Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:05:42 UTC

Update Date

2021-09-14 15:30:23 UTC

HMDB ID

HMDB0060894

Secondary Accession Numbers

HMDB60894

Metabolite Identification

Common Name

4-Hydroxyvoriconazole

Description

4-Hydroxyvoriconazole is a metabolite of voriconazole. Voriconazole is a triazole antifungal medication that is generally used to treat serious, invasive fungal infections. These are generally seen in patients who are immunocompromised, and include invasive candidiasis, invasive aspergillosis, and certain emerging fungal infections. (Wikipedia)

Structure

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


  Mrv0541 07091309052D          

 26 28  0  0  0  0            999 V2000
    4.1986    2.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1616   -0.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7491    0.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241   -0.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116    4.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7491    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -1.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646   -0.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0212    1.9745    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7491   -0.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241    0.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116   -0.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116    2.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7193    0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871    1.2568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3079   -1.5750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008   -0.5519    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2901    3.6265    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366    4.0827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2097   -1.2822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366    2.6538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1297   -0.4976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -0.0127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107    1.1650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3133    1.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  9  1  1  1  0  0  0
 10  2  1  0  0  0  0
 10  4  2  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12 11  2  0  0  0  0
 13  5  2  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 16  9  1  0  0  0  0
 16 11  1  1  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20  5  1  0  0  0  0
 20  6  2  0  0  0  0
 21  7  1  0  0  0  0
 21  8  2  0  0  0  0
 22  6  1  0  0  0  0
 22 14  2  0  0  0  0
 23  7  2  0  0  0  0
 24  8  1  0  0  0  0
 24 15  1  0  0  0  0
 24 23  1  0  0  0  0
 25 15  1  0  0  0  0
 16 26  1  6  0  0  0
M  END

HMDB0060894
     RDKit          3D
4-Hydroxyvoriconazole
 40 42  0  0  0  0  0  0  0  0999 V2000
    0.6830    0.0490    1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6837    0.4504    0.2729 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9146    0.0397   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9070   -0.3224    0.5835 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224   -0.7047    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.7673   -1.0169 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5793   -0.4300   -1.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2995   -0.0272   -1.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4010    0.3099   -2.5280 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729    0.1648   -0.2431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8753    0.5364   -1.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0472   -1.2700   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1655   -2.2627    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894   -3.6154    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7320   -4.0174   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415   -5.3480   -0.0667 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393   -3.0893   -0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909   -1.7321   -0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413   -0.9282   -1.0146 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876    1.0787    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082    1.0053    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2285    2.4963    0.4178 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6798    3.2613    1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971    4.5144    0.9693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280    4.5530   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3591    3.3273   -0.5971 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -0.5339    2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1647   -0.5976    1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608    0.9283    2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344    1.5973    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810   -0.9842    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8114   -0.4590   -2.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460    1.4785   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8269   -2.0310    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716   -4.3378    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267   -3.3765   -0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4962    0.8840    1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360    1.7391   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4130    2.9704    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9103    5.4507   -0.9382 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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  8  3  1  0
 18 12  1  0
 26 22  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  5 31  1  0
  7 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 20 37  1  0
 21 38  1  0
 23 39  1  0
 25 40  1  0
M  END


  Mrv0541 07091309052D          

 26 28  0  0  0  0            999 V2000
    4.1986    2.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1616   -0.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7491    0.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241   -0.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116    4.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7491    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -1.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646   -0.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0212    1.9745    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7491   -0.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241    0.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116   -0.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991    3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116    2.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7193    0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871    1.2568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3079   -1.5750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.7008   -0.5519    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2901    3.6265    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366    4.0827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2097   -1.2822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366    2.6538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1297   -0.4976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -0.0127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107    1.1650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3133    1.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  9  1  1  1  0  0  0
 10  2  1  0  0  0  0
 10  4  2  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12 11  2  0  0  0  0
 13  5  2  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 16  9  1  0  0  0  0
 16 11  1  1  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20  5  1  0  0  0  0
 20  6  2  0  0  0  0
 21  7  1  0  0  0  0
 21  8  2  0  0  0  0
 22  6  1  0  0  0  0
 22 14  2  0  0  0  0
 23  7  2  0  0  0  0
 24  8  1  0  0  0  0
 24 15  1  0  0  0  0
 24 23  1  0  0  0  0
 25 15  1  0  0  0  0
 16 26  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0060894

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](C1=NC=NC=C1F)[C@](O)(C(O)N1C=NC=N1)C1=C(F)C=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14F3N5O2/c1-9(14-13(19)5-20-6-22-14)16(26,15(25)24-8-21-7-23-24)11-3-2-10(17)4-12(11)18/h2-9,15,25-26H,1H3/t9-,15?,16+/m0/s1

> <INCHI_KEY>
ICGJRJXWKNVQMK-TXTOSPAFSA-N

> <FORMULA>
C16H14F3N5O2

> <MOLECULAR_WEIGHT>
365.3099

> <EXACT_MASS>
365.109959332

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.341417309054158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <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)butane-1,2-diol

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
1.4588086506666675

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.71737689781557

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.170028549596875

> <JCHEM_PKA_STRONGEST_BASIC>
1.9855215951266656

> <JCHEM_POLAR_SURFACE_AREA>
96.95

> <JCHEM_REFRACTIVITY>
96.30790000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butane-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060894
     RDKit          3D
4-Hydroxyvoriconazole
 40 42  0  0  0  0  0  0  0  0999 V2000
    0.6830    0.0490    1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6837    0.4504    0.2729 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9146    0.0397   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9070   -0.3224    0.5835 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224   -0.7047    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.7673   -1.0169 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5793   -0.4300   -1.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2995   -0.0272   -1.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4010    0.3099   -2.5280 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729    0.1648   -0.2431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8753    0.5364   -1.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0472   -1.2700   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1655   -2.2627    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894   -3.6154    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7320   -4.0174   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415   -5.3480   -0.0667 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393   -3.0893   -0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909   -1.7321   -0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413   -0.9282   -1.0146 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876    1.0787    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082    1.0053    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2285    2.4963    0.4178 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6798    3.2613    1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971    4.5144    0.9693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280    4.5530   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3591    3.3273   -0.5971 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -0.5339    2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1647   -0.5976    1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608    0.9283    2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344    1.5973    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810   -0.9842    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8114   -0.4590   -2.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460    1.4785   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8269   -2.0310    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716   -4.3378    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267   -3.3765   -0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4962    0.8840    1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360    1.7391   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4130    2.9704    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9103    5.4507   -0.9382 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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  8  3  1  0
 18 12  1  0
 26 22  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  5 31  1  0
  7 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 20 37  1  0
 21 38  1  0
 23 39  1  0
 25 40  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       7.837   4.161   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.368  -0.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.598   0.953   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.058  -1.715   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.288   7.621   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.598   6.287   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.185  -2.393   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.201  -0.929   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.373   3.686   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.598  -1.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.058   0.953   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.288  -0.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.518   6.287   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.288   4.954   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.809   1.615   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.243   2.346   0.000  0.00  0.00           C+0
HETATM   17  F   UNK     0      13.641  -2.940   0.000  0.00  0.00           F+0
HETATM   18  F   UNK     0       8.775  -1.030   0.000  0.00  0.00           F+0
HETATM   19  F   UNK     0       8.008   6.769   0.000  0.00  0.00           F+0
HETATM   20  N   UNK     0      11.828   7.621   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       9.725  -2.393   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      11.828   4.954   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       7.709  -0.929   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       8.955  -0.024   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       7.300   2.175   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      11.785   2.735   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    3   10                                                       
CONECT    3    2   11                                                       
CONECT    4   10   12                                                       
CONECT    5   13   20                                                       
CONECT    6   20   22                                                       
CONECT    7   21   23                                                       
CONECT    8   21   24                                                       
CONECT    9    1   14   16                                                  
CONECT   10    2    4   17                                                  
CONECT   11    3   12   16                                                  
CONECT   12    4   11   18                                                  
CONECT   13    5   14   19                                                  
CONECT   14    9   13   22                                                  
CONECT   15   16   24   25                                                  
CONECT   16    9   11   15   26                                             
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20    5    6                                                       
CONECT   21    7    8                                                       
CONECT   22    6   14                                                       
CONECT   23    7   24                                                       
CONECT   24    8   15   23                                                  
CONECT   25   15                                                            
CONECT   26   16                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0060894
HETATM    1  C1  UNL     1       0.683   0.049   1.736  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.684   0.450   0.273  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.915   0.040  -0.295  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.907  -0.322   0.584  1.00  0.00           N  
HETATM    5  C4  UNL     1       4.122  -0.705   0.274  1.00  0.00           C  
HETATM    6  N2  UNL     1       4.490  -0.767  -1.017  1.00  0.00           N  
HETATM    7  C5  UNL     1       3.579  -0.430  -1.933  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.299  -0.027  -1.612  1.00  0.00           C  
HETATM    9  F1  UNL     1       1.401   0.310  -2.528  1.00  0.00           F  
HETATM   10  C7  UNL     1      -0.673   0.165  -0.243  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.875   0.536  -1.569  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.047  -1.270  -0.211  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.165  -2.263   0.184  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.489  -3.615   0.234  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.732  -4.017  -0.120  1.00  0.00           C  
HETATM   16  F2  UNL     1      -2.041  -5.348  -0.067  1.00  0.00           F  
HETATM   17  C12 UNL     1      -2.639  -3.089  -0.518  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.291  -1.732  -0.560  1.00  0.00           C  
HETATM   19  F3  UNL     1      -3.241  -0.928  -1.015  1.00  0.00           F  
HETATM   20  C14 UNL     1      -1.588   1.079   0.525  1.00  0.00           C  
HETATM   21  O2  UNL     1      -2.908   1.005   0.139  1.00  0.00           O  
HETATM   22  N3  UNL     1      -1.228   2.496   0.418  1.00  0.00           N  
HETATM   23  C15 UNL     1      -0.680   3.261   1.408  1.00  0.00           C  
HETATM   24  N4  UNL     1      -0.497   4.514   0.969  1.00  0.00           N  
HETATM   25  C16 UNL     1      -0.928   4.553  -0.300  1.00  0.00           C  
HETATM   26  N5  UNL     1      -1.359   3.327  -0.597  1.00  0.00           N  
HETATM   27  H1  UNL     1       1.609  -0.534   2.013  1.00  0.00           H  
HETATM   28  H2  UNL     1      -0.165  -0.598   1.987  1.00  0.00           H  
HETATM   29  H3  UNL     1       0.761   0.928   2.421  1.00  0.00           H  
HETATM   30  H4  UNL     1       0.734   1.597   0.310  1.00  0.00           H  
HETATM   31  H5  UNL     1       4.881  -0.984   0.995  1.00  0.00           H  
HETATM   32  H6  UNL     1       3.811  -0.459  -2.991  1.00  0.00           H  
HETATM   33  H7  UNL     1      -0.846   1.479  -1.765  1.00  0.00           H  
HETATM   34  H8  UNL     1       0.827  -2.031   0.450  1.00  0.00           H  
HETATM   35  H9  UNL     1       0.272  -4.338   0.560  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.627  -3.376  -0.803  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.496   0.884   1.638  1.00  0.00           H  
HETATM   38  H12 UNL     1      -3.136   1.739  -0.454  1.00  0.00           H  
HETATM   39  H13 UNL     1      -0.413   2.970   2.416  1.00  0.00           H  
HETATM   40  H14 UNL     1      -0.910   5.451  -0.938  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   10   30
CONECT    3    4    4    8
CONECT    4    5
CONECT    5    6    6   31
CONECT    6    7
CONECT    7    8    8   32
CONECT    8    9
CONECT   10   11   12   20
CONECT   11   33
CONECT   12   13   13   18
CONECT   13   14   34
CONECT   14   15   15   35
CONECT   15   16   17
CONECT   17   18   18   36
CONECT   18   19
CONECT   20   21   22   37
CONECT   21   38
CONECT   22   23   26
CONECT   23   24   24   39
CONECT   24   25
CONECT   25   26   26   40
END

HMDB0060894
     RDKit          3D
4-Hydroxyvoriconazole
 40 42  0  0  0  0  0  0  0  0999 V2000
    0.6830    0.0490    1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6837    0.4504    0.2729 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9146    0.0397   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9070   -0.3224    0.5835 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224   -0.7047    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.7673   -1.0169 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5793   -0.4300   -1.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2995   -0.0272   -1.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4010    0.3099   -2.5280 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729    0.1648   -0.2431 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8753    0.5364   -1.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0472   -1.2700   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1655   -2.2627    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894   -3.6154    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7320   -4.0174   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415   -5.3480   -0.0667 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393   -3.0893   -0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909   -1.7321   -0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413   -0.9282   -1.0146 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876    1.0787    0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082    1.0053    0.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2285    2.4963    0.4178 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6798    3.2613    1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971    4.5144    0.9693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280    4.5530   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3591    3.3273   -0.5971 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -0.5339    2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1647   -0.5976    1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608    0.9283    2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344    1.5973    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810   -0.9842    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8114   -0.4590   -2.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460    1.4785   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8269   -2.0310    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716   -4.3378    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267   -3.3765   -0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4962    0.8840    1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1360    1.7391   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4130    2.9704    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9103    5.4507   -0.9382 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  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  8  3  1  0
 18 12  1  0
 26 22  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  5 31  1  0
  7 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 17 36  1  0
 20 37  1  0
 21 38  1  0
 23 39  1  0
 25 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄F₃N₅O₂

Average Molecular Weight

365.3099

Monoisotopic Molecular Weight

365.109959332

IUPAC Name

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

Traditional Name

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butane-1,2-diol

CAS Registry Number

Not Available

SMILES

C[C@@H](C1=NC=NC=C1F)[C@](O)(C(O)N1C=NC=N1)C1=C(F)C=C(F)C=C1

InChI Identifier

InChI=1S/C16H14F3N5O2/c1-9(14-13(19)5-20-6-22-14)16(26,15(25)24-8-21-7-23-24)11-3-2-10(17)4-12(11)18/h2-9,15,25-26H,1H3/t9-,15?,16+/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060894)
Liver (HMDB: HMDB0060894)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060894)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060894)

Cellular substructure

Cytoplasm (HMDB: HMDB0060894)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	1.28	ALOGPS
logP	1.46	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.17	ChemAxon
pKa (Strongest Basic)	1.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.95 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.31 m³·mol⁻¹	ChemAxon
Polarizability	31.34 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]+	179.328	30932474
DeepCCS	[M-H]-	176.933	30932474
DeepCCS	[M-2H]-	210.318	30932474
DeepCCS	[M+Na]+	185.241	30932474
AllCCS	[M+H]+	183.3	32859911
AllCCS	[M+H-H2O]+	180.1	32859911
AllCCS	[M+NH4]+	186.3	32859911
AllCCS	[M+Na]+	187.1	32859911
AllCCS	[M-H]-	180.8	32859911
AllCCS	[M+Na-2H]-	180.4	32859911
AllCCS	[M+HCOO]-	180.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyvoriconazole	C[C@@H](C1=NC=NC=C1F)[C@](O)(C(O)N1C=NC=N1)C1=C(F)C=C(F)C=C1	3113.3	Standard polar	33892256
4-Hydroxyvoriconazole	C[C@@H](C1=NC=NC=C1F)[C@](O)(C(O)N1C=NC=N1)C1=C(F)C=C(F)C=C1	2394.7	Standard non polar	33892256
4-Hydroxyvoriconazole	C[C@@H](C1=NC=NC=C1F)[C@](O)(C(O)N1C=NC=N1)C1=C(F)C=C(F)C=C1	2357.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyvoriconazole,1TMS,isomer #1	C[C@@H](C1=NC=NC=C1F)[C@@](O[Si](C)(C)C)(C1=CC=C(F)C=C1F)C(O)N1C=NC=N1	2500.8	Semi standard non polar	33892256
4-Hydroxyvoriconazole,1TMS,isomer #2	C[C@@H](C1=NC=NC=C1F)[C@@](O)(C1=CC=C(F)C=C1F)C(O[Si](C)(C)C)N1C=NC=N1	2491.8	Semi standard non polar	33892256
4-Hydroxyvoriconazole,2TMS,isomer #1	C[C@@H](C1=NC=NC=C1F)[C@@](O[Si](C)(C)C)(C1=CC=C(F)C=C1F)C(O[Si](C)(C)C)N1C=NC=N1	2504.4	Semi standard non polar	33892256
4-Hydroxyvoriconazole,1TBDMS,isomer #1	C[C@@H](C1=NC=NC=C1F)[C@@](O[Si](C)(C)C(C)(C)C)(C1=CC=C(F)C=C1F)C(O)N1C=NC=N1	2755.3	Semi standard non polar	33892256
4-Hydroxyvoriconazole,1TBDMS,isomer #2	C[C@@H](C1=NC=NC=C1F)[C@@](O)(C1=CC=C(F)C=C1F)C(O[Si](C)(C)C(C)(C)C)N1C=NC=N1	2730.5	Semi standard non polar	33892256
4-Hydroxyvoriconazole,2TBDMS,isomer #1	C[C@@H](C1=NC=NC=C1F)[C@@](O[Si](C)(C)C(C)(C)C)(C1=CC=C(F)C=C1F)C(O[Si](C)(C)C(C)(C)C)N1C=NC=N1	2949.3	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 - 4-Hydroxyvoriconazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kg-6961000000-87a426cedd8af2af831c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyvoriconazole GC-MS (2 TMS) - 70eV, Positive	splash10-00di-7859700000-b46f637cd2fb15c5c7f0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyvoriconazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 10V, Positive-QTOF	splash10-014i-1019000000-0410db0d0e0cc85b9510	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 20V, Positive-QTOF	splash10-00di-4139000000-443f98ffb3381a0031a2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 40V, Positive-QTOF	splash10-00r7-4390000000-93900d977c0d8c7a236f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 10V, Negative-QTOF	splash10-014i-9001000000-93fa9e2a84501a962986	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 20V, Negative-QTOF	splash10-014i-9021000000-5bcfcbb606ac5ec804a4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 40V, Negative-QTOF	splash10-016u-9000000000-10ee7f8aa517ec58e76b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 10V, Positive-QTOF	splash10-014i-0019000000-2af81cc02ba749ed408a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 20V, Positive-QTOF	splash10-014i-3469000000-a912962e849d21aa8d8a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 40V, Positive-QTOF	splash10-004i-2900000000-2ca5c3dddbd0976f7bd0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 10V, Negative-QTOF	splash10-01ot-2098000000-cd98d517126e994b7fd5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 20V, Negative-QTOF	splash10-014i-9650000000-4cca1ea215e87d5a0d9a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 40V, Negative-QTOF	splash10-014i-9110000000-fc49d2dea2018a43951e	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131769987

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 4-Hydroxyvoriconazole (HMDB0060894)

MOL for HMDB0060894 (4-Hydroxyvoriconazole)

3D MOL for HMDB0060894 (4-Hydroxyvoriconazole)

3D SDF for HMDB0060894 (4-Hydroxyvoriconazole)

3D-SDF for HMDB0060894 (4-Hydroxyvoriconazole)

PDB for HMDB0060894 (4-Hydroxyvoriconazole)

3D PDB for HMDB0060894 (4-Hydroxyvoriconazole)

SMILES for HMDB0060894 (4-Hydroxyvoriconazole)

INCHI for HMDB0060894 (4-Hydroxyvoriconazole)

Structure for HMDB0060894 (4-Hydroxyvoriconazole)

3D Structure for HMDB0060894 (4-Hydroxyvoriconazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra