Chrysene
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Basic Info
| Common Name | Chrysene(F03380) |
| 2D Structure | |
| Description | Chrysene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that 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 | F03380 |
| CAS Number | 218-01-9 |
| PubChem CID | 9171 |
| Formula | C18H12 |
| IUPAC Name | chrysene |
| InChI Key | WDECIBYCCFPHNR-UHFFFAOYSA-N |
| InChI | InChI=1S/C18H12/c1-3-7-15-13(5-1)9-11-18-16-8-4-2-6-14(16)10-12-17(15)18/h1-12H |
| Canonical SMILES | C1=CC=C2C(=C1)C=CC3=C2C=CC4=CC=CC=C43 |
| Isomeric SMILES | C1=CC=C2C(=C1)C=CC3=C2C=CC4=CC=CC=C43 |
| Wikipedia | Chrysene |
| Synonyms |
1,2-Benzphenanthrene
CHRYSENE
218-01-9
Benzo[a]phenanthrene
1,2-Benzophenanthrene
1,2,5,6-Dibenzonaphthalene
Benz(a)phenanthrene
Benz[a]phenanthrene
Chrysen
RCRA waste number U050
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenanthrenes and derivatives |
| Subclass | Chrysenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Chrysenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | Chrysene - Naphthalene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as chrysenes. These are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 228.294 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 264 |
| Monoisotopic Mass | 228.094 |
| Exact Mass | 228.094 |
| XLogP | 5.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 18 |
| 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 |
|---|---|---|---|
| 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 |
| A preliminary study of PCBs, PAHs, pesticides and trace metals contamination incold-pressed rapeseed oils from conventional and ecological cultivations. | J Food Sci Technol | 2017 Apr | 28416887 |
| Efficacy of Ozonation Treatments of Smoked Fish for Reducing Its Benzo[a]pyrene Concentration and Toxicity. | J Food Prot | 2016 Dec | 28221959 |
| Concentrations of Contaminants with Regulatory Limits in Samples of Clam(Chamelea gallina) Collected along the Abruzzi Region Coast in Central Italy. | J Food Prot | 2015 Sep | 26319726 |
| Determination of polycyclic aromatic hydrocarbons in dry tea. | J Environ Sci Health B | 2015 | 26065515 |
| Determination of polycyclic aromatic hydrocarbons in smoked and non-smoked black teas and tea infusions. | Food Chem | 2014 Feb 15 | 24128549 |
| Polycyclic aromatic hydrocarbons in fish from St Helena, South Atlantic, in relation to an historic wreck. | Mar Pollut Bull | 2014 Dec 15 | 25444627 |
| 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 |
| Carcinogenic polycyclic aromatic hydrocarbons in umbilical cord blood of human neonates from Guiyu, China. | Sci Total Environ | 2012 Jun 15 | 22542294 |
| Polycyclic aromatic hydrocarbons: bees, honey and pollen as sentinels forenvironmental chemical contaminants. | Chemosphere | 2012 Jan | 22051346 |
| Polycyclic aromatic hydrocarbons incidence in Portuguese traditional smoked meat products. | Food Chem Toxicol | 2011 Sep | 21722696 |
| Simultaneous mobilization of trace elements and polycyclic aromatic hydrocarbon(PAH) compounds from soil with a nonionic surfactant and [S,S]-EDDS in admixture:metals. | J Hazard Mater | 2011 Dec 15 | 22023908 |
| Assessment of hydrocarbons concentration in marine fauna due to Tasman Spirit oil spill along the Clifton beach at Karachi coast. | Environ Monit Assess | 2009 Jan | 18302003 |
| Polycyclic aromatic hydrocarbons in farmed rainbow trout (Oncorhynchus mykiss)processed by traditional flue gas smoking and by liquid smoke flavourings. | Food Chem Toxicol | 2008 May | 18262709 |
| A model for estimating the potential biomagnification of chemicals in a generic food web: preliminary development. | Environ Sci Pollut Res Int | 2008 Jan | 18306886 |
| Polymers imprinted with PAH mixtures--comparing fluorescence and QCM sensors. | Anal Bioanal Chem | 2008 Dec | 18985326 |
| DNA solution(R) in cigarette filters reduces polycyclic aromatic hydrocarbon (PAH) levels in mainstream tobacco smoke. | Food Chem Toxicol | 2007 Sep | 17459554 |
| An untargeted metabolomics approach to contaminant analysis: pinpointingpotential unknown compounds. | Anal Chim Acta | 2007 Feb 12 | 17386583 |
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:
- 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:
- Protein homodimerization activity
- Specific Function:
- Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
- Gene Name:
- HPRT1
- Uniprot ID:
- P00492
- Molecular Weight:
- 24579.155 Da
References
- Medrano FJ, Wenck MA, Engel JC, Craig SP 3rd: Analysis of 6-(2,2-Dichloroacetamido)chrysene interaction with the hypoxanthine phosphoribosyltransferase from Trypanosoma cruzi. J Med Chem. 2003 Jun 5;46(12):2548-50. [12773058 ]
- 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 ]