Showing Compound Card for Anthracene (CDB005863)

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Record Information
Version1.0
Created at2020-04-27 17:04:05 UTC
Updated at2021-01-06 19:06:58 UTC
CannabisDB IDCDB005863
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAnthracene
DescriptionAnthracene is a member of the class of compounds known as anthracenes. Anthracenes are organic compounds containing a system of three linearly fused benzene rings. Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10. It is a component of coal tar and it is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400-500 nm peak) fluorescence under ultraviolet radiation. Anthracene is formally rated as a non-carcinogenic (IARC 3) but potentially toxic compound. PAH metabolism occurs in all tissues, usually by cytochrome P-450, specifically by its associated enzymes CYP1A1 and CYP1B1 (PMID: 14720319 ). These enzymes metabolize PAH's into their toxic intermediates. The metabolites of PAHs, such as phenols, quinones, and dihydrodiols, can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. PAHs are generally considered as cancerogenic to varying degrees. Anthracene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AnthrazenChEBI
Anthracene, sodium salt, ion (1-)HMDB
Chemical FormulaC14H10
Average Molecular Weight178.23
Monoisotopic Molecular Weight178.0783
IUPAC Nameanthracene
Traditional Nameanthracene
CAS Registry Number120-12-7
SMILES
C1=CC2=CC3=CC=CC=C3C=C2C=C1
InChI Identifier
InChI=1S/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H
InChI KeyMWPLVEDNUUSJAV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassNot Available
Direct ParentAnthracenes
Alternative Parents
Substituents
  • 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 Point216 °C at 760 mmHgWikipedia
Boiling Point341.3 °C at 760 mmHgWikipedia
Water Solubility0.044 mg/L at 25 °CWikipedia
logP4.56Wikipedia
Predicted Properties
PropertyValueSource
logP4.56ALOGPS
logP3.95ChemAxon
logS-5.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity58.96 m³·mol⁻¹ChemAxon
Polarizability20.61 ųChemAxon
Number of Rings3ChemAxon
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-2900000000-675a19db0c1732536f9c2014-09-20View Spectrum
Predicted GC-MSAnthracene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-0900000000-d3d9e217ff8f2666316bSpectrum
Predicted GC-MSAnthracene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-57a407595d8d4d4f83602016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-57a407595d8d4d4f83602016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1900000000-7b27938dfa3a7a68eaf42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-1441cd503a5c1f7bffa72016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-1441cd503a5c1f7bffa72016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-d151e8f9f566ca0e402f2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2afa14fa908f69024c442021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-2afa14fa908f69024c442021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0900000000-86e8a779c98b6b6a02ab2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-a5c7c61e51665431ac9b2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-a5c7c61e51665431ac9b2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-a5c7c61e51665431ac9b2021-10-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 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 IDHMDB0248460
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006967
KNApSAcK IDC00002864
Chemspider ID8111
KEGG Compound IDC14315
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnthracene
METLIN IDNot Available
PubChem Compound8418
PDB IDNot Available
ChEBI ID35298
References
General References
  1. Shimada T, Fujii-Kuriyama Y: Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes P450 1A1 and 1B1. Cancer Sci. 2004 Jan;95(1):1-6. doi: 10.1111/j.1349-7006.2004.tb03162.x. [PubMed:14720319 ]