MiMeDB: Showing metabocard for voriconazole (MMDBc0054699)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:25:00 UTC

Update Date

2024-10-10 23:43:43 UTC

Metabolite ID

MMDBc0054699

Metabolite Identification

Common Name

voriconazole

Description

Voriconazole (Vfend, Pfizer) is a triazole antifungal medication used to treat serious fungal infections. It is used to treat invasive fungal infections that are generally seen in patients who are immunocompromised. These include invasive candidiasis, invasive aspergillosis, and emerging fungal infections.

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>
MMDBc0054699

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₆H₁₄F₃N₅O

Average Mass

349.3105

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-007o-9870000000-37f0e72d184d58adf95f	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00gs-9165100000-2b5d1149e34858faa6bb	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0fh9-2593000000-630f0453fb0da8e2745d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ikf-0094000000-e4b4765d05aa953ac516	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00c0-0690000000-54968439d5df7f27f9db	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0039000000-4831581820baa773cbd0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0249000000-d1f4e5629407a5b0f052	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9330000000-8840243a922d085b8d82	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9013000000-c8af89477bf516cdf196	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9014000000-947fc7640f570d4afdd7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-912a372757f51f1a9f40	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1009000000-f770d46865506a5b9cc2	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-e0260b8b6ec84bcf2c45	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-cd28fa5bc96d882612d5	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-9006000000-cc33590c7b94ecaefd7f	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9031000000-899de365c4e23b31ebf2	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9210000000-21d95020c2f323256ddf	2021-10-11	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191842	Dimethylaniline monooxygenase [N-oxide-forming] 3	Unknown	P31513	Homo sapiens
MMDBp0191856	Dimethylaniline monooxygenase [N-oxide-forming] 1	Unknown	Q01740	Homo sapiens
MMDBp0192588	Prostaglandin G/H synthase 1	Unknown	P23219	Homo sapiens
MMDBp0192630	Cytochrome P450 3A4	Unknown	P08684	Homo sapiens
MMDBp0192647	Cytochrome P450 2C9	Unknown	P11712	Homo sapiens
MMDBp0192649	Cytochrome P450 2C19	Unknown	P33261	Homo sapiens
MMDBp0193109	Cytochrome P450 3A5	Unknown	P20815	Homo sapiens
MMDBp0193112	Cytochrome P450 3A7	Unknown	P24462	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	6
Eukaryota/Fungi	Basidiomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0014720

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

References

Synthesis Reference

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. doi: 10.1086/322653. 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. doi: 10.1056/NEJM200201243460403. [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. doi: 10.1056/NEJMoa020191. [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. doi: 10.1086/497126. 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. doi: 10.1016/S0140-6736(05)67490-9. [PubMed:16243088 ]

Showing metabocard for voriconazole (MMDBc0054699)

MOL for #<Metabolite:0x00007f46987d8620>

3D MOL for #<Metabolite:0x00007f46987d8620>

3D SDF for #<Metabolite:0x00007f46987d8620>

3D-SDF for #<Metabolite:0x00007f46987d8620>

PDB for #<Metabolite:0x00007f46987d8620>

3D PDB for #<Metabolite:0x00007f46987d8620>

SMILES for #<Metabolite:0x00007f46987d8620>

INCHI for #<Metabolite:0x00007f46987d8620>

Structure for #<Metabolite:0x00007f46987d8620>

3D Structure for #<Metabolite:0x00007f46987d8620>