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Record Information
Version3.6
Creation Date2013-07-09 16:08:10 UTC
Update Date2016-02-11 08:15:40 UTC
HMDB IDHMDB60934
Secondary Accession NumbersNone
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=1/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+/s2
InChI KeyInChIKey=GZLIUWBDTXQVBY-LQKAMQBPNA-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
  • Phenethylamine
  • Cyclohexylamine
  • Cyclohexanol
  • Pyrazine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Cyclic alcohol
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility0.051 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity118.29 m3·mol-1ChemAxon
Polarizability47.69 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00205
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
NuGOwiki LinkHMDB60934
Metagene LinkHMDB60934
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