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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:46:37 UTC
Update Date2017-10-23 19:15:45 UTC
HMDB IDHMDB0060599
Secondary Accession Numbers
  • HMDB60599
Metabolite Identification
Common NameLamivudine sulfoxide
DescriptionLamivudine sulfoxide is a metabolite of nitazoxanide. Nitazoxanide, also known by the brand names Alinia and Annita (and by Daxon, Dexidex, Kidonax, Mitafar, Pacovanton, and Paramix in Mexico, by Nitax, Zox, Nitazox, Niazid and Toza in Bangladesh) is a synthetic nitrothiazolyl-salicylamide derivative and an antiprotozoal agent. Nitazoxanide is a light yellow crystalline powder. It is poorly soluble in ethanol and practically insoluble in water. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC8H11N3O4S
Average Molecular Weight245.256
Monoisotopic Molecular Weight245.047026545
IUPAC Name4-amino-1-[(2S,5R)-2-(hydroxymethyl)-3-oxo-1,3λ⁴-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
Traditional Name4-amino-1-[(2S,5R)-2-(hydroxymethyl)-3-oxo-1,3λ⁴-oxathiolan-5-yl]pyrimidin-2-one
CAS Registry NumberNot Available
SMILES
NC1=NC(=O)N(C=C1)[C@H]1CS(=O)[C@@H](CO)O1
InChI Identifier
InChI=1S/C8H11N3O4S/c9-5-1-2-11(8(13)10-5)6-4-16(14)7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+,16?/m1/s1
InChI KeyLJMQAXFNQNADRZ-FYZWQCAOSA-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
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Primary aromatic amine
  • Pyrimidine
  • Imidolactam
  • Monothioacetal
  • Oxathiolane
  • Heteroaromatic compound
  • Sulfoxide
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfinyl compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 Solubility60.6 g/LALOGPS
logP-2.1ALOGPS
logP-2.5ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)14.01ChemAxon
pKa (Strongest Basic)-0.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.12 m³·mol⁻¹ChemAxon
Polarizability21.74 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, Positivesplash10-03di-8910000000-0a97c81e597d46d13cecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0jbi-6900000000-73ae3c3a3bc573a6595dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910000000-63f9bb8a8fb1f78ab9f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-04a8a42440e410019507View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9700000000-c7cc0fb6f0db073b654fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-1970000000-742b32f84394a407678fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-4900000000-01d178cf401a4d93caf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9000000000-15e4d8cb62057a01e18eView in MoNA
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 IDDBMET00895
      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 Compound452020
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available