Anthracene
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Basic Info
| Common Name | Anthracene(F03759) |
| 2D Structure | |
| Description | Anthracene 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. (L10) |
| FRCD ID | F03759 |
| CAS Number | 120-12-7 |
| PubChem CID | 8418 |
| Formula | C14H10 |
| IUPAC Name | anthracene |
| InChI Key | MWPLVEDNUUSJAV-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H |
| Canonical SMILES | C1=CC=C2C=C3C=CC=CC3=CC2=C1 |
| Isomeric SMILES | C1=CC=C2C=C3C=CC=CC3=CC2=C1 |
| Wikipedia | Anthracene |
| Synonyms |
Anthracen [German]
ANTHRACENE
120-12-7
Paranaphthalene
Anthracin
Green Oil
Anthracen
Tetra Olive N2G
Anthrazen
Anthracene, pure
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Anthracenes |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Anthracenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | Anthracene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 178.234 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 154 |
| Monoisotopic Mass | 178.078 |
| Exact Mass | 178.078 |
| XLogP | 4.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| 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 |
| Simultaneous determination of organophosphorus pesticides and phthalates in baby food samples by ultrasound-vortex-assisted liquid-liquid microextraction andGC-IT/MS. | Anal Bioanal Chem | 2018 May | 29549507 |
| Effects of steaming on contaminants of emerging concern levels in seafood. | Food Chem Toxicol | 2018 Aug | 29787848 |
| Determination of the priority substances regulated by 2000/60/EC and 2008/105/EC Directives in the surface waters supplying water treatment plants of Athens, Greece. | J Environ Sci Health A Tox Hazard Subst Environ Eng | 2017 Mar 21 | 27973987 |
| Inhibition of Neoplastic Transformation and Chemically-Induced Skin Hyperplasia in Mice by Traditional Chinese Medicinal Formula Si-Wu-Tang. | Nutrients | 2017 Mar 18 | 28335476 |
| Characterization of particulate-phase polycyclic aromatic hydrocarbons emitted from incense burning and their bioreactivity in RAW264.7 macrophage. | Environ Pollut | 2017 Jan | 27865658 |
| Changes in the Bacterial Community Structure of RemediatedAnthracene-Contaminated Soils. | PLoS One | 2016 Oct 11 | 27727277 |
| Laccase oxidation and removal of toxicants released during combustion processes. | Chemosphere | 2016 Feb | 26408262 |
| 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 |
| Diversity of organotrophic bacteria, activity of dehydrogenases and urease as well as seed germination and root growth Lepidium sativum, Sorghum saccharatum and Sinapis alba under the influence of polycyclic aromatic hydrocarbons. | Environ Sci Pollut Res Int | 2015 Dec | 26341339 |
| Determination of polycyclic aromatic hydrocarbons in dry tea. | J Environ Sci Health B | 2015 | 26065515 |
| Trianthema portulacastrum Linn. exerts chemoprevention of 7,12-dimethylbenz(a)anthracene-induced mammary tumorigenesis in rats. | Mutat Res | 2014 Oct | 24451939 |
| Unraveling the toxicity mechanisms of the herbicide diclofop-methyl in rice: modulation of the activity of key enzymes involved in citrate metabolism and induction of cell membrane anion channels. | J Agric Food Chem | 2014 Nov 5 | 25307187 |
| Polycyclic aromatic hydrocarbons in fish from St Helena, South Atlantic, in relation to an historic wreck. | Mar Pollut Bull | 2014 Dec 15 | 25444627 |
| Ochratoxin A-induced cell proliferation and tumor promotion in mouse skin by activating the expression of cyclin-D1 and cyclooxygenase-2 through nuclear factor-kappa B and activator protein-1. | Carcinogenesis | 2013 Mar | 23172667 |
| 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 |
| The effect of Plantago major Linnaeus on serum total sialic acid, lipid-bound sialic acid, some trace elements and minerals after administration of 7,12-dimethylbenz(a)anthracene in rats. | Toxicol Ind Health | 2012 May | 21996710 |
| Carcinogenic polycyclic aromatic hydrocarbons in umbilical cord blood of human neonates from Guiyu, China. | Sci Total Environ | 2012 Jun 15 | 22542294 |
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:
- 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 ]