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Record Information
Version3.6
Creation Date2013-07-09 16:18:27 UTC
Update Date2016-02-11 08:18:30 UTC
HMDB IDHMDB61100
Secondary Accession NumbersNone
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 KeyInChIKey=KQURMIWGELPUHQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Hydroxypyrimidine
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Acetate salt
  • Imidazole
  • Azole
  • Carboxylic acid ester
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.81 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity93.91 m3·mol-1ChemAxon
Polarizability33.26 Å3ChemAxon
Number of Rings2ChemAxon
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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB61100
Metagene LinkHMDB61100
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