Dibenzo(a,h)pyrene (CHEM003182)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:54:16 UTC
Update Date2026-04-17 15:55:49 UTC
Accession NumberCHEM003182
Identification
Common NameDibenzo(a,h)pyrene
ClassSmall Molecule
DescriptionDibenzo(a,h)pyrene is a polycyclic aromatic hydrocarbon made of five fused benzene rings. It is a fused five ringed, cyclopenta, PAHs compound which is common as a pollutant of smoke and oils. It is white to light yellow crystalline solid. It is stable and highly genotoxic in bacterial and mammalian cell systems, as it intercalates into DNA and causes mutations.
Contaminant Sources
  • Clean Air Act Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • T3DB toxins
Contaminant Type
  • Cigarette Toxin
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3,4:8,9-DibenzopyreneKegg
3,4-8,9-DibenzopyreneMeSH
Dibenzo(a,H)pyreneMeSH
Chemical FormulaC24H14
Average Molecular Mass302.368 g/mol
Monoisotopic Mass302.110 g/mol
CAS Registry Number189-64-0
IUPAC Namehexacyclo[10.10.2.0²,⁷.0⁹,²³.0¹³,¹⁸.0²⁰,²⁴]tetracosa-1(23),2,4,6,8,10,12(24),13,15,17,19,21-dodecaene
Traditional Namedibenzo[a,h]pyrene
SMILESC1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC1=CC=CC=C31
InChI IdentifierInChI=1S/C24H14/c1-3-7-19-15(5-1)13-17-9-12-22-20-8-4-2-6-16(20)14-18-10-11-21(19)23(17)24(18)22/h1-14H
InChI KeyRXUSYFJGDZFVND-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPyrenes
Sub ClassBenzopyrenes
Direct ParentBenzopyrenes
Alternative Parents
Substituents
  • Benzo-a-pyrene
  • Chrysene
  • Phenanthrene
  • Anthracene
  • 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
  • Microsome
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Nucleotide Excision RepairSMP00478 map03420
Cell cycleNot Availablemap04110
Degradation Of Aromatic CompoundsNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.5e-07 g/LALOGPS
logP7.49ALOGPS
logP6.26ChemAxon
logS-8.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity99.62 m³·mol⁻¹ChemAxon
Polarizability35.52 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-b1b5fafa768a6638d4a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-f8a7b442bdaee00f0356Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-0059000000-c0001af367ed54224db9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-e12d0955684fc8ca7756Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-e12d0955684fc8ca7756Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0019000000-3fa0b6b7fbfdcc1545fbSpectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-0619000000-bcddb692f8bbef9eee44Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (2)
Uses/SourcesThis is a toxic chemical found in cigarettes or generated by tobacco combustion.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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 IDNot Available
ChEBI IDNot Available
PubChem Compound ID9108
Kegg Compound IDC19222
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available