Dibenzo(a,i)pyrene (CHEM003181)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:54:10 UTC
Update Date2026-04-17 15:55:49 UTC
Accession NumberCHEM003181
Identification
Common NameDibenzo(a,i)pyrene
ClassSmall Molecule
DescriptionDibenzo(a,i)pyrene belongs to the family of Benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system. It is an environmental polycyclic aromatic hydrocarbon, is the most potent carcinogen ever tested in mouse skin and rat mammary gland.
Contaminant Sources
  • Clean Air Act Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • T3DB toxins
Contaminant Type
  • Cigarette Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Benzo(RST)pentapheneMeSH
3,4-9,10-DibenzopyreneMeSH
Dibenzo(a,i)pyreneMeSH
Chemical FormulaC24H14
Average Molecular Mass302.368 g/mol
Monoisotopic Mass302.110 g/mol
CAS Registry Number189-55-9
IUPAC Namehexacyclo[10.10.2.0²,⁷.0⁹,²³.0¹⁴,¹⁹.0²⁰,²⁴]tetracosa-1(23),2,4,6,8,10,12,14,16,18,20(24),21-dodecaene
Traditional Namehexacyclo[10.10.2.0²,⁷.0⁹,²³.0¹⁴,¹⁹.0²⁰,²⁴]tetracosa-1(23),2,4,6,8,10,12,14,16,18,20(24),21-dodecaene
SMILESC1=CC=C2C(=C1)C=C1C=CC3=CC4=CC=CC=C4C4=C3C1=C2C=C4
InChI IdentifierInChI=1S/C24H14/c1-3-7-19-15(5-1)13-17-9-10-18-14-16-6-2-4-8-20(16)22-12-11-21(19)23(17)24(18)22/h1-14H
InChI KeyTUGYIJVAYAHHHM-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
  • Cytosol
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Nucleotide Excision RepairSMP00478 map03420
ApoptosisNot Availablemap04210
Cell cycleNot Availablemap04110
Base excision repairNot Availablemap03410
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
Polarizability35.48 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-c0171fab86acf676623fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-8c40a6a745f606d2a71cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-0098000000-cfe1c43f8ba27e43941bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-013e1ff6ef29d7cd1b94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-013e1ff6ef29d7cd1b94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0029000000-5b3d9560b833e62e5290Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-0319000000-92ab47c227d476a1acfaSpectrum
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. (3)
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 ID9106
Kegg Compound IDC19223
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available