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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:05:30 UTC

Update Date

2019-07-23 07:15:19 UTC

HMDB ID

HMDB0060890

Secondary Accession Numbers

HMDB60890

Metabolite Identification

Common Name

Hydroxyterbinafine

Description

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

Structure

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

HMDB0060890
     RDKit          3D
Hydroxyterbinafine
 48 49  0  0  0  0  0  0  0  0999 V2000
    0.9562   -2.0449   -0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -0.6886   -0.5346 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049   -0.2784    0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -0.3205    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.7442    0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588    0.5849    0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5410    0.4349    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9826    0.2326   -0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2890    0.3091   -1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642   -1.1586    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7851    1.2538    0.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4793    2.5498    0.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034    0.0386   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513   -0.4066   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -1.4583    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7782   -1.7766    1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9392   -1.0956    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8339   -0.0341    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9808    0.6842   -0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8353    1.7324   -1.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6429    2.0850   -1.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107    1.3708   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148    0.2996   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544   -2.3475   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6950   -2.7810   -0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767   -2.1304   -1.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657    0.8028    0.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5965   -0.7966    1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226   -1.2706    0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727    1.6901    0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2466    1.3186   -1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5852   -0.3314   -2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3360   -0.0966   -1.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4486   -1.3036    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0829   -1.2574    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7601   -1.9123   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8566    1.0451    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4059    1.1591    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5083    2.7005    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0617    1.1140   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3506    0.0102   -1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551   -2.0224    0.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8603   -2.6182    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9170   -1.3531    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9545    0.4328    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7137    2.3287   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227    2.9132   -2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5604    1.6484   -1.8630 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  0
  5  6  1  0
  6  7  3  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
  2 13  1  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 22  1  0
 22 23  2  0
 23 14  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
M  END

  Mrv0541 07091309052D          

 23 24  0  0  0  0            999 V2000
    6.7322   -5.6645    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
    5.0013   -1.2375    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
    7.8592   -5.3625    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
    8.5737   -4.9500    0.0000 O   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
 18 10  2  0  0  0  0
 18 11  1  0  0  0  0
 19 12  2  0  0  0  0
 19 16  1  0  0  0  0
 20 13  2  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 14  1  0  0  0  0
 21 17  1  0  0  0  0
 22  3  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060890

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C\C=C\C#CC(C)(C)CO)CC1=CC=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H25NO/c1-21(2,17-23)14-7-4-8-15-22(3)16-19-12-9-11-18-10-5-6-13-20(18)19/h4-6,8-13,23H,15-17H2,1-3H3/b8-4+

> <INCHI_KEY>
GPEJUKJZTGFNKY-XBXARRHUSA-N

> <FORMULA>
C21H25NO

> <MOLECULAR_WEIGHT>
307.4293

> <EXACT_MASS>
307.193614427

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.55677429146043

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-ol

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
4.246711876999999

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.145563242865748

> <JCHEM_PKA_STRONGEST_BASIC>
8.941442242579678

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
99.84989999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060890
     RDKit          3D
Hydroxyterbinafine
 48 49  0  0  0  0  0  0  0  0999 V2000
    0.9562   -2.0449   -0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -0.6886   -0.5346 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049   -0.2784    0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -0.3205    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.7442    0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588    0.5849    0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5410    0.4349    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9826    0.2326   -0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2890    0.3091   -1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642   -1.1586    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7851    1.2538    0.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4793    2.5498    0.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034    0.0386   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513   -0.4066   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -1.4583    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7782   -1.7766    1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9392   -1.0956    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8339   -0.0341    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9808    0.6842   -0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8353    1.7324   -1.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6429    2.0850   -1.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107    1.3708   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148    0.2996   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544   -2.3475   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6950   -2.7810   -0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767   -2.1304   -1.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657    0.8028    0.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5965   -0.7966    1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226   -1.2706    0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727    1.6901    0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2466    1.3186   -1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5852   -0.3314   -2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3360   -0.0966   -1.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4486   -1.3036    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0829   -1.2574    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7601   -1.9123   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8566    1.0451    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4059    1.1591    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5083    2.7005    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0617    1.1140   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3506    0.0102   -1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551   -2.0224    0.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8603   -2.6182    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9170   -1.3531    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9545    0.4328    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7137    2.3287   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227    2.9132   -2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5604    1.6484   -1.8630 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  0
  5  6  1  0
  6  7  3  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
  2 13  1  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 22  1  0
 22 23  2  0
 23 14  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  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      12.567 -10.574   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       9.336  -2.310   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      14.671 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       8.002  -3.080   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
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   18                                                       
CONECT   11    9   18                                                       
CONECT   12    9   19                                                       
CONECT   13    6   20                                                       
CONECT   14    7   21                                                       
CONECT   15    8   22                                                       
CONECT   16   19   22                                                       
CONECT   17   21   23                                                       
CONECT   18   10   11   20                                                  
CONECT   19   12   16   20                                                  
CONECT   20   13   18   19                                                  
CONECT   21    1    2   14   17                                             
CONECT   22    3   15   16                                                  
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0060890
HETATM    1  C1  UNL     1       0.956  -2.045  -0.914  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.032  -0.689  -0.535  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.305  -0.278   0.614  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.161  -0.321   0.405  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.931   0.744   0.505  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.359   0.585   0.279  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.541   0.435   0.107  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.983   0.233  -0.082  1.00  0.00           C  
HETATM    9  C8  UNL     1      -6.289   0.309  -1.541  1.00  0.00           C  
HETATM   10  C9  UNL     1      -6.364  -1.159   0.405  1.00  0.00           C  
HETATM   11  C10 UNL     1      -6.785   1.254   0.710  1.00  0.00           C  
HETATM   12  O1  UNL     1      -6.479   2.550   0.308  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.203   0.039  -0.846  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.451  -0.407  -0.222  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.550  -1.458   0.651  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.778  -1.777   1.180  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.939  -1.096   0.886  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.834  -0.034   0.003  1.00  0.00           C  
HETATM   19  C17 UNL     1       6.981   0.684  -0.325  1.00  0.00           C  
HETATM   20  C18 UNL     1       6.835   1.732  -1.206  1.00  0.00           C  
HETATM   21  C19 UNL     1       5.643   2.085  -1.756  1.00  0.00           C  
HETATM   22  C20 UNL     1       4.511   1.371  -1.428  1.00  0.00           C  
HETATM   23  C21 UNL     1       4.615   0.300  -0.537  1.00  0.00           C  
HETATM   24  H1  UNL     1       1.954  -2.348  -1.334  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.695  -2.781  -0.150  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.177  -2.130  -1.710  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.566   0.803   0.796  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.596  -0.797   1.550  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.623  -1.271   0.159  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.473   1.690   0.748  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.247   1.319  -1.983  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.585  -0.331  -2.101  1.00  0.00           H  
HETATM   33  H10 UNL     1      -7.336  -0.097  -1.668  1.00  0.00           H  
HETATM   34  H11 UNL     1      -7.449  -1.304   0.321  1.00  0.00           H  
HETATM   35  H12 UNL     1      -6.083  -1.257   1.481  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.760  -1.912  -0.134  1.00  0.00           H  
HETATM   37  H14 UNL     1      -7.857   1.045   0.664  1.00  0.00           H  
HETATM   38  H15 UNL     1      -6.406   1.159   1.769  1.00  0.00           H  
HETATM   39  H16 UNL     1      -5.508   2.701   0.250  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.062   1.114  -0.526  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.351   0.010  -1.949  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.655  -2.022   0.917  1.00  0.00           H  
HETATM   43  H20 UNL     1       4.860  -2.618   1.878  1.00  0.00           H  
HETATM   44  H21 UNL     1       6.917  -1.353   1.310  1.00  0.00           H  
HETATM   45  H22 UNL     1       7.955   0.433   0.097  1.00  0.00           H  
HETATM   46  H23 UNL     1       7.714   2.329  -1.495  1.00  0.00           H  
HETATM   47  H24 UNL     1       5.523   2.913  -2.454  1.00  0.00           H  
HETATM   48  H25 UNL     1       3.560   1.648  -1.863  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   13
CONECT    3    4   27   28
CONECT    4    5    5   29
CONECT    5    6   30
CONECT    6    7    7    7
CONECT    7    8
CONECT    8    9   10   11
CONECT    9   31   32   33
CONECT   10   34   35   36
CONECT   11   12   37   38
CONECT   12   39
CONECT   13   14   40   41
CONECT   14   15   15   23
CONECT   15   16   42
CONECT   16   17   17   43
CONECT   17   18   44
CONECT   18   19   19   23
CONECT   19   20   45
CONECT   20   21   21   46
CONECT   21   22   47
CONECT   22   23   23   48
END

HMDB0060890
     RDKit          3D
Hydroxyterbinafine
 48 49  0  0  0  0  0  0  0  0999 V2000
    0.9562   -2.0449   -0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -0.6886   -0.5346 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049   -0.2784    0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -0.3205    0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.7442    0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588    0.5849    0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5410    0.4349    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9826    0.2326   -0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2890    0.3091   -1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642   -1.1586    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7851    1.2538    0.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4793    2.5498    0.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034    0.0386   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513   -0.4066   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -1.4583    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7782   -1.7766    1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9392   -1.0956    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8339   -0.0341    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9808    0.6842   -0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8353    1.7324   -1.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6429    2.0850   -1.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107    1.3708   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148    0.2996   -0.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9544   -2.3475   -1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6950   -2.7810   -0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767   -2.1304   -1.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657    0.8028    0.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5965   -0.7966    1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226   -1.2706    0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727    1.6901    0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2466    1.3186   -1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5852   -0.3314   -2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3360   -0.0966   -1.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4486   -1.3036    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0829   -1.2574    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7601   -1.9123   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8566    1.0451    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4059    1.1591    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5083    2.7005    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0617    1.1140   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3506    0.0102   -1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551   -2.0224    0.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8603   -2.6182    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9170   -1.3531    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9545    0.4328    0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7137    2.3287   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227    2.9132   -2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5604    1.6484   -1.8630 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  0
  5  6  1  0
  6  7  3  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
  2 13  1  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 22  1  0
 22 23  2  0
 23 14  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₂₅NO

Average Molecular Weight

307.4293

Monoisotopic Molecular Weight

307.193614427

IUPAC Name

(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-ol

Traditional Name

(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-ol

CAS Registry Number

Not Available

SMILES

CN(C\C=C\C#CC(C)(C)CO)CC1=CC=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C21H25NO/c1-21(2,17-23)14-7-4-8-15-22(3)16-19-12-9-11-18-10-5-6-13-20(18)19/h4-6,8-13,23H,15-17H2,1-3H3/b8-4+

InChI Key

GPEJUKJZTGFNKY-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
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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: HMDB0060890)

Organ

Kidney (HMDB: HMDB0060890)
Liver (HMDB: HMDB0060890)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060890)

Cellular substructure

Cytoplasm (HMDB: HMDB0060890)
Membrane (HMDB: HMDB0060890)

Source

Endogenous

Endogenous (HMDB: HMDB0060890)

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	0.0023 g/L	ALOGPS
logP	4.86	ALOGPS
logP	4.25	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	17.15	ChemAxon
pKa (Strongest Basic)	8.94	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	99.85 m³·mol⁻¹	ChemAxon
Polarizability	36.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	176.991	31661259
DarkChem	[M-H]-	178.179	31661259
DeepCCS	[M-2H]-	199.909	30932474
DeepCCS	[M+Na]+	175.475	30932474
AllCCS	[M+H]+	176.8	32859911
AllCCS	[M+H-H2O]+	173.8	32859911
AllCCS	[M+NH4]+	179.7	32859911
AllCCS	[M+Na]+	180.5	32859911
AllCCS	[M-H]-	183.4	32859911
AllCCS	[M+Na-2H]-	183.3	32859911
AllCCS	[M+HCOO]-	183.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyterbinafine	CN(C\C=C\C#CC(C)(C)CO)CC1=CC=CC2=CC=CC=C12	3455.3	Standard polar	33892256
Hydroxyterbinafine	CN(C\C=C\C#CC(C)(C)CO)CC1=CC=CC2=CC=CC=C12	2545.8	Standard non polar	33892256
Hydroxyterbinafine	CN(C\C=C\C#CC(C)(C)CO)CC1=CC=CC2=CC=CC=C12	2494.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyterbinafine,1TMS,isomer #1	CN(C/C=C/C#CC(C)(C)CO[Si](C)(C)C)CC1=CC=CC2=CC=CC=C12	2499.1	Semi standard non polar	33892256
Hydroxyterbinafine,1TBDMS,isomer #1	CN(C/C=C/C#CC(C)(C)CO[Si](C)(C)C(C)(C)C)CC1=CC=CC2=CC=CC=C12	2737.0	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 - Hydroxyterbinafine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1930000000-1741131965fab9d0957d	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyterbinafine GC-MS (1 TMS) - 70eV, Positive	splash10-0006-4922000000-266e34d164a29c1768c7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyterbinafine 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 - Hydroxyterbinafine 10V, Positive-QTOF	splash10-052f-0689000000-5468bac84ff7c453b8aa	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 20V, Positive-QTOF	splash10-0006-1930000000-baba1f28622d10c533d5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 40V, Positive-QTOF	splash10-0006-2900000000-66e9152abfdc6560824a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 10V, Negative-QTOF	splash10-0a4i-0029000000-449a34723f4c945f15cf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 20V, Negative-QTOF	splash10-0adi-0796000000-05ed2fd15959c6ab3efd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 40V, Negative-QTOF	splash10-00fr-3900000000-c3e4bb0a920ce1a8057f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 10V, Positive-QTOF	splash10-0a4l-0619000000-58c776e9dc0774bb5e16	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 20V, Positive-QTOF	splash10-0006-0900000000-8e891456994f6e90397f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 40V, Positive-QTOF	splash10-0006-4900000000-66b8c641ee1a71484002	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 10V, Negative-QTOF	splash10-0a4i-0009000000-362958de4b63235619b6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 20V, Negative-QTOF	splash10-05dl-0954000000-09cc8da3daf481b64610	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyterbinafine 40V, Negative-QTOF	splash10-01r6-5921000000-b57a6384c56b450b70f1	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

21917706

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 Hydroxyterbinafine (HMDB0060890)

MOL for HMDB0060890 (Hydroxyterbinafine)

3D MOL for HMDB0060890 (Hydroxyterbinafine)

3D SDF for HMDB0060890 (Hydroxyterbinafine)

3D-SDF for HMDB0060890 (Hydroxyterbinafine)

PDB for HMDB0060890 (Hydroxyterbinafine)

3D PDB for HMDB0060890 (Hydroxyterbinafine)

SMILES for HMDB0060890 (Hydroxyterbinafine)

INCHI for HMDB0060890 (Hydroxyterbinafine)

Structure for HMDB0060890 (Hydroxyterbinafine)

3D Structure for HMDB0060890 (Hydroxyterbinafine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra