Dibenz[a,h]acridine (CHEM003588)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-09-08 02:38:28 UTC
Update Date2026-04-17 16:06:56 UTC
Accession NumberCHEM003588
Identification
Common NameDibenz[a,h]acridine
ClassSmall Molecule
DescriptionDibenz[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.
Contaminant Sources
  • Clean Air Act Chemicals
  • IARC Carcinogens Group 2B
  • T3DB toxins
Contaminant Type
  • Cigarette Toxin
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Dibenz(a,H)acridineMeSH
Dibenz(a,J)acridineMeSH
DibenzacridineMeSH
Chemical FormulaC21H13N
Average Molecular Mass279.335 g/mol
Monoisotopic Mass279.105 g/mol
CAS Registry Number226-36-8
IUPAC Name2-azapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaene
Traditional Name2-azapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaene
SMILESC1=CC=C2C(C=CC3=C2C=C2C=CC4=CC=CC=C4C2=N3)=C1
InChI IdentifierInChI=1S/C21H13N/c1-3-7-17-14(5-1)11-12-20-19(17)13-16-10-9-15-6-2-4-8-18(15)21(16)22-20/h1-13H
InChI KeyJNCSIWAONQTVCF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzacridines. These are organic heterocyclic compounds with a structure characterized by a benzene ring fused to an acridine ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentBenzacridines
Alternative Parents
Substituents
  • Benz-c-acridine
  • Benz-a-acridine
  • Naphthalene
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Microsome
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot 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 Solubility6.2e-06 g/LALOGPS
logP5.83ALOGPS
logP5.49ChemAxon
logS-7.6ALOGPS
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.96 m³·mol⁻¹ChemAxon
Polarizability32.24 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-555739c719ace9165596Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0090000000-39ab9be8543d133c66e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-0090000000-558f2a11f8e05f7183d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-ffae77def7653a96f574Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-a7eef4ee609ad8e8954dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-0090000000-67808fbc34bf9b84bed8Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-1590000000-1d6239c2696d50236a78Spectrum
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. (1)
Uses/SourcesNot Available
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 ID9183
Kegg Compound IDC19219
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available