Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:30 UTC
HMDB IDHMDB0014873
Secondary Accession Numbers
  • HMDB14873
Metabolite Identification
Common NameNaftifine
DescriptionNaftifine is only found in individuals that have used or taken this drug. It is a synthetic, broad spectrum, antifungal agent and allylamine derivative for the topical treatment of tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans and Epidermophyton floccosum.Although the exact mechanism of action against fungi is not known, naftifine appears to interfere with sterol biosynthesis by inhibiting the enzyme squalene 2,3-epoxidase. This inhibition of enzyme activity results in decreased amounts of sterols, especially ergosterol, and a corresponding accumulation of squalene in the cells.
Structure
Data?1582753230
SynonymsNot Available
Chemical FormulaC21H21N
Average Molecular Weight287.3981
Monoisotopic Molecular Weight287.167399677
IUPAC Namemethyl(naphthalen-1-ylmethyl)(3-phenylprop-2-en-1-yl)amine
Traditional Namenaftin
CAS Registry Number65472-88-0
SMILES
CN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C12
InChI Identifier
InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3
InChI KeyOZGNYLLQHRPOBR-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
  • Styrene
  • Aralkylamine
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00023 g/LNot Available
LogP5.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00023 g/LALOGPS
logP10(4.96) g/LALOGPS
logP10(5.24) g/LChemAxon
logS10(-6.1) g/LALOGPS
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.98 m³·mol⁻¹ChemAxon
Polarizability34.05 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.06131661259
DarkChem[M-H]-167.5631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NaftifineCN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C123554.6Standard polar33892256
NaftifineCN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C122529.8Standard non polar33892256
NaftifineCN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C122532.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Naftifine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1910000000-7366549496bd2c2788f52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naftifine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naftifine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOFsplash10-014r-0940000000-736e1306e0a1b21a69e52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-1a47528b60d38f7230ea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-db364fa78b21edf4eb3a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-43af6cd3170ea07037e02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOFsplash10-014l-0900000000-2a982f932855fa74205f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOFsplash10-014l-1900000000-6aded55bd308a6ddc1e82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOFsplash10-014l-4900000000-382482d4ffa5075b4d292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOFsplash10-014i-8900000000-ad11e6913754f48ce01d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOFsplash10-014i-9400000000-52e2c99bae16686c15b32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine 30V, Positive-QTOFsplash10-014i-0900000000-228745653af2f94f26a32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine 15V, Positive-QTOFsplash10-014r-0940000000-47ca7782d23a6ae4df712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine 45V, Positive-QTOFsplash10-014i-0900000000-d19a9de16f6c454753892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine 60V, Positive-QTOFsplash10-014i-0900000000-ba29235b5f67a54b69562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine 75V, Positive-QTOFsplash10-014l-0900000000-58fdc6592d74f0567c2f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naftifine 90V, Positive-QTOFsplash10-014l-1900000000-547e16d898f6a4479e7b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 10V, Positive-QTOFsplash10-000i-0190000000-fd201be8eee2bb433cb02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 20V, Positive-QTOFsplash10-014r-1960000000-35f1fa638d6e1dc5f4902017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 40V, Positive-QTOFsplash10-014l-4900000000-3a485b07ea52fcd7daa72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 10V, Negative-QTOFsplash10-000i-0090000000-9145fb80fdfbae4d7d882017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 20V, Negative-QTOFsplash10-0079-0890000000-02539444187b5684da242017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 40V, Negative-QTOFsplash10-004i-2900000000-5e6be894cea51a6b4aa62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 10V, Positive-QTOFsplash10-000l-0980000000-580dcbfcf6a7084da34e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 20V, Positive-QTOFsplash10-0006-1910000000-462012d44312e953acd02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 40V, Positive-QTOFsplash10-00kf-2900000000-b5cdb70d91b984020cba2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naftifine 10V, Negative-QTOFsplash10-000i-0090000000-26c7f893d45bf33544e22021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00735 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00735 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00735
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID66071
KEGG Compound IDC08071
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNaftifine
METLIN IDNot Available
PubChem Compound47641
PDB IDNot Available
ChEBI ID126722
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name:
SQLE
Uniprot ID:
Q14534
Molecular weight:
63922.505
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Favre B, Ryder NS: Characterization of squalene epoxidase activity from the dermatophyte Trichophyton rubrum and its inhibition by terbinafine and other antimycotic agents. Antimicrob Agents Chemother. 1996 Feb;40(2):443-7. [PubMed:8834895 ]
  3. Vanden Bossche H, Marichal P: Mode of action of anti-Candida drugs: focus on terconazole and other ergosterol biosynthesis inhibitors. Am J Obstet Gynecol. 1991 Oct;165(4 Pt 2):1193-9. [PubMed:1951574 ]
  4. Mukherjee PK, Leidich SD, Isham N, Leitner I, Ryder NS, Ghannoum MA: Clinical Trichophyton rubrum strain exhibiting primary resistance to terbinafine. Antimicrob Agents Chemother. 2003 Jan;47(1):82-6. [PubMed:12499173 ]
  5. Ryder NS, Dupont MC: Inhibition of squalene epoxidase by allylamine antimycotic compounds. A comparative study of the fungal and mammalian enzymes. Biochem J. 1985 Sep 15;230(3):765-70. [PubMed:3877503 ]
  6. Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [PubMed:1287164 ]