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Record Information
Version3.6
Creation Date2013-06-15 17:46:37 UTC
Update Date2016-02-11 08:09:04 UTC
HMDB IDHMDB60599
Secondary Accession NumbersNone
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 KeyInChIKey=LJMQAXFNQNADRZ-FYZWQCAOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub ClassNot Available
Direct ParentNucleoside and nucleotide analogues
Alternative Parents
Substituents
  • Pyrimidone
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Hydropyrimidine
  • Heteroaromatic compound
  • Oxathiolane
  • Monothioacetal
  • Sulfoxide
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfinyl compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility60.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.12 m3·mol-1ChemAxon
Polarizability21.74 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
Pathways
NameSMPDB LinkKEGG Link
Lamivudine Metabolism PathwaySMP00649Not 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 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
NuGOwiki LinkHMDB60599
Metagene LinkHMDB60599
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