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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014873

Secondary Accession Numbers

HMDB14873

Metabolite Identification

Common Name

Naftifine

Description

Naftifine 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014873
     RDKit          3D
Naftifine
 43 45  0  0  0  0  0  0  0  0999 V2000
    0.6236    0.4543    1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2364    0.8518    0.0678 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    0.1150    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -1.3079    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5360   -1.8189   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -0.9031   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9115   -0.1344   -1.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0271    0.6845   -1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9089    0.7571   -0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6127   -0.0065    0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4999   -0.8064    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5716   -0.0542   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030    0.6403   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076    1.9797   -0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    2.6788   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147    1.9601   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.5663    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2740   -0.1378    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1527   -1.5011    0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777   -2.1797    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978   -1.4245   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.0949   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745    0.9464    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023    0.8346    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5953   -0.6213    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663    0.6871   -0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905    0.3721    1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -1.9562    0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785   -2.8635   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109   -0.2050   -2.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2349    1.2952   -2.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7558    1.4155   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2779    0.0638    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154   -1.3943    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264   -1.0081   -0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115    0.2905   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0064    2.5505   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1149    3.7477   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1522    2.5076    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255    0.3390    0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9715   -2.1358    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062   -3.2465    0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605   -1.9378   -0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  6  1  0
 22 13  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END

735
  Mrv0541 02231214582D          

 22 24  0  0  1  0            999 V2000
    4.5079    0.3982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    2.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    1.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    3.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    3.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -3.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 12  2  0  0  0  0
  6 13  1  0  0  0  0
  7 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  3  0  0  0
 14 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014873

> <DATABASE_NAME>
hmdb

> <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_KEY>
OZGNYLLQHRPOBR-UHFFFAOYSA-N

> <FORMULA>
C21H21N

> <MOLECULAR_WEIGHT>
287.3981

> <EXACT_MASS>
287.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
34.04545714727199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl(naphthalen-1-ylmethyl)(3-phenylprop-2-en-1-yl)amine

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
5.238508130333333

> <ALOGPS_LOGS>
-6.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.076115733353172

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
95.98210000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naftin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014873
     RDKit          3D
Naftifine
 43 45  0  0  0  0  0  0  0  0999 V2000
    0.6236    0.4543    1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2364    0.8518    0.0678 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    0.1150    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -1.3079    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5360   -1.8189   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -0.9031   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9115   -0.1344   -1.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0271    0.6845   -1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9089    0.7571   -0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6127   -0.0065    0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4999   -0.8064    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5716   -0.0542   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030    0.6403   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076    1.9797   -0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    2.6788   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147    1.9601   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.5663    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2740   -0.1378    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1527   -1.5011    0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777   -2.1797    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978   -1.4245   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.0949   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745    0.9464    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023    0.8346    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5953   -0.6213    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663    0.6871   -0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905    0.3721    1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -1.9562    0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785   -2.8635   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109   -0.2050   -2.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2349    1.2952   -2.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7558    1.4155   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2779    0.0638    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154   -1.3943    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264   -1.0081   -0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115    0.2905   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0064    2.5505   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1149    3.7477   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1522    2.5076    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255    0.3390    0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9715   -2.1358    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062   -3.2465    0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605   -1.9378   -0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  6  1  0
 22 13  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 735                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       8.415   0.743   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       9.748   1.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.748   3.053   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.082   3.823   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.082   5.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415  -0.797   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   3.823   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   1.513   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.459   3.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   6.133   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   5.363   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.459   6.187   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -1.567   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.854   3.791   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.854   5.395   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -3.107   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747  -3.877   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747  -5.417   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -3.107   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -6.187   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080  -3.877   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -5.417   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4   10   12                                                  
CONECT    6    1   13                                                       
CONECT    7    3   11                                                       
CONECT    8    1                                                            
CONECT    9    4   14                                                       
CONECT   10    5   11                                                       
CONECT   11    7   10                                                       
CONECT   12    5   15                                                       
CONECT   13    6   16                                                       
CONECT   14    9   15                                                       
CONECT   15   12   14                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0014873
HETATM    1  C1  UNL     1       0.624   0.454   1.316  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.236   0.852   0.068  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.443   0.115   0.481  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.438  -1.308   0.225  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.536  -1.819  -0.336  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.597  -0.903  -0.584  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.911  -0.134  -1.656  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.027   0.684  -1.701  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.909   0.757  -0.603  1.00  0.00           C  
HETATM   10  C9  UNL     1      -5.613  -0.006   0.483  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.500  -0.806   0.503  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.572  -0.054  -0.887  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.903   0.640  -0.657  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.908   1.980  -0.715  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.097   2.679  -0.394  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.215   1.960  -0.029  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.196   0.566   0.018  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.274  -0.138   0.482  1.00  0.00           C  
HETATM   19  C18 UNL     1       5.153  -1.501   0.628  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.978  -2.180   0.312  1.00  0.00           C  
HETATM   21  C20 UNL     1       2.898  -1.424  -0.163  1.00  0.00           C  
HETATM   22  C21 UNL     1       3.009  -0.095  -0.307  1.00  0.00           C  
HETATM   23  H1  UNL     1       0.074   0.946   2.128  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.602   0.835   1.265  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.595  -0.621   1.367  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.266   0.687  -0.082  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.590   0.372   1.578  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.630  -1.956   0.489  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.578  -2.863  -0.560  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.211  -0.205  -2.506  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.235   1.295  -2.564  1.00  0.00           H  
HETATM   32  H10 UNL     1      -6.756   1.415  -0.638  1.00  0.00           H  
HETATM   33  H11 UNL     1      -6.278   0.064   1.356  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.315  -1.394   1.411  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.426  -1.008  -0.515  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.211   0.290  -1.853  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.006   2.550  -1.002  1.00  0.00           H  
HETATM   38  H16 UNL     1       3.115   3.748  -0.465  1.00  0.00           H  
HETATM   39  H17 UNL     1       5.152   2.508   0.225  1.00  0.00           H  
HETATM   40  H18 UNL     1       6.226   0.339   0.760  1.00  0.00           H  
HETATM   41  H19 UNL     1       5.972  -2.136   0.995  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.906  -3.246   0.443  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.961  -1.938  -0.422  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   12
CONECT    3    4   26   27
CONECT    4    5    5   28
CONECT    5    6   29
CONECT    6    7    7   11
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   34
CONECT   12   13   35   36
CONECT   13   14   14   22
CONECT   14   15   37
CONECT   15   16   16   38
CONECT   16   17   39
CONECT   17   18   18   22
CONECT   18   19   40
CONECT   19   20   20   41
CONECT   20   21   42
CONECT   21   22   22   43
END

HMDB0014873
     RDKit          3D
Naftifine
 43 45  0  0  0  0  0  0  0  0999 V2000
    0.6236    0.4543    1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2364    0.8518    0.0678 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    0.1150    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -1.3079    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5360   -1.8189   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5965   -0.9031   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9115   -0.1344   -1.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0271    0.6845   -1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9089    0.7571   -0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6127   -0.0065    0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4999   -0.8064    0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5716   -0.0542   -0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030    0.6403   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9076    1.9797   -0.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    2.6788   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147    1.9601   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.5663    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2740   -0.1378    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1527   -1.5011    0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777   -2.1797    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978   -1.4245   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.0949   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745    0.9464    2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023    0.8346    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5953   -0.6213    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663    0.6871   -0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905    0.3721    1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -1.9562    0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785   -2.8635   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2109   -0.2050   -2.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2349    1.2952   -2.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7558    1.4155   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2779    0.0638    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154   -1.3943    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264   -1.0081   -0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115    0.2905   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0064    2.5505   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1149    3.7477   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1522    2.5076    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255    0.3390    0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9715   -2.1358    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062   -3.2465    0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9605   -1.9378   -0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  6  1  0
 22 13  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₂₁N

Average Molecular Weight

287.3981

Monoisotopic Molecular Weight

287.167399677

IUPAC Name

methyl(naphthalen-1-ylmethyl)(3-phenylprop-2-en-1-yl)amine

Traditional Name

naftin

CAS Registry Number

65472-88-0

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 Key

OZGNYLLQHRPOBR-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

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 Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014873)
Membrane (HMDB: HMDB0014873)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00023 g/L	Not Available
LogP	5.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00023 g/L	ALOGPS
logP	4.96	ALOGPS
logP	5.24	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.98 m³·mol⁻¹	ChemAxon
Polarizability	34.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.061	31661259
DarkChem	[M-H]-	167.56	31661259
DeepCCS	[M-2H]-	195.576	30932474
DeepCCS	[M+Na]+	171.141	30932474
AllCCS	[M+H]+	171.5	32859911
AllCCS	[M+H-H2O]+	167.9	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.8	32859911
AllCCS	[M-H]-	177.5	32859911
AllCCS	[M+Na-2H]-	176.7	32859911
AllCCS	[M+HCOO]-	175.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naftifine	CN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C12	3554.6	Standard polar	33892256
Naftifine	CN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C12	2529.8	Standard non polar	33892256
Naftifine	CN(CC=CC1=CC=CC=C1)CC1=CC=CC2=CC=CC=C12	2532.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Naftifine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1910000000-7366549496bd2c2788f5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naftifine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naftifine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOF	splash10-014r-0940000000-736e1306e0a1b21a69e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-1a47528b60d38f7230ea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-db364fa78b21edf4eb3a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-43af6cd3170ea07037e0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOF	splash10-014l-0900000000-2a982f932855fa74205f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOF	splash10-014l-1900000000-6aded55bd308a6ddc1e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOF	splash10-014l-4900000000-382482d4ffa5075b4d29	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOF	splash10-014i-8900000000-ad11e6913754f48ce01d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine LC-ESI-QFT , positive-QTOF	splash10-014i-9400000000-52e2c99bae16686c15b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine 30V, Positive-QTOF	splash10-014i-0900000000-228745653af2f94f26a3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine 15V, Positive-QTOF	splash10-014r-0940000000-47ca7782d23a6ae4df71	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine 45V, Positive-QTOF	splash10-014i-0900000000-d19a9de16f6c45475389	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine 60V, Positive-QTOF	splash10-014i-0900000000-ba29235b5f67a54b6956	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine 75V, Positive-QTOF	splash10-014l-0900000000-58fdc6592d74f0567c2f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Naftifine 90V, Positive-QTOF	splash10-014l-1900000000-547e16d898f6a4479e7b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 10V, Positive-QTOF	splash10-000i-0190000000-fd201be8eee2bb433cb0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 20V, Positive-QTOF	splash10-014r-1960000000-35f1fa638d6e1dc5f490	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 40V, Positive-QTOF	splash10-014l-4900000000-3a485b07ea52fcd7daa7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 10V, Negative-QTOF	splash10-000i-0090000000-9145fb80fdfbae4d7d88	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 20V, Negative-QTOF	splash10-0079-0890000000-02539444187b5684da24	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 40V, Negative-QTOF	splash10-004i-2900000000-5e6be894cea51a6b4aa6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 10V, Positive-QTOF	splash10-000l-0980000000-580dcbfcf6a7084da34e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 20V, Positive-QTOF	splash10-0006-1910000000-462012d44312e953acd0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 40V, Positive-QTOF	splash10-00kf-2900000000-b5cdb70d91b984020cba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naftifine 10V, Negative-QTOF	splash10-000i-0090000000-26c7f893d45bf33544e2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00735	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00735	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00735

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

66071

KEGG Compound ID

C08071

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Naftifine

METLIN ID

Not Available

PubChem Compound

47641

PDB ID

Not Available

ChEBI ID

126722

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Squalene monooxygenase

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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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 ]
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 ]
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 ]
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 ]
Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [PubMed:1287164 ]

Showing metabocard for Naftifine (HMDB0014873)

MOL for HMDB0014873 (Naftifine)

3D MOL for HMDB0014873 (Naftifine)

3D SDF for HMDB0014873 (Naftifine)

3D-SDF for HMDB0014873 (Naftifine)

PDB for HMDB0014873 (Naftifine)

3D PDB for HMDB0014873 (Naftifine)

SMILES for HMDB0014873 (Naftifine)

INCHI for HMDB0014873 (Naftifine)

Structure for HMDB0014873 (Naftifine)

3D Structure for HMDB0014873 (Naftifine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References