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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:06:57 UTC
Update Date2019-07-23 07:15:22 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
Data?1563866122
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
Description belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
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

Source:

Biological location:

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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r6-9614000000-f1aa336ac18c1d5cf817Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-8941026000-03c8189ac740d9584fc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0719300000-4e34ca0476847f5d9c92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-1953000000-ab0bdba835d6bf9c99c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03g0-7900000000-7c5d68dabea029077fbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02tc-3239200000-0a4e2ca8f81249bd8d0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-9764000000-479864cd7f02f7d2de76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-15f38183e57982736ce3Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound71752997
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available