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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:08:10 UTC
Update Date2018-05-20 20:31:43 UTC
HMDB IDHMDB0060934
Secondary Accession Numbers
  • HMDB60934
Metabolite Identification
Common Name3-cis-Hydroxyglipizide
Description3-cis-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 NameN-(2-{4-[({[(1S,3R)-3-hydroxycyclohexyl]-C-hydroxycarbonimidoyl}amino)sulfonyl]phenyl}ethyl)-5-methylpyrazine-2-carboximidic acid
Traditional NameN-{2-[4-({[(1S,3R)-3-hydroxycyclohexyl]-C-hydroxycarbonimidoyl}aminosulfonyl)phenyl]ethyl}-5-methylpyrazine-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]1CCC[C@@H](O)C1
InChI Identifier
InChI=1S/C21H27N5O5S/c1-14-12-24-19(13-23-14)20(28)22-10-9-15-5-7-18(8-6-15)32(30,31)26-21(29)25-16-3-2-4-17(27)11-16/h5-8,12-13,16-17,27H,2-4,9-11H2,1H3,(H,22,28)(H2,25,26,29)/t16-,17+/m0/s1
InChI KeyGZLIUWBDTXQVBY-DLBZAZTESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
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

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 Solubility0.052 g/LALOGPS
logP1.32ALOGPS
logP1.61ChemAxon
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
Refractivity118.29 m³·mol⁻¹ChemAxon
Polarizability47.69 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, Positivesplash10-0f6x-9614500000-64150592b72e8acb8c57View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03k9-5423429000-df478a70bf2a61f95339View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2209600000-683041e6404b9a787419View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-6904000000-ef9d26224001b5f3f91cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9800000000-f60cca076e18f02c4d5aView 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-2519000000-56c5c8ff9d77d0391e67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9711000000-7c13c92514adb010c5b5View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound 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