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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-04-06 16:21:37 UTC

Update Date

2022-03-07 02:51:22 UTC

HMDB ID

HMDB0012242

Secondary Accession Numbers

HMDB12242

Metabolite Identification

Common Name

Ketoconazole

Description

Ketoconazole is only found in individuals that have used or taken this drug. It is a broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients. [PubChem]Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mechanisms may involve the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole can also inhibit the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone.

Structure

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


  Mrv0541 02241203522D          

 36 40  0  0  1  0            999 V2000
   14.0744  -13.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4869  -12.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0744  -11.6202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4869  -10.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0744  -10.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2494  -10.1912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8370  -10.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2494  -11.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8370   -9.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2494   -8.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8370   -8.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120   -8.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5995   -8.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120   -9.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5995   -7.3336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7746   -7.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3621   -6.6191    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6977   -5.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0848   -5.3134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3703   -5.7259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8853   -5.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2208   -4.3048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0278   -4.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1140   -3.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3604   -2.9775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8084   -3.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5497   -5.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0646   -5.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2447   -5.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091   -5.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3935   -6.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2142   -6.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6992   -7.2331    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0885   -6.0708    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.5415   -6.5328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3118  -12.3348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 36  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 17 35  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 27  1  0  0  0  0
 20 35  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 26  1  0  0  0  0
 23 24  2  0  0  0  0
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 30 31  1  0  0  0  0
 30 34  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0012242
     RDKit          3D
Ketoconazole
 64 68  0  0  0  0  0  0  0  0999 V2000
    7.9451    2.7620    1.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7288    1.3650    1.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1658    1.0678    3.1327 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0707    0.4035    1.1773 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5975    0.8338   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762   -0.3552   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0422   -0.9420    0.0480 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6389   -0.9335   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929   -0.0885   -1.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242   -0.0968   -1.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294   -0.9480   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335   -0.9017   -0.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603   -1.7168   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7734   -1.4647   -0.5268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9003   -1.5145   -2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -0.8728   -2.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3024   -0.0501   -1.0474 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6332    1.2982   -1.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8996    2.4152   -0.8185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9791    3.3057   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613    4.2698    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9615    3.9575    0.2837 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1472    2.8377   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4471   -0.6086   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2684   -1.5674   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4036   -2.0104   -0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7649   -1.5355    0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2042   -2.1037    1.7362 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.9801   -0.6092    1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8363   -0.1652    0.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8049    0.9112    1.8815 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643   -0.1329   -0.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021   -1.7888    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568   -1.8020    0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5908   -1.5677    1.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8963   -0.9267    1.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0005    2.8504    1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7928    3.4182    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2489    3.0292    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4182    1.2365   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8200    1.6112   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7904   -1.0808   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5068   -0.0132   -1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533    0.6073   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2906    0.5769   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2490   -1.6195    1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1228   -2.7693   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912   -2.1898   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5731    1.1376   -2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8477    1.5721   -2.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9149    3.2559   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277    5.1385    0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0816    2.3367   -0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9658   -1.9297   -1.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9982   -2.7460   -0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2739   -2.4655    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9473   -0.9091    2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 13 14  1  0
 14 15  1  0
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 16 17  1  0
 17 18  1  6
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 21 22  1  0
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 17 24  1  0
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 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 17 32  1  0
 11 33  1  0
 33 34  2  0
  7 35  1  0
 35 36  1  0
 36  4  1  0
 34  8  1  0
 32 14  1  0
 23 19  1  0
 30 24  1  0
  1 37  1  0
  1 38  1  0
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 33 59  1  0
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 35 61  1  0
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 36 63  1  0
 36 64  1  0
M  END


  Mrv0541 02241203522D          

 36 40  0  0  1  0            999 V2000
   14.0744  -13.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4869  -12.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0744  -11.6202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4869  -10.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0744  -10.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2494  -10.1912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8370  -10.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2494  -11.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8370   -9.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2494   -8.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8370   -8.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120   -8.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5995   -8.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120   -9.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5995   -7.3336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7746   -7.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3621   -6.6191    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6977   -5.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0848   -5.3134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3703   -5.7259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8853   -5.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2208   -4.3048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0278   -4.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1140   -3.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3604   -2.9775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8084   -3.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0646   -5.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2447   -5.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091   -5.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3935   -6.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2142   -6.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0885   -6.0708    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.5415   -6.5328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3118  -12.3348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 36  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
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 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 17 35  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 20 27  1  0  0  0  0
 20 35  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 26  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  2  0  0  0  0
 27 32  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 34  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012242

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1

> <INCHI_KEY>
XMAYWYJOQHXEEK-ZEQKJWHPSA-N

> <FORMULA>
C26H28Cl2N4O4

> <MOLECULAR_WEIGHT>
531.431

> <EXACT_MASS>
530.148760818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
54.666767639117076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
4.191597861333333

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.746571393297444

> <JCHEM_POLAR_SURFACE_AREA>
69.06

> <JCHEM_REFRACTIVITY>
138.06719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nizoral

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012242
     RDKit          3D
Ketoconazole
 64 68  0  0  0  0  0  0  0  0999 V2000
    7.9451    2.7620    1.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7288    1.3650    1.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1658    1.0678    3.1327 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0707    0.4035    1.1773 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5975    0.8338   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762   -0.3552   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0422   -0.9420    0.0480 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6389   -0.9335   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929   -0.0885   -1.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242   -0.0968   -1.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294   -0.9480   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335   -0.9017   -0.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603   -1.7168   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7734   -1.4647   -0.5268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9003   -1.5145   -2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -0.8728   -2.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3024   -0.0501   -1.0474 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6332    1.2982   -1.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8996    2.4152   -0.8185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9791    3.3057   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613    4.2698    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9615    3.9575    0.2837 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1472    2.8377   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4471   -0.6086   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2684   -1.5674   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4036   -2.0104   -0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7649   -1.5355    0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2042   -2.1037    1.7362 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.9801   -0.6092    1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8363   -0.1652    0.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8049    0.9112    1.8815 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643   -0.1329   -0.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021   -1.7888    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568   -1.8020    0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5908   -1.5677    1.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8963   -0.9267    1.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0005    2.8504    1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7928    3.4182    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2489    3.0292    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4182    1.2365   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8200    1.6112   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7904   -1.0808   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5068   -0.0132   -1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533    0.6073   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2906    0.5769   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2490   -1.6195    1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1228   -2.7693   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912   -2.1898   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -0.8583   -2.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -2.5389   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5731    1.1376   -2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8477    1.5721   -2.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9149    3.2559   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277    5.1385    0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0816    2.3367   -0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9658   -1.9297   -1.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9982   -2.7460   -0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2198   -0.2107    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8757   -2.4565    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2739   -2.4655    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8844   -1.5090    2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7416   -2.6379    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7313   -1.5610    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9473   -0.9091    2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 17 32  1  0
 11 33  1  0
 33 34  2  0
  7 35  1  0
 35 36  1  0
 36  4  1  0
 34  8  1  0
 32 14  1  0
 23 19  1  0
 30 24  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  9 44  1  0
 10 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  1
 15 49  1  0
 15 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 25 56  1  0
 26 57  1  0
 29 58  1  0
 33 59  1  0
 34 60  1  0
 35 61  1  0
 35 62  1  0
 36 63  1  0
 36 64  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      26.272 -24.358   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.042 -23.025   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      26.272 -21.691   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      27.042 -20.357   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.272 -19.024   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      24.732 -19.024   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      23.962 -20.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.732 -21.691   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.962 -17.690   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.732 -16.357   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.962 -15.023   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.422 -15.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.652 -16.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.422 -17.690   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.652 -13.689   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      20.113 -13.689   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.343 -12.356   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.969 -10.949   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.825  -9.918   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      17.491 -10.688   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.586  -9.443   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      17.212  -8.036   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      18.719  -7.716   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.879  -6.184   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      17.473  -5.558   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      16.442  -6.702   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.959 -10.849   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.054  -9.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.523  -9.764   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.897 -11.171   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.801 -12.417   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.333 -12.256   0.000  0.00  0.00           C+0
HETATM   33 Cl   UNK     0      16.239 -13.502   0.000  0.00  0.00          Cl+0
HETATM   34 Cl   UNK     0      11.365 -11.332   0.000  0.00  0.00          Cl+0
HETATM   35  O   UNK     0      17.811 -12.195   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      28.582 -23.025   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    3    7                                                       
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14    9   13                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   35                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27   35                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   22   25                                                       
CONECT   27   20   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   27   31   33                                                  
CONECT   33   32                                                            
CONECT   34   30                                                            
CONECT   35   17   20                                                       
CONECT   36    2                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0012242
HETATM    1  C1  UNL     1       7.945   2.762   1.536  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.729   1.365   1.983  1.00  0.00           C  
HETATM    3  O1  UNL     1       8.166   1.068   3.133  1.00  0.00           O  
HETATM    4  N1  UNL     1       7.071   0.404   1.177  1.00  0.00           N  
HETATM    5  C3  UNL     1       6.597   0.834  -0.139  1.00  0.00           C  
HETATM    6  C4  UNL     1       5.976  -0.355  -0.870  1.00  0.00           C  
HETATM    7  N2  UNL     1       5.042  -0.942   0.048  1.00  0.00           N  
HETATM    8  C5  UNL     1       3.639  -0.933  -0.143  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.093  -0.089  -1.071  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.724  -0.097  -1.258  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.929  -0.948  -0.516  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.433  -0.902  -0.757  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.360  -1.717  -0.070  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.773  -1.465  -0.527  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.900  -1.515  -2.034  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.116  -0.873  -2.232  1.00  0.00           O  
HETATM   17  C12 UNL     1      -4.302  -0.050  -1.047  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.633   1.298  -1.635  1.00  0.00           C  
HETATM   19  N3  UNL     1      -4.900   2.415  -0.819  1.00  0.00           N  
HETATM   20  C14 UNL     1      -3.979   3.306  -0.332  1.00  0.00           C  
HETATM   21  C15 UNL     1      -4.661   4.270   0.359  1.00  0.00           C  
HETATM   22  N4  UNL     1      -5.962   3.957   0.284  1.00  0.00           N  
HETATM   23  C16 UNL     1      -6.147   2.838  -0.423  1.00  0.00           C  
HETATM   24  C17 UNL     1      -5.447  -0.609  -0.305  1.00  0.00           C  
HETATM   25  C18 UNL     1      -6.268  -1.567  -0.924  1.00  0.00           C  
HETATM   26  C19 UNL     1      -7.404  -2.010  -0.291  1.00  0.00           C  
HETATM   27  C20 UNL     1      -7.765  -1.535   0.951  1.00  0.00           C  
HETATM   28 CL1  UNL     1      -9.204  -2.104   1.736  1.00  0.00          CL  
HETATM   29  C21 UNL     1      -6.980  -0.609   1.564  1.00  0.00           C  
HETATM   30  C22 UNL     1      -5.836  -0.165   0.927  1.00  0.00           C  
HETATM   31 CL2  UNL     1      -4.805   0.911   1.881  1.00  0.00          CL  
HETATM   32  O4  UNL     1      -3.164  -0.133  -0.316  1.00  0.00           O  
HETATM   33  C23 UNL     1       1.502  -1.789   0.412  1.00  0.00           C  
HETATM   34  C24 UNL     1       2.857  -1.802   0.619  1.00  0.00           C  
HETATM   35  C25 UNL     1       5.591  -1.568   1.248  1.00  0.00           C  
HETATM   36  C26 UNL     1       6.896  -0.927   1.669  1.00  0.00           C  
HETATM   37  H1  UNL     1       9.001   2.850   1.188  1.00  0.00           H  
HETATM   38  H2  UNL     1       7.793   3.418   2.412  1.00  0.00           H  
HETATM   39  H3  UNL     1       7.249   3.029   0.727  1.00  0.00           H  
HETATM   40  H4  UNL     1       7.418   1.236  -0.764  1.00  0.00           H  
HETATM   41  H5  UNL     1       5.820   1.611  -0.071  1.00  0.00           H  
HETATM   42  H6  UNL     1       6.790  -1.081  -1.148  1.00  0.00           H  
HETATM   43  H7  UNL     1       5.507  -0.013  -1.799  1.00  0.00           H  
HETATM   44  H8  UNL     1       3.653   0.607  -1.683  1.00  0.00           H  
HETATM   45  H9  UNL     1       1.291   0.577  -1.998  1.00  0.00           H  
HETATM   46  H10 UNL     1      -1.249  -1.619   1.027  1.00  0.00           H  
HETATM   47  H11 UNL     1      -1.123  -2.769  -0.327  1.00  0.00           H  
HETATM   48  H12 UNL     1      -3.491  -2.190  -0.121  1.00  0.00           H  
HETATM   49  H13 UNL     1      -2.127  -0.858  -2.522  1.00  0.00           H  
HETATM   50  H14 UNL     1      -2.873  -2.539  -2.427  1.00  0.00           H  
HETATM   51  H15 UNL     1      -5.573   1.138  -2.270  1.00  0.00           H  
HETATM   52  H16 UNL     1      -3.848   1.572  -2.406  1.00  0.00           H  
HETATM   53  H17 UNL     1      -2.915   3.256  -0.469  1.00  0.00           H  
HETATM   54  H18 UNL     1      -4.228   5.138   0.878  1.00  0.00           H  
HETATM   55  H19 UNL     1      -7.082   2.337  -0.656  1.00  0.00           H  
HETATM   56  H20 UNL     1      -5.966  -1.930  -1.904  1.00  0.00           H  
HETATM   57  H21 UNL     1      -7.998  -2.746  -0.809  1.00  0.00           H  
HETATM   58  H22 UNL     1      -7.220  -0.211   2.528  1.00  0.00           H  
HETATM   59  H23 UNL     1       0.876  -2.456   0.994  1.00  0.00           H  
HETATM   60  H24 UNL     1       3.274  -2.465   1.343  1.00  0.00           H  
HETATM   61  H25 UNL     1       4.884  -1.509   2.093  1.00  0.00           H  
HETATM   62  H26 UNL     1       5.742  -2.638   1.011  1.00  0.00           H  
HETATM   63  H27 UNL     1       7.731  -1.561   1.260  1.00  0.00           H  
HETATM   64  H28 UNL     1       6.947  -0.909   2.774  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3    3    4
CONECT    4    5   36
CONECT    5    6   40   41
CONECT    6    7   42   43
CONECT    7    8   35
CONECT    8    9    9   34
CONECT    9   10   44
CONECT   10   11   11   45
CONECT   11   12   33
CONECT   12   13
CONECT   13   14   46   47
CONECT   14   15   32   48
CONECT   15   16   49   50
CONECT   16   17
CONECT   17   18   24   32
CONECT   18   19   51   52
CONECT   19   20   23
CONECT   20   21   21   53
CONECT   21   22   54
CONECT   22   23   23
CONECT   23   55
CONECT   24   25   25   30
CONECT   25   26   56
CONECT   26   27   27   57
CONECT   27   28   29
CONECT   29   30   30   58
CONECT   30   31
CONECT   33   34   34   59
CONECT   34   60
CONECT   35   36   61   62
CONECT   36   63   64
END

HMDB0012242
     RDKit          3D
Ketoconazole
 64 68  0  0  0  0  0  0  0  0999 V2000
    7.9451    2.7620    1.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7288    1.3650    1.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1658    1.0678    3.1327 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0707    0.4035    1.1773 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5975    0.8338   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762   -0.3552   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0422   -0.9420    0.0480 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6389   -0.9335   -0.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929   -0.0885   -1.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242   -0.0968   -1.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294   -0.9480   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335   -0.9017   -0.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603   -1.7168   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7734   -1.4647   -0.5268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9003   -1.5145   -2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -0.8728   -2.2318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3024   -0.0501   -1.0474 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6332    1.2982   -1.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8996    2.4152   -0.8185 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9791    3.3057   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613    4.2698    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9615    3.9575    0.2837 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1472    2.8377   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4471   -0.6086   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2684   -1.5674   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4036   -2.0104   -0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7649   -1.5355    0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2042   -2.1037    1.7362 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.9801   -0.6092    1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8363   -0.1652    0.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8049    0.9112    1.8815 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643   -0.1329   -0.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021   -1.7888    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568   -1.8020    0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5908   -1.5677    1.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8963   -0.9267    1.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0005    2.8504    1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7928    3.4182    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2489    3.0292    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4182    1.2365   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8200    1.6112   -0.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7904   -1.0808   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5068   -0.0132   -1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533    0.6073   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2906    0.5769   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2490   -1.6195    1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1228   -2.7693   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912   -2.1898   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -0.8583   -2.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -2.5389   -2.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5731    1.1376   -2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8477    1.5721   -2.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9149    3.2559   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277    5.1385    0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0816    2.3367   -0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9658   -1.9297   -1.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9982   -2.7460   -0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2198   -0.2107    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8757   -2.4565    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2739   -2.4655    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8844   -1.5090    2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7416   -2.6379    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7313   -1.5610    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9473   -0.9091    2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 17 32  1  0
 11 33  1  0
 33 34  2  0
  7 35  1  0
 35 36  1  0
 36  4  1  0
 34  8  1  0
 32 14  1  0
 23 19  1  0
 30 24  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  9 44  1  0
 10 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  1
 15 49  1  0
 15 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 25 56  1  0
 26 57  1  0
 29 58  1  0
 33 59  1  0
 34 60  1  0
 35 61  1  0
 35 62  1  0
 36 63  1  0
 36 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,4R)-1-Acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine	ChEBI
1-ACETYL-4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine	ChEBI
Nizoral	Kegg
Xolegel	Kegg
ABBR KTC	Kegg
(+-)-cis-1-Acetyl-4-(P-((2-(2,4-dichlorophenyl)-2-(imidazol-1- ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine	HMDB
cis-1-Acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H- imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-ketoconazol	HMDB
Fungarest	HMDB
Fungoral	HMDB
Ketoderm	HMDB
Ketoisdin	HMDB
Orifungal m	HMDB
Panfungol	HMDB
Piperazine	HMDB
Janssen brand OF ketoconazole	MeSH, HMDB
Ketoconazole janssen brand	MeSH, HMDB
Ketoconazole	MeSH

Chemical Formula

C₂₆H₂₈Cl₂N₄O₄

Average Molecular Weight

531.431

Monoisotopic Molecular Weight

530.148760818

IUPAC Name

1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

Traditional Name

nizoral

CAS Registry Number

65277-42-1

SMILES

CC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1

InChI Identifier

InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1

InChI Key

XMAYWYJOQHXEEK-ZEQKJWHPSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Phenylpiperazines

Alternative Parents

Substituents

Phenylpiperazine
N-arylpiperazine
Aminophenyl ether
1,3-dichlorobenzene
Phenol ether
Tertiary aliphatic/aromatic amine
Phenoxy compound
Dialkylarylamine
Aniline or substituted anilines
Alkyl aryl ether
Ketal
Halobenzene
Chlorobenzene
Monocyclic benzene moiety
Aryl chloride
Aryl halide
N-substituted imidazole
Benzenoid
Meta-dioxolane
Heteroaromatic compound
Tertiary carboxylic acid amide
Imidazole
Azole
Acetamide
Carboxamide group
Amino acid or derivatives
Tertiary amine
Acetal
Oxacycle
Azacycle
Carboxylic acid derivative
Ether
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Organonitrogen compound
Organochloride
Organopnictogen compound
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cis-1-acetyl-4-(4-\{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy\}phenyl)piperazine (CHEBI:47518 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0012242)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 21543078)

Source

Exogenous

Exogenous (HMDB: HMDB0012242)

Process

Not Available

Role

Industrial application

Antifungal agent (HMDB: HMDB0012242)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0012242)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	146 °C	PhysProp
Boiling Point	753.37 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.087 mg/L	Not Available
LogP	4.35	SANGSTER (1993)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0093 g/L	ALOGPS
logP	4.3	ALOGPS
logP	4.19	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	6.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	138.07 m³·mol⁻¹	ChemAxon
Polarizability	54.67 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	209.114	30932474
DeepCCS	[M-H]-	206.719	30932474
DeepCCS	[M-2H]-	239.603	30932474
DeepCCS	[M+Na]+	215.027	30932474
AllCCS	[M+H]+	219.7	32859911
AllCCS	[M+H-H2O]+	218.1	32859911
AllCCS	[M+NH4]+	221.1	32859911
AllCCS	[M+Na]+	221.5	32859911
AllCCS	[M-H]-	211.0	32859911
AllCCS	[M+Na-2H]-	211.9	32859911
AllCCS	[M+HCOO]-	213.1	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.	5.89 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7351 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	59.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1560.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	195.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	87.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	444.5 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	473.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	194.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	873.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	396.4 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	1302.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	285.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	355.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	293.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	183.2 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ketoconazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9345700000-032f45d476928c144063	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoconazole LC-ESI-QFT , positive-QTOF	splash10-001i-3530190000-a2b05a2498270bcd4a7e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoconazole 35V, Positive-QTOF	splash10-001i-3430090000-055d7bbaadb1e1716a8b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 10V, Positive-QTOF	splash10-001i-0031490000-58a475e5974da2dfdc18	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 20V, Positive-QTOF	splash10-0ik9-5395740000-08c010ea5c947e1a62f5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 40V, Positive-QTOF	splash10-014i-9520100000-76672a88c60da8324f81	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 10V, Negative-QTOF	splash10-00or-2090150000-e4d86d7a4af384399254	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 20V, Negative-QTOF	splash10-014i-9240000000-92849351dd004ec26239	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 40V, Negative-QTOF	splash10-00or-5940000000-e2a0f55e6d356bbc9c0e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 10V, Negative-QTOF	splash10-004i-0010390000-00106b8b890fdebbf036	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 20V, Negative-QTOF	splash10-014i-9030210000-22cee3cdcfef8b4b8068	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 40V, Negative-QTOF	splash10-00o0-4930100000-6819285e7904a4b66c66	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 10V, Positive-QTOF	splash10-001i-0000090000-081787cba0594aced901	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 20V, Positive-QTOF	splash10-001i-0011980000-f9fa0eaf2d1b6889e098	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoconazole 40V, Positive-QTOF	splash10-066v-3140900000-ae27808322ff5c503bcf	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	Normal	21543078	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

DB05667

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028884

KNApSAcK ID

Not Available

Chemspider ID

43284

KEGG Compound ID

Not Available

BioCyc ID

CPD-4503

BiGG ID

Not Available

Wikipedia Link

Ketoconazole

METLIN ID

Not Available

PubChem Compound

47576

PDB ID

KLN

ChEBI ID

47518

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1670781

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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

Enzyme Details

2. Cytochrome P450 2C9

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Enzyme Details

5. Cytochrome P450 3A5

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

6. Cytochrome P450 1A1

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

Enzyme Details

7. Cytochrome P450 1A2

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

Enzyme Details

8. Cytochrome P450 2C8

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

Showing metabocard for Ketoconazole (HMDB0012242)

MOL for HMDB0012242 (Ketoconazole)

3D MOL for HMDB0012242 (Ketoconazole)

3D SDF for HMDB0012242 (Ketoconazole)

3D-SDF for HMDB0012242 (Ketoconazole)

PDB for HMDB0012242 (Ketoconazole)

3D PDB for HMDB0012242 (Ketoconazole)

SMILES for HMDB0012242 (Ketoconazole)

INCHI for HMDB0012242 (Ketoconazole)

Structure for HMDB0012242 (Ketoconazole)

3D Structure for HMDB0012242 (Ketoconazole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

Enzymes