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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (1) Show 9 proteins XML

enzymes (8)transporters (1) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015298

Secondary Accession Numbers

HMDB15298

Metabolite Identification

Common Name

Itraconazole

Description

Itraconazole is only found in individuals that have used or taken this drug. It is one of the triazole antifungal agents that inhibits cytochrome P-450-dependent enzymes resulting in impairment of ergosterol synthesis. It has been used against histoplasmosis, blastomycosis, cryptococcal meningitis & aspergillosis. [PubChem]Itraconazole 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. Itraconazole 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

1167
  Mrv0541 02231215172D          

 49 55  0  0  1  0            999 V2000
    2.8383   -1.7653    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -4.2403    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0923   -0.9403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0123   -0.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3034    0.9063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8172    2.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4420    1.9261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0113    2.4359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695   -0.6432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1498    3.4558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558    0.1773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4847    3.4558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2298    4.2403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -0.9403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3473   -0.1557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6798    0.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6135    2.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0551    1.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3981    2.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8397    1.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826   -1.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -1.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    0.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6573    1.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7959    2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -2.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9818   -2.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4858    0.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0443    2.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881    1.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4090    2.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9674    3.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7011    0.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2596    1.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3651    3.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1936    2.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7521    3.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9818   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2694    3.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -3.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8172    2.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8824    3.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021    0.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4047    4.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4409    2.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6671    3.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 43  1  0  0  0  0
  3 15  1  0  0  0  0
  3 16  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  5 24  1  0  0  0  0
  5 31  1  0  0  0  0
  6 44  2  0  0  0  0
  7 18  1  0  0  0  0
  7 19  1  0  0  0  0
  7 25  1  0  0  0  0
  8 20  1  0  0  0  0
  8 21  1  0  0  0  0
  8 26  1  0  0  0  0
  9 11  1  0  0  0  0
  9 22  1  0  0  0  0
  9 41  1  0  0  0  0
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 18 20  1  0  0  0  0
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 29 34  1  0  0  0  0
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 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 39 43  2  0  0  0  0
 40 43  1  0  0  0  0
 42 45  1  0  0  0  0
 42 48  1  0  0  0  0
 45 49  1  0  0  0  0
M  END

HMDB0015298
     RDKit          3D
Itraconazole
 87 93  0  0  0  0  0  0  0  0999 V2000
   12.6557   -0.4448   -0.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4809    0.9523    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3717    1.6228   -0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1264    3.0333   -0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1358    0.8599   -0.6130 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0249   -0.4779   -0.6219 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7335   -0.8389   -0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9907    0.2907   -0.4767 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5713    0.2977   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7138    0.1824   -1.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3367    0.1929   -1.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7499    0.3208   -0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3469    0.3148    0.1248 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009    0.8958    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.0326    1.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -0.9373    0.9623 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -1.2573    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912   -1.0754    2.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -1.3485    2.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911   -1.8266    1.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2932   -2.0720    1.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2892   -2.4976    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6696   -1.5404   -0.2065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9594   -2.0829   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7158   -0.9637   -1.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1679    0.1236   -0.4103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1558    0.7058    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4422   -0.3550    1.5360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8294   -0.6405    2.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4308   -1.7156    3.2709 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4220   -2.0790    2.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4142   -1.2509    1.4129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7024    1.1071   -1.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3847    1.5235   -1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847    2.4531   -2.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8876    2.9863   -3.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2913    4.1669   -4.4579 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -8.2000    2.5825   -3.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6050    1.6344   -2.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3021    1.1839   -2.3523 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.0916   -0.3361    0.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057   -2.0124    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0591   -1.7251    0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -1.5146   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099   -0.3265   -0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6199    0.4371    1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9851    0.4247    0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8677    1.3011   -0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5055    2.5046   -0.4844 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3144   -0.5084   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
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   13.4096    1.5156   -0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2578    0.9197    1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7138    1.6646   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4687    2.9920    0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3934    1.2661    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1506   -0.5615    2.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9884   -0.1149    3.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.8971    3.0118   -3.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9672   -2.3970   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2014    0.5342    2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6626    0.5178    1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
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 46 86  1  0
 47 87  1  0
M  END

1167
  Mrv0541 02231215172D          

 49 55  0  0  1  0            999 V2000
    2.8383   -1.7653    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -4.2403    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0923   -0.9403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0123   -0.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3034    0.9063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8172    2.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4420    1.9261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0113    2.4359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695   -0.6432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1498    3.4558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558    0.1773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4847    3.4558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2298    4.2403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -0.9403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3473   -0.1557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6798    0.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6135    2.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0551    1.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3981    2.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8397    1.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826   -1.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -1.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    0.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6573    1.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7959    2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -2.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9818   -2.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4858    0.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0443    2.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881    1.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4090    2.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9674    3.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7011    0.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2596    1.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3651    3.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1936    2.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7521    3.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9818   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2694    3.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -3.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8172    2.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8824    3.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021    0.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4047    4.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4409    2.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6671    3.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 43  1  0  0  0  0
  3 15  1  0  0  0  0
  3 16  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  5 24  1  0  0  0  0
  5 31  1  0  0  0  0
  6 44  2  0  0  0  0
  7 18  1  0  0  0  0
  7 19  1  0  0  0  0
  7 25  1  0  0  0  0
  8 20  1  0  0  0  0
  8 21  1  0  0  0  0
  8 26  1  0  0  0  0
  9 11  1  0  0  0  0
  9 22  1  0  0  0  0
  9 41  1  0  0  0  0
 10 36  1  0  0  0  0
 10 44  1  0  0  0  0
 10 47  1  0  0  0  0
 11 46  2  0  0  0  0
 12 14  1  0  0  0  0
 12 42  1  0  0  0  0
 12 44  1  0  0  0  0
 13 41  2  0  0  0  0
 13 46  1  0  0  0  0
 14 47  2  0  0  0  0
 15 22  1  6  0  0  0
 15 23  1  0  0  0  0
 16 17  1  0  0  0  0
 16 24  1  6  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 23 27  2  0  0  0  0
 23 28  1  0  0  0  0
 25 29  2  0  0  0  0
 25 30  1  0  0  0  0
 26 32  2  0  0  0  0
 26 33  1  0  0  0  0
 27 39  1  0  0  0  0
 28 40  2  0  0  0  0
 29 34  1  0  0  0  0
 30 35  2  0  0  0  0
 31 34  2  0  0  0  0
 31 35  1  0  0  0  0
 32 37  1  0  0  0  0
 33 38  2  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 39 43  2  0  0  0  0
 40 43  1  0  0  0  0
 42 45  1  0  0  0  0
 42 48  1  0  0  0  0
 45 49  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015298

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)N1N=CN(C1=O)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1

> <INCHI_KEY>
VHVPQPYKVGDNFY-ZPGVKDDISA-N

> <FORMULA>
C35H38Cl2N8O4

> <MOLECULAR_WEIGHT>
705.633

> <EXACT_MASS>
704.239307158

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
74.69824682545351

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one

> <ALOGPS_LOGP>
5.48

> <JCHEM_LOGP>
7.311371119666667

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.9185762016978543

> <JCHEM_POLAR_SURFACE_AREA>
100.79

> <JCHEM_REFRACTIVITY>
200.3999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
itraconazole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015298
     RDKit          3D
Itraconazole
 87 93  0  0  0  0  0  0  0  0999 V2000
   12.6557   -0.4448   -0.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4809    0.9523    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3717    1.6228   -0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1264    3.0333   -0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1358    0.8599   -0.6130 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0249   -0.4779   -0.6219 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7335   -0.8389   -0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9907    0.2907   -0.4767 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5713    0.2977   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7138    0.1824   -1.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3367    0.1929   -1.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7499    0.3208   -0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3469    0.3148    0.1248 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009    0.8958    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.0326    1.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -0.9373    0.9623 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -1.2573    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912   -1.0754    2.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -1.3485    2.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911   -1.8266    1.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2932   -2.0720    1.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2892   -2.4976    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6696   -1.5404   -0.2065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9594   -2.0829   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7158   -0.9637   -1.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1679    0.1236   -0.4103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1558    0.7058    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4422   -0.3550    1.5360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8294   -0.6405    2.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4308   -1.7156    3.2709 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4220   -2.0790    2.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4142   -1.2509    1.4129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7024    1.1071   -1.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3847    1.5235   -1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847    2.4531   -2.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8876    2.9863   -3.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2913    4.1669   -4.4579 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -8.2000    2.5825   -3.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6050    1.6344   -2.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3021    1.1839   -2.3523 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.0916   -0.3361    0.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057   -2.0124    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0591   -1.7251    0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -1.5146   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099   -0.3265   -0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6199    0.4371    1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9851    0.4247    0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8677    1.3011   -0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5055    2.5046   -0.4844 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3144   -0.5084   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1396   -1.1599    0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7519   -0.6848   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4096    1.5156   -0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2578    0.9197    1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7138    1.6646   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4687    2.9920    0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1006    3.5364    0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7224    3.6134   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3250   -1.8390   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1645    0.0803   -2.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331    0.1028   -2.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1741    1.8262    0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3934    1.2661    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1506   -0.5615    2.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    0.6258    2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2963   -0.7164    3.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7213   -1.2168    3.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2352   -2.7832    1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9742   -3.4646    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9158   -1.3822   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5008   -2.7142   -0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7436   -2.6561   -1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0880    1.0306    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7387    1.5842    1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9884   -0.1149    3.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0925   -2.8962    2.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6994    1.0834   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9507    2.7616   -2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8971    3.0118   -3.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9672   -2.3970   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -1.8770   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7906   -2.0413    0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324   -2.1553   -0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6756    0.4043   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9879   -0.6484   -1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014    0.5342    2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6626    0.5178    1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
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  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
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 41 23  1  0
 32 28  1  0
 39 33  1  0
  1 50  1  0
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 47 87  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1167                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.298  -3.295   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       7.965  -7.915   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       9.506  -1.755   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.490  -0.291   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.766   1.692   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      27.659   4.005   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      17.625   3.595   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      20.554   4.547   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       5.356  -1.201   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      26.413   6.451   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       5.517   0.331   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      28.905   6.451   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       3.080  -0.187   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      28.429   7.915   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       7.965  -1.755   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.982  -0.291   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.736   0.615   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.945   5.102   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.770   2.565   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.410   5.578   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.234   3.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.501  -2.231   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.965  -3.295   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.446   0.185   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.160   3.119   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.019   5.023   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.632  -4.065   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.299  -4.065   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.840   1.613   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.016   4.150   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.231   2.168   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      23.163   3.993   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      22.339   6.529   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.375   1.137   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.551   3.674   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      24.948   5.975   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      24.628   4.468   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      23.804   7.005   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.632  -5.605   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.299  -5.605   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.850  -1.521   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      30.370   5.975   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.965  -6.375   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      27.659   5.545   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      31.514   7.005   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.111   0.957   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      26.889   7.915   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      30.690   4.468   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      32.979   6.529   0.000  0.00  0.00           C+0
CONECT    1   27                                                            
CONECT    2   43                                                            
CONECT    3   15   16                                                       
CONECT    4   15   17                                                       
CONECT    5   24   31                                                       
CONECT    6   44                                                            
CONECT    7   18   19   25                                                  
CONECT    8   20   21   26                                                  
CONECT    9   11   22   41                                                  
CONECT   10   36   44   47                                                  
CONECT   11    9   46                                                       
CONECT   12   14   42   44                                                  
CONECT   13   41   46                                                       
CONECT   14   12   47                                                       
CONECT   15    3    4   22   23                                             
CONECT   16    3   17   24                                                  
CONECT   17    4   16                                                       
CONECT   18    7   20                                                       
CONECT   19    7   21                                                       
CONECT   20    8   18                                                       
CONECT   21    8   19                                                       
CONECT   22    9   15                                                       
CONECT   23   15   27   28                                                  
CONECT   24    5   16                                                       
CONECT   25    7   29   30                                                  
CONECT   26    8   32   33                                                  
CONECT   27    1   23   39                                                  
CONECT   28   23   40                                                       
CONECT   29   25   34                                                       
CONECT   30   25   35                                                       
CONECT   31    5   34   35                                                  
CONECT   32   26   37                                                       
CONECT   33   26   38                                                       
CONECT   34   29   31                                                       
CONECT   35   30   31                                                       
CONECT   36   10   37   38                                                  
CONECT   37   32   36                                                       
CONECT   38   33   36                                                       
CONECT   39   27   43                                                       
CONECT   40   28   43                                                       
CONECT   41    9   13                                                       
CONECT   42   12   45   48                                                  
CONECT   43    2   39   40                                                  
CONECT   44    6   10   12                                                  
CONECT   45   42   49                                                       
CONECT   46   11   13                                                       
CONECT   47   10   14                                                       
CONECT   48   42                                                            
CONECT   49   45                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  110    0
END

COMPND    HMDB0015298
HETATM    1  C1  UNL     1      12.656  -0.445  -0.451  1.00  0.00           C  
HETATM    2  C2  UNL     1      12.481   0.952   0.097  1.00  0.00           C  
HETATM    3  C3  UNL     1      11.372   1.623  -0.686  1.00  0.00           C  
HETATM    4  C4  UNL     1      11.126   3.033  -0.201  1.00  0.00           C  
HETATM    5  N1  UNL     1      10.136   0.860  -0.613  1.00  0.00           N  
HETATM    6  N2  UNL     1      10.025  -0.478  -0.622  1.00  0.00           N  
HETATM    7  C5  UNL     1       8.734  -0.839  -0.540  1.00  0.00           C  
HETATM    8  N3  UNL     1       7.991   0.291  -0.477  1.00  0.00           N  
HETATM    9  C6  UNL     1       6.571   0.298  -0.378  1.00  0.00           C  
HETATM   10  C7  UNL     1       5.714   0.182  -1.448  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.337   0.193  -1.297  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.750   0.321  -0.051  1.00  0.00           C  
HETATM   13  N4  UNL     1       2.347   0.315   0.125  1.00  0.00           N  
HETATM   14  C10 UNL     1       1.701   0.896   1.252  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.709  -0.033   1.916  1.00  0.00           C  
HETATM   16  N5  UNL     1       0.096  -0.937   0.962  1.00  0.00           N  
HETATM   17  C12 UNL     1      -1.284  -1.257   1.105  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.891  -1.075   2.339  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.200  -1.348   2.508  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.991  -1.827   1.438  1.00  0.00           C  
HETATM   21  O1  UNL     1      -5.293  -2.072   1.716  1.00  0.00           O  
HETATM   22  C16 UNL     1      -6.289  -2.498   0.895  1.00  0.00           C  
HETATM   23  C17 UNL     1      -6.670  -1.540  -0.206  1.00  0.00           C  
HETATM   24  C18 UNL     1      -7.959  -2.083  -0.810  1.00  0.00           C  
HETATM   25  O2  UNL     1      -8.716  -0.964  -1.027  1.00  0.00           O  
HETATM   26  C19 UNL     1      -8.168   0.124  -0.410  1.00  0.00           C  
HETATM   27  C20 UNL     1      -9.156   0.706   0.569  1.00  0.00           C  
HETATM   28  N6  UNL     1      -9.442  -0.355   1.536  1.00  0.00           N  
HETATM   29  C21 UNL     1      -8.829  -0.641   2.689  1.00  0.00           C  
HETATM   30  N7  UNL     1      -9.431  -1.716   3.271  1.00  0.00           N  
HETATM   31  C22 UNL     1     -10.422  -2.079   2.449  1.00  0.00           C  
HETATM   32  N8  UNL     1     -10.414  -1.251   1.413  1.00  0.00           N  
HETATM   33  C23 UNL     1      -7.702   1.107  -1.415  1.00  0.00           C  
HETATM   34  C24 UNL     1      -6.385   1.524  -1.477  1.00  0.00           C  
HETATM   35  C25 UNL     1      -5.985   2.453  -2.412  1.00  0.00           C  
HETATM   36  C26 UNL     1      -6.888   2.986  -3.302  1.00  0.00           C  
HETATM   37 CL1  UNL     1      -6.291   4.167  -4.458  1.00  0.00          CL  
HETATM   38  C27 UNL     1      -8.200   2.583  -3.252  1.00  0.00           C  
HETATM   39  C28 UNL     1      -8.605   1.634  -2.299  1.00  0.00           C  
HETATM   40 CL2  UNL     1     -10.302   1.184  -2.352  1.00  0.00          CL  
HETATM   41  O3  UNL     1      -7.092  -0.336   0.367  1.00  0.00           O  
HETATM   42  C29 UNL     1      -3.406  -2.012   0.215  1.00  0.00           C  
HETATM   43  C30 UNL     1      -2.059  -1.725   0.062  1.00  0.00           C  
HETATM   44  C31 UNL     1       0.887  -1.515  -0.101  1.00  0.00           C  
HETATM   45  C32 UNL     1       1.510  -0.326  -0.860  1.00  0.00           C  
HETATM   46  C33 UNL     1       4.620   0.437   1.033  1.00  0.00           C  
HETATM   47  C34 UNL     1       5.985   0.425   0.862  1.00  0.00           C  
HETATM   48  C35 UNL     1       8.868   1.301  -0.523  1.00  0.00           C  
HETATM   49  O4  UNL     1       8.506   2.505  -0.484  1.00  0.00           O  
HETATM   50  H1  UNL     1      12.314  -0.508  -1.495  1.00  0.00           H  
HETATM   51  H2  UNL     1      12.140  -1.160   0.224  1.00  0.00           H  
HETATM   52  H3  UNL     1      13.752  -0.685  -0.465  1.00  0.00           H  
HETATM   53  H4  UNL     1      13.410   1.516  -0.129  1.00  0.00           H  
HETATM   54  H5  UNL     1      12.258   0.920   1.184  1.00  0.00           H  
HETATM   55  H6  UNL     1      11.714   1.665  -1.740  1.00  0.00           H  
HETATM   56  H7  UNL     1      10.469   2.992   0.674  1.00  0.00           H  
HETATM   57  H8  UNL     1      12.101   3.536   0.052  1.00  0.00           H  
HETATM   58  H9  UNL     1      10.722   3.613  -1.052  1.00  0.00           H  
HETATM   59  H10 UNL     1       8.325  -1.839  -0.525  1.00  0.00           H  
HETATM   60  H11 UNL     1       6.164   0.080  -2.449  1.00  0.00           H  
HETATM   61  H12 UNL     1       3.733   0.103  -2.200  1.00  0.00           H  
HETATM   62  H13 UNL     1       1.174   1.826   0.874  1.00  0.00           H  
HETATM   63  H14 UNL     1       2.393   1.266   2.017  1.00  0.00           H  
HETATM   64  H15 UNL     1       1.151  -0.562   2.781  1.00  0.00           H  
HETATM   65  H16 UNL     1      -0.092   0.626   2.314  1.00  0.00           H  
HETATM   66  H17 UNL     1      -1.296  -0.716   3.163  1.00  0.00           H  
HETATM   67  H18 UNL     1      -3.721  -1.217   3.476  1.00  0.00           H  
HETATM   68  H19 UNL     1      -7.235  -2.783   1.446  1.00  0.00           H  
HETATM   69  H20 UNL     1      -5.974  -3.465   0.415  1.00  0.00           H  
HETATM   70  H21 UNL     1      -5.916  -1.382  -0.963  1.00  0.00           H  
HETATM   71  H22 UNL     1      -8.501  -2.714  -0.058  1.00  0.00           H  
HETATM   72  H23 UNL     1      -7.744  -2.656  -1.709  1.00  0.00           H  
HETATM   73  H24 UNL     1     -10.088   1.031   0.117  1.00  0.00           H  
HETATM   74  H25 UNL     1      -8.739   1.584   1.109  1.00  0.00           H  
HETATM   75  H26 UNL     1      -7.988  -0.115   3.110  1.00  0.00           H  
HETATM   76  H27 UNL     1     -11.092  -2.896   2.615  1.00  0.00           H  
HETATM   77  H28 UNL     1      -5.699   1.083  -0.761  1.00  0.00           H  
HETATM   78  H29 UNL     1      -4.951   2.762  -2.441  1.00  0.00           H  
HETATM   79  H30 UNL     1      -8.897   3.012  -3.958  1.00  0.00           H  
HETATM   80  H31 UNL     1      -3.967  -2.397  -0.620  1.00  0.00           H  
HETATM   81  H32 UNL     1      -1.618  -1.877  -0.931  1.00  0.00           H  
HETATM   82  H33 UNL     1       1.791  -2.041   0.334  1.00  0.00           H  
HETATM   83  H34 UNL     1       0.332  -2.155  -0.773  1.00  0.00           H  
HETATM   84  H35 UNL     1       0.676   0.404  -1.061  1.00  0.00           H  
HETATM   85  H36 UNL     1       1.988  -0.648  -1.772  1.00  0.00           H  
HETATM   86  H37 UNL     1       4.201   0.534   2.038  1.00  0.00           H  
HETATM   87  H38 UNL     1       6.663   0.518   1.727  1.00  0.00           H  
CONECT    1    2   50   51   52
CONECT    2    3   53   54
CONECT    3    4    5   55
CONECT    4   56   57   58
CONECT    5    6   48
CONECT    6    7    7
CONECT    7    8   59
CONECT    8    9   48
CONECT    9   10   10   47
CONECT   10   11   60
CONECT   11   12   12   61
CONECT   12   13   46
CONECT   13   14   45
CONECT   14   15   62   63
CONECT   15   16   64   65
CONECT   16   17   44
CONECT   17   18   18   43
CONECT   18   19   66
CONECT   19   20   20   67
CONECT   20   21   42
CONECT   21   22
CONECT   22   23   68   69
CONECT   23   24   41   70
CONECT   24   25   71   72
CONECT   25   26
CONECT   26   27   33   41
CONECT   27   28   73   74
CONECT   28   29   32
CONECT   29   30   30   75
CONECT   30   31
CONECT   31   32   32   76
CONECT   33   34   34   39
CONECT   34   35   77
CONECT   35   36   36   78
CONECT   36   37   38
CONECT   38   39   39   79
CONECT   39   40
CONECT   42   43   43   80
CONECT   43   81
CONECT   44   45   82   83
CONECT   45   84   85
CONECT   46   47   47   86
CONECT   47   87
CONECT   48   49   49
END

HMDB0015298
     RDKit          3D
Itraconazole
 87 93  0  0  0  0  0  0  0  0999 V2000
   12.6557   -0.4448   -0.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4809    0.9523    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3717    1.6228   -0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1264    3.0333   -0.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1358    0.8599   -0.6130 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0249   -0.4779   -0.6219 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7335   -0.8389   -0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9907    0.2907   -0.4767 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5713    0.2977   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7138    0.1824   -1.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3367    0.1929   -1.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7499    0.3208   -0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3469    0.3148    0.1248 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009    0.8958    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.0326    1.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -0.9373    0.9623 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -1.2573    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912   -1.0754    2.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -1.3485    2.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911   -1.8266    1.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2932   -2.0720    1.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2892   -2.4976    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6696   -1.5404   -0.2065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9594   -2.0829   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7158   -0.9637   -1.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1679    0.1236   -0.4103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1558    0.7058    0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4422   -0.3550    1.5360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8294   -0.6405    2.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4308   -1.7156    3.2709 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4220   -2.0790    2.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4142   -1.2509    1.4129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7024    1.1071   -1.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3847    1.5235   -1.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847    2.4531   -2.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8876    2.9863   -3.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2913    4.1669   -4.4579 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -8.2000    2.5825   -3.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6050    1.6344   -2.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3021    1.1839   -2.3523 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.0916   -0.3361    0.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057   -2.0124    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0591   -1.7251    0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -1.5146   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099   -0.3265   -0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6199    0.4371    1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9851    0.4247    0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8677    1.3011   -0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5055    2.5046   -0.4844 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3144   -0.5084   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1396   -1.1599    0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7519   -0.6848   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4096    1.5156   -0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2578    0.9197    1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7138    1.6646   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4687    2.9920    0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1006    3.5364    0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7224    3.6134   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3250   -1.8390   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1645    0.0803   -2.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7331    0.1028   -2.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1741    1.8262    0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3934    1.2661    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1506   -0.5615    2.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    0.6258    2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2963   -0.7164    3.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7213   -1.2168    3.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2352   -2.7832    1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9742   -3.4646    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9158   -1.3822   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5008   -2.7142   -0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7436   -2.6561   -1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0880    1.0306    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7387    1.5842    1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9884   -0.1149    3.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0925   -2.8962    2.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6994    1.0834   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9507    2.7616   -2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8971    3.0118   -3.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9672   -2.3970   -0.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -1.8770   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7906   -2.0413    0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324   -2.1553   -0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6756    0.4043   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9879   -0.6484   -1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2014    0.5342    2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6626    0.5178    1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 26 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 39 40  1  0
 26 41  1  0
 20 42  1  0
 42 43  2  0
 16 44  1  0
 44 45  1  0
 12 46  1  0
 46 47  2  0
  8 48  1  0
 48 49  2  0
 48  5  1  0
 47  9  1  0
 45 13  1  0
 43 17  1  0
 41 23  1  0
 32 28  1  0
 39 33  1  0
  1 50  1  0
  1 51  1  0
  1 52  1  0
  2 53  1  0
  2 54  1  0
  3 55  1  0
  4 56  1  0
  4 57  1  0
  4 58  1  0
  7 59  1  0
 10 60  1  0
 11 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  0
 15 65  1  0
 18 66  1  0
 19 67  1  0
 22 68  1  0
 22 69  1  0
 23 70  1  6
 24 71  1  0
 24 72  1  0
 27 73  1  0
 27 74  1  0
 29 75  1  0
 31 76  1  0
 34 77  1  0
 35 78  1  0
 38 79  1  0
 42 80  1  0
 43 81  1  0
 44 82  1  0
 44 83  1  0
 45 84  1  0
 45 85  1  0
 46 86  1  0
 47 87  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Itrizole	ChEBI
Oriconazole	ChEBI
Sporanox	ChEBI
ITC	HMDB
ITCZ	HMDB
ITZ	HMDB
Orungal	HMDB
Itraconazole janssen brand	HMDB
Janssen brand OF itraconazole	HMDB
Janssen cilag brand OF itraconazole	HMDB
Janssen-cilag brand OF itraconazole	HMDB

Chemical Formula

C₃₅H₃₈Cl₂N₈O₄

Average Molecular Weight

705.633

Monoisotopic Molecular Weight

704.239307158

IUPAC Name

1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one

Traditional Name

itraconazole

CAS Registry Number

84625-61-6

SMILES

CCC(C)N1N=CN(C1=O)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1

InChI Identifier

InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:6076 )
triazole antifungal drug (CHEBI:6076 )
conazole antifungal drug (CHEBI:6076 )
dioxolane (CHEBI:6076 )
dichlorobenzene (CHEBI:6076 )
triazoles (CHEBI:6076 )
cyclic ketal (CHEBI:6076 )

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

Cytoplasm (HMDB: HMDB0015298)
Membrane (HMDB: HMDB0015298)

Source

Exogenous

Exogenous (HMDB: HMDB0015298)

Process

Not Available

Role

Industrial application

Antifungal agent (HMDB: HMDB0015298)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	166.2 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0096 g/L	Not Available
LogP	6.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0096 g/L	ALOGPS
logP	5.48	ALOGPS
logP	7.31	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	3.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	100.79 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	200.4 m³·mol⁻¹	ChemAxon
Polarizability	74.7 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	251.414	30932474
DeepCCS	[M-H]-	249.59	30932474
DeepCCS	[M-2H]-	283.11	30932474
DeepCCS	[M+Na]+	257.02	30932474
AllCCS	[M+H]+	255.1	32859911
AllCCS	[M+H-H2O]+	254.7	32859911
AllCCS	[M+NH4]+	255.4	32859911
AllCCS	[M+Na]+	255.4	32859911
AllCCS	[M-H]-	224.0	32859911
AllCCS	[M+Na-2H]-	226.4	32859911
AllCCS	[M+HCOO]-	229.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.15 minutes	32390414
Predicted by Siyang on May 30, 2022	18.4977 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3205.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	235.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	268.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	192.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	974.9 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	876.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1614.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	725.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2159.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	527.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	568.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	188.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	68.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Itraconazole	CCC(C)N1N=CN(C1=O)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1	6499.7	Standard polar	33892256
Itraconazole	CCC(C)N1N=CN(C1=O)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1	5223.9	Standard non polar	33892256
Itraconazole	CCC(C)N1N=CN(C1=O)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1	6441.8	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 - Itraconazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-6214197000-1ee5b13e7088e9cfe8f4	2017-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Itraconazole LC-ESI-qTof , Positive-QTOF	splash10-0lz0-0594300000-f8fca354ab686af07f2d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Itraconazole LC-ESI-qTof , Positive-QTOF	splash10-0lz0-0594300000-f8fca354ab686af07f2d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Itraconazole , positive-QTOF	splash10-0udi-0329000000-18fc35342fd0b509b439	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Itraconazole , positive-QTOF	splash10-0a4i-0112100900-c45b863fbc00a8c449b4	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 10V, Positive-QTOF	splash10-0a4i-2014019700-85126d2b5b6964cb167d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 20V, Positive-QTOF	splash10-03di-4911034000-399215ad81f2268c5d61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 40V, Positive-QTOF	splash10-00di-9132010000-ae7c2d5fe82a8f94b236	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 10V, Negative-QTOF	splash10-014i-9013020100-071002be4024d571dbb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 20V, Negative-QTOF	splash10-014i-9011000000-14b98a8a8e8671d57c64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 40V, Negative-QTOF	splash10-00or-7094010000-5df5528d83df0744427a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 10V, Negative-QTOF	splash10-0udi-1000002900-92f9c0efb49798e3bcf6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 20V, Negative-QTOF	splash10-0ufr-2020019400-0234895cdc4dcdafd7ad	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 40V, Negative-QTOF	splash10-0uyl-5284109100-cbdacae0a2b5183f54c6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 10V, Positive-QTOF	splash10-0a4i-0000001900-c0509f1b5423bc42d985	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 20V, Positive-QTOF	splash10-0a4i-0000037900-6204ee9c5fe37a35c4f4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Itraconazole 40V, Positive-QTOF	splash10-00di-9040343100-71b0ddcafedcd83a768c	2021-10-11	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	Taking drug identified by DrugBank entry DB01167	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01167	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

DB01167

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

49927

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Itraconazole

METLIN ID

Not Available

PubChem Compound

55283

PDB ID

Not Available

ChEBI ID

6076

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)

Download (PDF)

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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Cotrim PC, Garrity LK, Beverley SM: Isolation of genes mediating resistance to inhibitors of nucleoside and ergosterol metabolism in Leishmania by overexpression/selection. J Biol Chem. 1999 Dec 31;274(53):37723-30. [PubMed:10608831 ]
Carrillo-Munoz AJ, Giusiano G, Ezkurra PA, Quindos G: Antifungal agents: mode of action in yeast cells. Rev Esp Quimioter. 2006 Jun;19(2):130-9. [PubMed:16964330 ]

Enzyme Details

2. 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

Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567 ]
Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [PubMed:15969931 ]
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 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

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

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

5. Cytochrome P450 2B6

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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742 ]

Enzyme Details

6. 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

7. 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

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

8. Cytochrome P450 3A7

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:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
Wang EJ, Lew K, Casciano CN, Clement RP, Johnson WW: Interaction of common azole antifungals with P glycoprotein. Antimicrob Agents Chemother. 2002 Jan;46(1):160-5. [PubMed:11751127 ]
Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
Takara K, Tanigawara Y, Komada F, Nishiguchi K, Sakaeda T, Okumura K: Cellular pharmacokinetic aspects of reversal effect of itraconazole on P-glycoprotein-mediated resistance of anticancer drugs. Biol Pharm Bull. 1999 Dec;22(12):1355-9. [PubMed:10746169 ]
Masuda S, Inui K: [Molecular mechanisms on drug transporters in the drug absorption and disposition]. Nihon Rinsho. 2002 Jan;60(1):65-73. [PubMed:11808341 ]
Lilja JJ, Backman JT, Laitila J, Luurila H, Neuvonen PJ: Itraconazole increases but grapefruit juice greatly decreases plasma concentrations of celiprolol. Clin Pharmacol Ther. 2003 Mar;73(3):192-8. [PubMed:12621384 ]
Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [PubMed:15969931 ]
Saito M, Hirata-Koizumi M, Miyake S, Hasegawa R: Comparison of information on the pharmacokinetic interactions of Ca antagonists in the package inserts from three countries (Japan, USA and UK). Eur J Clin Pharmacol. 2005 Aug;61(7):531-6. Epub 2005 Jul 23. [PubMed:16041596 ]
Shon JH, Yoon YR, Hong WS, Nguyen PM, Lee SS, Choi YG, Cha IJ, Shin JG: Effect of itraconazole on the pharmacokinetics and pharmacodynamics of fexofenadine in relation to the MDR1 genetic polymorphism. Clin Pharmacol Ther. 2005 Aug;78(2):191-201. [PubMed:16084853 ]

Showing metabocard for Itraconazole (HMDB0015298)

MOL for HMDB0015298 (Itraconazole)

3D MOL for HMDB0015298 (Itraconazole)

3D SDF for HMDB0015298 (Itraconazole)

3D-SDF for HMDB0015298 (Itraconazole)

PDB for HMDB0015298 (Itraconazole)

3D PDB for HMDB0015298 (Itraconazole)

SMILES for HMDB0015298 (Itraconazole)

INCHI for HMDB0015298 (Itraconazole)

Structure for HMDB0015298 (Itraconazole)

3D Structure for HMDB0015298 (Itraconazole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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