8481Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-3d5f8e3c5b92e6bffb78Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-3d5f8e3c5b92e6bffb78Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-563e7d9b4b491a60a828Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-563e7d9b4b491a60a828Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-563e7d9b4b491a60a828Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-e7a28a8ea0101bc97aa6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-e7a28a8ea0101bc97aa6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-e7a28a8ea0101bc97aa6Not AvailableView Spectrum
MSMS Spectrumsplash10-014i-3590000000-1be327edcf96b221d568Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityPentachlorophenol is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (14)
Minimum Risk LevelAcute Oral: 0.005 mg/kg/day (13) Intermediate Oral: 0.001 mg/kg/day (13) Chronic Oral: 0.001 mg/kg/day (13)
SymptomsExposure to high levels of pentachlorophenol can cause the cells in the body to produce excess heat, resulting in a very high fever, profuse sweating, and difficulty breathing. Contact with pentachlorophenol, particularly in the form of vapor can irritate the skin, eyes, and mouth. (11, 12)
TreatmentIf the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
27.0mg/kgNot AvailableRatLD50OralexperimentalT26
96.0mg/kgNot AvailableRatLD50DermalexperimentalT26
56.0mg/kgNot AvailableRatLD50IntraperitonealexperimentalT26
58.0mg/kgNot AvailableRatLD50SubcutaneousexperimentalT26
Health Effects
Health EffectRelationshipDirectionReference
lymphomaassociated_withNot AvailablePMC5453502 , PMC6625894
non-Hodgkin lymphomaassociated_withincreasePMC10598475
kidney cancerassociated_withNot AvailablePMC5453502
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
572Credit Card HoldersHousehold itemsNot Available
573Key RingsHousehold itemsNot Available
577Watch ChainsHousehold itemsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
586Fishing BoatsMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
590Lifeboat EquipmentMarine, shipping & aquacultureNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
599Harvesters For PeanutsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
622Game AccessoriesRecreation & sports surfacesNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
627Roulette GamesRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
639Degreasing LeatherTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
641Foam DyeingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
644Hook Or Eye FastenersTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
648Nitro DyesTextiles, leather & furnishingsNot Available
649Pins ClothesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)5860.33
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)6823.8
Click to view 3D structureThromboxane-A synthaseP24557HumansPredicted (SEA)2222.36
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)6400.76
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)7293.85
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)5564.82
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)5635.04
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)6394.15
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)6375.31
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)6537.62
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)6423.34
Tyrosine-protein kinase Fyn structureClick to view 3D structureTyrosine-protein kinase FynP06241HumansPredicted (SEA)7331.61
Click to view 3D structureCarbonic anhydraseQ2PCB5Dicentrarchus labraxPredicted (SEA)130.787
Substance-K receptor structureClick to view 3D structureSubstance-K receptorP21452HumansPredicted (SEA)5198.62
Click to view 3D structureCalpain-2 catalytic subunitP43367Sus scrofaPredicted (SEA)3674.56
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)5974.15
Click to view 3D structureEnvelope glycoprotein gp160Q6QLK5Human immunodeficiency virus 1Predicted (SEA)2194.73
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)3447.32
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)6131.64
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)2884.94
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)2719.51
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)6504.93
Click to view 3D structureVacuolar aminopeptidase 1P14904Saccharomyces cerevisiae S288cPredicted (SEA)44.2184
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)6778.25
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)6765.64
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansKnownCauses endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansKnownCauses endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansKnownPentachlorophenol inhibits acetylcholinesterase in erythrocyte membranes. (A93)
Calcium-transporting ATPase type 2C member 1 structureClick to view 3D structureCalcium-transporting ATPase type 2C member 1P98194HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Carnitine O-acetyltransferase structureClick to view 3D structureCarnitine O-acetyltransferaseP43155HumansKnownPentachlorophenol inhibits O-acetyltransferases. (A94)
Choline O-acetyltransferase structureClick to view 3D structureCholine O-acetyltransferaseP28329HumansKnownPentachlorophenol inhibits O-acetyltransferases. (A94)
Gamma-aminobutyric acid receptor subunit alpha-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-1P14867HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit alpha-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-2P47869HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit alpha-3 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-3P34903HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit alpha-4 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-4P48169HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit alpha-5 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-5P31644HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-6Q16445HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit beta-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-1P18505HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit beta-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-2P47870HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit beta-3 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-3P28472HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit delta structureClick to view 3D structureGamma-aminobutyric acid receptor subunit deltaO14764HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structureGamma-aminobutyric acid receptor subunit epsilonP78334HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structureGamma-aminobutyric acid receptor subunit gamma-1Q8N1C3HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit gamma-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit gamma-2P18507HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structureGamma-aminobutyric acid receptor subunit gamma-3Q99928HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit pi structureClick to view 3D structureGamma-aminobutyric acid receptor subunit piO00591HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Gamma-aminobutyric acid receptor subunit rho-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit rho-1P24046HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structureGamma-aminobutyric acid receptor subunit rho-2P28476HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structureGamma-aminobutyric acid receptor subunit rho-3A8MPY1HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structureGamma-aminobutyric acid receptor subunit thetaQ9UN88HumansKnownThis organochloride antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. (T10)
Click to view 3D structurePotassium-transporting ATPase alpha chain 1P20648HumansKnownPentachlorophenol inhibits mitochondrial ATP-ase activity, preventing the the formation of ATP and the release of energy to the cell from the breakdown of ATP to ADP. (A95)
Click to view 3D structurePotassium-transporting ATPase subunit betaP51164HumansKnownPentachlorophenol inhibits mitochondrial ATP-ase activity, preventing the the formation of ATP and the release of energy to the cell from the breakdown of ATP to ADP. (A95)
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansKnownPentachlorophenol is an antagonist of progesterone receptor (PR). It inhibits the gene expression via the PR in a dose-dependent manner.
Click to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 1O14983HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 structureClick to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 2P16615HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Sodium/potassium-transporting ATPase subunit alpha-1 structureClick to view 3D structureSodium/potassium-transporting ATPase subunit alpha-1P05023HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structureSodium/potassium-transporting ATPase subunit alpha-2P50993HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Sodium/potassium-transporting ATPase subunit alpha-3 structureClick to view 3D structureSodium/potassium-transporting ATPase subunit alpha-3P13637HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Sodium/potassium-transporting ATPase subunit alpha-4 structureClick to view 3D structureSodium/potassium-transporting ATPase subunit alpha-4Q13733HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Sodium/potassium-transporting ATPase subunit beta-1 structureClick to view 3D structureSodium/potassium-transporting ATPase subunit beta-1P05026HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structureSodium/potassium-transporting ATPase subunit beta-2P14415HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Click to view 3D structureSodium/potassium-transporting ATPase subunit beta-3P54709HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Sodium/potassium-transporting ATPase subunit gamma structureClick to view 3D structureSodium/potassium-transporting ATPase subunit gammaP54710HumansKnownThis organochloride inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
Sulfotransferase 1A1 structureClick to view 3D structureSulfotransferase 1A1P50225HumansKnownPentachlorophenol prevents sulfation by inhibiting phenol-sulfotransferases. (A92)
Sulfotransferase 1A3 structureClick to view 3D structureSulfotransferase 1A3P0DMM9HumansKnownPentachlorophenol prevents sulfation by inhibiting phenol-sulfotransferases. (A92)
Thyroxine-binding globulin structureClick to view 3D structureThyroxine-binding globulinP05543HumansKnownPentachlorophenol causes adverse effects on thyroid homeostasis, decreasing serum thyroxine by competing for serum protein thyroxine binding sites. (L127)
Transient receptor potential cation channel subfamily A member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily A member 1O75762HumansKnownNot Available
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansKnownPentachlorophenol competes with thyroxine for uptake into cerebrospinal fluid at the T4 binding site of transthyretin. (L127)
Click to view 3D structureNuclear receptor ROR-betaQ92753HumansKnownNot Available
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansKnownNot Available
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansKnownNot Available
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansKnownNot Available
Estrogen-related receptor gamma structureClick to view 3D structureEstrogen-related receptor gammaP62508HumansKnownNot Available
Protein c-Fos structureClick to view 3D structureProtein c-FosP01100HumansKnownNot Available
Transforming growth factor beta-1 proprotein structureClick to view 3D structureTransforming growth factor beta-1 proproteinP01137HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0041974
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00007496
BiGG IDNot Available
BioCyc IDPENTACHLOROPHENOL
METLIN IDNot Available
PDB IDPCI
Wikipedia LinkPentachlorophenol
Chemspider ID967
ChEBI ID17642
PubChem Compound ID992
Kegg Compound IDC02575
YMDB IDNot Available
ECMDB IDM2MDB005730
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17497895
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23636589
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24123209
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. Gonczi C, Hollo A, Komaromi S, Molnar J: [Elevated pentachlorphenol in urine following Fungifen therapy]. Orv Hetil. 1991 Feb 17;132(7):361-3.
11. Kalman DA, Horstman SW: Persistence of tetrachlorophenol and pentachlorophenol in exposed woodworkers. J Toxicol Clin Toxicol. 1983 Jun;20(4):343-52.
12. 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.