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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014777

Secondary Accession Numbers

HMDB14777

Metabolite Identification

Common Name

Butoconazole

Description

Butoconazole is only found in individuals that have used or taken this drug. It is an imidazole antifungal used in gynecology.The exact mechanism of the antifungal action of butoconazole is unknown, however, it is presumed to function as other imidazole derivatives via inhibition of steroid synthesis. Imidazoles generally inhibit the conversion of lanosterol to ergosterol via the inhibition of the enzyme cytochrome P450 14α-demethylase, resulting in a change in fungal cell membrane lipid composition. This structural change alters cell permeability and, ultimately, results in the osmotic disruption or growth inhibition of the fungal cell.

Structure

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

HMDB0014777
     RDKit          3D
Butoconazole
 42 44  0  0  0  0  0  0  0  0999 V2000
    6.0955   -3.9793   -0.0386 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8931   -2.7124    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -1.7484   -0.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856   -0.7487   -0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9283   -0.7063    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8749    0.3650    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5898   -0.0761   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4302    1.0196   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    2.2923   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662    3.3363   -0.6459 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    4.2255    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422    5.0364    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042    4.6470   -1.0201 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9776    3.5961   -1.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9431    0.4969   -1.0033 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6870   -0.9068   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6051   -0.7675    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0393    0.8435    1.3466 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089   -1.8372    1.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8738   -3.1032    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639   -3.2586   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3655   -2.1707   -0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -2.4916   -1.9574 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0862   -1.6815    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0322   -2.6784    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.7668   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6846    0.0041   -1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    1.2238   -0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    0.5256    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2358   -1.0182    0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087   -0.2678   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    1.2159    0.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2465    2.1718   -1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    2.7138   -0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    4.2632    1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4533    5.8365    0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    3.1061   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9217   -1.7029    2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3577   -3.9361    1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108   -4.2589   -0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252   -1.6625    2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489   -3.4396    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  5 24  1  0
 24 25  2  0
 25  2  1  0
 14 10  1  0
 22 16  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 24 41  1  0
 25 42  1  0
M  END

639
  Mrv0541 02231214512D          

 25 27  0  0  1  0            999 V2000
    4.5080   -0.9085    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.9085    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.3210    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.0835    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.5665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012    2.5585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2616    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942    2.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    1.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4  7  1  0  0  0  0
  4 12  1  0  0  0  0
  5  9  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 14  2  0  0  0  0
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 20  2  0  0  0  0
 12 21  1  0  0  0  0
 13 17  2  0  0  0  0
 15 18  1  0  0  0  0
 16 19  2  0  0  0  0
 18 22  2  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  2  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014777

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2

> <INCHI_KEY>
SWLMUYACZKCSHZ-UHFFFAOYSA-N

> <FORMULA>
C19H17Cl3N2S

> <MOLECULAR_WEIGHT>
411.776

> <EXACT_MASS>
410.017802365

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
41.00664949220142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-imidazole

> <ALOGPS_LOGP>
6.70

> <JCHEM_LOGP>
6.552484297333333

> <ALOGPS_LOGS>
-5.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.7811216992495575

> <JCHEM_POLAR_SURFACE_AREA>
17.82

> <JCHEM_REFRACTIVITY>
108.986

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.18e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butoconazole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014777
     RDKit          3D
Butoconazole
 42 44  0  0  0  0  0  0  0  0999 V2000
    6.0955   -3.9793   -0.0386 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8931   -2.7124    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -1.7484   -0.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856   -0.7487   -0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9283   -0.7063    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8749    0.3650    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5898   -0.0761   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4302    1.0196   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    2.2923   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662    3.3363   -0.6459 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    4.2255    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422    5.0364    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042    4.6470   -1.0201 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9776    3.5961   -1.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9431    0.4969   -1.0033 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6870   -0.9068   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6051   -0.7675    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0393    0.8435    1.3466 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089   -1.8372    1.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8738   -3.1032    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639   -3.2586   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3655   -2.1707   -0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -2.4916   -1.9574 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0862   -1.6815    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0322   -2.6784    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.7668   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6846    0.0041   -1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    1.2238   -0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    0.5256    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2358   -1.0182    0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087   -0.2678   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    1.2159    0.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2465    2.1718   -1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    2.7138   -0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    4.2632    1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4533    5.8365    0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    3.1061   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9217   -1.7029    2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3577   -3.9361    1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108   -4.2589   -0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252   -1.6625    2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489   -3.4396    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  5 24  1  0
 24 25  2  0
 25  2  1  0
 14 10  1  0
 22 16  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 24 41  1  0
 25 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 639                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.415  -1.696   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       3.080  -1.696   0.000  0.00  0.00          Cl+0
HETATM    3 Cl   UNK     0      15.083  -2.466   0.000  0.00  0.00          Cl+0
HETATM    4  S   UNK     0       5.748  -0.156   0.000  0.00  0.00           S+0
HETATM    5  N   UNK     0       8.415   2.924   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      10.082   4.776   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081   0.614   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -0.156   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   2.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   0.614   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082  -0.156   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -1.696   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.822   2.298   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.576   4.456   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.416   0.614   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082  -1.696   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.852   3.442   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.750  -0.156   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.416  -2.466   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081  -2.466   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -2.466   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.750  -1.696   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081  -4.006   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -4.006   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.748  -4.776   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    7   12                                                       
CONECT    5    9   13   14                                                  
CONECT    6   14   17                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    5    7                                                       
CONECT   10    8   11                                                       
CONECT   11   10   15   16                                                  
CONECT   12    4   20   21                                                  
CONECT   13    5   17                                                       
CONECT   14    5    6                                                       
CONECT   15   11   18                                                       
CONECT   16   11   19                                                       
CONECT   17    6   13                                                       
CONECT   18   15   22                                                       
CONECT   19   16   22                                                       
CONECT   20    1   12   23                                                  
CONECT   21    2   12   24                                                  
CONECT   22    3   18   19                                                  
CONECT   23   20   25                                                       
CONECT   24   21   25                                                       
CONECT   25   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0014777
HETATM    1 CL1  UNL     1       6.096  -3.979  -0.039  1.00  0.00          CL  
HETATM    2  C1  UNL     1       4.893  -2.712   0.039  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.755  -1.748  -0.930  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.786  -0.749  -0.841  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.928  -0.706   0.241  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.875   0.365   0.352  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.590  -0.076  -0.299  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.430   1.020  -0.147  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.033   2.292  -0.797  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.966   3.336  -0.646  1.00  0.00           N  
HETATM   11  C9  UNL     1      -1.075   4.225   0.352  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.142   5.036   0.130  1.00  0.00           C  
HETATM   13  N2  UNL     1      -2.704   4.647  -1.020  1.00  0.00           N  
HETATM   14  C11 UNL     1      -1.978   3.596  -1.500  1.00  0.00           C  
HETATM   15  S1  UNL     1      -1.943   0.497  -1.003  1.00  0.00           S  
HETATM   16  C12 UNL     1      -2.687  -0.907  -0.238  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.605  -0.767   0.785  1.00  0.00           C  
HETATM   18 CL2  UNL     1      -4.039   0.843   1.347  1.00  0.00          CL  
HETATM   19  C14 UNL     1      -4.209  -1.837   1.400  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.874  -3.103   0.967  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.964  -3.259  -0.048  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.365  -2.171  -0.657  1.00  0.00           C  
HETATM   23 CL3  UNL     1      -1.219  -2.492  -1.957  1.00  0.00          CL  
HETATM   24  C18 UNL     1       3.086  -1.681   1.197  1.00  0.00           C  
HETATM   25  C19 UNL     1       4.032  -2.678   1.137  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.422  -1.767  -1.790  1.00  0.00           H  
HETATM   27  H2  UNL     1       3.685   0.004  -1.605  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.294   1.224  -0.189  1.00  0.00           H  
HETATM   29  H4  UNL     1       1.704   0.526   1.430  1.00  0.00           H  
HETATM   30  H5  UNL     1       0.236  -1.018   0.181  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.709  -0.268  -1.384  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.636   1.216   0.925  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.247   2.172  -1.862  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.958   2.714  -0.311  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.386   4.263   1.205  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.453   5.837   0.778  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.235   3.106  -2.422  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.922  -1.703   2.196  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.358  -3.936   1.461  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.711  -4.259  -0.378  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.425  -1.663   2.047  1.00  0.00           H  
HETATM   42  H17 UNL     1       4.149  -3.440   1.893  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   25
CONECT    3    4   26
CONECT    4    5    5   27
CONECT    5    6   24
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   15   32
CONECT    9   10   33   34
CONECT   10   11   14
CONECT   11   12   12   35
CONECT   12   13   36
CONECT   13   14   14
CONECT   14   37
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   19
CONECT   19   20   20   38
CONECT   20   21   39
CONECT   21   22   22   40
CONECT   22   23
CONECT   24   25   25   41
CONECT   25   42
END

HMDB0014777
     RDKit          3D
Butoconazole
 42 44  0  0  0  0  0  0  0  0999 V2000
    6.0955   -3.9793   -0.0386 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8931   -2.7124    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -1.7484   -0.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856   -0.7487   -0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9283   -0.7063    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8749    0.3650    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5898   -0.0761   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4302    1.0196   -0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    2.2923   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662    3.3363   -0.6459 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    4.2255    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422    5.0364    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042    4.6470   -1.0201 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9776    3.5961   -1.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9431    0.4969   -1.0033 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6870   -0.9068   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6051   -0.7675    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0393    0.8435    1.3466 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089   -1.8372    1.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8738   -3.1032    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639   -3.2586   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3655   -2.1707   -0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -2.4916   -1.9574 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0862   -1.6815    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0322   -2.6784    1.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.7668   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6846    0.0041   -1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    1.2238   -0.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    0.5256    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2358   -1.0182    0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087   -0.2678   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    1.2159    0.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2465    2.1718   -1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    2.7138   -0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    4.2632    1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4533    5.8365    0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    3.1061   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9217   -1.7029    2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3577   -3.9361    1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108   -4.2589   -0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252   -1.6625    2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489   -3.4396    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  5 24  1  0
 24 25  2  0
 25  2  1  0
 14 10  1  0
 22 16  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 24 41  1  0
 25 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulfanyl)-butyl]-1H-imidazole	ChEBI
Butoconazol	ChEBI
Butoconazolum	ChEBI
Gynofort	Kegg
1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulphanyl)-butyl]-1H-imidazole	Generator
Butoconazole nitrate	HMDB
Bayer brand 1 OF butoconazole nitrate	HMDB
Mycelex-3	HMDB
1-(4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-N-butyl)-1H-imidazole	HMDB
Bayer brand 2 OF butoconazole nitrate	HMDB
Gynomyk	HMDB
Ther-RX brand OF butoconazole nitrate	HMDB
Femstal	HMDB
Aventis brand OF butoconazole nitrate	HMDB
Femstat	HMDB
Gynazole-1	HMDB
Syntex brand OF butoconazole nitrate	HMDB
Will brand OF butoconazole nitrate	HMDB

Chemical Formula

C₁₉H₁₇Cl₃N₂S

Average Molecular Weight

411.776

Monoisotopic Molecular Weight

410.017802365

IUPAC Name

1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-imidazole

Traditional Name

butoconazole

CAS Registry Number

64872-77-1

SMILES

ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1

InChI Identifier

InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2

InChI Key

SWLMUYACZKCSHZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Aryl thioether
1,3-dichlorobenzene
Thiophenol ether
Chlorobenzene
Alkylarylthioether
Halobenzene
Aryl chloride
Aryl halide
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thioether
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organosulfur compound
Organohalogen compound
Organochloride
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

conazole antifungal drug (CHEBI:3240 )
aryl sulfide (CHEBI:3240 )
imidazoles (CHEBI:3240 )
imidazole antifungal drug (CHEBI:3240 )
dichlorobenzene (CHEBI:3240 )
monochlorobenzenes (CHEBI:3240 )

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: HMDB0014777)

Source

Exogenous

Exogenous (HMDB: HMDB0014777)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	159 °C (decomposition)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00082 g/L	Not Available
LogP	6.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	186.525	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000799

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00082 g/L	ALOGPS
logP	6.7	ALOGPS
logP	6.55	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	6.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	108.99 m³·mol⁻¹	ChemAxon
Polarizability	41.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	184.013	30932474
DeepCCS	[M-H]-	181.655	30932474
DeepCCS	[M-2H]-	215.358	30932474
DeepCCS	[M+Na]+	190.665	30932474
AllCCS	[M+H]+	188.7	32859911
AllCCS	[M+H-H2O]+	186.1	32859911
AllCCS	[M+NH4]+	191.1	32859911
AllCCS	[M+Na]+	191.8	32859911
AllCCS	[M-H]-	179.1	32859911
AllCCS	[M+Na-2H]-	178.5	32859911
AllCCS	[M+HCOO]-	178.1	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.	8.72 minutes	32390414
Predicted by Siyang on May 30, 2022	14.9574 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2360.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	408.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	186.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	242.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	292.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	629.8 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	644.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1417.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	620.6 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	1519.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	283.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	79.0 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butoconazole	ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1	4231.6	Standard polar	33892256
Butoconazole	ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1	3051.5	Standard non polar	33892256
Butoconazole	ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1	3229.4	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 - Butoconazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0059-6921000000-df9fbb2ed1919d5db32d	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butoconazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butoconazole 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 - Butoconazole 10V, Positive-QTOF	splash10-03e9-0291800000-175d20ae946894d63ff0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 20V, Positive-QTOF	splash10-02di-6966500000-99152c227089dc60fc64	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 40V, Positive-QTOF	splash10-016r-6900000000-33b44a1350666f009c48	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 10V, Negative-QTOF	splash10-0a4i-1110900000-66f5c95ad320950db5ee	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 20V, Negative-QTOF	splash10-014i-9330100000-d4e9c87c57f1a3ccac9d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 40V, Negative-QTOF	splash10-016u-7900000000-e6e65ee82f67ecda0db0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 10V, Positive-QTOF	splash10-03ec-0045900000-1fac55efca4ba6eccc60	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 20V, Positive-QTOF	splash10-03di-0212900000-f208005b553e381d5f6e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 40V, Positive-QTOF	splash10-05r0-0903000000-5bc7d62d0a3041507d6a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 10V, Negative-QTOF	splash10-0a4i-0200900000-432e3f6045e38ec2662a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 20V, Negative-QTOF	splash10-069r-9520300000-1f132112bc9ce64d1aa1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butoconazole 40V, Negative-QTOF	splash10-001i-9100000000-a40b7e0b888e3f9f6938	2021-10-11	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 DB00639	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00639	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00639

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

43192

KEGG Compound ID

C08065

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butoconazole

METLIN ID

Not Available

PubChem Compound

47472

PDB ID

Not Available

ChEBI ID

3240

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 Butoconazole (HMDB0014777)

MOL for HMDB0014777 (Butoconazole)

3D MOL for HMDB0014777 (Butoconazole)

3D SDF for HMDB0014777 (Butoconazole)

3D-SDF for HMDB0014777 (Butoconazole)

PDB for HMDB0014777 (Butoconazole)

3D PDB for HMDB0014777 (Butoconazole)

SMILES for HMDB0014777 (Butoconazole)

INCHI for HMDB0014777 (Butoconazole)

Structure for HMDB0014777 (Butoconazole)

3D Structure for HMDB0014777 (Butoconazole)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra