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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:24 UTC
Update Date2019-07-31 22:49:59 UTC
HMDB IDHMDB0029751
Secondary Accession Numbers
  • HMDB29751
Metabolite Identification
Common NameNaphthalene
DescriptionNaphthalene is found in black walnut. Naphthalene is found in many essential oils.Naphthalene is an organic compound with formula C10H8. It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. Trace amounts of naphthalene are produced by magnolias and specific types of deer, as well as the Formosan subterranean termite. Some strains of the endophytic fungus Muscodor albus produce naphthalene among a range of volatile organic compounds, while Muscodor vitigenus produces naphthalene almost exclusively (Wikipedia
Structure
Data?1563861887
Synonyms
ValueSource
NaftalenoChEBI
NaftalinaChEBI
NaphtaleneChEBI
NaphtalineChEBI
NaphthalenChEBI
NaphthalinChEBI
AlbocarbonHMDB
Camphor tarHMDB
Moth ballsHMDB
Moth flakesHMDB
MothballsHMDB
NaftalenHMDB
NaphthalineHMDB
NaphtheneHMDB
Tar camphorHMDB
TolboxaneHMDB
White tarHMDB
Chemical FormulaC10H8
Average Molecular Weight128.1705
Monoisotopic Molecular Weight128.062600256
IUPAC Namenaphthalene
Traditional Namenaphthalene
CAS Registry Number91-20-3
SMILES
C1=CC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
InChI KeyUFWIBTONFRDIAS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point80.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.031 mg/mL at 25 °CNot Available
LogP3.30Not Available
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-28274068093bf0319e30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-10810744223497787156JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-f640b15d5ebd285008e9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-837afe39d2806871be73JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-262e4b8e72f3d3fa0593JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-3900000000-0e32d0a2d4bb6373bea3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-34ade0e20ab7aa4d4e7fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-c780f74ca6838fbab7d8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-b2e474b4d7508faeddc3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-43781a61560faeff786dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-7a87251d344c519a4335JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-0900000000-0532459557fd0c543587JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-1900000000-5a22b095f0a190f1b978JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-28274068093bf0319e30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-10810744223497787156JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-f640b15d5ebd285008e9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-837afe39d2806871be73JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-262e4b8e72f3d3fa0593JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-3900000000-0e32d0a2d4bb6373bea3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-34ade0e20ab7aa4d4e7fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-c780f74ca6838fbab7d8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-b2e474b4d7508faeddc3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-43781a61560faeff786dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-7a87251d344c519a4335JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1900000000-35bf92cf7a210b27759bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9058dd9b60d558e52773JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-9058dd9b60d558e52773JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1900000000-91e4df79f1f59e0c0465JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8575b97da509996b8151JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-8575b97da509996b8151JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-ff7fd755c09159064a33JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-1f03568d4331683921b4JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not Quantified Children (1-13 years old)BothAsthma details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Asthma
  1. van de Kant KD, van Berkel JJ, Jobsis Q, Lima Passos V, Klaassen EM, van der Sande L, van Schayck OC, de Jongste JC, van Schooten FJ, Derks E, Dompeling E, Dallinga JW: Exhaled breath profiling in diagnosing wheezy preschool children. Eur Respir J. 2013 Jan;41(1):183-8. doi: 10.1183/09031936.00122411. [PubMed:23277518 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000954
KNApSAcK IDC00001259
Chemspider ID906
KEGG Compound IDC00829
BioCyc IDNAPHTHALENE
BiGG IDNot Available
Wikipedia LinkNaphthalene
METLIN IDNot Available
PubChem Compound931
PDB IDNPY
ChEBI ID16482
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:10814889 ]
  2. Yen KM, Serdar CM: Genetics of naphthalene catabolism in pseudomonads. Crit Rev Microbiol. 1988;15(3):247-68. [PubMed:3288442 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .