Showing Compound Card for Chrysene (CDB005898)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-04-27 17:07:34 UTC
Updated at2021-01-06 19:06:58 UTC
CannabisDB IDCDB005898
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameChrysene
DescriptionChrysene belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. They may also cause reproductive effects and depress the immune system. Chrysene is possibly neutral. Chrysene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. They are usually found as a mixture containing two or more of these compounds. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. Chrysene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers (T3DB). Chrysene 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-DibenzonaphthaleneChEBI
1,2-BenzophenanthreneChEBI
Benz[a]phenanthreneChEBI
Benzo[a]phenanthreneChEBI
ChrysenChEBI
Chemical FormulaC18H12
Average Molecular Weight228.29
Monoisotopic Molecular Weight228.0939
IUPAC Namechrysene
Traditional Namechrysene
CAS Registry Number218-01-9
SMILES
C1=CC2=CC=C3C4=CC=CC=C4C=CC3=C2C=C1
InChI Identifier
InChI=1S/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H
InChI KeyWDECIBYCCFPHNR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassChrysenes
Direct ParentChrysenes
Alternative Parents
Substituents
  • Chrysene
  • Naphthalene
  • 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 Point254 °CWikipedia
Boiling Point448 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.71ALOGPS
logP4.94ChemAxon
logS-7.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity75.41 m³·mol⁻¹ChemAxon
Polarizability26.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-0090000000-008c5314ed8ae5725e3a2014-09-20View Spectrum
Predicted GC-MSChrysene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-0190000000-feb74c065b2ddee5d227Spectrum
Predicted GC-MSChrysene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-b7159ca7c08c3b71bd952016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-d6a81f78e33eddf5f6232016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-0090000000-0ac1df0c431c6c8220362016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-3a53674e8156110b1bed2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-3a53674e8156110b1bed2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-b07df02ba42d338087292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-1345c9a6e6eae72769592021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-1345c9a6e6eae72769592021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0090000000-96fab4943b7ee18d243f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-21ab23fa1007795bd0da2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-21ab23fa1007795bd0da2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-8062207992d5862f74bb2021-10-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 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 IDHMDB0250216
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8817
KEGG Compound IDC14222
BioCyc IDCPD-13772
BiGG IDNot Available
Wikipedia LinkChrysene
METLIN IDNot Available
PubChem Compound9171
PDB IDNot Available
ChEBI ID51687
References
General ReferencesNot Available