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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:18:27 UTC
Update Date2017-10-23 19:15:52 UTC
HMDB IDHMDB0061100
Secondary Accession Numbers
  • HMDB61100
Metabolite Identification
Common Name6-oxo-famciclovir
Description6-oxo-famciclovir is a metabolite of famciclovir. Famciclovir is a guanine analogue antiviral drug used for the treatment of various herpesvirus infections, most commonly for herpes zoster (shingles). It is a prodrug form of penciclovir with improved oral bioavailability. Famciclovir is marketed under the trade name Famvir. On August 24, 2007, the United States Food and Drug Administration approved the first generic version of famciclovir. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC14H19N5O5
Average Molecular Weight337.3312
Monoisotopic Molecular Weight337.138618743
IUPAC Name2-[(acetyloxy)methyl]-4-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)butyl acetate
Traditional Name2-[(acetyloxy)methyl]-4-(6-hydroxy-2-imino-3H-purin-9-yl)butyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OCC(CCN1C=NC2=C1NC(=N)N=C2O)COC(C)=O
InChI Identifier
InChI=1S/C14H19N5O5/c1-8(20)23-5-10(6-24-9(2)21)3-4-19-7-16-11-12(19)17-14(15)18-13(11)22/h7,10H,3-6H2,1-2H3,(H3,15,17,18,22)
InChI KeyKQURMIWGELPUHQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Aminopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Primary aromatic amine
  • Dicarboxylic acid or derivatives
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.81 g/LALOGPS
logP-0.07ALOGPS
logP-0.79ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.25ChemAxon
pKa (Strongest Basic)5.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area138.89 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity93.91 m³·mol⁻¹ChemAxon
Polarizability33.26 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r6-9881000000-7b9ac30f11371010ebdbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fdo-8149000000-28c0e149facf37e1f9d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0079000000-d92c38520a4531bff2c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0961000000-432457b11ec0e8d5d92dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w4i-1920000000-d93419f4384fe5413ea5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-4019000000-78cc30d6fa88605159e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-8922000000-f09fc841b532c140b35aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-7900000000-23f1ad945928a2e9605dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00463
      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
      METLIN IDNot Available
      PubChem Compound11724611
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available