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Record Information
Version4.0
Creation Date2013-07-09 16:08:14 UTC
Update Date2017-10-23 19:15:50 UTC
HMDB IDHMDB0060935
Secondary Accession Numbers
  • HMDB60935
Metabolite Identification
Common Name4-trans-Hydroxyglipizide
Description4-trans-Hydroxyglipizide is a metabolite of glipizide. Glipizide is an oral rapid- and short-acting anti-diabetic drug from the sulfonylurea class. It is classified as a second generation sulfonylurea, which means that it undergoes enterohepatic circulation. Second-generation sulfonylureas are both more potent and have shorter half-lives than the first-generation sulfonylureas. Mechanism of action is produced by blocking potassium channels in the beta cells of the islets of Langerhans. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H27N5O5S
Average Molecular Weight461.535
Monoisotopic Molecular Weight461.173289689
IUPAC Name5-methyl-N-(2-{4-[({[(1r,4r)-4-hydroxycyclohexyl]-C-hydroxycarbonimidoyl}amino)sulfonyl]phenyl}ethyl)pyrazine-2-carboximidic acid
Traditional Name5-methyl-N-{2-[4-({[(1r,4r)-4-hydroxycyclohexyl]-C-hydroxycarbonimidoyl}aminosulfonyl)phenyl]ethyl}pyrazine-2-carboximidic acid
CAS Registry NumberNot Available
SMILES
CC1=CN=C(C=N1)C(O)=NCCC1=CC=C(C=C1)S(=O)(=O)NC(O)=N[C@H]1CC[C@H](O)CC1
InChI Identifier
InChI=1S/C21H27N5O5S/c1-14-12-24-19(13-23-14)20(28)22-11-10-15-2-8-18(9-3-15)32(30,31)26-21(29)25-16-4-6-17(27)7-5-16/h2-3,8-9,12-13,16-17,27H,4-7,10-11H2,1H3,(H,22,28)(H2,25,26,29)/t16-,17-
InChI KeyWPQWQJBFAJEUHS-QAQDUYKDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Cyclohexanol
  • Sulfonylurea
  • Pyrazine
  • Cyclic alcohol
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboximidic acid derivative
  • Azacycle
  • Carboximidic acid
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Alcohol
  • 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 Solubility0.048 g/LALOGPS
logP1.29ALOGPS
logP1.68ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)5.44ChemAxon
pKa (Strongest Basic)2.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area157.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity118.33 m³·mol⁻¹ChemAxon
Polarizability47.83 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, Positivesplash10-0w93-8926500000-b1f77e53010b280710f4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03k9-4523429000-e0ccdaeb3933e5beef25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2209600000-5aad21e860dae640443cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-6904000000-afb161cdc06418ce541dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-8901000000-4c0c19b86495d3dbc461View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1407900000-992c1bfeea2fffc14ebdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2519000000-308dc505af787a161469View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9811000000-3e4f38aa86f3824ab46eView 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 IDDBMET00206
      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