Benzo[k]fluoranthene (CED0000044)

Record Information
Version1.0
Creation Date2009-03-06 18:58:00 UTC
Update Date2026-08-20 04:27:28 UTC
Accession NumberCHEM000058
Identification
Common NameBenzo[k]fluoranthene
ClassSmall Molecule
Description
Benzo[k]fluoranthene (C20H12) is a solid at room temperature with an average molecular weight of 252.31 g/mol. Benzo[k]fluoranthene belongs to the naphthalenes, a class of benzenoids within the organic compounds. This exogenous compound is used in various plastics, including High-Density Polyethylene, Low-Density Polyethylene, Polypropylene, Polystyrene, Expanded polystyrene, Polyvinyl Chloride, Polyamide, Polyurethane, Acrylonitrile butadiene styrene, and Polycarbonate. It is present in High impact polystyrene and is released in Polyethylene Terephthalate, while its presence in Superabsorbent polymer is inconclusive. The compound is found in or released from 19 recorded sources, including indoor air, drinking water, fencing, food preservation, food contact materials, and household cleaning and consumer products such as cigar cigarettes, tobacco pipes, pipe accessories, other smoking requisites, and non-electric simulated smoking devices. It is also associated with electrical and electronic equipment, such as electrodes, hybrid capacitors, radio transmission systems, conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. Exposure routes include oral, touch, and inhalation. Benzo[k]fluoranthene interacts with two recorded protein targets: the aryl hydrocarbon receptor (AHR) and glycine N-methyltransferase (GNMT). Binding to these proteins induces the expression of cytochrome P450 enzymes, specifically CYP1A1, CYP1A2, and CYP1B1, which metabolize the compound into toxic intermediates. These reactive metabolites, which include phenols, quinones, dihydrodiols, epoxide intermediates, and various combinations thereof, covalently bind to other cellular macromolecules and DNA, initiating carcinogenesis and mutagenesis.
Contaminant Type
  • Aromatic Hydrocarbon
  • Cigarette Toxin
  • Food Toxin
  • Industrial By-product/Pollutant
  • Industrial/Workplace Toxin
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical Structure
Synonyms
ValueSource
11,12-BenzofluorantheneKegg
benzo(K)FluorantheneMeSH
Chemical FormulaC20H12
Average Molecular Mass252.309 g/mol
Monoisotopic Mass252.094 g/mol
CAS Registry Number207-08-9
IUPAC Namepentacyclo[10.7.1.0^{2,11}.0^{4,9}.0^{16,20}]icosa-1(19),2,4,6,8,10,12,14,16(20),17-decaene
Traditional Namepentacyclo[10.7.1.0^{2,11}.0^{4,9}.0^{16,20}]icosa-1(19),2,4,6,8,10,12,14,16(20),17-decaene
SMILESC1=CC=C2C=C3C(=CC2=C1)C1=CC=CC2=CC=CC3=C12
InChI IdentifierInChI=1S/C20H12/c1-2-6-15-12-19-17-10-4-8-13-7-3-9-16(20(13)17)18(19)11-14(15)5-1/h1-12H
InChI KeyHAXBIWFMXWRORI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearancePale yellow solid.
Experimental Properties
PropertyValue
Melting Point217°C
Boiling PointNot Available
Solubility8e-07 mg/mL at 25 °C [PEARLMAN,RS et al. (1984)]
Predicted Properties
PropertyValueSource
Water Solubility4.9e-06 g/LALOGPS
logP6.13ALOGPS
logP5.27ChemAxon
logS-7.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.17 m³·mol⁻¹ChemAxon
Polarizability29.59 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0udi-0090000000-0fb1e10e7f5d139722afNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-f612ac63f25ab09a3fb7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-f612ac63f25ab09a3fb7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-da998b0ead23206d1398Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-31f8cde7b8fb38348ad0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-31f8cde7b8fb38348ad0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-a7dc66f1d25898e30831Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-b5f9e841f69a96c6392aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-b5f9e841f69a96c6392aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-15c41a541f380aede3e0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-969da6c938a324fffb4fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-969da6c938a324fffb4fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-969da6c938a324fffb4fNot AvailableView Spectrum
MSMS Spectrumsplash10-0udi-0390000000-7fadd00de7b666c8d6a4Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityThe ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (4, 5, 2, 3)
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (6)
Minimum Risk LevelNot Available
SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)
TreatmentThere is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (4)
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
115Drinking waterDrinking water & water supplyNot Available
494Food contact materialsFood, food processing & cookwareNot Available
496FencingBuilding & ConstructionNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureNAD-dependent histone deacetylase SIR2P06700Saccharomyces cerevisiae S288cPredicted (SEA)0.0778492
Click to view 3D structureSecernin-3Q0VDG4HumansPredicted (SEA)0.467095
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP04818HumansPredicted (SEA)14.48
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)653.856
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)231.601
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)327.2
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)350.088
Click to view 3D structurePeptidoglycan-N-acetylglucosamine deacetylase BC_1974Q81EJ6Bacillus cereus (strain ATCC 14579 / DSM 31 / JCM 2152 / NBRC 15305 /NCIMB 9373 / NRRL B-3711)Predicted (SEA)33.7087
Click to view 3D structureCytochrome P450 2A5P20852Mus musculusPredicted (SEA)6.77288
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP00469Lactobacillus caseiPredicted (SEA)27.6365
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)2169.03
Aryl hydrocarbon receptor structureClick to view 3D structureAryl hydrocarbon receptorP35869HumansPredicted (SEA)53.4824
Click to view 3D structureNa(+)/H(+) antiporter NhaAP13738Escherichia coli K-12Predicted (SEA)0.700643
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)101.671
Click to view 3D structureFemale germline-specific tumor suppressor gld-1Q17339Caenorhabditis elegansPredicted (SEA)6.53933
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)1222.47
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)735.753
Click to view 3D structureThymidylate synthaseC3SWJ7Escherichia coliPredicted (SEA)24.4447
Cysteine protease ATG4B structureClick to view 3D structureCysteine protease ATG4BQ9Y4P1HumansPredicted (SEA)91.5507
Click to view 3D structureThymidylate synthaseP0CS13Cryptococcus neoformans var. neoformans B-3501APredicted (SEA)1.24559
Protein S100-A4 structureClick to view 3D structureProtein S100-A4P26447HumansPredicted (SEA)9.10836
Cytochrome P450 2A6 structureClick to view 3D structureCytochrome P450 2A6P11509HumansPredicted (SEA)64.8484
Indoleamine 2,3-dioxygenase 1 structureClick to view 3D structureIndoleamine 2,3-dioxygenase 1P14902HumansPredicted (SEA)197.036
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)1226.83
Tyrosyl-DNA phosphodiesterase 2 structureClick to view 3D structureTyrosyl-DNA phosphodiesterase 2O95551HumansPredicted (SEA)53.9495
Aryl hydrocarbon receptor structureClick to view 3D structureAryl hydrocarbon receptorP35869HumansKnownMany PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)
Glycine N-methyltransferase structureClick to view 3D structureGlycine N-methyltransferaseQ14749HumansKnownMany PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8804
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC14321
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References