Pyrene
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Basic Info
| Common Name | Pyrene(F03460) |
| 2D Structure | |
| Description | Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is C16H10. This colourless solid is the smallest peri-fused PAH (one where the rings are fused through more than one face). Pyrene forms during incomplete combustion of organic compounds. Although it is not as problematic as benzopyrene, animal studies have shown pyrene is toxic to the kidneys and the liver. |
| FRCD ID | F03460 |
| CAS Number | 129-00-0 |
| PubChem CID | 31423 |
| Formula | C16H10 |
| IUPAC Name | pyrene |
| InChI Key | BBEAQIROQSPTKN-UHFFFAOYSA-N |
| InChI | InChI=1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H |
| Canonical SMILES | C1=CC2=C3C(=C1)C=CC4=CC=CC(=C43)C=C2 |
| Isomeric SMILES | C1=CC2=C3C(=C1)C=CC4=CC=CC(=C43)C=C2 |
| Wikipedia | Pyrene |
| Synonyms |
.beta.-Pyrene
PYRENE
129-00-0
Benzo[def]phenanthrene
Pyren
beta-Pyrene
Pyren [German]
Benzo(def)phenanthrene
UNII-9E0T7WFW93
CCRIS 1256
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Pyrenes |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyrenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | Pyrene - Phenanthrene - Naphthalene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyrenes. These are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 202.256 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 217 |
| Monoisotopic Mass | 202.078 |
| Exact Mass | 202.078 |
| XLogP | 4.9 |
| 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+ | 0.9728 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8537 |
| P-glycoprotein Substrate | Non-substrate | 0.7437 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9276 |
| Non-inhibitor | 0.9361 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8178 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.8244 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8091 |
| CYP450 2D6 Substrate | Non-substrate | 0.8874 |
| CYP450 3A4 Substrate | Non-substrate | 0.7722 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6798 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9070 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8548 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9288 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5335 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9317 |
| Non-inhibitor | 0.9054 | |
| AMES Toxicity | AMES toxic | 0.9118 |
| Carcinogens | Non-carcinogens | 0.7059 |
| Fish Toxicity | High FHMT | 0.9391 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9959 |
| Honey Bee Toxicity | High HBT | 0.7822 |
| Biodegradation | Not ready biodegradable | 0.8151 |
| Acute Oral Toxicity | III | 0.7913 |
| Carcinogenicity (Three-class) | Warning | 0.4954 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -6.2526 | LogS |
| Caco-2 Permeability | 1.9501 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9645 | LD50, mol/kg |
| Fish Toxicity | 0.5157 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9399 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Photodegradation Rate Constants for Anthracene and Pyrene Are Similar in/on Ice and in Aqueous Solution. | Environ Sci Technol | 2018 Oct 9 | 30251528 |
| Assessment of shorebird migratory fuelling physiology and departure timing in relation to polycyclic aromatic hydrocarbon contamination in the Gulf of Mexico. | Environ Sci Technol | 2018 Oct 26 | 30362719 |
| Polycyclic aromatic hydrocarbons in fruits and vegetables: Origin, analysis, and occurrence. | Environ Pollut | 2018 Mar | 29172043 |
| Covalent organic framework as efficient desorption/ionization matrix for directdetection of small molecules by laser desorption/ionization mass spectrometry. | Anal Chim Acta | 2018 Jul 19 | 29523252 |
| The intervention mechanism of folic acid for benzo(a)pyrene toxic effects in vitro and in vivo. | Eur J Cancer Prev | 2018 Jul 16 | 30020114 |
| Comparison of xenobiotic metabolism in phase I oxidation and phase II conjugation between rats and bird species. | Comp Biochem Physiol C Toxicol Pharmacol | 2018 Dec | 30176376 |
| Effects of steaming on contaminants of emerging concern levels in seafood. | Food Chem Toxicol | 2018 Aug | 29787848 |
| Individual and Combined Toxicities of Benzo[a]pyrene and 2,2',4,4'-Tetrabromodiphenyl Ether on Early Life Stages of the Pacific Oyster, Crassostrea gigas. | Bull Environ Contam Toxicol | 2017 Nov | 28889174 |
| The endophytic bacterium Serratia sp. PW7 degrades pyrene in wheat. | Environ Sci Pollut Res Int | 2017 Mar | 28083742 |
| The toxic effects of benzo[a]pyrene on activated mouse T cells in vitro. | Immunopharmacol Immunotoxicol | 2017 Jun | 28290727 |
| Potent mutagenicity of some non-planar tri- and tetrachlorinated biphenyls in mammalian cells, human CYP2E1 being a major activating enzyme. | Arch Toxicol | 2017 Jul | 27913846 |
| Determination of kinetic bioconcentration in mussels after short term exposure to polycyclic aromatic hydrocarbons. | Heliyon | 2017 Jan | 28203639 |
| Characterization of particulate-phase polycyclic aromatic hydrocarbons emitted from incense burning and their bioreactivity in RAW264.7 macrophage. | Environ Pollut | 2017 Jan | 27865658 |
| Influence of multiwalled carbon nanotubes and sodium dodecyl benzene sulfonate onbioaccumulation and translocation of pyrene and 1-methylpyrene in maize (Zeamays) seedlings. | Environ Pollut | 2017 Jan | 27836475 |
| Benzo[a]pyrene-induced DNA damage associated with mutagenesis in primary human activated T lymphocytes. | Biochem Pharmacol | 2017 Aug 1 | 28461126 |
| Elements of kitchen toxicology to exploit the value of traditional (African) recipes: The case of <i>Egusi Okra</i> meal in the diet of HIV+/AIDS subjects. | Toxicol Rep | 2017 | 28959677 |
| Docosahexaenoic acid attenuates in endocannabinoid synthesis in RAW 264.7 macrophages activated with benzo(a)pyrene and lipopolysaccharide. | Toxicol Lett | 2016 Sep 6 | 27329536 |
| Vesicles from pH-regulated reversible gemini amino-acid surfactants asnanocapsules for delivery. | Colloids Surf B Biointerfaces | 2016 Oct 1 | 27419647 |
| Potential pitfalls associated with testing of enzyme preparations in the Salmonella/microsome assay. | Regul Toxicol Pharmacol | 2016 Oct | 27330008 |
| Polycyclic aromatic hydrocarbons and trace metals in mosque's carpet dust ofRiyadh, Saudi Arabia, and their health risk implications. | Environ Sci Pollut Res Int | 2016 Nov | 27497850 |
Targets
- 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:
- Vitamin d 24-hydroxylase activity
- 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:
- 58164.815 Da
References
- Bruno RD, Njar VC: Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development. Bioorg Med Chem. 2007 Aug 1;15(15):5047-60. Epub 2007 May 23. [17544277 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Bruno RD, Njar VC: Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development. Bioorg Med Chem. 2007 Aug 1;15(15):5047-60. Epub 2007 May 23. [17544277 ]
- General Function:
- Zinc ion binding
- 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:
- 39942.145 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:
- 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:
- Oxygen binding
- 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, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compounds to their activated forms, including polycyclic aromatic hydrocarbons. Promotes angiogenesis by removing cellular oxygenation products, thereby decreasing oxidative stress, release of antiangiogenic factor THBS2, then allowing endothelial cells migration, cell adhesion and capillary morphogenesis. These changes are concommitant with the endothelial nitric oxide synthase activity and nitric oxide synthesis. Plays an important role in the regulation of perivascular cell proliferation, migration, and survival through modulation of the intracellular oxidative state and NF-kappa-B expression and/or activity, during angiogenesis. Contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression.
- Gene Name:
- CYP1B1
- Uniprot ID:
- Q16678
- Molecular Weight:
- 60845.33 Da
References
- Bruno RD, Njar VC: Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development. Bioorg Med Chem. 2007 Aug 1;15(15):5047-60. Epub 2007 May 23. [17544277 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 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 ]