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T3D0010 - Benzo[b]fluoranthene

Record Information
Version 1.0
Creation Date 2009-03-06 18:57:55 UTC
Update Date 2013-04-25 08:32:26 UTC
Accession Number T3D0010
Identification
Common Name Benzo[b]fluoranthene
Description Benzo[b]fluoranthene 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. (R028)
Compound Type
  • Organic Compound
  • Aromatic Hydrocarbon
  • Industrial By-product/Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms
  1. 2, 3-Benzofluoranthene
  2. 2,3-Benzofluoranthene
  3. 2,3-Benzofluoranthrene
  4. 3,4-Benz(e)acephenanthrylene
  5. 3,4-Benzfluoranthene
  6. 3,4-Benzofluoranthene
  7. 3,4-Benzofluoranthrene
  8. 3,{4-Benz[e]acephenanthrylene}
  9. 4,5-Benzofluoranthene
  10. Benz(e)acephenanthrylene
  11. Benzo(b)fluoranthene
  12. Benzo(b)fluoranthene [polycyclic aromatic compounds]
  13. Benzo(b)fluoranthene [polycyclic aromatic hydrocarbons]
  14. Benzo(e)fluoranthene
  15. Benzo[b]fluoranthene
  16. Benzo[b]fluoranthene solution
  17. Benzo[e]acephenanthrylene
  18. benzo[e]acephenanthrylene
  19. Benzo[e]fluoranthene
  20. Benz[b]fluoranthene
Chemical Formula C20H12
Average Molecular Weight 252.3093
Monoisotopic Molecular Weight 252.093900384
Chemical IUPAC Name
benzo[b]fluoranthene
CAS Registry Number 205-99-2
SMILES
C1=CC=C2C(=C1)C1=CC3=CC=CC=C3C3=CC=CC2=C13
InChI Identifier
InChI=1S/C20H12/c1-2-7-14-13(6-1)12-19-16-9-4-3-8-15(16)18-11-5-10-17(14)20(18)19/h1-12H
InChI Key InChIKey=FTOVXSOBNPWTSH-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Benzenoids
Class Phenanthrenes and Derivatives
Sub Class Not Available
Direct Parent Phenanthrenes and Derivatives
Alternative Parents
  • Naphthalenes
  • Benzene and Substituted Derivatives
  • Cycloalkenes
Molecular Framework Aromatic Homopolycyclic Compounds
Substituents
  • benzene
  • naphthalene
  • cycloalkene
External Descriptors
  • ortho- and peri-fused polycyclic arene(ChEBI)
DrugBank ID Not Available
PubChem Compound ID 9153 Link_out
KEGG ID C14320 Link_out
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 34565 Link_out
BioCyc ID Not Available
CTD ID C006703 Link_out
Stitch ID Benzo[b]fluoranthene Link_out
PDB ID Not Available
ACToR ID 6380
Wikipedia Link Not Available
Physical Properties
Appearance Colorless solid.
Melting Point 168 C
Solubility 1.5e-06 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted LogP 5.273404237333333
Toxicity Profile
Route of Exposure Oral (R028) ; inhalation (R028)
Mechanism of Action 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. (R028, R060, R068, R073)
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. (R028)
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) 2B, possibly carcinogenic to humans. (R264)
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 volcanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (R028)
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. (R028)
Symptoms Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (R034)
Treatment There is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (R028)
References
General References
  • R028 — 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]
  • R060 — Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
  • R068 — 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 Link_out]
  • R073 — 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 Link_out]
  • R264 — International Agency for Research on Cancer (2009). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  • R034 — 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 Link_out]

Targets

1. Aryl hydrocarbon receptor

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.

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. (R028, R060, R068, R073)
UniProt ID: P35869 Link_out
Gene: AHR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R028 — 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]
  • R060 — Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
  • R068 — 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 Link_out]
  • R073 — 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 Link_out]

2. Glycine N-methyltransferase

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.

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. (R028, R060, R068, R073)
UniProt ID: Q14749 Link_out
Gene: GNMT Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R028 — 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]
  • R060 — Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
  • R068 — 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 Link_out]
  • R073 — 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 Link_out]

3. Cytokine receptor common subunit beta

High affinity receptor for interleukin-3, interleukin-5 and granulocyte-macrophage colony-stimulating factor.

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. (R028, R060, R068, R073)
UniProt ID: P32927 Link_out
Gene: CSF2RB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • R028 — 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]
  • R060 — Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
  • R068 — 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 Link_out]
  • R073 — 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 Link_out]