Dibenzo[a,l]pyrene (CHEM003183)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:54:24 UTC
Update Date2026-04-17 15:57:01 UTC
Accession NumberCHEM003183
Identification
Common NameDibenzo[a,l]pyrene
ClassSmall Molecule
DescriptionThis compound belongs to the family of Benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.
Contaminant Sources
  • Clean Air Act Chemicals
  • IARC Carcinogens Group 2A
  • My Exposome Chemicals
  • T3DB toxins
Contaminant Type
  • Cigarette Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3,4-DibenzpyreneChEBI
1,2,9,10-DibenzopyreneChEBI
1,2:3,4-DibenzopyreneChEBI
1,2:9,10-DibenzopyreneChEBI
2,3:4,5-DibenzopyreneChEBI
4,5,6,7-DibenzpyreneChEBI
DB(a,L)pChEBI
DBPChEBI
Dibenzo(D,e,F,p)chryseneChEBI
Dibenzo[def,p]chryseneChEBI
Dibenzo(a,L)pyreneHMDB
1,2,3,4-DibenzopyreneHMDB
Dibenzo(def,p)chryseneHMDB
Chemical FormulaC24H14
Average Molecular Mass302.368 g/mol
Monoisotopic Mass302.110 g/mol
CAS Registry Number191-30-0
IUPAC Namehexacyclo[10.10.2.0²,⁷.0⁸,²⁴.0¹⁵,²³.0¹⁷,²²]tetracosa-1(23),2,4,6,8,10,12(24),13,15,17,19,21-dodecaene
Traditional NameDIBENZO[a,l]PYRENE
SMILESC1=CC=C2C(=C1)C=C1C=CC3=C4C(=CC=C3)C3=CC=CC=C3C2=C14
InChI IdentifierInChI=1S/C24H14/c1-2-8-18-16(6-1)14-17-13-12-15-7-5-11-20-19-9-3-4-10-21(19)24(18)23(17)22(15)20/h1-14H
InChI KeyJNTHRSHGARDABO-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-e-pyrene
  • Benzo-a-pyrene
  • Triphenylene
  • 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
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.6e-07 g/LALOGPS
logP7.45ALOGPS
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
Polarizability34.99 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0069000000-79ffc5ceeae8bcda5804Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-47a15bfb48ded410fec5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019000000-f65c65a5ce298114108aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0093000000-09920bc24c1bd8854810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-e12220354769bce9257fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-e12220354769bce9257fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0069000000-c0191e32f85fb011592bSpectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-0419000000-f51bcd5a2a855e4946b6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2A, probably 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 IDHMDB0060116
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 ID35861
PubChem Compound ID9119
Kegg Compound IDC19174
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.