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Record Information
Version3.6
Creation Date2013-06-15 17:43:22 UTC
Update Date2017-03-02 22:05:14 UTC
HMDB IDHMDB60597
Secondary Accession NumbersNone
Metabolite Identification
Common NameDesacetyl-nitazoxanide
DescriptionDesacetyl-nitazoxanide 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 FormulaC10H7N3O4S
Average Molecular Weight265.245
Monoisotopic Molecular Weight265.015726417
IUPAC Name2-hydroxy-N-(5-nitro-1,3-thiazol-2-yl)benzamide
Traditional Nametizoxanide
CAS Registry NumberNot Available
SMILES
OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O
InChI Identifier
InChI=1S/C10H7N3O4S/c14-7-4-2-1-3-6(7)9(15)12-10-11-5-8(18-10)13(16)17/h1-5,14H,(H,11,12,15)
InChI KeyFDTZUTSGGSRHQF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentSalicylamides
Alternative Parents
Substituents
  • Salicylamide
  • Benzamide
  • Nitroaromatic compound
  • Benzoyl
  • Nitrothiazole
  • 2,5-disubstituted 1,3-thiazole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Vinylogous acid
  • Organic nitro compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxoazanium
  • Organic zwitterion
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • 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
  • Membrane (predicted from logP)
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 Solubility0.042 mg/mLALOGPS
logP2ALOGPS
logP2.21ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.81ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area108.04 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.74 m3·mol-1ChemAxon
Polarizability24.1 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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 IDDBMET01012
      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 LinkHMDB60597
      Metagene LinkHMDB60597
      METLIN IDNot Available
      PubChem Compound394397
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available