ContaminantDB: Picene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:59:17 UTC

Update Date

2026-04-04 18:38:26 UTC

Accession Number

CHEM000565

Identification

Common Name

Picene

Class

Small Molecule

Description

Picene 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

HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
T3DB toxins

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Natural Compound
Organic Compound
Pollutant
Polycyclic Aromatic Hydrocarbon

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2:7,8-Dibenzophenanthrene	ChEBI
3,4-Benzchrysene	ChEBI
Benzo[a]chrysene	ChEBI
beta,beta-Binaphthyleneethene	ChEBI
b,b-Binaphthyleneethene	Generator
Β,β-binaphthyleneethene	Generator
benzo(a)Chrysene	MeSH

Chemical Formula

C₂₂H₁₄

Average Molecular Mass

278.347 g/mol

Monoisotopic Mass

278.110 g/mol

CAS Registry Number

213-46-7

IUPAC Name

picene

Traditional Name

picene

SMILES

C1=CC=C2C(C=CC3=C2C=CC2=C3C=CC3=CC=CC=C23)=C1

InChI Identifier

InChI=1S/C22H14/c1-3-7-17-15(5-1)9-11-21-19(17)13-14-20-18-8-4-2-6-16(18)10-12-22(20)21/h1-14H

InChI Key

GBROPGWFBFCKAG-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Chrysenes

Direct Parent

Chrysenes

Alternative Parents

Substituents

Chrysene
Naphthalene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

ortho-fused polycyclic arene (CHEBI:33090 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless solid.

Experimental Properties

Property	Value
Melting Point	368°C
Boiling Point	518-520°C
Solubility	4.31e-06 mg/mL at 20°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Predicted Properties

Property	Value	Source
Water Solubility	5.9e-07 g/L	ALOGPS
logP	6.83	ALOGPS
logP	5.93	ChemAxon
logS	-8.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.86 m³·mol⁻¹	ChemAxon
Polarizability	32.81 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-3115bf003b9cee611609	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0090000000-fd8727b37afa5ed60851	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-0090000000-4f621a25e1efa21249fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-773f4e4ef9823ddfdea3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0090000000-773f4e4ef9823ddfdea3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0090000000-8294fe5cc03241a498dc	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-0390000000-cf7598276086d4ecfed4	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4)

Mechanism of Toxicity

The 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)

Metabolism

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. (4)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (6)

Uses/Sources

PAHs 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 Level

Not Available

Health Effects

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. (4)

Symptoms

Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)

Treatment

There is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (4)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Picene

Chemspider ID

Not Available

ChEBI ID

33090

PubChem Compound ID

9162

Kegg Compound ID

C19500

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Picene (CHEM000565)

Structure for CHEM000565: Picene