You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2013-06-15 18:25:20 UTC
Update Date2017-09-27 08:43:51 UTC
HMDB IDHMDB0060643
Secondary Accession Numbers
  • HMDB60643
Metabolite Identification
Common NameTizoxanide glucuronide
DescriptionTizoxanide glucuronide 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 FormulaC16H15N3O10S
Average Molecular Weight441.369
Monoisotopic Molecular Weight441.047814405
IUPAC Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenoxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenoxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@H]1C(OC2=CC=CC=C2C(=O)NC2=NC=C(S2)[N+]([O-])=O)O[C@@H]([C@@H](O)[C@@H]1O)C(O)=O
InChI Identifier
InChI=1S/C16H15N3O10S/c20-9-10(21)12(14(24)25)29-15(11(9)22)28-7-4-2-1-3-6(7)13(23)18-16-17-5-8(30-16)19(26)27/h1-5,9-12,15,20-22H,(H,24,25)(H,17,18,23)/t9-,10-,11+,12-,15?/m0/s1
InChI KeyUJTOVSZPBVTOMC-VDQYPUQXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Benzamide
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Nitroaromatic compound
  • Benzoyl
  • Nitrothiazole
  • Phenol ether
  • 2,5-disubstituted 1,3-thiazole
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Pyran
  • Benzenoid
  • Hydroxy acid
  • Heteroaromatic compound
  • Thiazole
  • Azole
  • Carboxamide group
  • Organic nitro compound
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • C-nitro compound
  • Acetal
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Polyol
  • Monocarboxylic acid or derivatives
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
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 Solubility0.096 g/LALOGPS
logP-0.31ALOGPS
logP0.26ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area204.26 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.75 m³·mol⁻¹ChemAxon
Polarizability39.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-05fr-9413300000-b8cd7da8e2e5ca4a3e4aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00ec-4941046000-63ed9c126ceb01bb423cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-0270900000-b658c9053286dde72a26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-0691000000-85d34de1d1be43ab5d1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00r5-8940000000-f91824bcd9e2c6dad37fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-2203900000-1e0dce80cee816703d95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9305400000-4c473d7730e922675086View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06s9-9661000000-fdc4ff7e16e6035e3649View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET01013
      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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available