Pentacene (CHEM000558)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-03-06 18:59:16 UTC
Update Date2026-04-03 14:12:51 UTC
Accession NumberCHEM000558
Identification
Common NamePentacene
ClassSmall Molecule
DescriptionPentacene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. (4)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3:6,7-DibenzanthraceneChEBI
Benzo[b]naphthaceneChEBI
Chemical FormulaC22H14
Average Molecular Mass278.347 g/mol
Monoisotopic Mass278.110 g/mol
CAS Registry Number135-48-8
IUPAC Namepentacene
Traditional Namepentacene
SMILESC1=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C2C=C1
InChI IdentifierInChI=1S/C22H14/c1-2-6-16-10-20-14-22-12-18-8-4-3-7-17(18)11-21(22)13-19(20)9-15(16)5-1/h1-14H
InChI KeySLIUAWYAILUBJU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentacenes. Pentacenes are compounds containing a pentacene moiety, which is consists of five linearly fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPentacenes
Sub ClassNot Available
Direct ParentPentacenes
Alternative Parents
Substituents
  • Pentacene
  • 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 RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless solid.
Experimental Properties
PropertyValue
Melting Point257°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.8e-07 g/LALOGPS
logP6.85ALOGPS
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
Polarizability33.39 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-765bfbf382ddedaf2ac7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-765bfbf382ddedaf2ac7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0090000000-5c8af8b3a4272e203973Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-773f4e4ef9823ddfdea3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-773f4e4ef9823ddfdea3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-b5308c827319619051efSpectrum
MSMass Spectrum (Electron Ionization)splash10-004i-0390000000-31e35f7a29c246e88f9fSpectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4)
Mechanism of ToxicityThe ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. 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. (4, 5, 2, 3)
MetabolismPAH 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. (4)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC. IARC has evaluated other PAHs (6).
Uses/SourcesPAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (4)
Minimum Risk LevelNot Available
Health EffectsPAHs 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. (4)
SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)
TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (4)
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 LinkPentacene
Chemspider IDNot Available
ChEBI ID33148
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20699485