Record Information
Version2.0
Creation Date2009-03-06 11:57:54 -0700
Update Date2014-11-04 15:48:28 -0700
Accession NumberT3D0009
Identification
Common NameBenzo[a]pyrene
ClassSmall Molecule
DescriptionBenzo[a]pyrene 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. It is one ingredient of cigarette. (5)
Compound Type
  • Aromatic Hydrocarbon
  • Cigarette Toxin
  • Food Toxin
  • Industrial By-product/Pollutant
  • Industrial/Workplace Toxin
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical Structure
Thumb
Synonyms
Synonym
1,2-Benzpyrene
3,4 Benzopyrene
3,4 Benzpyrene
3,4-Benz(a)pyrene
3,4-Benzo(a)pyrene
3,4-Benzopyrene
3,4-Benzpyrene
3,4-benzylpyrene
3,4-Benzypyrene
3,4-BP
4,5-Benzpyrene
6,7-Benzopyrene
Benz(a)pyrene
Benzo(a)pyrene
Benzo(d,e,f)chrysene
Benzo(def)chrysene
Benzopyrene
Benzo[a]pyrene solution
Benzo[d,e,f]chrysene
Benzo[def]chrysene
Benzo[PQR]tetraphene
Benzpyrene
BP
Chemical FormulaC20H12
Average Molecular Mass252.309 g/mol
Monoisotopic Mass252.094 g/mol
CAS Registry Number50-32-8
IUPAC Namepentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,8,10,12(20),13,15,17-decaene
Traditional Namebenzo(A)pyrene
SMILESC1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C3
InChI IdentifierInChI=1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H
InChI KeyInChIKey=FMMWHPNWAFZXNH-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassBenzenoids
ClassPyrenes
Sub ClassBenzopyrenes
Direct ParentBenzopyrenes
Alternative Parents
Substituents
  • Chrysene
  • Anthracene
  • Phenanthrene
  • Aromatic Homopolycyclic Compound
  • Hydrocarbon
  • Benzo-a-pyrene
Molecular FrameworkAromatic Homopolycyclic Compounds
External Descriptors
  • Ortho- and Peri-fused Polycyclic Arene (ChEBI)
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearancePale yellow solid.
Experimental Properties
PropertyValue
Melting Point176.5°C
Boiling Point495 °C
Solubility1.62e-06 mg/mL at 25 °C [MAY,WE et al. (1983)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.25e-06ALOGPS
logP6.39ALOGPS
logP5.27ChemAxon
logS-8.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.17 m3·mol-1ChemAxon
Polarizability29.09 Å3ChemAxon
Spectra
SpectraMS1D NMR
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
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. The main carcinogenic metabolite of benzo(a)pyrene is the diol-epoxide trans-9,10-epoxy-7,8-dihydrodiol. (5, 6, 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. (5)
Toxicity ValuesLD50: 250 mg/kg (Intraperitoneal, Mouse) (8)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (7)
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 volcanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (5)
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. (5)
SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)
TreatmentThere is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID2336
ChEMBL IDCHEMBL31184
ChemSpider ID2246
KEGG IDC07535
UniProt IDNot Available
OMIM ID
ChEBI ID29865
BioCyc IDNot Available
CTD IDD001564
Stitch IDBenzo[a]pyrene
PDB IDNot Available
ACToR ID141
Wikipedia LinkBenzo(a)pyrene
References
Synthesis ReferenceNot Available
MSDST3D0009.pdf
General References
  1. Santodonato J, Howard P, Basu D: Health and ecological assessment of polynuclear aromatic hydrocarbons. J Environ Pathol Toxicol. 1981 Sep;5(1):1-364. [7310260 ]
  2. Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]
  3. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  4. Phillips DH: Smoking-related DNA and protein adducts in human tissues. Carcinogenesis. 2002 Dec;23(12):1979-2004. [12507921 ]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  6. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
  7. International Agency for Research on Cancer (2009). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  8. HSDB: Hazardous Substances Data Bank. National Library of Medicine (2001). [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

General Function:
Involved in Hsp90 protein binding
Specific Function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular Weight:
96146.7 Da
References
  1. Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]
  2. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  3. Kizu R, Okamura K, Toriba A, Kakishima H, Mizokami A, Burnstein KL, Hayakawa K: A role of aryl hydrocarbon receptor in the antiandrogenic effects of polycyclic aromatic hydrocarbons in LNCaP human prostate carcinoma cells. Arch Toxicol. 2003 Jun;77(6):335-43. Epub 2003 Mar 12. [12799773 ]
  4. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  5. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]
  2. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
General Function:
Secondary metabolites biosynthesis, transport and catabolism
Specific Function:
Catalyzes the methylation of glycine by using S- adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine
Gene Name:
GNMT
Uniprot ID:
Q14749
Molecular Weight:
32611.0 Da
References
  1. Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]
  2. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
General Function:
Involved in DNA binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Activated, but not phosphorylated, by HIPK3
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98990.0 Da
References
  1. Vinggaard AM, Hnida C, Larsen JC: Environmental polycyclic aromatic hydrocarbons affect androgen receptor activation in vitro. Toxicology. 2000 Apr 14;145(2-3):173-83. [10771140 ]
General Function:
Involved in beta2-adrenergic receptor activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46557.0 Da
References
  1. Mayati A, Levoin N, Paris H, N'Diaye M, Courtois A, Uriac P, Lagadic-Gossmann D, Fardel O, Le Ferrec E: Induction of intracellular calcium concentration by environmental benzo(a)pyrene involves a beta2-adrenergic receptor/adenylyl cyclase/Epac-1/inositol 1,4,5-trisphosphate pathway in endothelial cells. J Biol Chem. 2012 Feb 3;287(6):4041-52. doi: 10.1074/jbc.M111.319970. Epub 2011 Dec 13. [22167199 ]
General Function:
Secondary metabolites biosynthesis, transport and catabolism
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.8 Da
References
  1. Adachi J, Mori Y, Matsui S, Matsuda T: Comparison of gene expression patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a natural arylhydrocarbon receptor ligand, indirubin. Toxicol Sci. 2004 Jul;80(1):161-9. Epub 2004 Mar 31. [15056799 ]
General Function:
Involved in transcription factor activity
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66217.0 Da
References
  1. Liu S, Abdelrahim M, Khan S, Ariazi E, Jordan VC, Safe S: Aryl hydrocarbon receptor agonists directly activate estrogen receptor alpha in MCF-7 breast cancer cells. Biol Chem. 2006 Sep;387(9):1209-13. [16972788 ]
General Function:
Involved in establishment of epithelial cell polarity
Specific Function:
Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
Gene Name:
FBF1
Uniprot ID:
Q8TES7
Molecular Weight:
125445.19 Da
References
  1. Skupinska K, Zylm M, Misiewicz I, Kasprzycka-Guttman T: Interaction of anthracene and its oxidative derivatives with human serum albumin. Acta Biochim Pol. 2006;53(1):101-12. Epub 2006 Jan 9. [16404478 ]
General Function:
Involved in transcription factor activity
Specific Function:
Orphan receptor; its natural ligand is probably pregnane. Binds to a response element in the CYP3A4 and ABCB1/MDR1 genes promoter. Activates its expression in response to a wide variety of endobiotics and xenobiotics
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49762.0 Da
References
  1. Luckert C, Ehlers A, Buhrke T, Seidel A, Lampen A, Hessel S: Polycyclic aromatic hydrocarbons stimulate human CYP3A4 promoter activity via PXR. Toxicol Lett. 2013 Oct 24;222(2):180-8. doi: 10.1016/j.toxlet.2013.06.243. Epub 2013 Jul 8. [23845848 ]