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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:05:33 UTC

Update Date

2019-07-23 07:15:19 UTC

HMDB ID

HMDB0060891

Secondary Accession Numbers

HMDB60891

Metabolite Identification

Common Name

N-Desmethylterbinafine

Description

N-Desmethylterbinafine belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. N-Desmethylterbinafine is a very strong basic compound (based on its pKa). It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. N-Desmethylterbinafine is a metabolite of terbinafine. Terbinafine hydrochloride is a synthetic allylamine antifungal from Novartis.

Structure

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

HMDB0060891
     RDKit          3D
N-Desmethylterbinafine
 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.8192   -0.8150   -0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6649    0.3977    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2212    1.6492   -0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3817    0.1193    1.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2445    0.6100    0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722    0.7570    0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    0.9228    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    0.3634   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4072    0.3549   -0.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792    0.9522   -0.3128 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322    0.6215    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499   -0.4818    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5285   -1.7773    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4169   -2.7975    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7258   -2.4876   -0.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1622   -1.2073    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4835   -0.9167   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8556    0.4070   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9752    1.4303    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6739    1.1157    0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2699   -0.1845    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8557   -1.7097   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -0.8992   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6013   -0.6882   -1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8540    2.2595    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6996    1.3383   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3303    2.3294   -0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4104   -0.2717    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246   -0.6885    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5646    1.0387    1.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0499    1.4061    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6745   -0.1383   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024    0.6392   -2.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531   -0.8027   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0749    1.5641   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0652    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224    1.3710    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999   -2.0694    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -3.8036    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4409   -3.2954   -0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1840   -1.6801   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8680    0.6458   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3384    2.4390    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846    1.9176    0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  3  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 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
 21 12  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END


  Mrv0541 07091309052D          

 21 22  0  0  0  0            999 V2000
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7322   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  8  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  3  0  0  0  0
 15  8  1  0  0  0  0
 17 10  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 18 16  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060891

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)C#C\C=C\CNCC1=CC=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N/c1-20(2,3)14-7-4-8-15-21-16-18-12-9-11-17-10-5-6-13-19(17)18/h4-6,8-13,21H,15-16H2,1-3H3/b8-4+

> <INCHI_KEY>
IZJZLXQHMWUCIC-XBXARRHUSA-N

> <FORMULA>
C20H23N

> <MOLECULAR_WEIGHT>
277.4033

> <EXACT_MASS>
277.183049741

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
33.77982797528381

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](naphthalen-1-ylmethyl)amine

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
5.144435096333334

> <ALOGPS_LOGS>
-5.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.28967830235928

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
92.7805

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](naphthalen-1-ylmethyl)amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060891
     RDKit          3D
N-Desmethylterbinafine
 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.8192   -0.8150   -0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6649    0.3977    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2212    1.6492   -0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3817    0.1193    1.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2445    0.6100    0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722    0.7570    0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    0.9228    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    0.3634   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4072    0.3549   -0.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792    0.9522   -0.3128 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322    0.6215    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499   -0.4818    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5285   -1.7773    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4169   -2.7975    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7258   -2.4876   -0.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1622   -1.2073    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4835   -0.9167   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8556    0.4070   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9752    1.4303    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6739    1.1157    0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2699   -0.1845    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8557   -1.7097   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -0.8992   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6013   -0.6882   -1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8540    2.2595    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6996    1.3383   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3303    2.3294   -0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4104   -0.2717    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246   -0.6885    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5646    1.0387    1.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0499    1.4061    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6745   -0.1383   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024    0.6392   -2.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531   -0.8027   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0749    1.5641   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0652    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224    1.3710    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999   -2.0694    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -3.8036    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4409   -3.2954   -0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1840   -1.6801   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8680    0.6458   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3384    2.4390    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846    1.9176    0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  3  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 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
 21 12  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      14.671 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.107  -7.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.567 -10.574   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       8.002  -3.080   0.000  0.00  0.00           N+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4    7    8                                                       
CONECT    5    6   10                                                       
CONECT    6    5   13                                                       
CONECT    7    4   14                                                       
CONECT    8    4   15                                                       
CONECT    9   11   12                                                       
CONECT   10    5   17                                                       
CONECT   11    9   17                                                       
CONECT   12    9   18                                                       
CONECT   13    6   19                                                       
CONECT   14    7   20                                                       
CONECT   15    8   21                                                       
CONECT   16   18   21                                                       
CONECT   17   10   11   19                                                  
CONECT   18   12   16   19                                                  
CONECT   19   13   17   18                                                  
CONECT   20    1    2    3   14                                             
CONECT   21   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0060891
HETATM    1  C1  UNL     1      -5.819  -0.815  -0.901  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.665   0.398   0.012  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.221   1.649  -0.639  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.382   0.119   1.270  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.245   0.610   0.279  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.072   0.757   0.381  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.618   0.923   0.376  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.010   0.363  -0.687  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.407   0.355  -0.998  1.00  0.00           C  
HETATM   10  N1  UNL     1       1.379   0.952  -0.313  1.00  0.00           N  
HETATM   11  C10 UNL     1       1.932   0.622   0.946  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.950  -0.482   0.591  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.528  -1.777   0.483  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.417  -2.798   0.171  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.726  -2.488  -0.031  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.162  -1.207   0.074  1.00  0.00           C  
HETATM   17  C16 UNL     1       6.483  -0.917  -0.250  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.856   0.407  -0.243  1.00  0.00           C  
HETATM   19  C18 UNL     1       5.975   1.430   0.076  1.00  0.00           C  
HETATM   20  C19 UNL     1       4.674   1.116   0.396  1.00  0.00           C  
HETATM   21  C20 UNL     1       4.270  -0.185   0.393  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.856  -1.710  -0.262  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.813  -0.899  -1.420  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.601  -0.688  -1.633  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.854   2.259   0.025  1.00  0.00           H  
HETATM   26  H5  UNL     1      -6.700   1.338  -1.562  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.330   2.329  -0.850  1.00  0.00           H  
HETATM   28  H7  UNL     1      -7.410  -0.272   0.984  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.925  -0.689   1.838  1.00  0.00           H  
HETATM   30  H9  UNL     1      -6.565   1.039   1.864  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.050   1.406   1.097  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.674  -0.138  -1.436  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.502   0.639  -2.135  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.653  -0.803  -1.144  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.075   1.564  -0.864  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.127   0.065   1.522  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.322   1.371   1.584  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.500  -2.069   0.652  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.055  -3.804   0.109  1.00  0.00           H  
HETATM   40  H19 UNL     1       5.441  -3.295  -0.292  1.00  0.00           H  
HETATM   41  H20 UNL     1       7.184  -1.680  -0.516  1.00  0.00           H  
HETATM   42  H21 UNL     1       7.868   0.646  -0.509  1.00  0.00           H  
HETATM   43  H22 UNL     1       6.338   2.439   0.062  1.00  0.00           H  
HETATM   44  H23 UNL     1       3.985   1.918   0.647  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    5
CONECT    3   25   26   27
CONECT    4   28   29   30
CONECT    5    6    6    6
CONECT    6    7
CONECT    7    8    8   31
CONECT    8    9   32
CONECT    9   10   33   34
CONECT   10   11   35
CONECT   11   12   36   37
CONECT   12   13   13   21
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   16   40
CONECT   16   17   17   21
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   43
CONECT   20   21   21   44
END

HMDB0060891
     RDKit          3D
N-Desmethylterbinafine
 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.8192   -0.8150   -0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6649    0.3977    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2212    1.6492   -0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3817    0.1193    1.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2445    0.6100    0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722    0.7570    0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    0.9228    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    0.3634   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4072    0.3549   -0.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792    0.9522   -0.3128 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322    0.6215    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499   -0.4818    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5285   -1.7773    0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4169   -2.7975    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7258   -2.4876   -0.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1622   -1.2073    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4835   -0.9167   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8556    0.4070   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9752    1.4303    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6739    1.1157    0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2699   -0.1845    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8557   -1.7097   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -0.8992   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6013   -0.6882   -1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8540    2.2595    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6996    1.3383   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3303    2.3294   -0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4104   -0.2717    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246   -0.6885    1.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5646    1.0387    1.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0499    1.4061    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6745   -0.1383   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024    0.6392   -2.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531   -0.8027   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0749    1.5641   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0652    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224    1.3710    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999   -2.0694    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -3.8036    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4409   -3.2954   -0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1840   -1.6801   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8680    0.6458   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3384    2.4390    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9846    1.9176    0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  3  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 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
 21 12  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Desmethylterbinafine, (e)-isomer	HMDB
Desmethylterbinafine hydrochloride, (e)-isomer	HMDB
Desmethylterbinafine	MeSH

Chemical Formula

C₂₀H₂₃N

Average Molecular Weight

277.4033

Monoisotopic Molecular Weight

277.183049741

IUPAC Name

[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](naphthalen-1-ylmethyl)amine

Traditional Name

[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](naphthalen-1-ylmethyl)amine

CAS Registry Number

Not Available

SMILES

CC(C)(C)C#C\C=C\CNCC1=CC=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C20H23N/c1-20(2,3)14-7-4-8-15-21-16-18-12-9-11-17-10-5-6-13-19(17)18/h4-6,8-13,21H,15-16H2,1-3H3/b8-4+

InChI Key

IZJZLXQHMWUCIC-XBXARRHUSA-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
Aralkylamine
Secondary amine
Secondary aliphatic 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 (HMDB: HMDB0060891)

Organ

Kidney (HMDB: HMDB0060891)
Liver (HMDB: HMDB0060891)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060891)

Cellular substructure

Cytoplasm (HMDB: HMDB0060891)
Membrane (HMDB: HMDB0060891)

Source

Endogenous

Endogenous (HMDB: HMDB0060891)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00071 g/L	ALOGPS
logP	5.5	ALOGPS
logP	5.14	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	9.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	92.78 m³·mol⁻¹	ChemAxon
Polarizability	33.78 Å³	ChemAxon
Number of Rings	2	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]+	172.44	31661259
DarkChem	[M-H]-	173.475	31661259
DeepCCS	[M-2H]-	196.886	30932474
DeepCCS	[M+Na]+	172.452	30932474
AllCCS	[M+H]+	167.8	32859911
AllCCS	[M+H-H2O]+	164.5	32859911
AllCCS	[M+NH4]+	170.9	32859911
AllCCS	[M+Na]+	171.8	32859911
AllCCS	[M-H]-	176.2	32859911
AllCCS	[M+Na-2H]-	175.8	32859911
AllCCS	[M+HCOO]-	175.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.1 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9853 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.77 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2063.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	392.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	210.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	215.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	124.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	729.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	593.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1236.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	615.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1646.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	401.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	276.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	289.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethylterbinafine	CC(C)(C)C#C\C=C\CNCC1=CC=CC2=CC=CC=C12	3163.1	Standard polar	33892256
N-Desmethylterbinafine	CC(C)(C)C#C\C=C\CNCC1=CC=CC2=CC=CC=C12	2384.9	Standard non polar	33892256
N-Desmethylterbinafine	CC(C)(C)C#C\C=C\CNCC1=CC=CC2=CC=CC=C12	2327.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethylterbinafine,1TMS,isomer #1	CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C	2318.0	Semi standard non polar	33892256
N-Desmethylterbinafine,1TMS,isomer #1	CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C	2495.1	Standard non polar	33892256
N-Desmethylterbinafine,1TMS,isomer #1	CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C	3190.2	Standard polar	33892256
N-Desmethylterbinafine,1TBDMS,isomer #1	CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2556.2	Semi standard non polar	33892256
N-Desmethylterbinafine,1TBDMS,isomer #1	CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2682.7	Standard non polar	33892256
N-Desmethylterbinafine,1TBDMS,isomer #1	CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3260.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylterbinafine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-1930000000-cd75c3521c488cd06441	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylterbinafine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 10V, Positive-QTOF	splash10-004l-0790000000-48cf9a06ce59d2b5cec9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 20V, Positive-QTOF	splash10-0006-0910000000-7dd31856f24ef0b93957	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 40V, Positive-QTOF	splash10-0006-2900000000-8576e3e9be6070199004	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 10V, Negative-QTOF	splash10-004i-0190000000-a2cc4270b6d348b87c9c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 20V, Negative-QTOF	splash10-056r-0980000000-d7b29ca9e90d2e10614a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 40V, Negative-QTOF	splash10-056r-0900000000-b30cc7379173d05ec4fd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 10V, Positive-QTOF	splash10-0006-0930000000-f6db78b9e73cd09bed17	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 20V, Positive-QTOF	splash10-004i-3940000000-8d1d265c93e478ef1ef6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 40V, Positive-QTOF	splash10-0006-5900000000-d4a57ea4dff3a9f5ef36	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 10V, Negative-QTOF	splash10-004i-0090000000-c524df0015f139e69d14	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 20V, Negative-QTOF	splash10-004i-0690000000-d35bfcf98df5aa8e7567	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylterbinafine 40V, Negative-QTOF	splash10-0fbc-0910000000-6f3bd0a35275de042a7a	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443233

PDB ID

Not Available

ChEBI ID

Not Available

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

Showing metabocard for N-Desmethylterbinafine (HMDB0060891)

MOL for HMDB0060891 (N-Desmethylterbinafine)

3D MOL for HMDB0060891 (N-Desmethylterbinafine)

3D SDF for HMDB0060891 (N-Desmethylterbinafine)

3D-SDF for HMDB0060891 (N-Desmethylterbinafine)

PDB for HMDB0060891 (N-Desmethylterbinafine)

3D PDB for HMDB0060891 (N-Desmethylterbinafine)

SMILES for HMDB0060891 (N-Desmethylterbinafine)

INCHI for HMDB0060891 (N-Desmethylterbinafine)

Structure for HMDB0060891 (N-Desmethylterbinafine)

3D Structure for HMDB0060891 (N-Desmethylterbinafine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra