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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:05:42 UTC
Update Date2021-09-14 15:30:23 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
Data?1563866119
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
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.31 m³·mol⁻¹ChemAxon
Polarizability31.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+179.32830932474
DeepCCS[M-H]-176.93330932474
DeepCCS[M-2H]-210.31830932474
DeepCCS[M+Na]+185.24130932474
AllCCS[M+H]+183.332859911
AllCCS[M+H-H2O]+180.132859911
AllCCS[M+NH4]+186.332859911
AllCCS[M+Na]+187.132859911
AllCCS[M-H]-180.832859911
AllCCS[M+Na-2H]-180.432859911
AllCCS[M+HCOO]-180.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxyvoriconazoleC[C@@H](C1=NC=NC=C1F)[C@](O)(C(O)N1C=NC=N1)C1=C(F)C=C(F)C=C13113.3Standard polar33892256
4-HydroxyvoriconazoleC[C@@H](C1=NC=NC=C1F)[C@](O)(C(O)N1C=NC=N1)C1=C(F)C=C(F)C=C12394.7Standard non polar33892256
4-HydroxyvoriconazoleC[C@@H](C1=NC=NC=C1F)[C@](O)(C(O)N1C=NC=N1)C1=C(F)C=C(F)C=C12357.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyvoriconazole,1TMS,isomer #1C[C@@H](C1=NC=NC=C1F)[C@@](O[Si](C)(C)C)(C1=CC=C(F)C=C1F)C(O)N1C=NC=N12500.8Semi standard non polar33892256
4-Hydroxyvoriconazole,1TMS,isomer #2C[C@@H](C1=NC=NC=C1F)[C@@](O)(C1=CC=C(F)C=C1F)C(O[Si](C)(C)C)N1C=NC=N12491.8Semi standard non polar33892256
4-Hydroxyvoriconazole,2TMS,isomer #1C[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=N12504.4Semi standard non polar33892256
4-Hydroxyvoriconazole,1TBDMS,isomer #1C[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=N12755.3Semi standard non polar33892256
4-Hydroxyvoriconazole,1TBDMS,isomer #2C[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=N12730.5Semi standard non polar33892256
4-Hydroxyvoriconazole,2TBDMS,isomer #1C[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=N12949.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyvoriconazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kg-6961000000-87a426cedd8af2af831c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyvoriconazole GC-MS (2 TMS) - 70eV, Positivesplash10-00di-7859700000-b46f637cd2fb15c5c7f02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyvoriconazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 10V, Positive-QTOFsplash10-014i-1019000000-0410db0d0e0cc85b95102017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 20V, Positive-QTOFsplash10-00di-4139000000-443f98ffb3381a0031a22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 40V, Positive-QTOFsplash10-00r7-4390000000-93900d977c0d8c7a236f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 10V, Negative-QTOFsplash10-014i-9001000000-93fa9e2a84501a9629862017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 20V, Negative-QTOFsplash10-014i-9021000000-5bcfcbb606ac5ec804a42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 40V, Negative-QTOFsplash10-016u-9000000000-10ee7f8aa517ec58e76b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 10V, Positive-QTOFsplash10-014i-0019000000-2af81cc02ba749ed408a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 20V, Positive-QTOFsplash10-014i-3469000000-a912962e849d21aa8d8a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 40V, Positive-QTOFsplash10-004i-2900000000-2ca5c3dddbd0976f7bd02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 10V, Negative-QTOFsplash10-01ot-2098000000-cd98d517126e994b7fd52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 20V, Negative-QTOFsplash10-014i-9650000000-4cca1ea215e87d5a0d9a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyvoriconazole 40V, Negative-QTOFsplash10-014i-9110000000-fc49d2dea2018a43951e2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769987
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available