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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014396

Secondary Accession Numbers

HMDB14396

Metabolite Identification

Common Name

Terconazole

Description

Terconazole is only found in individuals that have used or taken this drug. It is an anti-fungal medication, primarily used to treat vaginal fungal infections. [Wikipedia ]Terconazole may exert its antifungal activity by disrupting normal fungal cell membrane permeability. Terconazole and other triazole antifungal agents inhibit cytochrome P450 14-alpha-demethylase in susceptible fungi, which leads to the accumulation of lanosterol and other methylated sterols and a decrease in ergosterol concentration. Depletion of ergosterol in the membrane disrupts the structure and function of the fungal cell leading to a decrease or inhibition of fungal growth.

Structure

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

251
  Mrv0541 02231214332D          

 36 40  0  0  1  0            999 V2000
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    4.2672   -3.8691    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    6.3034    1.2775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0113    2.8072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4420    2.2973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695   -0.2719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558    0.5486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0014396
     RDKit          3D
Terconazole
 67 71  0  0  0  0  0  0  0  0999 V2000
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M  END

251
  Mrv0541 02231214332D          

 36 40  0  0  1  0            999 V2000
    2.8383   -1.3940    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -3.8691    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0014396

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H31Cl2N5O3/c1-19(2)31-9-11-32(12-10-31)21-4-6-22(7-5-21)34-14-23-15-35-26(36-23,16-33-18-29-17-30-33)24-8-3-20(27)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/m0/s1

> <INCHI_KEY>
BLSQLHNBWJLIBQ-OZXSUGGESA-N

> <FORMULA>
C26H31Cl2N5O3

> <MOLECULAR_WEIGHT>
532.462

> <EXACT_MASS>
531.180395297

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
56.15330616306304

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propan-2-yl)piperazine

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
5.374220876333333

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.409370512807275

> <JCHEM_POLAR_SURFACE_AREA>
64.88

> <JCHEM_REFRACTIVITY>
153.18939999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
terconazole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014396
     RDKit          3D
Terconazole
 67 71  0  0  0  0  0  0  0  0999 V2000
   -9.2668   -1.3583   -0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5949   -0.1902   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5946    0.9796   -1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3236   -0.5357    0.2897 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6183    0.5255    0.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1730    0.1551    1.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5114   -0.3519    0.0204 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0977   -0.3018   -0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3047    0.1750    0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9248    0.2325    0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2960   -0.2174   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0942   -0.1815   -0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    0.3073    0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3551    0.2004    0.2475 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6236    1.1525   -0.9027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9282    1.5273   -0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4263    0.9167    0.4269 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3175    1.6866    1.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5325    2.1738    0.7526 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7192    3.3350    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0127    3.4748   -0.2377 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6612    2.3998    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7545    1.6139    0.8039 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9432   -0.4571    0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5533   -1.5174    0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0587   -2.7806    0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0123   -3.0416   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6629   -4.6531   -0.1876 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4143   -2.0060   -0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8904   -0.7210   -0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4020    0.5138   -1.9051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2206    0.6590    1.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552   -0.7014   -1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4388   -0.7495   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2854   -0.9120   -1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5594   -1.4681   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0423   -2.3307   -0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3643   -1.2090   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0543   -1.3864   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2474    0.1101    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8442    1.9326   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4221    0.8606   -1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6697    1.1173   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6843    1.4995    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0768    0.6765    1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6945    1.0845    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1564   -0.6220    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7575    0.5337    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463    0.6258    1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.3015    1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513    1.3597    0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960   -0.8181   -0.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4898    0.6449   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9528    2.0281   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7690    2.5865    1.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5726    1.1106    2.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708    4.0810   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7229    2.1479    0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8048   -1.3657    1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7132   -3.5852    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1739   -2.2029   -1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5448   -1.0524   -2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9433   -1.1441   -2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4642   -0.2142   -1.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -1.8128   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2453   -2.2972    0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1754   -1.9412   -1.2491 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 17 32  1  0
 11 33  1  0
 33 34  2  0
  7 35  1  0
 35 36  1  0
 36  4  1  0
 34  8  1  0
 32 14  1  0
 23 19  1  0
 30 24  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  9 48  1  0
 10 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 15 53  1  0
 15 54  1  0
 18 55  1  0
 18 56  1  0
 20 57  1  0
 22 58  1  0
 25 59  1  0
 26 60  1  0
 29 61  1  0
 33 62  1  0
 34 63  1  0
 35 64  1  0
 35 65  1  0
 36 66  1  0
 36 67  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 251                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.298  -2.602   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       7.965  -7.222   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       9.506  -1.062   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.490   0.402   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.766   2.385   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      20.554   5.240   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      17.625   4.288   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       5.356  -0.508   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       5.517   1.024   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       3.080   0.506   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      20.234   3.734   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.410   6.271   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.770   3.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.945   5.795   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.965  -1.062   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.019   5.716   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.982   0.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.736   1.308   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.501  -1.538   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.160   3.812   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.965  -2.602   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.446   0.878   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.339   7.222   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.163   4.686   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.840   2.306   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.016   4.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.231   2.861   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.632  -3.372   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.299  -3.372   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.375   1.830   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.551   4.367   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.632  -4.912   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.299  -4.912   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.850  -0.828   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.965  -5.682   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.111   1.650   0.000  0.00  0.00           C+0
CONECT    1   28                                                            
CONECT    2   35                                                            
CONECT    3   15   17                                                       
CONECT    4   15   18                                                       
CONECT    5   22   27                                                       
CONECT    6   11   12   16                                                  
CONECT    7   13   14   20                                                  
CONECT    8    9   19   34                                                  
CONECT    9    8   36                                                       
CONECT   10   34   36                                                       
CONECT   11    6   13                                                       
CONECT   12    6   14                                                       
CONECT   13    7   11                                                       
CONECT   14    7   12                                                       
CONECT   15    3    4   19   21                                             
CONECT   16    6   23   24                                                  
CONECT   17    3   18   22                                                  
CONECT   18    4   17                                                       
CONECT   19    8   15                                                       
CONECT   20    7   25   26                                                  
CONECT   21   15   28   29                                                  
CONECT   22    5   17                                                       
CONECT   23   16                                                            
CONECT   24   16                                                            
CONECT   25   20   30                                                       
CONECT   26   20   31                                                       
CONECT   27    5   30   31                                                  
CONECT   28    1   21   32                                                  
CONECT   29   21   33                                                       
CONECT   30   25   27                                                       
CONECT   31   26   27                                                       
CONECT   32   28   35                                                       
CONECT   33   29   35                                                       
CONECT   34    8   10                                                       
CONECT   35    2   32   33                                                  
CONECT   36    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0014396
HETATM    1  C1  UNL     1      -9.267  -1.358  -0.885  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.595  -0.190  -0.236  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.595   0.980  -1.178  1.00  0.00           C  
HETATM    4  N1  UNL     1      -7.324  -0.536   0.290  1.00  0.00           N  
HETATM    5  C4  UNL     1      -6.618   0.525   0.916  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.173   0.155   1.178  1.00  0.00           C  
HETATM    7  N2  UNL     1      -4.511  -0.352   0.020  1.00  0.00           N  
HETATM    8  C6  UNL     1      -3.098  -0.302  -0.053  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.305   0.175   0.957  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.925   0.233   0.903  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.296  -0.217  -0.239  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.094  -0.181  -0.345  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.905   0.307   0.691  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.355   0.200   0.248  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.624   1.152  -0.903  1.00  0.00           C  
HETATM   16  O2  UNL     1       4.928   1.527  -0.688  1.00  0.00           O  
HETATM   17  C13 UNL     1       5.426   0.917   0.427  1.00  0.00           C  
HETATM   18  C14 UNL     1       6.318   1.687   1.315  1.00  0.00           C  
HETATM   19  N3  UNL     1       7.532   2.174   0.753  1.00  0.00           N  
HETATM   20  C15 UNL     1       7.719   3.335   0.098  1.00  0.00           C  
HETATM   21  N4  UNL     1       9.013   3.475  -0.238  1.00  0.00           N  
HETATM   22  C16 UNL     1       9.661   2.400   0.203  1.00  0.00           C  
HETATM   23  N5  UNL     1       8.754   1.614   0.804  1.00  0.00           N  
HETATM   24  C17 UNL     1       5.943  -0.457   0.191  1.00  0.00           C  
HETATM   25  C18 UNL     1       5.553  -1.517   0.996  1.00  0.00           C  
HETATM   26  C19 UNL     1       6.059  -2.781   0.895  1.00  0.00           C  
HETATM   27  C20 UNL     1       7.012  -3.042  -0.055  1.00  0.00           C  
HETATM   28 CL1  UNL     1       7.663  -4.653  -0.188  1.00  0.00          CL  
HETATM   29  C21 UNL     1       7.414  -2.006  -0.866  1.00  0.00           C  
HETATM   30  C22 UNL     1       6.890  -0.721  -0.755  1.00  0.00           C  
HETATM   31 CL2  UNL     1       7.402   0.514  -1.905  1.00  0.00          CL  
HETATM   32  O3  UNL     1       4.221   0.659   1.205  1.00  0.00           O  
HETATM   33  C23 UNL     1      -1.055  -0.701  -1.270  1.00  0.00           C  
HETATM   34  C24 UNL     1      -2.439  -0.749  -1.194  1.00  0.00           C  
HETATM   35  C25 UNL     1      -5.285  -0.912  -1.062  1.00  0.00           C  
HETATM   36  C26 UNL     1      -6.559  -1.468  -0.458  1.00  0.00           C  
HETATM   37  H1  UNL     1      -9.042  -2.331  -0.412  1.00  0.00           H  
HETATM   38  H2  UNL     1     -10.364  -1.209  -0.811  1.00  0.00           H  
HETATM   39  H3  UNL     1      -9.054  -1.386  -1.994  1.00  0.00           H  
HETATM   40  H4  UNL     1      -9.247   0.110   0.636  1.00  0.00           H  
HETATM   41  H5  UNL     1      -8.844   1.933  -0.628  1.00  0.00           H  
HETATM   42  H6  UNL     1      -9.422   0.861  -1.919  1.00  0.00           H  
HETATM   43  H7  UNL     1      -7.670   1.117  -1.738  1.00  0.00           H  
HETATM   44  H8  UNL     1      -6.684   1.499   0.413  1.00  0.00           H  
HETATM   45  H9  UNL     1      -7.077   0.677   1.936  1.00  0.00           H  
HETATM   46  H10 UNL     1      -4.694   1.084   1.578  1.00  0.00           H  
HETATM   47  H11 UNL     1      -5.156  -0.622   1.969  1.00  0.00           H  
HETATM   48  H12 UNL     1      -2.758   0.534   1.861  1.00  0.00           H  
HETATM   49  H13 UNL     1      -0.346   0.626   1.746  1.00  0.00           H  
HETATM   50  H14 UNL     1       1.754  -0.302   1.590  1.00  0.00           H  
HETATM   51  H15 UNL     1       1.651   1.360   0.960  1.00  0.00           H  
HETATM   52  H16 UNL     1       3.496  -0.818  -0.103  1.00  0.00           H  
HETATM   53  H17 UNL     1       3.490   0.645  -1.886  1.00  0.00           H  
HETATM   54  H18 UNL     1       2.953   2.028  -0.811  1.00  0.00           H  
HETATM   55  H19 UNL     1       5.769   2.586   1.745  1.00  0.00           H  
HETATM   56  H20 UNL     1       6.573   1.111   2.260  1.00  0.00           H  
HETATM   57  H21 UNL     1       6.971   4.081  -0.148  1.00  0.00           H  
HETATM   58  H22 UNL     1      10.723   2.148   0.123  1.00  0.00           H  
HETATM   59  H23 UNL     1       4.805  -1.366   1.774  1.00  0.00           H  
HETATM   60  H24 UNL     1       5.713  -3.585   1.560  1.00  0.00           H  
HETATM   61  H25 UNL     1       8.174  -2.203  -1.626  1.00  0.00           H  
HETATM   62  H26 UNL     1      -0.545  -1.052  -2.163  1.00  0.00           H  
HETATM   63  H27 UNL     1      -2.943  -1.144  -2.053  1.00  0.00           H  
HETATM   64  H28 UNL     1      -5.464  -0.214  -1.889  1.00  0.00           H  
HETATM   65  H29 UNL     1      -4.782  -1.813  -1.524  1.00  0.00           H  
HETATM   66  H30 UNL     1      -6.245  -2.297   0.216  1.00  0.00           H  
HETATM   67  H31 UNL     1      -7.175  -1.941  -1.249  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3    4   40
CONECT    3   41   42   43
CONECT    4    5   36
CONECT    5    6   44   45
CONECT    6    7   46   47
CONECT    7    8   35
CONECT    8    9    9   34
CONECT    9   10   48
CONECT   10   11   11   49
CONECT   11   12   33
CONECT   12   13
CONECT   13   14   50   51
CONECT   14   15   32   52
CONECT   15   16   53   54
CONECT   16   17
CONECT   17   18   24   32
CONECT   18   19   55   56
CONECT   19   20   23
CONECT   20   21   21   57
CONECT   21   22
CONECT   22   23   23   58
CONECT   24   25   25   30
CONECT   25   26   59
CONECT   26   27   27   60
CONECT   27   28   29
CONECT   29   30   30   61
CONECT   30   31
CONECT   33   34   34   62
CONECT   34   63
CONECT   35   36   64   65
CONECT   36   66   67
END

HMDB0014396
     RDKit          3D
Terconazole
 67 71  0  0  0  0  0  0  0  0999 V2000
   -9.2668   -1.3583   -0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5949   -0.1902   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5946    0.9796   -1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3236   -0.5357    0.2897 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6183    0.5255    0.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1730    0.1551    1.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5114   -0.3519    0.0204 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0977   -0.3018   -0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3047    0.1750    0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9248    0.2325    0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2960   -0.2174   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0942   -0.1815   -0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    0.3073    0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3551    0.2004    0.2475 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6236    1.1525   -0.9027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9282    1.5273   -0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4263    0.9167    0.4269 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3175    1.6866    1.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5325    2.1738    0.7526 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7192    3.3350    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0127    3.4748   -0.2377 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6612    2.3998    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7545    1.6139    0.8039 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9432   -0.4571    0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5533   -1.5174    0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0587   -2.7806    0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0123   -3.0416   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6629   -4.6531   -0.1876 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4143   -2.0060   -0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8904   -0.7210   -0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4020    0.5138   -1.9051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2206    0.6590    1.2050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552   -0.7014   -1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4388   -0.7495   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2854   -0.9120   -1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5594   -1.4681   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0423   -2.3307   -0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3643   -1.2090   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0543   -1.3864   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2474    0.1101    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8442    1.9326   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4221    0.8606   -1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6697    1.1173   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6843    1.4995    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0768    0.6765    1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6945    1.0845    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1564   -0.6220    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7575    0.5337    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463    0.6258    1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.3015    1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513    1.3597    0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960   -0.8181   -0.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4898    0.6449   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9528    2.0281   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7690    2.5865    1.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5726    1.1106    2.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708    4.0810   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7229    2.1479    0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8048   -1.3657    1.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7132   -3.5852    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1739   -2.2029   -1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5448   -1.0524   -2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9433   -1.1441   -2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4642   -0.2142   -1.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815   -1.8128   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2453   -2.2972    0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1754   -1.9412   -1.2491 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 17 32  1  0
 11 33  1  0
 33 34  2  0
  7 35  1  0
 35 36  1  0
 36  4  1  0
 34  8  1  0
 32 14  1  0
 23 19  1  0
 30 24  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  9 48  1  0
 10 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  6
 15 53  1  0
 15 54  1  0
 18 55  1  0
 18 56  1  0
 20 57  1  0
 22 58  1  0
 25 59  1  0
 26 60  1  0
 29 61  1  0
 33 62  1  0
 34 63  1  0
 35 64  1  0
 35 65  1  0
 36 66  1  0
 36 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Terazol 3	Kegg
Triaconazole	HMDB
1-(4-((2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(1-methylethyl)piperazine	HMDB
Cilag brand OF terconazole	HMDB
Janssen brand OF terconazole	HMDB
Fungistat	HMDB
Ortho brand OF terconazole	HMDB
Gyno-terazol	HMDB
Terazol	HMDB
Terconazole	MeSH

Chemical Formula

C₂₆H₃₁Cl₂N₅O₃

Average Molecular Weight

532.462

Monoisotopic Molecular Weight

531.180395297

IUPAC Name

1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propan-2-yl)piperazine

Traditional Name

terconazole

CAS Registry Number

67915-31-5

SMILES

CC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1

InChI Identifier

InChI=1S/C26H31Cl2N5O3/c1-19(2)31-9-11-32(12-10-31)21-4-6-22(7-5-21)34-14-23-15-35-26(36-23,16-33-18-29-17-30-33)24-8-3-20(27)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/m0/s1

InChI Key

BLSQLHNBWJLIBQ-OZXSUGGESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Phenylpiperazines

Alternative Parents

Substituents

Phenylpiperazine
N-arylpiperazine
Aminophenyl ether
1,3-dichlorobenzene
Phenoxy compound
Phenol ether
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aniline or substituted anilines
Alkyl aryl ether
Chlorobenzene
Halobenzene
Ketal
N-alkylpiperazine
Benzenoid
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Heteroaromatic compound
1,2,4-triazole
Azole
Meta-dioxolane
Tertiary amine
Tertiary aliphatic amine
Ether
Acetal
Azacycle
Oxacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-(4-\{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy\}phenyl)-4-isopropylpiperazine (CHEBI:82980 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014396)

Source

Exogenous

Exogenous (HMDB: HMDB0014396)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	126.3 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.012 g/L	Not Available
LogP	4.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	4.58	ALOGPS
logP	5.37	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	8.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	64.88 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	153.19 m³·mol⁻¹	ChemAxon
Polarizability	56.15 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	212.818	30932474
DeepCCS	[M-H]-	210.423	30932474
DeepCCS	[M-2H]-	243.328	30932474
DeepCCS	[M+Na]+	218.731	30932474
AllCCS	[M+H]+	223.2	32859911
AllCCS	[M+H-H2O]+	221.7	32859911
AllCCS	[M+NH4]+	224.6	32859911
AllCCS	[M+Na]+	225.0	32859911
AllCCS	[M-H]-	212.6	32859911
AllCCS	[M+Na-2H]-	213.7	32859911
AllCCS	[M+HCOO]-	215.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Terconazole	CC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1	5032.4	Standard polar	33892256
Terconazole	CC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1	3671.6	Standard non polar	33892256
Terconazole	CC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1	4286.0	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 - Terconazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9443500000-9564806da5509b610135	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Terconazole , positive-QTOF	splash10-00o0-3971230000-dd66741ee49b1efec5ef	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 10V, Positive-QTOF	splash10-001i-1031290000-ae9cf158d06c702d6779	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 20V, Positive-QTOF	splash10-006y-2030900000-107157b00d324c679eaf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 40V, Positive-QTOF	splash10-00di-9650000000-20fe5c34ac5ea92694b0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 10V, Negative-QTOF	splash10-014i-9040020000-0b48b94660b9f3ef6e8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 20V, Negative-QTOF	splash10-014i-9020000000-63022b7fa681bfa05832	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 40V, Negative-QTOF	splash10-014i-9430000000-2d5aaa4b68e19d7bf8e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 10V, Positive-QTOF	splash10-001i-0000290000-f3aef95a41e4260dde02	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 20V, Positive-QTOF	splash10-001i-0001590000-49599976d635f6aacd4b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 40V, Positive-QTOF	splash10-0c0r-5589830000-780cdd0e0d8417618e23	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 10V, Negative-QTOF	splash10-001i-2000090000-c74ac4cbd2cd12fcbaeb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 20V, Negative-QTOF	splash10-00lr-6190360000-c1e756aeed62c3137090	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terconazole 40V, Negative-QTOF	splash10-00o0-3920210000-06b53e2e06769acd7c3c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00251	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00251	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00251

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

390122

KEGG Compound ID

C08080

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Terconazole

METLIN ID

Not Available

PubChem Compound

441383

PDB ID

Not Available

ChEBI ID

82980

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 Terconazole (HMDB0014396)

MOL for HMDB0014396 (Terconazole)

3D MOL for HMDB0014396 (Terconazole)

3D SDF for HMDB0014396 (Terconazole)

3D-SDF for HMDB0014396 (Terconazole)

PDB for HMDB0014396 (Terconazole)

3D PDB for HMDB0014396 (Terconazole)

SMILES for HMDB0014396 (Terconazole)

INCHI for HMDB0014396 (Terconazole)

Structure for HMDB0014396 (Terconazole)

3D Structure for HMDB0014396 (Terconazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra