Showing Compound Card for Dibenz[a,h]anthracene (CDB005926)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-04-27 17:10:23 UTC
Updated at2021-01-06 19:06:59 UTC
CannabisDB IDCDB005926
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDibenz[a,h]anthracene
DescriptionDibenzo[a,h]anthracene, also known as 1,2:5,6-dibenzanthracene or DBA, belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. Dibenzo[a,h]anthracene is possibly neutral. Dibenz[a,h]anthracene is an organic compound with the chemical formula C22H14. It 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. Dibenzo[a,h]anthracene is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. It is one ingredient of cigarette. Dibenzo[a,h]anthracene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning of organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates (T3DB). Dibenzo[a,h]anthracene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2:5,6-DibenzanthraceneChEBI
DBAChEBI
1,2,5,6-DibenzanthraceneMeSH
1,2,5,6-Dibenzanthracene, ion(1+)MeSH
1,2,5,6-Dibenzanthracene, ion(1-)MeSH
Dibenz(a,H)anthraceneMeSH
dibenzo(a,H)AnthraceneMeSH
Chemical FormulaC22H14
Average Molecular Weight278.35
Monoisotopic Molecular Weight278.1096
IUPAC Namepentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene
Traditional Namepentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene
CAS Registry Number56-56-4
SMILES
C1=CC2=CC=C3C=C4C(C=CC5=CC=CC=C45)=CC3=C2C=C1
InChI Identifier
InChI=1S/C22H14/c1-3-7-19-15(5-1)9-11-17-14-22-18(13-21(17)19)12-10-16-6-2-4-8-20(16)22/h1-14H
InChI KeyLHRCREOYAASXPZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Anthracene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.93ALOGPS
logP5.93ChemAxon
logS-8.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.86 m³·mol⁻¹ChemAxon
Polarizability32.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-0190000000-84d24efcba4eb6b8512e2014-09-20View Spectrum
Predicted GC-MSDibenz[a,h]anthracene , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-0090000000-81693ebd93637cbc7080Spectrum
Predicted GC-MSDibenz[a,h]anthracene , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-3115bf003b9cee6116092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-749c760f7a5a9c1aeeb02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0090000000-e058e0550d22fa7479e52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-773f4e4ef9823ddfdea32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-773f4e4ef9823ddfdea32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-910a1e5be083829e55352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-3ca26a652eff5433f50a2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-3ca26a652eff5433f50a2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0090000000-27ab7759f478445cae3f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1f000ca3cb2151d263d2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-f1f000ca3cb2151d263d2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-0090000000-46f199df2f90ecf72a7d2021-10-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0251159
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00017098
Chemspider ID5678
KEGG Compound IDC14325
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID35299
References
General ReferencesNot Available