Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:02 UTC
Update Date2014-12-24 20:21:03 UTC
Accession NumberT3D0078
Identification
Common NameNaphthalene
ClassSmall Molecule
DescriptionNaphthalene 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.
Compound Type
  • Aromatic Hydrocarbon
  • Food Toxin
  • Household Toxin
  • Industrial By-product/Pollutant
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical Structure
Thumb
Synonyms
Synonym
Albocarbon
Camphor tar
Moth balls
Moth flakes
Mothballs
Naftalen
Naphtalene
Naphthalin
Naphthaline
Naphthene
Tar camphor
Tolboxane
White tar
Chemical FormulaC10H8
Average Molecular Mass128.171 g/mol
Monoisotopic Mass128.063 g/mol
CAS Registry Number91-20-3
IUPAC Namenaphthalene
Traditional Namenaphthalene
SMILESC1=CC2=CC=CC=C2C=C1
InChI IdentifierInChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
InChI KeyInChIKey=UFWIBTONFRDIAS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite crystals.
Experimental Properties
PropertyValue
Melting Point80.3°C
Boiling Point218°C (424.4°F)
Solubility0.031 mg/mL at 25°C
LogP3.3
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP3.33ALOGPS
logP2.96ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.51 m³·mol⁻¹ChemAxon
Polarizability14.56 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-28274068093bf0319e30View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-10810744223497787156View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-f640b15d5ebd285008e9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-837afe39d2806871be73View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-262e4b8e72f3d3fa0593View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-3900000000-0e32d0a2d4bb6373bea3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-34ade0e20ab7aa4d4e7fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-c780f74ca6838fbab7d8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-b2e474b4d7508faeddc3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-43781a61560faeff786dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-7a87251d344c519a4335View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-0900000000-0532459557fd0c543587View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-1900000000-5a22b095f0a190f1b978View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-28274068093bf0319e30View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-10810744223497787156View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-f640b15d5ebd285008e9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-837afe39d2806871be73View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-262e4b8e72f3d3fa0593View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-3900000000-0e32d0a2d4bb6373bea3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-34ade0e20ab7aa4d4e7fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-c780f74ca6838fbab7d8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-b2e474b4d7508faeddc3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-43781a61560faeff786dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-7a87251d344c519a4335View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1900000000-35bf92cf7a210b27759bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9058dd9b60d558e52773View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-9058dd9b60d558e52773View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1900000000-91e4df79f1f59e0c0465View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8575b97da509996b8151View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-8575b97da509996b8151View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-ff7fd755c09159064a33View in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-1f03568d4331683921b4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (10); inhalation (10)
Mechanism of ToxicityPAH's such as naphthalene are transported throughout the body after binding blood proteins such as albumin. Binding to the aryl hydrocarbon receptor or glycine N-methyltransferase induces the expression of cytochrome P450 enzymes (especially CYP1A1, CYP1A2, and CYP1B1). These cytochrome enzymes metabolize PAH's into various toxic intermediates (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations). The reactive metabolites of PAHs covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (10, 12, 2, 3). In humans, the metabolite alpha-naphthol has been linked to the development of hemolytic anemia in some cases following ingestion or extensive dermal or inhalation exposure. Susceptibility appears to be exacerbated by a deficiency in the glucose 6-phosphate dehydrogenase enzyme, or G-6-PD. Over 400 million people have an inherited condition called glucose-6-phosphate dehydrogenase deficiency. Exposure to naphthalene is more harmful for these people and may cause hemolytic anemia at lower doses. Some naphthalene metabolites deplete glutathione stores in affected tissues such as the lungs, leading to toxicity. The metabolites responsible for glutathione depletion have been identified as naphthalene oxide or 1,2-naphthoquinone and 1,4-naphthoquinone.
MetabolismPAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can be conjugated to glucuronides and sulfate esters; and the quinones can form glutathione conjugates. (10)
Toxicity ValuesLD50: 490 mg/kg (Oral, Rat) (8) LD50: >20 g/kg (Dermal, Rabbit) (8) LD50: 150 mg/kg (Intraperitoneal, Mouse) (7) LD50: 969 mg/kg (Subcutaneous, Mouse) (7) LD50: 100 mg/kg (Intravenous, Mouse) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (13)
Uses/SourcesIndustrially, naphthalene is used in the production of phthalic anhydride, as a solvent for chemical reactions, as a wetting agent and as a fumigant. Naphthalene is produced industrially via coal tar and naturally with trace amounts of naphthalene being produced by black walnuts, magnolias and specific types of deer.
Minimum Risk LevelNot Available
Health EffectsInhalation of naphthalene vapor has been associated with headaches, nausea, vomiting and dizziness. Hemolysis, the abnormal breakdown of red blood cells, may occur following ingestion or sufficient dermal exposure to either naphthalene or to naphthalene-treated fabric. In humans, cataracts and other ocular injury have been reported following acute and chronic occupational exposure to naphthalene. Additional signs of toxicity in children include convulsions and coma. Infants may develop encephalopathy and kernicterus, a form of brain damage, due to the presence of increased levels of methemoglobin, hemoglobin, and bilirubin in their plasma. Naphthalene appears to be mildly carcinogenic. Rats exposed to naphthalene vapors at 10, 30, or 60 ppm for 6 hours a day, five days a week for two years developed respiratory epithelial adenomas and olfactory epithelial neuroblastomas.
SymptomsSymptoms of hemolytic anemia include fatigue, lack of appetite, restlessness, and pale skin. Exposure to large amounts of naphthalene may cause confusion, nausea, vomiting, diarrhea, blood in the urine, and jaundice (yellow coloration of the skin).
TreatmentThere is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (10)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB29751
PubChem Compound ID931
ChEMBL IDCHEMBL16293
ChemSpider ID906
KEGG IDC00829
UniProt IDNot Available
OMIM ID
ChEBI ID16482
BioCyc IDALPHA-NAPHTHALENEACETAMIDE
CTD IDC031721
Stitch IDNaphthalene
PDB IDNPY
ACToR ID934
Wikipedia LinkNaphthalene
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Santodonato J, Howard P, Basu D: Health and ecological assessment of polynuclear aromatic hydrocarbons. J Environ Pathol Toxicol. 1981 Sep;5(1):1-364. [7310260 ]
  2. 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 ]
  3. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  4. Pandya U, Saini MK, Jin GF, Awasthi S, Godley BF, Awasthi YC: Dietary curcumin prevents ocular toxicity of naphthalene in rats. Toxicol Lett. 2000 Jun 5;115(3):195-204. [10814889 ]
  5. Yen KM, Serdar CM: Genetics of naphthalene catabolism in pseudomonads. Crit Rev Microbiol. 1988;15(3):247-68. [3288442 ]
  6. Waidyanatha S, Zheng Y, Serdar B, Rappaport SM: Albumin adducts of naphthalene metabolites as biomarkers of exposure to polycyclic aromatic hydrocarbons. Cancer Epidemiol Biomarkers Prev. 2004 Jan;13(1):117-24. [14744742 ]
  7. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  8. Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  10. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  11. ATSDR - Agency for Toxic Substances and Disease Registry (2005). Toxicological profile for naphthalene, 1-methylnaphthalene, and 2-methyl-naphthalene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  12. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
  13. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

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
References
  1. 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 ]
  2. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. 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 ]
  2. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
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
References
  1. 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 ]
  2. Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51. [11460716 ]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50700 uMNot AvailableBindingDB 50159249
References
  1. 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:
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
  1. 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 ]
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
  1. 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:
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
  1. 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 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
  1. 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
  1. 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
  1. 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:
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.32 uMATG_PPARa_TRANSAttagene
References
  1. 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:
Not Available
Specific Function:
Not Available
Gene Name:
TP53
Uniprot ID:
P04637
Molecular Weight:
43652.79 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.85 uMAPR_p53Act_72h_upApredica
References
  1. 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 ]