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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

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014720

Secondary Accession Numbers

HMDB14720

Metabolite Identification

Common Name

Voriconazole

Description

Voriconazole, also known as vfend or VCZ, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Voriconazole is a drug which is used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by scedosporium apiospermum and fusarium spp. Voriconazole is a moderately basic compound (based on its pKa).

Structure

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

HMDB0014720
     RDKit          3D
Voriconazole
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.7180    0.9239   -2.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702   -0.2080   -1.4235 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0434   -0.4691   -0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9339    0.5059   -0.0007 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172    0.4108    0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8492   -0.7142    1.7294 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -1.7197    1.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679   -1.6130    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692   -2.6752    0.1778 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262    0.3523   -0.8958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0652    0.7617   -1.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385    1.4747    0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134    2.1625    0.5113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    2.1424    1.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0502    3.0995    1.3452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7323    3.7251    0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547    3.1891   -0.2892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721   -0.7777   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1627   -0.9017    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750   -2.0216    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1960   -3.0298    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7933   -4.1143    1.4384 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111   -2.9260   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4144   -1.8358   -1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331   -1.7393   -2.4032 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5756    0.4269   -2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    1.2916   -2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1539    1.6704   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283   -1.0428   -2.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233    1.1995    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0050   -2.6241    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9749    1.7296   -2.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4795    1.0951    0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992    2.2036   -0.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1120    1.4980    2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3296    4.5618   -0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035   -0.1959    1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053   -2.0658    2.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558   -3.7505   -1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  2 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
  8  3  1  0
 17 13  1  0
 24 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  6
  5 30  1  0
  7 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 16 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
M  END

582
  Mrv0541 02231214472D          

 25 27  0  0  1  0            999 V2000
    1.6500   -0.4125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.4125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.8875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5359   -0.1178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3364    0.0818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433   -1.2499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0790    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9040    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4784   -0.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7736   -0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2 18  1  0  0  0  0
  3 22  1  0  0  0  0
 10  4  1  1  0  0  0
  5  7  1  0  0  0  0
  5 12  1  0  0  0  0
  5 21  1  0  0  0  0
  6 15  2  0  0  0  0
  6 24  1  0  0  0  0
  7 25  2  0  0  0  0
  8 21  2  0  0  0  0
  8 25  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  1  0  0  0
 11 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 23  2  0  0  0  0
 19 22  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014720

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](C1=NC=NC=C1F)[C@](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/m0/s1

> <INCHI_KEY>
BCEHBSKCWLPMDN-MGPLVRAMSA-N

> <FORMULA>
C16H14F3N5O

> <MOLECULAR_WEIGHT>
349.3105

> <EXACT_MASS>
349.11504471

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.54426257953428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.8230325923333337

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.708208344255155

> <JCHEM_PKA_STRONGEST_BASIC>
2.268914242488986

> <JCHEM_POLAR_SURFACE_AREA>
76.72

> <JCHEM_REFRACTIVITY>
95.27799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
voriconazole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014720
     RDKit          3D
Voriconazole
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.7180    0.9239   -2.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702   -0.2080   -1.4235 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0434   -0.4691   -0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9339    0.5059   -0.0007 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172    0.4108    0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8492   -0.7142    1.7294 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -1.7197    1.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679   -1.6130    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692   -2.6752    0.1778 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262    0.3523   -0.8958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0652    0.7617   -1.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385    1.4747    0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134    2.1625    0.5113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    2.1424    1.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0502    3.0995    1.3452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7323    3.7251    0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547    3.1891   -0.2892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721   -0.7777   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1627   -0.9017    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750   -2.0216    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1960   -3.0298    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7933   -4.1143    1.4384 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111   -2.9260   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4144   -1.8358   -1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331   -1.7393   -2.4032 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5756    0.4269   -2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    1.2916   -2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1539    1.6704   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283   -1.0428   -2.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233    1.1995    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0050   -2.6241    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9749    1.7296   -2.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4795    1.0951    0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992    2.2036   -0.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1120    1.4980    2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3296    4.5618   -0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035   -0.1959    1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053   -2.0658    2.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558   -3.7505   -1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  2 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
  8  3  1  0
 17 13  1  0
 24 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  6
  5 30  1  0
  7 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 16 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 582                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       3.080  -0.770   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       8.415   0.770   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       5.747  -5.390   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0       4.207   0.770   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.467  -0.220   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.081   4.620   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.961   0.153   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       9.787  -2.333   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.748   4.620   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.747   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.287   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.360  -1.756   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.747  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748   3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.415   5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.777  -1.153   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   18                                                            
CONECT    3   22                                                            
CONECT    4   10                                                            
CONECT    5    7   12   21                                                  
CONECT    6   15   24                                                       
CONECT    7    5   25                                                       
CONECT    8   21   25                                                       
CONECT    9   23   24                                                       
CONECT   10    4   11   12   13                                             
CONECT   11   10   14   15                                                  
CONECT   12    5   10                                                       
CONECT   13   10   16   17                                                  
CONECT   14   11                                                            
CONECT   15    6   11   18                                                  
CONECT   16    1   13   19                                                  
CONECT   17   13   20                                                       
CONECT   18    2   15   23                                                  
CONECT   19   16   22                                                       
CONECT   20   17   22                                                       
CONECT   21    5    8                                                       
CONECT   22    3   19   20                                                  
CONECT   23    9   18                                                       
CONECT   24    6    9                                                       
CONECT   25    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0014720
HETATM    1  C1  UNL     1       1.718   0.924  -2.301  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.070  -0.208  -1.424  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.043  -0.469  -0.329  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.934   0.506  -0.001  1.00  0.00           N  
HETATM    5  C4  UNL     1       3.817   0.411   0.991  1.00  0.00           C  
HETATM    6  N2  UNL     1       3.849  -0.714   1.729  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.998  -1.720   1.459  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.068  -1.613   0.410  1.00  0.00           C  
HETATM    9  F1  UNL     1       1.269  -2.675   0.178  1.00  0.00           F  
HETATM   10  C7  UNL     1      -0.226   0.352  -0.896  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.065   0.762  -1.939  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.039   1.475   0.064  1.00  0.00           C  
HETATM   13  N3  UNL     1      -1.213   2.162   0.511  1.00  0.00           N  
HETATM   14  C9  UNL     1      -2.084   2.142   1.486  1.00  0.00           C  
HETATM   15  N4  UNL     1      -3.050   3.100   1.345  1.00  0.00           N  
HETATM   16  C10 UNL     1      -2.732   3.725   0.217  1.00  0.00           C  
HETATM   17  N5  UNL     1      -1.655   3.189  -0.289  1.00  0.00           N  
HETATM   18  C11 UNL     1      -0.972  -0.778  -0.257  1.00  0.00           C  
HETATM   19  C12 UNL     1      -1.163  -0.902   1.079  1.00  0.00           C  
HETATM   20  C13 UNL     1      -1.775  -2.022   1.660  1.00  0.00           C  
HETATM   21  C14 UNL     1      -2.196  -3.030   0.859  1.00  0.00           C  
HETATM   22  F2  UNL     1      -2.793  -4.114   1.438  1.00  0.00           F  
HETATM   23  C15 UNL     1      -2.011  -2.926  -0.487  1.00  0.00           C  
HETATM   24  C16 UNL     1      -1.414  -1.836  -1.064  1.00  0.00           C  
HETATM   25  F3  UNL     1      -1.233  -1.739  -2.403  1.00  0.00           F  
HETATM   26  H1  UNL     1       2.576   0.427  -2.821  1.00  0.00           H  
HETATM   27  H2  UNL     1       0.971   1.292  -2.997  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.154   1.670  -1.624  1.00  0.00           H  
HETATM   29  H4  UNL     1       0.928  -1.043  -2.086  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.523   1.199   1.244  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.005  -2.624   2.033  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.975   1.730  -2.053  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.479   1.095   0.999  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.699   2.204  -0.346  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.112   1.498   2.344  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.330   4.562  -0.173  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.803  -0.196   1.814  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.905  -2.066   2.753  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.356  -3.751  -1.128  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   10   29
CONECT    3    4    4    8
CONECT    4    5
CONECT    5    6    6   30
CONECT    6    7
CONECT    7    8    8   31
CONECT    8    9
CONECT   10   11   12   18
CONECT   11   32
CONECT   12   13   33   34
CONECT   13   14   17
CONECT   14   15   15   35
CONECT   15   16
CONECT   16   17   17   36
CONECT   18   19   19   24
CONECT   19   20   37
CONECT   20   21   21   38
CONECT   21   22   23
CONECT   23   24   24   39
CONECT   24   25
END

HMDB0014720
     RDKit          3D
Voriconazole
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.7180    0.9239   -2.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702   -0.2080   -1.4235 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0434   -0.4691   -0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9339    0.5059   -0.0007 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172    0.4108    0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8492   -0.7142    1.7294 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -1.7197    1.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679   -1.6130    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692   -2.6752    0.1778 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262    0.3523   -0.8958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0652    0.7617   -1.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385    1.4747    0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134    2.1625    0.5113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    2.1424    1.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0502    3.0995    1.3452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7323    3.7251    0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547    3.1891   -0.2892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721   -0.7777   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1627   -0.9017    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750   -2.0216    1.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1960   -3.0298    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7933   -4.1143    1.4384 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111   -2.9260   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4144   -1.8358   -1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331   -1.7393   -2.4032 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5756    0.4269   -2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    1.2916   -2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1539    1.6704   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283   -1.0428   -2.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233    1.1995    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0050   -2.6241    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9749    1.7296   -2.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4795    1.0951    0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992    2.2036   -0.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1120    1.4980    2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3296    4.5618   -0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035   -0.1959    1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053   -2.0658    2.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558   -3.7505   -1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  2 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
  8  3  1  0
 17 13  1  0
 24 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  6
  5 30  1  0
  7 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 16 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(AlphaR,betas)-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	ChEBI
(R-(R,s))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	ChEBI
VCZ	ChEBI
Vfend	ChEBI
Voriconazol	ChEBI
Voriconazolum	ChEBI
(AlphaR,betas)-a-(2,4-difluorophenyl)-5-fluoro-b-methyl-a(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	Generator
(AlphaR,betas)-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	Generator
(R-(R,s))-a-(2,4-difluorophenyl)-5-fluoro-b-methyl-a-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	Generator
(R-(R,s))-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	Generator

Chemical Formula

C₁₆H₁₄F₃N₅O

Average Molecular Weight

349.3105

Monoisotopic Molecular Weight

349.11504471

IUPAC Name

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Traditional Name

voriconazole

CAS Registry Number

137234-62-9

SMILES

C[C@@H](C1=NC=NC=C1F)[C@](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1

InChI Identifier

InChI=1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/m0/s1

InChI Key

BCEHBSKCWLPMDN-MGPLVRAMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Fluorobenzene
Halobenzene
Halopyrimidine
Aryl halide
Pyrimidine
Aryl fluoride
Heteroaromatic compound
1,2,4-triazole
Tertiary alcohol
Azole
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organooxygen compound
Alcohol
Organic nitrogen compound
Aromatic alcohol
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary alcohol (CHEBI:10023 )
triazole antifungal drug (CHEBI:10023 )
conazole antifungal drug (CHEBI:10023 )
pyrimidines (CHEBI:10023 )
difluorobenzene (CHEBI:10023 )

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: HMDB0014720)
Membrane (HMDB: HMDB0014720)

Source

Exogenous

Exogenous (HMDB: HMDB0014720)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	127 - 130 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.098 g/L	Not Available
LogP	1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.098 g/L	ALOGPS
logP	1.65	ALOGPS
logP	1.82	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.71	ChemAxon
pKa (Strongest Basic)	2.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.72 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.28 m³·mol⁻¹	ChemAxon
Polarizability	30.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	176.566	30932474
DeepCCS	[M-H]-	174.208	30932474
DeepCCS	[M-2H]-	208.029	30932474
DeepCCS	[M+Na]+	183.125	30932474
AllCCS	[M+H]+	179.7	32859911
AllCCS	[M+H-H2O]+	176.3	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.6	32859911
AllCCS	[M-H]-	178.7	32859911
AllCCS	[M+Na-2H]-	178.3	32859911
AllCCS	[M+HCOO]-	178.0	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.	2.94 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1131 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.47 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1897.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	289.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	132.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	502.6 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	554.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	68.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	956.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	423.0 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	1427.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	309.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	321.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	255.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	204.7 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	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Voriconazole	C[C@@H](C1=NC=NC=C1F)[C@](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1	2911.4	Standard polar	33892256
Voriconazole	C[C@@H](C1=NC=NC=C1F)[C@](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1	2308.9	Standard non polar	33892256
Voriconazole	C[C@@H](C1=NC=NC=C1F)[C@](O)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1	2271.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Voriconazole,1TMS,isomer #1	C[C@@H](C1=NC=NC=C1F)[C@@](CN1C=NC=N1)(O[Si](C)(C)C)C1=CC=C(F)C=C1F	2455.3	Semi standard non polar	33892256
Voriconazole,1TBDMS,isomer #1	C[C@@H](C1=NC=NC=C1F)[C@@](CN1C=NC=N1)(O[Si](C)(C)C(C)(C)C)C1=CC=C(F)C=C1F	2688.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Voriconazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-007o-9870000000-37f0e72d184d58adf95f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Voriconazole GC-MS (1 TMS) - 70eV, Positive	splash10-00gs-9165100000-2b5d1149e34858faa6bb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Voriconazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Voriconazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Voriconazole , positive-QTOF	splash10-0fh9-2593000000-630f0453fb0da8e2745d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Voriconazole 35V, Negative-QTOF	splash10-0ikf-0094000000-e4b4765d05aa953ac516	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Voriconazole 35V, Positive-QTOF	splash10-00c0-0690000000-54968439d5df7f27f9db	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 10V, Positive-QTOF	splash10-0udi-0039000000-4831581820baa773cbd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 20V, Positive-QTOF	splash10-0a4i-0249000000-d1f4e5629407a5b0f052	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 40V, Positive-QTOF	splash10-00di-9330000000-8840243a922d085b8d82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 10V, Negative-QTOF	splash10-014i-9013000000-c8af89477bf516cdf196	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 20V, Negative-QTOF	splash10-014i-9014000000-947fc7640f570d4afdd7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 40V, Negative-QTOF	splash10-00kf-9000000000-912a372757f51f1a9f40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 10V, Positive-QTOF	splash10-0udi-1009000000-f770d46865506a5b9cc2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 20V, Positive-QTOF	splash10-00di-9000000000-e0260b8b6ec84bcf2c45	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 40V, Positive-QTOF	splash10-00di-9000000000-cd28fa5bc96d882612d5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 10V, Negative-QTOF	splash10-014i-9006000000-cc33590c7b94ecaefd7f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 20V, Negative-QTOF	splash10-014i-9031000000-899de365c4e23b31ebf2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voriconazole 40V, Negative-QTOF	splash10-014i-9210000000-21d95020c2f323256ddf	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 DB00582	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00582	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00582

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

64684

KEGG Compound ID

C07622

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Voriconazole

METLIN ID

Not Available

PubChem Compound

71616

PDB ID

VOR

ChEBI ID

10023

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ally R, Schurmann D, Kreisel W, Carosi G, Aguirrebengoa K, Dupont B, Hodges M, Troke P, Romero AJ: A randomized, double-blind, double-dummy, multicenter trial of voriconazole and fluconazole in the treatment of esophageal candidiasis in immunocompromised patients. Clin Infect Dis. 2001 Nov 1;33(9):1447-54. Epub 2001 Sep 26. [PubMed:11577374 ]
Walsh TJ, Pappas P, Winston DJ, Lazarus HM, Petersen F, Raffalli J, Yanovich S, Stiff P, Greenberg R, Donowitz G, Schuster M, Reboli A, Wingard J, Arndt C, Reinhardt J, Hadley S, Finberg R, Laverdiere M, Perfect J, Garber G, Fioritoni G, Anaissie E, Lee J: Voriconazole compared with liposomal amphotericin B for empirical antifungal therapy in patients with neutropenia and persistent fever. N Engl J Med. 2002 Jan 24;346(4):225-34. [PubMed:11807146 ]
Herbrecht R, Denning DW, Patterson TF, Bennett JE, Greene RE, Oestmann JW, Kern WV, Marr KA, Ribaud P, Lortholary O, Sylvester R, Rubin RH, Wingard JR, Stark P, Durand C, Caillot D, Thiel E, Chandrasekar PH, Hodges MR, Schlamm HT, Troke PF, de Pauw B: Voriconazole versus amphotericin B for primary therapy of invasive aspergillosis. N Engl J Med. 2002 Aug 8;347(6):408-15. [PubMed:12167683 ]
Patterson TF, Boucher HW, Herbrecht R, Denning DW, Lortholary O, Ribaud P, Rubin RH, Wingard JR, DePauw B, Schlamm HT, Troke P, Bennett JE: Strategy of following voriconazole versus amphotericin B therapy with other licensed antifungal therapy for primary treatment of invasive aspergillosis: impact of other therapies on outcome. Clin Infect Dis. 2005 Nov 15;41(10):1448-52. Epub 2005 Oct 13. [PubMed:16231256 ]
Kullberg BJ, Sobel JD, Ruhnke M, Pappas PG, Viscoli C, Rex JH, Cleary JD, Rubinstein E, Church LW, Brown JM, Schlamm HT, Oborska IT, Hilton F, Hodges MR: Voriconazole versus a regimen of amphotericin B followed by fluconazole for candidaemia in non-neutropenic patients: a randomised non-inferiority trial. Lancet. 2005 Oct 22-28;366(9495):1435-42. [PubMed:16243088 ]

Enzymes

Enzyme Details

1. Dimethylaniline monooxygenase [N-oxide-forming] 3

General function:: Involved in flavin-containing monooxygenase activity
Specific function:: Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
Gene Name:: FMO3
Uniprot ID:: P31513
Molecular weight:: 60032.975

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. Dimethylaniline monooxygenase [N-oxide-forming] 1

General function:: Involved in flavin-containing monooxygenase activity
Specific function:: This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name:: FMO1
Uniprot ID:: Q01740
Molecular weight:: 60310.285

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

3. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

4. 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

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

6. 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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

7. 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

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

Showing metabocard for Voriconazole (HMDB0014720)

MOL for HMDB0014720 (Voriconazole)

3D MOL for HMDB0014720 (Voriconazole)

3D SDF for HMDB0014720 (Voriconazole)

3D-SDF for HMDB0014720 (Voriconazole)

PDB for HMDB0014720 (Voriconazole)

3D PDB for HMDB0014720 (Voriconazole)

SMILES for HMDB0014720 (Voriconazole)

INCHI for HMDB0014720 (Voriconazole)

Structure for HMDB0014720 (Voriconazole)

3D Structure for HMDB0014720 (Voriconazole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References