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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:24 UTC
Update Date2021-10-13 06:02:51 UTC
HMDB IDHMDB0029751
Secondary Accession Numbers
  • HMDB29751
Metabolite Identification
Common NameNaphthalene
DescriptionNaphthalene, also known as naftaleno or albocarbon, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Naphthalene is possibly neutral. Naphthalene is a dry, pungent, and tar tasting compound. Naphthalene is found, on average, in the highest concentration within a few different foods, such as black walnuts, corns, and cloves. Naphthalene has also been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, rices, yellow bell peppers, and red bell peppers. This could make naphthalene a potential biomarker for the consumption of these foods. Naphthalene was once the primary ingredient in mothballs, though its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. Naphthalene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Inhalation of naphthalene vapor has been associated with headaches, nausea, vomiting and dizziness. Naphthalene is the most abundant single component of coal tar so most of it is now industrially derived from coal tar. Aside from coal tar, trace amounts of naphthalene are produced by magnolias and some species of deer, as well as the Formosan subterranean termite, possibly produced by the termite as a repellant against "ants, poisonous fungi and nematode worms."[23] Some strains of the endophytic fungus Muscodor albus produce naphthalene among a range of volatile organic compounds, while Muscodor vitigenus produces naphthalene almost exclusively (PMID:12427963 ).
Structure
Data?1582753459
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
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point80.3 °CNot Available
Boiling Point217.00 to 219.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.031 mg/mL at 25 °CNot Available
LogP3.30Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available120.276http://allccs.zhulab.cn/database/detail?ID=AllCCS00002018
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP10(3.33) g/LALOGPS
logP10(2.96) g/LChemAxon
logS10(-3.3) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.22731661259
DarkChem[M-H]-122.64831661259
DeepCCS[M+H]+128.01730932474
DeepCCS[M-H]-125.03430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NaphthaleneC1=CC2=CC=CC=C2C=C11782.1Standard polar33892256
NaphthaleneC1=CC2=CC=CC=C2C=C11174.8Standard non polar33892256
NaphthaleneC1=CC2=CC=CC=C2C=C11187.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-4900000000-28274068093bf0319e302017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-4900000000-108107442234977871562017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-0900000000-f640b15d5ebd285008e92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-2900000000-837afe39d2806871be732017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-5900000000-262e4b8e72f3d3fa05932017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-3900000000-0e32d0a2d4bb6373bea32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-4900000000-34ade0e20ab7aa4d4e7f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-4900000000-c780f74ca6838fbab7d82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-000i-4900000000-b2e474b4d7508faeddc32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-7900000000-43781a61560faeff786d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-000i-0900000000-7a87251d344c519a43352017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene CI-B (Non-derivatized)splash10-004i-0900000000-0532459557fd0c5435872017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene GC-EI-TOF (Non-derivatized)splash10-004i-1900000000-5a22b095f0a190f1b9782017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-4900000000-28274068093bf0319e302018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-4900000000-108107442234977871562018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-0900000000-f640b15d5ebd285008e92018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-2900000000-837afe39d2806871be732018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-5900000000-262e4b8e72f3d3fa05932018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-3900000000-0e32d0a2d4bb6373bea32018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-4900000000-34ade0e20ab7aa4d4e7f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-4900000000-c780f74ca6838fbab7d82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-000i-4900000000-b2e474b4d7508faeddc32018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-004i-7900000000-43781a61560faeff786d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naphthalene EI-B (Non-derivatized)splash10-000i-0900000000-7a87251d344c519a43352018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naphthalene GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1900000000-35bf92cf7a210b27759b2016-09-22Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-1f03568d4331683921b42014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 10V, Positive-QTOFsplash10-004i-0900000000-9058dd9b60d558e527732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 20V, Positive-QTOFsplash10-004i-0900000000-9058dd9b60d558e527732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 40V, Positive-QTOFsplash10-004i-1900000000-91e4df79f1f59e0c04652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 10V, Negative-QTOFsplash10-004i-0900000000-8575b97da509996b81512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 20V, Negative-QTOFsplash10-004i-0900000000-8575b97da509996b81512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 40V, Negative-QTOFsplash10-004i-0900000000-ff7fd755c09159064a332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 10V, Positive-QTOFsplash10-004i-0900000000-71e8922109bea9aa624a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 20V, Positive-QTOFsplash10-004i-6900000000-6558deffdb05b27a632e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 40V, Positive-QTOFsplash10-004i-3900000000-f1f49df790d7f67edbc02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 10V, Negative-QTOFsplash10-004i-0900000000-ec6816397577a7beb93f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 20V, Negative-QTOFsplash10-004i-0900000000-ec6816397577a7beb93f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naphthalene 40V, Negative-QTOFsplash10-004i-0900000000-ec6816397577a7beb93f2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB000954
KNApSAcK IDC00001259
Chemspider ID906
KEGG Compound IDC00829
BioCyc IDNAPHTHALENE
BiGG IDNot Available
Wikipedia LinkNaphthalene
METLIN IDNot Available
PubChem Compound931
PDB IDNPY
ChEBI ID16482
Food Biomarker OntologyNot Available
VMH IDNPTHL
MarkerDB IDNot Available
Good Scents IDrw1268211
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. Daisy BH, Strobel GA, Castillo U, Ezra D, Sears J, Weaver DK, Runyon JB: Naphthalene, an insect repellent, is produced by Muscodor vitigenus, a novel endophytic fungus. Microbiology (Reading). 2002 Nov;148(Pt 11):3737-3741. doi: 10.1099/00221287-148-11-3737. [PubMed:12427963 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .