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Record Information
Version3.6
Creation Date2012-09-11 17:32:24 UTC
Update Date2016-02-11 01:43:04 UTC
HMDB IDHMDB29751
Secondary Accession NumbersNone
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) Naphthalene has been shown to exhibit apoptotic and catabolic functions (PMID 10814889 , 3288442 ). Naphthalene belongs to the family of Naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Structure
Thumb
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=C(C=C1)C=CC=C2
InChI Identifier
InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
InChI KeyInChIKey=UFWIBTONFRDIAS-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
  • Polycyclic hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • apoptotic
  • catabolic
Application
  • Nutrient
Cellular locations
  • Membrane
Physical Properties
StateNot Available
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 mg/mLALOGPS
logP3.33ALOGPS
logP2.96ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.51 m3·mol-1ChemAxon
Polarizability14.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-1f03568d4331683921b4View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000954
KNApSAcK IDC00001259
Chemspider ID906
KEGG Compound IDC00829
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNaphthalene
NuGOwiki LinkHMDB29751
Metagene LinkHMDB29751
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. [10814889 ]
  2. Yen KM, Serdar CM: Genetics of naphthalene catabolism in pseudomonads. Crit Rev Microbiol. 1988;15(3):247-68. [3288442 ]
  3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.