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Record Information
Version3.6
Creation Date2013-07-09 16:05:42 UTC
Update Date2017-08-18 12:52:36 UTC
HMDB IDHMDB0060894
Secondary Accession Numbers
  • HMDB60894
Metabolite Identification
Common Name4-Hydroxyvoriconazole
Description4-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
Thumb
SynonymsNot Available
Chemical FormulaC16H14F3N5O2
Average Molecular Weight365.3099
Monoisotopic Molecular Weight365.109959332
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 NumberNot 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 KeyICGJRJXWKNVQMK-TXTOSPAFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpropanes
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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.19 mg/mLALOGPS
logP1.28ALOGPS
logP1.46ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.17ChemAxon
pKa (Strongest Basic)1.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area96.95 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.31 m3·mol-1ChemAxon
Polarizability31.34 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00072
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060894
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available