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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-16 12:15:48 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005005

Secondary Accession Numbers

HMDB05005

Metabolite Identification

Common Name

Tolnaftate

Description

Tolnaftate is a synthetic over-the-counter anti-fungal agent. It may come as a cream, powder, spray, or liquid aerosol, and is used to treat jock itch, athlete's foot and ringworm. It is sold under several brand names, most notably Tinactin (Schering-Plough Corporation) and Odor-Eaters (Combe Incorporated). Other brands are Absorbine, Aftate, Desenex, Genaspor, NP 27, and Ting.and Odor-Eaters (Combe Incorporated). Other brands are Absorbine, Aftate, Desenex, Genaspor, NP 27, and Ting.

Structure

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

HMDB0005005
     RDKit          3D
Tolnaftate
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.9073    2.7031    0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    1.2696    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6144    0.3299    0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4121   -1.0196    0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.4109   -0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1700   -0.4652   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.8438   -0.8129 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5905   -1.3641   -2.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466   -0.7123    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -0.1227    1.5977 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5053   -1.0658   -0.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7138   -0.4995   -0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8928    0.6118    0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691    1.0841    0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    0.4842    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586    0.9404    0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6723    0.2983    0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4984   -0.8137   -0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2201   -1.2638   -0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -0.6295   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431   -1.1340   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841    0.8850   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5226    3.3258   -0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9764    2.8972    0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192    2.9058    1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5848    0.6359    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1588   -1.7728    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9181   -2.4196   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -0.7801   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -2.4648   -2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -1.3322   -2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241    1.1240    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842    1.9770    1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6855    1.8118    1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6413    0.6886    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3766   -1.3126   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1024   -2.1513   -1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7085   -2.0075   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924    1.6134   -0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  6 22  2  0
 22  2  1  0
 21 12  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 22 39  1  0
M  END

525
  Mrv1652305271900312D          

 22 24  0  0  0  0            999 V2000
    5.2224    0.8107    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.4268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180   -0.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654   -0.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    0.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  2  0  0  0  0
  2  7  1  0  0  0  0
  2 16  1  0  0  0  0
  3  6  1  0  0  0  0
  3 16  1  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4 13  2  0  0  0  0
  5 11  1  0  0  0  0
  5 15  2  0  0  0  0
  6  9  1  0  0  0  0
  6 14  2  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  9 10  2  0  0  0  0
 10 17  1  0  0  0  0
 10 22  1  0  0  0  0
 11 12  2  0  0  0  0
 13 20  1  0  0  0  0
 14 18  1  0  0  0  0
 15 21  1  0  0  0  0
 17 18  2  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005005

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3

> <INCHI_KEY>
FUSNMLFNXJSCDI-UHFFFAOYSA-N

> <FORMULA>
C19H17NOS

> <MOLECULAR_WEIGHT>
307.409

> <EXACT_MASS>
307.103084861

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.22480823447255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
5.745039567000001

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.07504048749554171

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
94.92040000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.46e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tolnaftate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0005005
     RDKit          3D
Tolnaftate
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.9073    2.7031    0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    1.2696    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6144    0.3299    0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4121   -1.0196    0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.4109   -0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1700   -0.4652   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.8438   -0.8129 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5905   -1.3641   -2.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466   -0.7123    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -0.1227    1.5977 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5053   -1.0658   -0.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7138   -0.4995   -0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8928    0.6118    0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691    1.0841    0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    0.4842    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586    0.9404    0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6723    0.2983    0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4984   -0.8137   -0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2201   -1.2638   -0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -0.6295   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431   -1.1340   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841    0.8850   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5226    3.3258   -0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9764    2.8972    0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192    2.9058    1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5848    0.6359    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1588   -1.7728    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9181   -2.4196   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -0.7801   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -2.4648   -2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -1.3322   -2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241    1.1240    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842    1.9770    1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6855    1.8118    1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6413    0.6886    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3766   -1.3126   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1024   -2.1513   -1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7085   -2.0075   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924    1.6134   -0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  6 22  2  0
 22  2  1  0
 21 12  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 22 39  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 525                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0       9.748   1.513   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      11.082  -0.797   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.415  -0.797   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      15.083  -0.027   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.083   1.513   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -0.027   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.416  -0.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.750  -0.797   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -0.797   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -0.027   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.750   2.283   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.416   1.513   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.460  -0.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   1.513   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.460   2.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -0.027   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   1.513   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   2.283   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -2.337   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.855  -0.059   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.855   1.545   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -0.797   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2    7   16                                                       
CONECT    3    6   16   19                                                  
CONECT    4    5    8   13                                                  
CONECT    5    4   11   15                                                  
CONECT    6    3    9   14                                                  
CONECT    7    2    8   12                                                  
CONECT    8    4    7                                                       
CONECT    9    6   10                                                       
CONECT   10    9   17   22                                                  
CONECT   11    5   12                                                       
CONECT   12    7   11                                                       
CONECT   13    4   20                                                       
CONECT   14    6   18                                                       
CONECT   15    5   21                                                       
CONECT   16    1    2    3                                                  
CONECT   17   10   18                                                       
CONECT   18   14   17                                                       
CONECT   19    3                                                            
CONECT   20   13   21                                                       
CONECT   21   15   20                                                       
CONECT   22   10                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0005005
HETATM    1  C1  UNL     1       4.907   2.703   0.698  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.623   1.270   0.367  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.614   0.330   0.532  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.412  -1.020   0.250  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.154  -1.411  -0.214  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.170  -0.465  -0.375  1.00  0.00           C  
HETATM    7  N1  UNL     1       1.858  -0.844  -0.813  1.00  0.00           N  
HETATM    8  C7  UNL     1       1.590  -1.364  -2.131  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.747  -0.712   0.084  1.00  0.00           C  
HETATM   10  S1  UNL     1       1.053  -0.123   1.598  1.00  0.00           S  
HETATM   11  O1  UNL     1      -0.505  -1.066  -0.312  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.714  -0.499  -0.022  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.893   0.612   0.766  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.169   1.084   0.991  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.280   0.484   0.456  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.559   0.940   0.688  1.00  0.00           C  
HETATM   17  C14 UNL     1      -6.672   0.298   0.140  1.00  0.00           C  
HETATM   18  C15 UNL     1      -6.498  -0.814  -0.650  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.220  -1.264  -0.878  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.096  -0.629  -0.335  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.843  -1.134  -0.586  1.00  0.00           C  
HETATM   22  C19 UNL     1       3.384   0.885  -0.090  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.523   3.326  -0.127  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.976   2.897   0.833  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.419   2.906   1.674  1.00  0.00           H  
HETATM   26  H4  UNL     1       6.585   0.636   0.894  1.00  0.00           H  
HETATM   27  H5  UNL     1       6.159  -1.773   0.364  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.918  -2.420  -0.455  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.792  -0.780  -2.627  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.316  -2.465  -2.045  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.479  -1.332  -2.796  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.024   1.124   1.207  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.284   1.977   1.627  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.685   1.812   1.312  1.00  0.00           H  
HETATM   35  H13 UNL     1      -7.641   0.689   0.352  1.00  0.00           H  
HETATM   36  H14 UNL     1      -7.377  -1.313  -1.077  1.00  0.00           H  
HETATM   37  H15 UNL     1      -5.102  -2.151  -1.508  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.709  -2.008  -1.208  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.592   1.613  -0.223  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   22
CONECT    3    4   26
CONECT    4    5    5   27
CONECT    5    6   28
CONECT    6    7   22   22
CONECT    7    8    9
CONECT    8   29   30   31
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   13   21
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16   20
CONECT   16   17   17   34
CONECT   17   18   35
CONECT   18   19   19   36
CONECT   19   20   37
CONECT   20   21   21
CONECT   21   38
CONECT   22   39
END

HMDB0005005
     RDKit          3D
Tolnaftate
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.9073    2.7031    0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    1.2696    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6144    0.3299    0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4121   -1.0196    0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.4109   -0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1700   -0.4652   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.8438   -0.8129 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5905   -1.3641   -2.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466   -0.7123    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -0.1227    1.5977 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5053   -1.0658   -0.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7138   -0.4995   -0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8928    0.6118    0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691    1.0841    0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    0.4842    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586    0.9404    0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6723    0.2983    0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4984   -0.8137   -0.6496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2201   -1.2638   -0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -0.6295   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431   -1.1340   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841    0.8850   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5226    3.3258   -0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9764    2.8972    0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192    2.9058    1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5848    0.6359    0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1588   -1.7728    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9181   -2.4196   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -0.7801   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -2.4648   -2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -1.3322   -2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241    1.1240    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842    1.9770    1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6855    1.8118    1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6413    0.6886    0.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3766   -1.3126   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1024   -2.1513   -1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7085   -2.0075   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924    1.6134   -0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  6 22  2  0
 22  2  1  0
 21 12  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 22 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate	ChEBI
m,N-Dimethylthiocarbanilic acid O-2-naphthyl ester	ChEBI
Methyl (3-methylphenyl)carbamothioic acid O-2-naphthalenyl ester	ChEBI
N-Methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide	ChEBI
O-2-Naphthyl m,N-dimethylthiocarbanilate	ChEBI
Separin	ChEBI
Tinactin	ChEBI
Tolnaftato	ChEBI
Tolnaftatum	ChEBI
Tolnaphthate	ChEBI
2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamic acid	Generator
m,N-Dimethylthiocarbanilate O-2-naphthyl ester	Generator
Methyl (3-methylphenyl)carbamothioate O-2-naphthalenyl ester	Generator
O-2-Naphthyl m,N-dimethylthiocarbanilic acid	Generator
Tolnaphthic acid	Generator
Tolnaftic acid	Generator
Aftate	HMDB, MeSH
Aftate for athlete's foot gel	HMDB
Aftate for jock itch aerosol spray powder	HMDB
Aftate for jock itch gel	HMDB
Aftate for jock itch sprinkle powder	HMDB
Chinofungin	HMDB, MeSH
Dermoxin	HMDB
Dr. scholl's athlete's foot spray	HMDB
Dungistop	HMDB
Focusan	HMDB
Fungistop	HMDB
Genaspore cream	HMDB
Hi-alarzin	HMDB
Hi-alazin	HMDB
Naphthiomate T	HMDB
Naphthiomate-T	HMDB
NP-27 Cream	HMDB
NP-27 Powder	HMDB
NP-27 Solution	HMDB
NP-27 Spray powder	HMDB
Phytoderm	HMDB
Pitrex	HMDB
Pitrex cream	HMDB
Prestwick_472	HMDB
Sorgoa	HMDB
Sporiline	HMDB, MeSH
Timoped	HMDB
Tinactin aerosol liquid	HMDB
Tinactin aerosol powder	HMDB
Tinactin antifungal deodorant powder aerosol	HMDB
Tinactin cream	HMDB
Tinactin jock itch aerosol powder	HMDB
Tinactin jock itch cream	HMDB
Tinactin jock itch spray powder	HMDB
Tinactin plus aerosol powder	HMDB
Tinactin plus powder	HMDB
Tinactin powder	HMDB
Tinactin solution	HMDB
Tinaderm	HMDB, MeSH
Tinavet	HMDB
Ting antifungal cream	HMDB
Ting antifungal powder	HMDB
Ting antifungal spray liquid	HMDB
Ting antifungal spray powder	HMDB
Ting products	HMDB
Tniaderm	HMDB
Tolsanil	HMDB
Tonoftal	HMDB, MeSH
Tritin	HMDB
Zeasorb-af	HMDB
Zeasorb-af powder	HMDB
Chinosol brand OF tolnaftate	MeSH, HMDB
Genaspor	MeSH, HMDB
Pedinol brand 2 OF tolnaftate	MeSH, HMDB
Purder N, tolnaftat	MeSH, HMDB
Tolnaftat purder N	MeSH, HMDB
Wernigerode brand OF tolnaftate	MeSH, HMDB
Bioglan brand OF tolnaftate	MeSH, HMDB
Chlorisept	MeSH, HMDB
Curatin	MeSH, HMDB
Douglas brand OF tolnaftate	MeSH, HMDB
Insight brand OF tolnaftate	MeSH, HMDB
Isdin brand OF tolnaftate	MeSH, HMDB
NP 27	MeSH, HMDB
Ony-clear	MeSH, HMDB
Pedinol brand 1 OF tolnaftate	MeSH, HMDB
Schering-plough brand 1 OF tolnaftate	MeSH, HMDB
Thompson brand OF tolnaftate	MeSH, HMDB
Tinatox	MeSH, HMDB
Tineafax	MeSH, HMDB
Zenith brand OF tolnaftate	MeSH, HMDB
Breezee	MeSH, HMDB
Essex brand OF tolnaftate	MeSH, HMDB
Schering brand OF tolnaftate	MeSH, HMDB
Stiefel brand OF tolnaftate	MeSH, HMDB
Tolnaftate douglas brand	MeSH, HMDB
ZeaSorb	MeSH, HMDB
Carter wallace brand OF tolnaftate	MeSH, HMDB
Micoisdin	MeSH, HMDB
NP-27	MeSH, HMDB
Ony clear	MeSH, HMDB
Schering-plough brand 2 OF tolnaftate	MeSH, HMDB
Ting	MeSH, HMDB
Tolnaftate schering brand	MeSH, HMDB

Chemical Formula

C₁₉H₁₇NOS

Average Molecular Weight

307.409

Monoisotopic Molecular Weight

307.103084861

IUPAC Name

N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide

Traditional Name

tolnaftate

CAS Registry Number

2398-96-1

SMILES

CN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1

InChI Identifier

InChI=1S/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3

InChI Key

FUSNMLFNXJSCDI-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
Toluene
Monocyclic benzene moiety
Thiocarbamic acid ester
Thiocarbamic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

monothiocarbamic ester (CHEBI:9620 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0005005)

Cellular substructure

Membrane (HMDB: HMDB0005005)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005005)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	111 °C	Not Available
Boiling Point	453.38 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.12 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.142 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	173.639	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000723

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00055 g/L	ALOGPS
logP	4.87	ALOGPS
logP	5.75	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	0.075	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.92 m³·mol⁻¹	ChemAxon
Polarizability	34.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	170.771	31661259
DarkChem	[M-H]-	172.799	31661259
DeepCCS	[M+H]+	170.857	30932474
DeepCCS	[M-H]-	168.499	30932474
DeepCCS	[M-2H]-	201.385	30932474
DeepCCS	[M+Na]+	176.95	30932474
AllCCS	[M+H]+	171.9	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	175.1	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	171.0	32859911
AllCCS	[M+Na-2H]-	169.8	32859911
AllCCS	[M+HCOO]-	168.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tolnaftate	CN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1	3830.8	Standard polar	33892256
Tolnaftate	CN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1	2525.4	Standard non polar	33892256
Tolnaftate	CN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1	2742.3	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 - Tolnaftate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-0900000000-79ecbdc568d82d58099c	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolnaftate 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 - Tolnaftate Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-052b-0905000000-19e117da217d372632e2	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00kb-0900000000-a065921efa544c82d972	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9600000000-19faf0e6dcd285dad8d1	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-c4dd1b126170bea2c620	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-b026e71179265a982a40	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOF	splash10-00di-0900000000-a17707ff263e82d6e00e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOF	splash10-00di-3900000000-d0563822804c2844660b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOF	splash10-006x-9700000000-a217b6444068e1406235	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOF	splash10-00kf-9200000000-dc89d8219d5ce2567f3c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate , positive-QTOF	splash10-01ot-0901000000-c6fc83b073e80d5851f5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 30V, Positive-QTOF	splash10-0002-0900000000-b026e71179265a982a40	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 15V, Positive-QTOF	splash10-0002-0900000000-c4dd1b126170bea2c620	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 90V, Positive-QTOF	splash10-00kf-9200000000-dc89d8219d5ce2567f3c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 75V, Positive-QTOF	splash10-006x-9700000000-a217b6444068e1406235	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 15V, Positive-QTOF	splash10-0a4j-0908000000-5202387eefde386bfb1a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 30V, Positive-QTOF	splash10-0002-0900000000-02d86c1363cdce6a1254	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 15V, Positive-QTOF	splash10-0a4j-0908000000-2d24973a40475e59d8cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 45V, Positive-QTOF	splash10-006t-0900000000-cc4b44219e6a91aa19ef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 60V, Positive-QTOF	splash10-00di-1900000000-b191679e9b4cb68f451f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 75V, Positive-QTOF	splash10-00dl-7900000000-07c809cbb632cbfb9a84	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 90V, Positive-QTOF	splash10-0006-9300000000-d629934791b126cd7d9b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 60V, Positive-QTOF	splash10-00di-3900000000-d0563822804c2844660b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolnaftate 45V, Positive-QTOF	splash10-00di-0900000000-a17707ff263e82d6e00e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolnaftate 10V, Negative-QTOF	splash10-0a4i-0009000000-007340f99a6e585a149c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolnaftate 20V, Negative-QTOF	splash10-0a4i-0309000000-2d03a82089f2eff29cff	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00525

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023578

KNApSAcK ID

Not Available

Chemspider ID

5309

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tolnaftate

METLIN ID

Not Available

PubChem Compound

5510

PDB ID

Not Available

ChEBI ID

9620

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1539591

References

Synthesis Reference

Ayyangar, N. R.; Wakharkar, R. D.; Deshpande, V. H.; Rai, B. An alternative method for tolnaftate. Organic Preparations and Procedures International (1990), 22(1), 128-30.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Showing metabocard for Tolnaftate (HMDB0005005)

MOL for HMDB0005005 (Tolnaftate)

3D MOL for HMDB0005005 (Tolnaftate)

3D SDF for HMDB0005005 (Tolnaftate)

3D-SDF for HMDB0005005 (Tolnaftate)

PDB for HMDB0005005 (Tolnaftate)

3D PDB for HMDB0005005 (Tolnaftate)

SMILES for HMDB0005005 (Tolnaftate)

INCHI for HMDB0005005 (Tolnaftate)

Structure for HMDB0005005 (Tolnaftate)

3D Structure for HMDB0005005 (Tolnaftate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra