Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015259

Secondary Accession Numbers

HMDB15259

Metabolite Identification

Common Name

Econazole

Description

Econazole is only found in individuals that have used or taken this drug. It is a broad spectrum antimycotic with some action against Gram positive bacteria. It is used topically in dermatomycoses also orally and parenterally. [PubChem]Econazole interacts with 14-alpha demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Econazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.

Structure

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

HMDB0015259
     RDKit          3D
Econazole
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.4867    0.2810    1.3598 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9595    0.0069    0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581   -0.8049    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7557   -1.0100    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5526   -0.4199   -0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2858   -0.5797   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2682   -0.5240   -0.6492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -0.3625   -1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613   -1.4759   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -1.7914    0.4484 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3500   -1.2145    1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5141   -1.8245    2.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251   -2.7424    2.4246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106   -2.6719    1.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    0.9493   -0.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4109    0.9938    0.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    2.1546    1.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7297    3.3290    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9479    4.8290    1.6630 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968    3.2990   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    2.1380   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319    2.0835   -3.0939 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5395    0.3846   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    0.5812   -0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1080   -1.2882    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -1.6742    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372   -1.6736   -1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396    0.1222   -2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -0.2657   -2.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -2.4259   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7841   -1.6054   -1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -0.4429    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3117   -1.5438    2.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368   -3.3538    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2086    0.1128    1.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    2.0930    2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    4.2271   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050    0.8847   -2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5149    1.2256   -1.0890 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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
  5 23  1  0
 23 24  2  0
 24  2  1  0
 14 10  1  0
 21 15  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 23 38  1  0
 24 39  1  0
M  END

1127
  Mrv0541 02231215162D          

 24 26  0  0  1  0            999 V2000
    3.7934   -0.6188    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -3.0938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3494    2.7133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2694    1.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6043    1.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5244    2.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 18  1  0  0  0  0
  3 24  1  0  0  0  0
  4  7  1  0  0  0  0
  4 10  1  0  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5 15  1  0  0  0  0
  6 15  2  0  0  0  0
  6 19  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  2  0  0  0  0
 13 20  2  0  0  0  0
 13 21  1  0  0  0  0
 14 19  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015259

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H15Cl3N2O/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2

> <INCHI_KEY>
LEZWWPYKPKIXLL-UHFFFAOYSA-N

> <FORMULA>
C18H15Cl3N2O

> <MOLECULAR_WEIGHT>
381.684

> <EXACT_MASS>
380.024996233

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.37246253608513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

> <ALOGPS_LOGP>
4.67

> <JCHEM_LOGP>
5.352323684

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.767291901775012

> <JCHEM_POLAR_SURFACE_AREA>
27.05

> <JCHEM_REFRACTIVITY>
98.26280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
econazole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015259
     RDKit          3D
Econazole
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.4867    0.2810    1.3598 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9595    0.0069    0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581   -0.8049    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7557   -1.0100    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5526   -0.4199   -0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2858   -0.5797   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2682   -0.5240   -0.6492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -0.3625   -1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613   -1.4759   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -1.7914    0.4484 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3500   -1.2145    1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5141   -1.8245    2.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251   -2.7424    2.4246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106   -2.6719    1.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    0.9493   -0.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4109    0.9938    0.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    2.1546    1.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7297    3.3290    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9479    4.8290    1.6630 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968    3.2990   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    2.1380   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319    2.0835   -3.0939 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5395    0.3846   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    0.5812   -0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1080   -1.2882    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -1.6742    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372   -1.6736   -1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396    0.1222   -2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -0.2657   -2.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -2.4259   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7841   -1.6054   -1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -0.4429    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3117   -1.5438    2.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368   -3.3538    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2086    0.1128    1.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    2.0930    2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    4.2271   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050    0.8847   -2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5149    1.2256   -1.0890 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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
  5 23  1  0
 23 24  2  0
 24  2  1  0
 14 10  1  0
 21 15  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 23 38  1  0
 24 39  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1127                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       7.081  -1.155   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       9.748  -5.775   0.000  0.00  0.00          Cl+0
HETATM    3 Cl   UNK     0       3.080   5.775   0.000  0.00  0.00          Cl+0
HETATM    4  O   UNK     0       8.415   1.155   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.082   2.695   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      11.852   5.065   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748  -1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081   3.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.836   3.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.328   3.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -3.465   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082  -3.465   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748  -4.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.312   5.065   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.747   2.695   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.081   5.005   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414   3.465   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.747   5.775   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414   5.005   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   18                                                            
CONECT    3   24                                                            
CONECT    4    7   10                                                       
CONECT    5    8   14   15                                                  
CONECT    6   15   19                                                       
CONECT    7    4    8    9                                                  
CONECT    8    5    7                                                       
CONECT    9    7   11   12                                                  
CONECT   10    4   13                                                       
CONECT   11    1    9   16                                                  
CONECT   12    9   17                                                       
CONECT   13   10   20   21                                                  
CONECT   14    5   19                                                       
CONECT   15    5    6                                                       
CONECT   16   11   18                                                       
CONECT   17   12   18                                                       
CONECT   18    2   16   17                                                  
CONECT   19    6   14                                                       
CONECT   20   13   22                                                       
CONECT   21   13   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   24                                                       
CONECT   24    3   22   23                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0015259
HETATM    1 CL1  UNL     1       6.487   0.281   1.360  1.00  0.00          CL  
HETATM    2  C1  UNL     1       4.959   0.007   0.513  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.958  -0.805   1.057  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.756  -1.010   0.381  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.553  -0.420  -0.820  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.286  -0.580  -1.552  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.268  -0.524  -0.649  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.034  -0.363  -1.275  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.861  -1.476  -0.862  1.00  0.00           C  
HETATM   10  N1  UNL     1      -2.252  -1.791   0.448  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.350  -1.215   1.042  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.514  -1.825   2.299  1.00  0.00           C  
HETATM   13  N2  UNL     1      -2.525  -2.742   2.425  1.00  0.00           N  
HETATM   14  C10 UNL     1      -1.811  -2.672   1.303  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.385   0.949  -0.643  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.411   0.994   0.714  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.582   2.155   1.474  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.730   3.329   0.784  1.00  0.00           C  
HETATM   19 CL2  UNL     1      -1.948   4.829   1.663  1.00  0.00          CL  
HETATM   20  C15 UNL     1      -1.697   3.299  -0.608  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.530   2.138  -1.334  1.00  0.00           C  
HETATM   22 CL3  UNL     1      -1.532   2.083  -3.094  1.00  0.00          CL  
HETATM   23  C17 UNL     1       3.540   0.385  -1.366  1.00  0.00           C  
HETATM   24  C18 UNL     1       4.704   0.581  -0.703  1.00  0.00           C  
HETATM   25  H1  UNL     1       4.108  -1.288   2.023  1.00  0.00           H  
HETATM   26  H2  UNL     1       1.979  -1.674   0.847  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.237  -1.674  -1.953  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.240   0.122  -2.402  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.954  -0.266  -2.351  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.298  -2.426  -1.242  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.784  -1.605  -1.561  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.946  -0.443   0.610  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.312  -1.544   2.971  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.937  -3.354   1.129  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.209   0.113   1.368  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.597   2.093   2.570  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.798   4.227  -1.148  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.405   0.885  -2.330  1.00  0.00           H  
HETATM   39  H15 UNL     1       5.515   1.226  -1.089  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   24
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   23
CONECT    6    7   27   28
CONECT    7    8
CONECT    8    9   15   29
CONECT    9   10   30   31
CONECT   10   11   14
CONECT   11   12   12   32
CONECT   12   13   33
CONECT   13   14   14
CONECT   14   34
CONECT   15   16   16   21
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   20
CONECT   20   21   21   37
CONECT   21   22
CONECT   23   24   24   38
CONECT   24   39
END

HMDB0015259
     RDKit          3D
Econazole
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.4867    0.2810    1.3598 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9595    0.0069    0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581   -0.8049    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7557   -1.0100    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5526   -0.4199   -0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2858   -0.5797   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2682   -0.5240   -0.6492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -0.3625   -1.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613   -1.4759   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -1.7914    0.4484 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3500   -1.2145    1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5141   -1.8245    2.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251   -2.7424    2.4246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8106   -2.6719    1.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    0.9493   -0.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4109    0.9938    0.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    2.1546    1.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7297    3.3290    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9479    4.8290    1.6630 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968    3.2990   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    2.1380   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5319    2.0835   -3.0939 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5395    0.3846   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    0.5812   -0.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1080   -1.2882    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -1.6742    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372   -1.6736   -1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2396    0.1222   -2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -0.2657   -2.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -2.4259   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7841   -1.6054   -1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -0.4429    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3117   -1.5438    2.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368   -3.3538    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2086    0.1128    1.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    2.0930    2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978    4.2271   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050    0.8847   -2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5149    1.2256   -1.0890 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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
  5 23  1  0
 23 24  2  0
 24  2  1  0
 14 10  1  0
 21 15  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 23 38  1  0
 24 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Spectazole	ChEMBL, HMDB
gyno Pevaryl	MeSH, HMDB
gyno-Pervaryl 150	MeSH, HMDB
gyno-Pevaryl	MeSH, HMDB
Econazole nitrate	MeSH, HMDB
gyno Pevaril	MeSH, HMDB
gyno-Pevaril	MeSH, HMDB
Nitrate, econazole	MeSH, HMDB
Pevaryl	MeSH, HMDB
Ekonazole	MeSH, HMDB
gyno Pervaryl 150	MeSH, HMDB
GynoPevaril	MeSH, HMDB
Econazole	MeSH

Chemical Formula

C₁₈H₁₅Cl₃N₂O

Average Molecular Weight

381.684

Monoisotopic Molecular Weight

380.024996233

IUPAC Name

1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

Traditional Name

econazole

CAS Registry Number

27220-47-9

SMILES

ClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

InChI Identifier

InChI=1S/C18H15Cl3N2O/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2

InChI Key

LEZWWPYKPKIXLL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
N-substituted imidazole
Imidazole
Azole
Heteroaromatic compound
Ether
Dialkyl ether
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:82873 )
ether (CHEBI:82873 )
dichlorobenzene (CHEBI:82873 )
monochlorobenzenes (CHEBI:82873 )

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: HMDB0015259)

Source

Exogenous

Exogenous (HMDB: HMDB0015259)

Process

Not Available

Role

Industrial application

Antifungal agent (HMDB: HMDB0015259)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0015 g/L	Not Available
LogP	5.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	184.751	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000734

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	4.67	ALOGPS
logP	5.35	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	6.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	98.26 m³·mol⁻¹	ChemAxon
Polarizability	37.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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]+	185.317	30932474
DeepCCS	[M-H]-	182.865	30932474
DeepCCS	[M-2H]-	217.015	30932474
DeepCCS	[M+Na]+	193.306	30932474
AllCCS	[M+H]+	182.2	32859911
AllCCS	[M+H-H2O]+	179.3	32859911
AllCCS	[M+NH4]+	184.8	32859911
AllCCS	[M+Na]+	185.6	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	175.6	32859911
AllCCS	[M+HCOO]-	175.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Econazole	ClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1	4094.2	Standard polar	33892256
Econazole	ClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1	2849.0	Standard non polar	33892256
Econazole	ClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1	2904.5	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 - Econazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9341000000-4ffb0473a31cea3f8c18	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Econazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Econazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Econazole , positive-QTOF	splash10-001i-0209000000-dd9a7887032ba981630f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Econazole 75V, Positive-QTOF	splash10-004i-1900000000-28f4c0046949a5e27ab1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Econazole 60V, Positive-QTOF	splash10-004i-0900000000-f00842704123db9b0465	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Econazole 30V, Positive-QTOF	splash10-004i-0903000000-6c5549ea79b88c593f2e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Econazole 15V, Positive-QTOF	splash10-001i-0009000000-0e20351a1183f50f888e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Econazole 90V, Positive-QTOF	splash10-004i-5900000000-bb76504dc81de5c3b579	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Econazole 45V, Positive-QTOF	splash10-004i-0900000000-a667527ad6d687e25400	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 10V, Positive-QTOF	splash10-001i-0019000000-e4e35751739b91041ba8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 20V, Positive-QTOF	splash10-00m0-5169000000-ef3cb4a26c4fda6ee25d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 40V, Positive-QTOF	splash10-014i-9310000000-88884e5d802b100711cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 10V, Negative-QTOF	splash10-004i-1009000000-cef44f57a37b6b00c969	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 20V, Negative-QTOF	splash10-014i-9001000000-7c677fea699efb1a72f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 40V, Negative-QTOF	splash10-014l-9310000000-1d15b5e04ae4eb7ad414	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 10V, Negative-QTOF	splash10-004i-2039000000-17f63aee73e32a973719	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 20V, Negative-QTOF	splash10-001i-9551000000-33222b3a25a12499d2cb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 40V, Negative-QTOF	splash10-00lr-9000000000-cd84e8c432915c9cc869	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 10V, Positive-QTOF	splash10-001i-0009000000-7996a613e7d9dea8ceba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 20V, Positive-QTOF	splash10-001i-1219000000-1878634d92d58865370e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Econazole 40V, Positive-QTOF	splash10-00or-6910000000-84c9b556f80d88764610	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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 DB01127	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01127	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01127

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3086

KEGG Compound ID

C08068

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Econazole

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

82873

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

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Econazole (HMDB0015259)

MOL for HMDB0015259 (Econazole)

3D MOL for HMDB0015259 (Econazole)

3D SDF for HMDB0015259 (Econazole)

3D-SDF for HMDB0015259 (Econazole)

PDB for HMDB0015259 (Econazole)

3D PDB for HMDB0015259 (Econazole)

SMILES for HMDB0015259 (Econazole)

INCHI for HMDB0015259 (Econazole)

Structure for HMDB0015259 (Econazole)

3D Structure for HMDB0015259 (Econazole)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References