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Record Information
Version4.0
Creation Date2013-06-15 18:25:14 UTC
Update Date2017-09-23 14:27:22 UTC
HMDB IDHMDB0060641
Secondary Accession Numbers
  • HMDB60641
Metabolite Identification
Common NameLamivudine-monophosphate
DescriptionLamivudine-monophosphate is a metabolite of lamivudine. Lamivudine (2',3'-dideoxy-3'-thiacytidine, commonly called 3TC) is a potent nucleoside analog reverse transcriptase inhibitor (nRTI). It is marketed by GlaxoSmithKline with the brand names Zeffix, Heptovir, Epivir, and Epivir-HBV. Lamivudine has been used for treatment of chronic hepatitis B at a lower dose than for treatment of HIV. It improves the seroconversion of e-antigen positive hepatitis B and also improves histology staging of the liver. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC8H12N3O6PS
Average Molecular Weight309.236
Monoisotopic Molecular Weight309.018442333
IUPAC Name{[5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxy}phosphonic acid
Traditional Name[5-(4-amino-2-oxopyrimidin-1-yl)-1,3-oxathiolan-2-yl]methoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
NC1=NC(=O)N(C=C1)C1CSC(COP(O)(O)=O)O1
InChI Identifier
InChI=1S/C8H12N3O6PS/c9-5-1-2-11(8(12)10-5)6-4-19-7(17-6)3-16-18(13,14)15/h1-2,6-7H,3-4H2,(H2,9,10,12)(H2,13,14,15)
InChI KeyWUMZLKDCOINBEA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassNucleoside and nucleotide analogues
Direct ParentNucleoside and nucleotide analogues
Alternative Parents
Substituents
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Monothioacetal
  • Oxathiolane
  • Heteroaromatic compound
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
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 Solubility17.4 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.6ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.09ChemAxon
pKa (Strongest Basic)0.07ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area134.68 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.04 m3·mol-1ChemAxon
Polarizability26.44 Å3ChemAxon
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-MSNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Lamivudine Metabolism PathwayPw000625Pw000625 greyscalePw000625 simpleNot Available
Displaying 1 entry
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 IDDBMET00898
      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 LinkHMDB0060641
      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