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
StatusExpected but not Quantified
Creation Date2013-07-09 16:06:57 UTC
Update Date2017-10-23 19:15:49 UTC
HMDB IDHMDB0060914
Secondary Accession Numbers
  • HMDB60914
Metabolite Identification
Common NameZileuton O-glucuronide
DescriptionZileuton O-glucuronide is a metabolite of zileuton. Zileuton (trade name ZYFLO) is an orally active inhibitor of 5-lipoxygenase, and thus inhibits leukotrienes (LTB4, LTC4, LTD4, and LTE4) formation. Zileuton is used for the maintenance treatment of asthma. Zileuton was introduced in 1996 by Abbott Laboratories and is now marketed in two formulations by Cornerstone Therapeutics Inc. under the brand names ZYFLO and ZYFLO CR. The original immediate-release formulation of zileuton, known as ZYFLO, is taken four times per day. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H20N2O8S
Average Molecular Weight412.414
Monoisotopic Molecular Weight412.094036316
IUPAC Name(2S,3S,4S,5R,6S)-6-({[1-(1-benzothiophen-2-yl)ethyl](C-hydroxycarbonimidoyl)amino}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-({[1-(1-benzothiophen-2-yl)ethyl](C-hydroxycarbonimidoyl)amino}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(N(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(O)=N)C1=CC2=CC=CC=C2S1
InChI Identifier
InChI=1S/C17H20N2O8S/c1-7(10-6-8-4-2-3-5-9(8)28-10)19(17(18)25)27-16-13(22)11(20)12(21)14(26-16)15(23)24/h2-7,11-14,16,20-22H,1H3,(H2,18,25)(H,23,24)/t7?,11-,12-,13+,14-,16-/m0/s1
InChI KeyCYYKQHWQVGZJRJ-UPZRFPAJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glucuronic acid derivatives. These are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentGlucuronic acid derivatives
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Benzothiophene
  • 1-benzothiophene
  • 2,3,5-trisubstituted thiophene
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Thiophene
  • Secondary alcohol
  • Carbonic acid derivative
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.14 g/LALOGPS
logP0.07ALOGPS
logP0.77ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)3.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area163.77 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity104.91 m³·mol⁻¹ChemAxon
Polarizability39.39 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-06r6-9614000000-f1aa336ac18c1d5cf817View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-8941026000-03c8189ac740d9584fc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0719300000-4e34ca0476847f5d9c92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-1953000000-ab0bdba835d6bf9c99c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03g0-7900000000-7c5d68dabea029077fbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02tc-3239200000-0a4e2ca8f81249bd8d0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-9764000000-479864cd7f02f7d2de76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-15f38183e57982736ce3View 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 IDDBMET00141
      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