Fluoranthene
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Basic Info
| Common Name | Fluoranthene(F03355) |
| 2D Structure | |
| Description | Fluoranthene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are are formed during the incomplete burning of organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. (L10) |
| FRCD ID | F03355 |
| CAS Number | 206-44-0 |
| PubChem CID | 9154 |
| Formula | C16H10 |
| IUPAC Name | fluoranthene |
| InChI Key | GVEPBJHOBDJJJI-UHFFFAOYSA-N |
| InChI | InChI=1S/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H |
| Canonical SMILES | C1=CC=C2C(=C1)C3=CC=CC4=C3C2=CC=C4 |
| Isomeric SMILES | C1=CC=C2C(=C1)C3=CC=CC4=C3C2=CC=C4 |
| Wikipedia | Fluoranthene |
| Synonyms |
RCRA waste number U120
FLUORANTHENE
206-44-0
Idryl
1,2-Benzacenaphthene
Benzo[jk]fluorene
Benzo(jk)fluorene
1,2-(1,8-Naphthylene)benzene
Benzene, 1,2-(1,8-naphthalenediyl)-
NSC 6803
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Naphthalenes |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Naphthalenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | Naphthalene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 202.256 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 243 |
| Monoisotopic Mass | 202.078 |
| Exact Mass | 202.078 |
| XLogP | 5.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9848 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.7795 |
| P-glycoprotein Substrate | Non-substrate | 0.7611 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8926 |
| Non-inhibitor | 0.9519 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7999 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.7333 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7989 |
| CYP450 2D6 Substrate | Non-substrate | 0.8684 |
| CYP450 3A4 Substrate | Non-substrate | 0.7639 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8047 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6504 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.7662 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5184 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6841 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9560 |
| Non-inhibitor | 0.8676 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.7763 |
| Fish Toxicity | High FHMT | 0.9528 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9975 |
| Honey Bee Toxicity | High HBT | 0.7511 |
| Biodegradation | Not ready biodegradable | 0.7808 |
| Acute Oral Toxicity | III | 0.7918 |
| Carcinogenicity (Three-class) | Warning | 0.3871 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -6.7426 | LogS |
| Caco-2 Permeability | 1.7942 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0363 | LD50, mol/kg |
| Fish Toxicity | 0.0092 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.3025 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Polycyclic aromatic hydrocarbons in fruits and vegetables: Origin, analysis, and occurrence. | Environ Pollut | 2018 Mar | 29172043 |
| Effects of steaming on contaminants of emerging concern levels in seafood. | Food Chem Toxicol | 2018 Aug | 29787848 |
| Characterization of particulate-phase polycyclic aromatic hydrocarbons emitted from incense burning and their bioreactivity in RAW264.7 macrophage. | Environ Pollut | 2017 Jan | 27865658 |
| Surface enhanced Raman spectroscopy hyphenated with surface microextraction forin-situ detection of polycyclic aromatic hydrocarbons on food contact materials. | Talanta | 2016 Sep 1 | 27343612 |
| Exposure of marine mussels Mytilus spp. to polystyrene microplastics: Toxicity and influence on fluoranthene bioaccumulation. | Environ Pollut | 2016 Sep | 27372385 |
| Evaluation of genotoxicity using automated detection of γH2AX in metabolically competent HepaRG cells. | Mutagenesis | 2016 Jan | 26282955 |
| Efficacy of Ozonation Treatments of Smoked Fish for Reducing Its Benzo[a]pyrene Concentration and Toxicity. | J Food Prot | 2016 Dec | 28221959 |
| Polycyclic aromatic hydrocarbons in Haliotis tuberculata (Linnaeus, 1758)(Mollusca, Gastropoda): Considerations on food safety and source investigation. | Food Chem Toxicol | 2016 Aug | 27235950 |
| Application of sewage sludge and sewage sludge biochar to reduce polycyclic aromatic hydrocarbons (PAH) and potentially toxic elements (PTE) accumulation in tomato. | Environ Sci Pollut Res Int | 2015 Aug | 25877899 |
| Differential degradation of polycyclic aromatic hydrocarbon mixtures byindigenous microbial assemblages in soil. | Lett Appl Microbiol | 2015 Aug | 26031321 |
| Fluoranthene, a polycyclic aromatic hydrocarbon, inhibits light as well as dark reactions of photosynthesis in wheat (Triticum aestivum). | Ecotoxicol Environ Saf | 2014 Nov | 25173746 |
| Polycyclic aromatic hydrocarbons in fish from St Helena, South Atlantic, in relation to an historic wreck. | Mar Pollut Bull | 2014 Dec 15 | 25444627 |
| Multi-residue method for the determination of 57 persistent organic pollutants inhuman milk and colostrum using a QuEChERS-based extraction procedure. | Anal Bioanal Chem | 2013 Nov | 24162817 |
| Relations of oxidative stress in freshwater phytoplankton with heavy metals and polycyclic aromatic hydrocarbons. | Comp Biochem Physiol A Mol Integr Physiol | 2013 Aug | 23415686 |
| Effects of crude oil exposure on bioaccumulation of polycyclic aromatic hydrocarbons and survival of adult and larval stages of gelatinous zooplankton. | PLoS One | 2013 | 24116004 |
| Interactions between zooplankton and crude oil: toxic effects and bioaccumulation of polycyclic aromatic hydrocarbons. | PLoS One | 2013 | 23840628 |
| Application of gas chromatography time-of-flight mass spectrometry for target andnon-target analysis of pesticide residues in fruits and vegetables. | J Chromatogr A | 2012 Jun 29 | 22608778 |
| Novel multifunctional acceptor phase additive of water-miscible ionic liquid inhollow-fiber protected liquid phase microextraction. | Talanta | 2012 Jan 15 | 22265467 |
| Maternal exposure to benzo[b]fluoranthene disturbs reproductive performance in male offspring mice. | Toxicol Lett | 2011 May 30 | 21392559 |
| Body burden of POPs of Hong Kong residents, based on human milk, maternal andcord serum. | Environ Int | 2011 Jan | 20828823 |
Targets
- General Function:
- Transcription regulatory region dna 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. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
- Mechanism of Action:
- 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.
References
- 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 ]
- General Function:
- Glycine n-methyltransferase activity
- 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:
- 32742.0 Da
- Mechanism of Action:
- 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.
References
- 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 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- 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:
- Peptidase activity
- Specific Function:
- Responsible for the proteolytic processing of the amyloid precursor protein (APP). Cleaves at the N-terminus of the A-beta peptide sequence, between residues 671 and 672 of APP, leads to the generation and extracellular release of beta-cleaved soluble APP, and a corresponding cell-associated C-terminal fragment which is later released by gamma-secretase.
- Gene Name:
- BACE1
- Uniprot ID:
- P56817
- Molecular Weight:
- 55710.28 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
- Gene Name:
- MMP3
- Uniprot ID:
- P08254
- Molecular Weight:
- 53976.84 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]