Record Information
Version2.0 (beta)
Creation Date2009-03-06 11:57:55 -0700
Update Date2014-09-29 09:37:44 -0600
Accession NumberT3D0010
Identification
Common NameBenzo[b]fluoranthene
ClassSmall Molecule
DescriptionBenzo[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. It is one ingredient of cigarette. (4)
Compound Type
  • Organic Compound
  • Aromatic Hydrocarbon
  • Industrial By-product/Pollutant
  • Polycyclic Aromatic Hydrocarbon
  • Pollutant
  • Food Toxin
  • Cigarette Toxin
  • Industrial/Workplace Toxin
  • Natural Compound
Chemical Structure
Thumb
Synonyms
  1. 2, 3-Benzofluoranthene
  2. 2,3-Benzofluoranthene
  3. 2,3-Benzofluoranthrene
  4. 3,{4-Benz[e]acephenanthrylene}
  5. 3,4-Benz(e)acephenanthrylene
  6. 3,4-Benzfluoranthene
  7. 3,4-Benzofluoranthene
  8. 3,4-Benzofluoranthrene
  9. 4,5-Benzofluoranthene
  10. Benz(e)acephenanthrylene
  11. Benz[b]fluoranthene
  12. Benzo(b)fluoranthene
  13. Benzo(b)fluoranthene [polycyclic aromatic compounds]
  14. Benzo(b)fluoranthene [polycyclic aromatic hydrocarbons]
  15. Benzo(e)fluoranthene
  16. Benzo[b]fluoranthene
  17. Benzo[b]fluoranthene solution
  18. Benzo[e]acephenanthrylene
  19. Benzo[e]fluoranthene
  20. benzo[e]acephenanthrylene
  21. 2,3-Benzfluoranthene
  22. b(b)F
  23. BF
Chemical FormulaC20H12
Average Molecular Mass252.30930 g/mol
Monoisotopic Mass252.093900384 g/mol
CAS Registry Number205-99-2
IUPAC Namepentacyclo[10.7.1.0²,⁷.0⁸,²⁰.0¹³,¹⁸]icosa-1(19),2,4,6,8(20),9,11,13,15,17-decaene
Traditional IUPAC Namebenzo(B)fluoranthene
SMILESC1=CC=C2C(=C1)C1=CC3=CC=CC=C3C3=CC=CC2=C13
InChI IdentifierInChI=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 KeyInChIKey=FTOVXSOBNPWTSH-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassBenzenoids
ClassPhenanthrenes and Derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and Derivatives
Alternative Parents
  • Naphthalenes
  • Heterocyclic Compounds
  • Hydrocarbons
Substituents
  • phenanthrene
  • naphthalene
  • Heterocycle
  • Aromatic Homopolycyclic Compound
  • Hydrocarbon
External Descriptors
  • ortho- and peri-fused polycyclic arene(ChEBI)
Biological Properties
StatusDetected and Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless solid.
Experimental Properties
PropertyValue
Melting Point168 C
Boiling PointNot Available
Solubility1.5e-06 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.21e-06 g/lALOGPS
logP6.23ALOGPS
logP5.27ChemAxon
logS-7.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ÅChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.17 m3·mol-1ChemAxon
Polarizability29.45 C·m2·V−1ChemAxon
Spectra
SpectraMS
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)2B, possibly carcinogenic to humans. (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 volcanic 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 known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (4)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID9153
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC14320
UniProt IDNot Available
OMIM IDNot Available
ChEBI ID34565
BioCyc IDNot Available
CTD IDC006703
Stitch IDBenzo[b]fluoranthene
PDB IDNot Available
ACToR ID6380
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
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. 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]
  6. International Agency for Research on Cancer (2009). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [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

Constants

TypeValueAssay TypeAssay Source
AC500.98 uMATG_Ahr_CISAttagene
AC500.75 uMTox21_AhRTox21/NCGC
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]
  5. ToxCastDB (EPA, United States Environmental Protection Agency) [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 transcription from RNA polymerase II promoter
Specific Function:
Transcription activator that binds to antioxidant response (ARE) elements in the promoter regions of target genes. Important for the coordinated up-regulation of genes in response to oxidative stress. May be involved in the transcriptional activation of genes of the beta-globin cluster by mediating enhancer activity of hypersensitive site 2 of the beta-globin locus control region.
Gene Name:
NFE2L2
Uniprot ID:
Q16236
Molecular Weight:
67825.9 Da

Constants

TypeValueAssay TypeAssay Source
AC500.37 uMATG_NRF2_ARE_CISAttagene
References
  1. ToxCastDB (EPA, United States Environmental Protection Agency) [Link]
General Function:
Involved in androgen receptor activity
Specific Function:
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element
Gene Name:
NR1I3
Uniprot ID:
Q14994
Molecular Weight:
39942.1 Da

Constants

TypeValueAssay TypeAssay Source
AC500.61 uMATG_CAR_TRANSAttagene
References
  1. ToxCastDB (EPA, United States Environmental Protection Agency) [Link]