Naphthalene
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Basic Info
| Common Name | Naphthalene(F03331) |
| 2D Structure | |
| Description | Naphthalene is the simplest polyaromatic hydrocarbon (PAH) consisting of two fused benzene rings. It has a distinct, pungent odor that can be detected at levels as low as 0.08 ppm. Naphthalene is the most abundant single component of coal tar so most of it is now industrially derived from coal tar. From the 1960s until the 1990s, significant amounts of naphthalene were also produced from heavy petroleum fractions during petroleum refining, but today petroleum-derived naphthalene represents only a minor component of naphthalene production. Naphthalene is also produced naturally with trace amounts of naphthalene being produced by black walnuts, magnolias and specific types of deer, as well as the Formosan subterranean termite. Some strains of the endophytic fungus (Muscodor albus) also produce naphthalene. Naphthalene and other polycyclic aromatic hydrocarbons (PAHs) are released from incomplete combustion processes originating in industry, cigarette smoke and motor vehicle exhaust, as well as natural events such as forest fires. Industrially, naphthalene is used in the production of phthalic anhydride, as a solvent for chemical reactions, as a wetting agent and as a fumigant. It is also used in pyrotechnic special effects such as the generation of black smoke and simulated explosions. In the past, naphthalene was administered orally to kill parasitic worms in livestock. Naphthalene was once the primary ingredient in mothballs, though its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. In a sealed container containing naphthalene pellets, naphthalene vapors build up to levels that are toxic to both the adult and larval forms of many moths. Naphthalene has been shown to exhibit apoptotic and catabolic functions (4, 5). Exposure to large amounts of naphthalene may damage or destroy red blood cells. Humans, in particular children, have developed this condition, known as hemolytic anemia, after ingesting mothballs or deodorant blocks containing naphthalene. |
| FRCD ID | F03331 |
| CAS Number | 91-20-3 |
| PubChem CID | 931 |
| Formula | C10H8 |
| IUPAC Name | naphthalene |
| InChI Key | UFWIBTONFRDIAS-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H |
| Canonical SMILES | C1=CC=C2C=CC=CC2=C1 |
| Isomeric SMILES | C1=CC=C2C=CC=CC2=C1 |
| Wikipedia | Naphthalene |
| Synonyms |
Naphthalin
naphthalene
91-20-3
Naphthene
Camphor tar
Tar camphor
White tar
Albocarbon
Naphthaline
Moth flakes
|
| 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 | 128.174 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 80.6 |
| Monoisotopic Mass | 128.063 |
| Exact Mass | 128.063 |
| XLogP | 3.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| 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 |
|---|---|---|---|
| Urban honey - the aspects of its safety. | Arh Hig Rada Toksikol | 2018 Sep 1 | 30285946 |
| Polycyclic aromatic hydrocarbons in fruits and vegetables: Origin, analysis, and occurrence. | Environ Pollut | 2018 Mar | 29172043 |
| Density functional theory study of adsorption geometries and electronicstructures of azo-dye-based molecules on anatase TiO2 surface for dye-sensitized solar cell applications. | J Mol Graph Model | 2017 Sep | 28688705 |
| Non-target evaluation of contaminants in honey bees and pollen samples by gaschromatography time-of-flight mass spectrometry. | Chemosphere | 2017 Oct | 28679151 |
| A risk-based approach for developing standards for irrigation with reclaimed water. | Water Res | 2017 Dec 1 | 28985601 |
| 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 |
| Active biomonitoring with Corbicula for USEPA priority pollutant and metal sources in the Anacostia River (DC, Maryland, USA). | Integr Environ Assess Manag | 2016 Jul | 26425991 |
| Biointeractions of C.I. Acid Red 2 and its structural analogues with transporter albumin: Fluorescence, circular dichroism, and ligand docking approaches. | J Photochem Photobiol B | 2016 Jan | 26682933 |
| Binding interaction of differently charged fluorescent probes with egg yolk phosphatidylcholine and the effect of β-cyclodextrin on the lipid-probe complexes: a fluorometric investigation. | Spectrochim Acta A Mol Biomol Spectrosc | 2015 May 5 | 25698439 |
| 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 |
| 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 |
| Effect of alpha-naphthalene acetic acid and thidiazuron on seedling of economic crops grown in endosulfan sulfate-spiked sand. | J Environ Biol | 2014 Nov | 25522501 |
| Polycyclic aromatic compounds (PAHs and oxygenated PAHs) and trace metals in fishspecies from Ghana (West Africa): bioaccumulation and health risk assessment. | Environ Int | 2014 Apr | 24486971 |
| Relations of oxidative stress in freshwater phytoplankton with heavy metals and polycyclic aromatic hydrocarbons. | Comp Biochem Physiol A Mol Integr Physiol | 2013 Aug | 23415686 |
| Polycyclic aromatic hydrocarbons in some grounded coffee brands. | Environ Monit Assess | 2013 Aug | 23242460 |
| Determination of cadmium and zinc in vegetables with online FAAS aftersimultaneous pre-concentration with 1,5-diphenylthiocarbazone immobilised onnaphthalene. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2013 | 23043611 |
| The constituents of essential oil: antimicrobial and antioxidant activity ofMicromeria congesta Boiss. & Hausskn. ex Boiss. from East Anatolia. | J Med Food | 2012 Sep | 22871061 |
| Simplified MPN method for enumeration of soil naphthalene degraders using gaseous substrate. | Biodegradation | 2012 Feb | 21626282 |
| County-scale distribution of polycyclic aromatic hydrocarbons in topsoil of the Yellow River Delta Region. | J Environ Sci Health A Tox Hazard Subst Environ Eng | 2012 | 22571530 |
| Identification of bacteria utilizing biphenyl, benzoate, and naphthalene inlong-term contaminated soil. | PLoS One | 2012 | 22808223 |
Targets
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor specific to the heptapeptide core common to adrenocorticotropic hormone and alpha-, beta-, and gamma-MSH. Plays a central role in energy homeostasis and somatic growth. This receptor is mediated by G proteins that stimulate adenylate cyclase (cAMP).
- Gene Name:
- MC4R
- Uniprot ID:
- P32245
- Molecular Weight:
- 36942.325 Da
References
- Mutulis F, Mutule I, Lapins M, Wikberg JE: Reductive amination products containing naphthalene and indole moieties bind to melanocortin receptors. Bioorg Med Chem Lett. 2002 Apr 8;12(7):1035-8. [11909711 ]
- General Function:
- Melanocortin receptor activity
- Specific Function:
- Receptor for MSH (alpha, beta and gamma) and ACTH. The activity of this receptor is mediated by G proteins which activate adenylate cyclase. This receptor is a possible mediator of the immunomodulation properties of melanocortins.
- Gene Name:
- MC5R
- Uniprot ID:
- P33032
- Molecular Weight:
- 36600.21 Da
References
- Mutulis F, Mutule I, Lapins M, Wikberg JE: Reductive amination products containing naphthalene and indole moieties bind to melanocortin receptors. Bioorg Med Chem Lett. 2002 Apr 8;12(7):1035-8. [11909711 ]
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor for MSH (alpha, beta and gamma) and ACTH. The activity of this receptor is mediated by G proteins which activate adenylate cyclase.
- Gene Name:
- MC1R
- Uniprot ID:
- Q01726
- Molecular Weight:
- 34705.04 Da
References
- Mutulis F, Mutule I, Lapins M, Wikberg JE: Reductive amination products containing naphthalene and indole moieties bind to melanocortin receptors. Bioorg Med Chem Lett. 2002 Apr 8;12(7):1035-8. [11909711 ]
- General Function:
- Peptide hormone binding
- Specific Function:
- Receptor for MSH (alpha, beta and gamma) and ACTH. This receptor is mediated by G proteins which activate adenylate cyclase. Required for expression of anticipatory patterns of activity and wakefulness during periods of limited nutrient availability and for the normal regulation of circadian clock activity in the brain.
- Gene Name:
- MC3R
- Uniprot ID:
- P41968
- Molecular Weight:
- 36042.75 Da
References
- Mutulis F, Mutule I, Lapins M, Wikberg JE: Reductive amination products containing naphthalene and indole moieties bind to melanocortin receptors. Bioorg Med Chem Lett. 2002 Apr 8;12(7):1035-8. [11909711 ]
- General Function:
- Peptide hormone binding
- Specific Function:
- G-protein coupled receptor for glucagon that plays a central role in the regulation of blood glucose levels and glucose homeostasis. Regulates the rate of hepatic glucose production by promoting glycogen hydrolysis and gluconeogenesis. Plays an important role in mediating the responses to fasting. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Promotes activation of adenylate cyclase. Besides, plays a role in signaling via a phosphatidylinositol-calcium second messenger system.
- Gene Name:
- GCGR
- Uniprot ID:
- P47871
- Molecular Weight:
- 54008.44 Da
References
- Kumar A, Pathak SR, Ahmad P, Ray S, Tewari P, Srivastava AK: Novel substituted naphthalen-1-yl-methanone derivatives as anti-hyperglycemic agents. Bioorg Med Chem Lett. 2006 May 15;16(10):2719-23. Epub 2006 Feb 24. [16500101 ]
- 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:
- 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
- Korhonen LE, Rahnasto M, Mahonen NJ, Wittekindt C, Poso A, Juvonen RO, Raunio H: Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15. [15916432 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
- Gene Name:
- PPARA
- Uniprot ID:
- Q07869
- Molecular Weight:
- 52224.595 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 ]
- Gene Name:
- TP53
- Uniprot ID:
- P04637
- Molecular Weight:
- 43652.79 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
- Shimada T, Tanaka K, Takenaka S, Foroozesh MK, Murayama N, Yamazaki H, Guengerich FP, Komori M: Reverse type I binding spectra of human cytochrome P450 1B1 induced by flavonoid, stilbene, pyrene, naphthalene, phenanthrene, and biphenyl derivatives that inhibit catalytic activity: a structure-function relationship study. Chem Res Toxicol. 2009 Jul;22(7):1325-33. doi: 10.1021/tx900127s. [19563207 ]