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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

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

HMDB0015284

Secondary Accession Numbers

HMDB15284

Metabolite Identification

Common Name

Sertaconazole

Description

Sertaconazole is only found in individuals that have used or taken this drug. Sertaconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athlete's foot. [Wikipedia]Sertaconazole 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. Sertaconazole 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

1153
  Mrv0541 02231215172D          

 27 30  0  0  1  0            999 V2000
    6.2815   -0.5684    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.3928    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4087    1.3402    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.4067    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -0.1246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8848    2.0579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    3.1366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286    1.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868    0.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -1.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379    0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2432    1.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4011    2.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6699    2.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3451    0.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    1.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6014    1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872    3.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  6 18  1  0  0  0  0
  6 19  1  0  0  0  0
  7 19  2  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 13 16  2  0  0  0  0
 13 20  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  2  0  0  0  0
 16 23  1  0  0  0  0
 18 25  2  0  0  0  0
 20 26  2  0  0  0  0
 21 24  2  0  0  0  0
 22 24  1  0  0  0  0
 23 27  2  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0015284
     RDKit          3D
Sertaconazole
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.6707   -5.9669    0.7724 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4282   -4.2264    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082   -3.3568    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -1.9900    1.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309   -1.5201    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258   -0.0764    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7625    0.8147    0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4970    2.2189    0.2853 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238    3.0792    1.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145    4.3419    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978    4.2697   -0.4315 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    2.9990   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282    0.1796   -0.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953    0.6253   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -0.2197   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   -1.3679    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9683   -1.8965    0.7607 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855   -0.6618    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623   -0.3601    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2944   -1.5063    0.8583 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7478    0.7626   -0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8189    1.5749   -1.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4605    1.2958   -1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633    0.1688   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657   -2.3949   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -1.6927   -2.3419 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9399   -3.7568   -0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0979   -3.7254    2.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -1.3445    2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874    0.0640    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5315    0.6142   -0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    0.5287    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896    2.8490    2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9730    5.2510    1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870    2.6305   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805    1.6340   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7772    1.0067   -1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4674   -1.9009    0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8175    0.9532   -0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680    2.4828   -1.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172    2.0178   -1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7178   -4.3981   -1.4945 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  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  5 25  1  0
 25 26  1  0
 25 27  2  0
 27  2  1  0
 12  8  1  0
 24 15  1  0
 24 18  1  0
  3 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 27 42  1  0
M  END

1153
  Mrv0541 02231215172D          

 27 30  0  0  1  0            999 V2000
    6.2815   -0.5684    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.3928    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4087    1.3402    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.4067    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -0.1246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8848    2.0579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    3.1366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286    1.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868    0.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -1.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379    0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2432    1.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4011    2.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6699    2.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3451    0.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    1.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6014    1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872    3.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  6 18  1  0  0  0  0
  6 19  1  0  0  0  0
  7 19  2  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 13 16  2  0  0  0  0
 13 20  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  2  0  0  0  0
 16 23  1  0  0  0  0
 18 25  2  0  0  0  0
 20 26  2  0  0  0  0
 21 24  2  0  0  0  0
 22 24  1  0  0  0  0
 23 27  2  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015284

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl

> <INCHI_IDENTIFIER>
InChI=1S/C20H15Cl3N2OS/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22/h1-8,11-12,19H,9-10H2

> <INCHI_KEY>
JLGKQTAYUIMGRK-UHFFFAOYSA-N

> <FORMULA>
C20H15Cl3N2OS

> <MOLECULAR_WEIGHT>
437.77

> <EXACT_MASS>
435.997066923

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
42.931925497274996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
6.228348480333333

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.767291901573991

> <JCHEM_POLAR_SURFACE_AREA>
27.05

> <JCHEM_REFRACTIVITY>
111.60290000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sertaconazole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015284
     RDKit          3D
Sertaconazole
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.6707   -5.9669    0.7724 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4282   -4.2264    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082   -3.3568    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -1.9900    1.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309   -1.5201    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258   -0.0764    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7625    0.8147    0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4970    2.2189    0.2853 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238    3.0792    1.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145    4.3419    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978    4.2697   -0.4315 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    2.9990   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282    0.1796   -0.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953    0.6253   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -0.2197   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   -1.3679    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9683   -1.8965    0.7607 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855   -0.6618    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623   -0.3601    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2944   -1.5063    0.8583 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7478    0.7626   -0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8189    1.5749   -1.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4605    1.2958   -1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633    0.1688   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657   -2.3949   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -1.6927   -2.3419 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9399   -3.7568   -0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0979   -3.7254    2.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -1.3445    2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874    0.0640    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5315    0.6142   -0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    0.5287    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896    2.8490    2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9730    5.2510    1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870    2.6305   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805    1.6340   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7772    1.0067   -1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4674   -1.9009    0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8175    0.9532   -0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680    2.4828   -1.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172    2.0178   -1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7178   -4.3981   -1.4945 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  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  5 25  1  0
 25 26  1  0
 25 27  2  0
 27  2  1  0
 12  8  1  0
 24 15  1  0
 24 18  1  0
  3 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 27 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1153                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      11.725  -1.061   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       4.414  -6.333   0.000  0.00  0.00          Cl+0
HETATM    3 Cl   UNK     0      15.696   2.502   0.000  0.00  0.00          Cl+0
HETATM    4  S   UNK     0       7.205  -4.493   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0       9.190  -0.233   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       9.118   3.841   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      10.586   5.855   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.668   1.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.640   2.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.175   1.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.683  -0.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.205  -2.014   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -2.483   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.204   0.403   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.654   3.013   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -4.023   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.104  -3.253   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.215   5.089   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.584   4.315   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -1.713   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.711   0.720   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.161   3.330   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -4.793   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.189   2.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.123   6.333   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080  -2.483   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080  -4.023   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   16   17                                                       
CONECT    5    8   11                                                       
CONECT    6    9   18   19                                                  
CONECT    7   19   25                                                       
CONECT    8    5    9   10                                                  
CONECT    9    6    8                                                       
CONECT   10    8   14   15                                                  
CONECT   11    5   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   16   20                                                  
CONECT   14    1   10   21                                                  
CONECT   15   10   22                                                       
CONECT   16    4   13   23                                                  
CONECT   17    4   12                                                       
CONECT   18    6   25                                                       
CONECT   19    6    7                                                       
CONECT   20   13   26                                                       
CONECT   21   14   24                                                       
CONECT   22   15   24                                                       
CONECT   23    2   16   27                                                  
CONECT   24    3   21   22                                                  
CONECT   25    7   18                                                       
CONECT   26   20   27                                                       
CONECT   27   23   26                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0015284
HETATM    1 CL1  UNL     1      -2.671  -5.967   0.772  1.00  0.00          CL  
HETATM    2  C1  UNL     1      -2.428  -4.226   0.580  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.708  -3.357   1.609  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.501  -1.990   1.396  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.031  -1.520   0.200  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.526  -0.076   0.110  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.763   0.815   0.305  1.00  0.00           C  
HETATM    8  N1  UNL     1      -2.497   2.219   0.285  1.00  0.00           N  
HETATM    9  C7  UNL     1      -2.424   3.079   1.351  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.114   4.342   0.906  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.998   4.270  -0.431  1.00  0.00           N  
HETATM   12  C9  UNL     1      -2.227   2.999  -0.808  1.00  0.00           C  
HETATM   13  O1  UNL     1      -0.728   0.180  -0.900  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.495   0.625  -0.951  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.638  -0.220  -0.390  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.398  -1.368   0.292  1.00  0.00           C  
HETATM   17  S1  UNL     1       2.968  -1.897   0.761  1.00  0.00           S  
HETATM   18  C13 UNL     1       3.885  -0.662   0.093  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.262  -0.360   0.053  1.00  0.00           C  
HETATM   20 CL2  UNL     1       6.294  -1.506   0.858  1.00  0.00          CL  
HETATM   21  C15 UNL     1       5.748   0.763  -0.573  1.00  0.00           C  
HETATM   22  C16 UNL     1       4.819   1.575  -1.157  1.00  0.00           C  
HETATM   23  C17 UNL     1       3.461   1.296  -1.133  1.00  0.00           C  
HETATM   24  C18 UNL     1       2.963   0.169  -0.503  1.00  0.00           C  
HETATM   25  C19 UNL     1      -1.766  -2.395  -0.812  1.00  0.00           C  
HETATM   26 CL3  UNL     1      -1.235  -1.693  -2.342  1.00  0.00          CL  
HETATM   27  C20 UNL     1      -1.940  -3.757  -0.679  1.00  0.00           C  
HETATM   28  H1  UNL     1      -3.098  -3.725   2.529  1.00  0.00           H  
HETATM   29  H2  UNL     1      -2.706  -1.344   2.236  1.00  0.00           H  
HETATM   30  H3  UNL     1      -0.987   0.064   1.121  1.00  0.00           H  
HETATM   31  H4  UNL     1      -3.531   0.614  -0.507  1.00  0.00           H  
HETATM   32  H5  UNL     1      -3.213   0.529   1.299  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.590   2.849   2.409  1.00  0.00           H  
HETATM   34  H7  UNL     1      -1.973   5.251   1.469  1.00  0.00           H  
HETATM   35  H8  UNL     1      -2.187   2.630  -1.816  1.00  0.00           H  
HETATM   36  H9  UNL     1       0.580   1.634  -0.339  1.00  0.00           H  
HETATM   37  H10 UNL     1       0.777   1.007  -1.971  1.00  0.00           H  
HETATM   38  H11 UNL     1       0.467  -1.901   0.540  1.00  0.00           H  
HETATM   39  H12 UNL     1       6.818   0.953  -0.583  1.00  0.00           H  
HETATM   40  H13 UNL     1       5.168   2.483  -1.656  1.00  0.00           H  
HETATM   41  H14 UNL     1       2.817   2.018  -1.637  1.00  0.00           H  
HETATM   42  H15 UNL     1      -1.718  -4.398  -1.495  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   27
CONECT    3    4   28
CONECT    4    5    5   29
CONECT    5    6   25
CONECT    6    7   13   30
CONECT    7    8   31   32
CONECT    8    9   12
CONECT    9   10   10   33
CONECT   10   11   34
CONECT   11   12   12
CONECT   12   35
CONECT   13   14
CONECT   14   15   36   37
CONECT   15   16   16   24
CONECT   16   17   38
CONECT   17   18
CONECT   18   19   19   24
CONECT   19   20   21
CONECT   21   22   22   39
CONECT   22   23   40
CONECT   23   24   24   41
CONECT   25   26   27   27
CONECT   27   42
END

HMDB0015284
     RDKit          3D
Sertaconazole
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.6707   -5.9669    0.7724 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4282   -4.2264    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082   -3.3568    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -1.9900    1.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0309   -1.5201    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258   -0.0764    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7625    0.8147    0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4970    2.2189    0.2853 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238    3.0792    1.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145    4.3419    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978    4.2697   -0.4315 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272    2.9990   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282    0.1796   -0.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953    0.6253   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -0.2197   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   -1.3679    0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9683   -1.8965    0.7607 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855   -0.6618    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2623   -0.3601    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2944   -1.5063    0.8583 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7478    0.7626   -0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8189    1.5749   -1.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4605    1.2958   -1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633    0.1688   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7657   -2.3949   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348   -1.6927   -2.3419 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9399   -3.7568   -0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0979   -3.7254    2.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -1.3445    2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874    0.0640    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5315    0.6142   -0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    0.5287    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896    2.8490    2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9730    5.2510    1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1870    2.6305   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805    1.6340   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7772    1.0067   -1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4674   -1.9009    0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8175    0.9532   -0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1680    2.4828   -1.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172    2.0178   -1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7178   -4.3981   -1.4945 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  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  5 25  1  0
 25 26  1  0
 25 27  2  0
 27  2  1  0
 12  8  1  0
 24 15  1  0
 24 18  1  0
  3 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 27 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dermofix	MeSH
Dermoseptic	MeSH
Ginedermofix	MeSH
Mykosert	MeSH
Zalain	MeSH
Sertaconazole mononitrate	MeSH
Sertaconazole nitrate	MeSH
Demofix	ChEMBL, HMDB
Ertaczo	ChEMBL, HMDB
Sertaconazole	MeSH

Chemical Formula

C₂₀H₁₅Cl₃N₂OS

Average Molecular Weight

437.77

Monoisotopic Molecular Weight

435.997066923

IUPAC Name

1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

Traditional Name

sertaconazole

CAS Registry Number

99592-32-2

SMILES

ClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl

InChI Identifier

InChI=1S/C20H15Cl3N2OS/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22/h1-8,11-12,19H,9-10H2

InChI Key

JLGKQTAYUIMGRK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiophenes

Sub Class

1-benzothiophenes

Direct Parent

1-benzothiophenes

Alternative Parents

Substituents

1-benzothiophene
Benzylether
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
N-substituted imidazole
Azole
Heteroaromatic compound
Thiophene
Imidazole
Azacycle
Dialkyl ether
Ether
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organochloride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazoles (CHEBI:83682 )
1-benzothiophenes (CHEBI:83682 )
ether (CHEBI:83682 )
dichlorobenzene (CHEBI:83682 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0064 g/L	Not Available
LogP	6.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0064 g/L	ALOGPS
logP	5.74	ALOGPS
logP	6.23	ChemAxon
logS	-4.8	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	111.6 m³·mol⁻¹	ChemAxon
Polarizability	42.93 Å³	ChemAxon
Number of Rings	4	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]+	183.449	30932474
DeepCCS	[M-H]-	181.091	30932474
DeepCCS	[M-2H]-	215.201	30932474
DeepCCS	[M+Na]+	190.651	30932474
AllCCS	[M+H]+	192.9	32859911
AllCCS	[M+H-H2O]+	190.5	32859911
AllCCS	[M+NH4]+	195.1	32859911
AllCCS	[M+Na]+	195.7	32859911
AllCCS	[M-H]-	174.1	32859911
AllCCS	[M+Na-2H]-	173.1	32859911
AllCCS	[M+HCOO]-	172.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sertaconazole	ClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl	4700.3	Standard polar	33892256
Sertaconazole	ClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl	3324.6	Standard non polar	33892256
Sertaconazole	ClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=CSC2=C1C=CC=C2Cl	3443.0	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 - Sertaconazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-8921000000-652bd3da9533b5e7b49c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sertaconazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sertaconazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sertaconazole 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 - Sertaconazole 10V, Positive-QTOF	splash10-000i-0010900000-e80248766f0207aed747	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 20V, Positive-QTOF	splash10-00kr-7172900000-fb816c23af8617fb0dfb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 40V, Positive-QTOF	splash10-014i-9230000000-a5524f8d3df959952f87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 10V, Negative-QTOF	splash10-001i-1000900000-8d6b59997574a7df6e25	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 20V, Negative-QTOF	splash10-014i-9000100000-00203eccb064d3b38462	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 40V, Negative-QTOF	splash10-014l-9210000000-31fa2b0a7600382a9cf4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 10V, Positive-QTOF	splash10-0019-0920800000-325d5bb8842de14747ea	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 20V, Positive-QTOF	splash10-001r-1902200000-221501bc20a8a810369b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 40V, Positive-QTOF	splash10-00ls-4900000000-0394fe97ab0550a97abd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 10V, Negative-QTOF	splash10-000i-2390400000-66e76245f92d693d9a99	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 20V, Negative-QTOF	splash10-001i-9300000000-64f716aeb89d151ae51f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sertaconazole 40V, Negative-QTOF	splash10-014i-9100000000-6151c3cb1b71a9e4e4ca	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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 DB01153	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01153	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59273

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65863

PDB ID

Not Available

ChEBI ID

83682

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. Lanosterol 14-alpha demethylase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:: CYP51A1
Uniprot ID:: Q16850
Molecular weight:: 57277.81

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 Sertaconazole (HMDB0015284)

MOL for HMDB0015284 (Sertaconazole)

3D MOL for HMDB0015284 (Sertaconazole)

3D SDF for HMDB0015284 (Sertaconazole)

3D-SDF for HMDB0015284 (Sertaconazole)

PDB for HMDB0015284 (Sertaconazole)

3D PDB for HMDB0015284 (Sertaconazole)

SMILES for HMDB0015284 (Sertaconazole)

INCHI for HMDB0015284 (Sertaconazole)

Structure for HMDB0015284 (Sertaconazole)

3D Structure for HMDB0015284 (Sertaconazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References