1-Methylnaphthalene (T3D0628)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (5)XML
Targets (5)
Record Information
Version2.0
Creation Date2009-03-06 18:59:15 UTC
Update Date2014-12-24 20:22:26 UTC
Accession NumberT3D0628
Identification
Common Name1-Methylnaphthalene
ClassSmall Molecule
Description1-Methylnaphthalene is found in black walnut. 1-Methylnaphthalene is a flavouring ingredient.
Compound Type
  • Aromatic Hydrocarbon
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1-Methyl naphthalene
1-Methyl-Naphthalene
a-Methyl-Naphthalene
a-Methylnaphthalene
alpha-Methyl-Naphthalene
alpha-Methylnaphthalene
Methyl naphthalene
Methyl-1-naphthalene
Methyl-Naphthalene
Chemical FormulaC11H10
Average Molecular Mass142.197 g/mol
Monoisotopic Mass142.078 g/mol
CAS Registry Number90-12-0
IUPAC Name1-methylnaphthalene
Traditional Name1-methylnaphthalene
SMILESCC1=CC=CC2=CC=CC=C12
InChI IdentifierInChI=1S/C11H10/c1-9-5-4-7-10-6-2-3-8-11(9)10/h2-8H,1H3
InChI KeyInChIKey=QPUYECUOLPXSFR-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 RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless solid.
Experimental Properties
PropertyValue
Melting Point-22°C
Boiling Point244.6°C (472.3°F)
Solubility0.0258 mg/mL at 25°C
LogP3.87
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.84ALOGPS
logP3.48ChemAxon
logS-3.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.55 m³·mol⁻¹ChemAxon
Polarizability16.61 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-5900000000-1053593aad42a77aa98b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2900000000-56264ce7fb87f61d59e32017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-3900000000-466eebbbc710f9d74e3b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-3900000000-5b7a1e8903022a3f5a572017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-e017871c9adc6ee00fb92017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0006-0900000000-e2ebef06c838787a17202017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-5900000000-1053593aad42a77aa98b2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2900000000-56264ce7fb87f61d59e32018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-3900000000-466eebbbc710f9d74e3b2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-3900000000-5b7a1e8903022a3f5a572018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-e017871c9adc6ee00fb92018-05-18View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0006-0900000000-e2ebef06c838787a17202018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-0da70ea2233c3affb6382017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-9a9a9f94bee2dbaba3c02015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5692907557a9baf3d2572015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-3900000000-7eef39e40fe85545ba502015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-4b4ea885969f2a72f1b72015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-4b4ea885969f2a72f1b72015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-e204af06be24fa547ed92015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-c989a442d4404542ed612021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2900000000-4c5f4b7cbec6cfd38b142021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9800000000-c7005946673c7bd7a9262021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-84dab5fd9e005e323db02021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-84dab5fd9e005e323db02021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-3a4e7194998e40dc39cf2021-09-25View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-2900000000-53cda581a6605326e48c2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (21) ; inhalation (21)
Mechanism of ToxicityThe ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. 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. (21, 22, 2, 3)
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 all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (21)
Toxicity ValuesLD50: 1840 mg/kg (Oral, Rat) (18)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (23)
Uses/SourcesPAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (21)
Minimum Risk LevelNot Available
Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (21)
SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)
TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (21)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB32860
PubChem Compound ID7002
ChEMBL IDCHEMBL383808
ChemSpider ID6736
KEGG IDC14082
UniProt IDNot Available
OMIM ID
ChEBI ID50717
BioCyc IDALPHA-NAPHTHALENEACETAMIDE
CTD IDC025968
Stitch ID1-Methylnaphthalene
PDB IDNot Available
ACToR IDNot Available
Wikipedia Link1-Methylnaphthalene
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. Adachi K: Mass fragmentographic determination of polymethylnaphthalene and polymethylphenanthrene in a crude oil and in marine organisms. Bull Environ Contam Toxicol. 1980 Sep;25(3):416-23. [6893557 ]
  5. Jin M, Kijima A, Suzuki Y, Hibi D, Ishii Y, Nohmi T, Nishikawa A, Ogawa K, Umemura T: In vivo genotoxicity of 1-methylnaphthalene from comprehensive toxicity studies with B6C3F1 gpt delta mice. J Toxicol Sci. 2012;37(4):711-21. [22863852 ]
  6. Kameda T, Inazu K, Asano K, Murota M, Takenaka N, Sadanaga Y, Hisamatsu Y, Bandow H: Prediction of rate constants for the gas phase reactions of triphenylene with OH and NO3 radicals using a relative rate method in CCl4 liquid phase-system. Chemosphere. 2013 Jan;90(2):766-71. doi: 10.1016/j.chemosphere.2012.09.071. Epub 2012 Oct 22. [23084261 ]
  7. Kwon HC, Kwon JH: Measuring aqueous solubility in the presence of small cosolvent volume fractions by passive dosing. Environ Sci Technol. 2012 Nov 20;46(22):12550-6. doi: 10.1021/es3035363. Epub 2012 Oct 29. [23088587 ]
  8. Wang Y, Lonard DM, Yu Y, Chow DC, Palzkill TG, O'Malley BW: Small molecule inhibition of the steroid receptor coactivators, SRC-3 and SRC-1. Mol Endocrinol. 2011 Dec;25(12):2041-53. doi: 10.1210/me.2011-1222. Epub 2011 Nov 3. [22053001 ]
  9. Shintani M, Matsuo Y, Sakuraba S, Matubayasi N: Interaction of naphthalene derivatives with lipids in membranes studied by the 1H-nuclear Overhauser effect and molecular dynamics simulation. Phys Chem Chem Phys. 2012 Oct 28;14(40):14049-60. Epub 2012 Sep 17. [22983117 ]
  10. Kleemann R, Meckenstock RU: Anaerobic naphthalene degradation by Gram-positive, iron-reducing bacteria. FEMS Microbiol Ecol. 2011 Dec;78(3):488-96. doi: 10.1111/j.1574-6941.2011.01193.x. Epub 2011 Sep 22. [22066721 ]
  11. Govindarajan M, Karabacak M: FT-IR, FT-Raman and UV spectral investigation: computed frequency estimation analysis and electronic structure calculations on 1-bromo-2-methylnaphthalene. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Jan 15;101:314-24. doi: 10.1016/j.saa.2012.09.099. Epub 2012 Oct 12. [23123238 ]
  12. Lopez ER, Pensado AS, Fernandez J, Harris KR: On the density scaling of pVT data and transport properties for molecular and ionic liquids. J Chem Phys. 2012 Jun 7;136(21):214502. doi: 10.1063/1.4720070. [22697553 ]
  13. Wang LF, Wu QJ, Zu LL: [Laser-induced fluorescence of 1-methylnaphthalene in a supersonic jet expansion]. Guang Pu Xue Yu Guang Pu Fen Xi. 2011 Nov;31(11):2965-8. [22242496 ]
  14. Liu J, Tang X, Zhang Y, Zhao W: Determination of the volatile composition in brown millet, milled millet and millet bran by gas chromatography/mass spectrometry. Molecules. 2012 Feb 24;17(3):2271-82. doi: 10.3390/molecules17032271. [22367023 ]
  15. Molloy JK, Kotova O, Peacock RD, Gunnlaugsson T: Synthesis of luminescent homo-dinuclear cationic lanthanide cyclen complexes bearing amide pendant arms through the use of copper catalysed (1,3-Huisgen, CuAAC) click chemistry. Org Biomol Chem. 2012 Jan 14;10(2):314-22. doi: 10.1039/c1ob06203d. Epub 2011 Nov 9. [22071980 ]
  16. Berdugo-Clavijo C, Dong X, Soh J, Sensen CW, Gieg LM: Methanogenic biodegradation of two-ringed polycyclic aromatic hydrocarbons. FEMS Microbiol Ecol. 2012 Jul;81(1):124-33. doi: 10.1111/j.1574-6941.2012.01328.x. Epub 2012 Mar 8. [22324881 ]
  17. Baedecker MJ, Eganhouse RP, Bekins BA, Delin GN: Loss of volatile hydrocarbons from an LNAPL oil source. J Contam Hydrol. 2011 Nov 1;126(3-4):140-52. doi: 10.1016/j.jconhyd.2011.06.006. Epub 2011 Jul 19. [22115081 ]
  18. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  19. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  20. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  21. 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]
  22. Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
  23. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Aryl hydrocarbon receptor
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]
Target Details
3. Glycine N-methyltransferase
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]
Target Details
4. Cytochrome P450 1A2
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
IC50110 uMNot AvailableBindingDB 50159279
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 ]
Target Details
5. Cellular tumor antigen p53
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
TP53
Uniprot ID:
P04637
Molecular Weight:
43652.79 Da