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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:08:10 UTC
Update Date2021-09-14 15:43:20 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
Data?1563866124
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
Description 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.55231661259
DarkChem[M-H]-198.68431661259
DeepCCS[M+H]+196.84530932474
DeepCCS[M-H]-194.44930932474
DeepCCS[M-2H]-227.33230932474
DeepCCS[M+Na]+202.75730932474
AllCCS[M+H]+206.632859911
AllCCS[M+H-H2O]+204.732859911
AllCCS[M+NH4]+208.432859911
AllCCS[M+Na]+208.932859911
AllCCS[M-H]-197.832859911
AllCCS[M+Na-2H]-198.832859911
AllCCS[M+HCOO]-200.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-cis-HydroxyglipizideCC1=CN=C(C=N1)C(O)=NCCC1=CC=C(C=C1)S(=O)(=O)NC(O)=N[C@H]1CCC[C@@H](O)C15041.4Standard polar33892256
3-cis-HydroxyglipizideCC1=CN=C(C=N1)C(O)=NCCC1=CC=C(C=C1)S(=O)(=O)NC(O)=N[C@H]1CCC[C@@H](O)C13249.1Standard non polar33892256
3-cis-HydroxyglipizideCC1=CN=C(C=N1)C(O)=NCCC1=CC=C(C=C1)S(=O)(=O)NC(O)=N[C@H]1CCC[C@@H](O)C14120.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-cis-Hydroxyglipizide,1TMS,isomer #1CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)NC(O)=N[C@H]3CCC[C@@H](O)C3)C=C2)O[Si](C)(C)C)C=N14157.4Semi standard non polar33892256
3-cis-Hydroxyglipizide,1TMS,isomer #2CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)NC(=N[C@H]3CCC[C@@H](O)C3)O[Si](C)(C)C)C=C2)C=N14200.5Semi standard non polar33892256
3-cis-Hydroxyglipizide,1TMS,isomer #3CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)NC(O)=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)C=C2)C=N14181.0Semi standard non polar33892256
3-cis-Hydroxyglipizide,1TMS,isomer #4CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)N(C(O)=N[C@H]3CCC[C@@H](O)C3)[Si](C)(C)C)C=C2)C=N14191.4Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TMS,isomer #1CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)NC(=N[C@H]3CCC[C@@H](O)C3)O[Si](C)(C)C)C=C2)O[Si](C)(C)C)C=N14011.5Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TMS,isomer #2CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)NC(O)=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)C=C2)O[Si](C)(C)C)C=N13966.2Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TMS,isomer #3CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)N(C(O)=N[C@H]3CCC[C@@H](O)C3)[Si](C)(C)C)C=C2)O[Si](C)(C)C)C=N13980.6Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TMS,isomer #4CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)NC(=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)O[Si](C)(C)C)C=C2)C=N13990.2Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TMS,isomer #5CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)N(C(=N[C@H]3CCC[C@@H](O)C3)O[Si](C)(C)C)[Si](C)(C)C)C=C2)C=N14023.2Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TMS,isomer #6CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)N(C(O)=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)[Si](C)(C)C)C=C2)C=N13977.9Semi standard non polar33892256
3-cis-Hydroxyglipizide,3TMS,isomer #1CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)NC(=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)O[Si](C)(C)C)C=C2)O[Si](C)(C)C)C=N13850.8Semi standard non polar33892256
3-cis-Hydroxyglipizide,3TMS,isomer #2CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)N(C(=N[C@H]3CCC[C@@H](O)C3)O[Si](C)(C)C)[Si](C)(C)C)C=C2)O[Si](C)(C)C)C=N13893.2Semi standard non polar33892256
3-cis-Hydroxyglipizide,3TMS,isomer #3CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)N(C(O)=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)[Si](C)(C)C)C=C2)O[Si](C)(C)C)C=N13846.2Semi standard non polar33892256
3-cis-Hydroxyglipizide,3TMS,isomer #4CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)N(C(=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)O[Si](C)(C)C)[Si](C)(C)C)C=C2)C=N13851.7Semi standard non polar33892256
3-cis-Hydroxyglipizide,4TMS,isomer #1CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)N(C(=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)O[Si](C)(C)C)[Si](C)(C)C)C=C2)O[Si](C)(C)C)C=N13786.3Semi standard non polar33892256
3-cis-Hydroxyglipizide,4TMS,isomer #1CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)N(C(=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)O[Si](C)(C)C)[Si](C)(C)C)C=C2)O[Si](C)(C)C)C=N13518.6Standard non polar33892256
3-cis-Hydroxyglipizide,4TMS,isomer #1CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)N(C(=N[C@H]3CCC[C@@H](O[Si](C)(C)C)C3)O[Si](C)(C)C)[Si](C)(C)C)C=C2)O[Si](C)(C)C)C=N15380.1Standard polar33892256
3-cis-Hydroxyglipizide,1TBDMS,isomer #1CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)NC(O)=N[C@H]3CCC[C@@H](O)C3)C=C2)O[Si](C)(C)C(C)(C)C)C=N14359.0Semi standard non polar33892256
3-cis-Hydroxyglipizide,1TBDMS,isomer #2CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)NC(=N[C@H]3CCC[C@@H](O)C3)O[Si](C)(C)C(C)(C)C)C=C2)C=N14410.2Semi standard non polar33892256
3-cis-Hydroxyglipizide,1TBDMS,isomer #3CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)NC(O)=N[C@H]3CCC[C@@H](O[Si](C)(C)C(C)(C)C)C3)C=C2)C=N14367.2Semi standard non polar33892256
3-cis-Hydroxyglipizide,1TBDMS,isomer #4CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)N(C(O)=N[C@H]3CCC[C@@H](O)C3)[Si](C)(C)C(C)(C)C)C=C2)C=N14435.6Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TBDMS,isomer #1CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)NC(=N[C@H]3CCC[C@@H](O)C3)O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)C=N14394.4Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TBDMS,isomer #2CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)NC(O)=N[C@H]3CCC[C@@H](O[Si](C)(C)C(C)(C)C)C3)C=C2)O[Si](C)(C)C(C)(C)C)C=N14355.6Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TBDMS,isomer #3CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)N(C(O)=N[C@H]3CCC[C@@H](O)C3)[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)C=N14422.9Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TBDMS,isomer #4CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)NC(=N[C@H]3CCC[C@@H](O[Si](C)(C)C(C)(C)C)C3)O[Si](C)(C)C(C)(C)C)C=C2)C=N14394.9Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TBDMS,isomer #5CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)N(C(=N[C@H]3CCC[C@@H](O)C3)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=N14450.1Semi standard non polar33892256
3-cis-Hydroxyglipizide,2TBDMS,isomer #6CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)N(C(O)=N[C@H]3CCC[C@@H](O[Si](C)(C)C(C)(C)C)C3)[Si](C)(C)C(C)(C)C)C=C2)C=N14426.2Semi standard non polar33892256
3-cis-Hydroxyglipizide,3TBDMS,isomer #1CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)NC(=N[C@H]3CCC[C@@H](O[Si](C)(C)C(C)(C)C)C3)O[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)C=N14401.9Semi standard non polar33892256
3-cis-Hydroxyglipizide,3TBDMS,isomer #2CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)N(C(=N[C@H]3CCC[C@@H](O)C3)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)C=N14495.9Semi standard non polar33892256
3-cis-Hydroxyglipizide,3TBDMS,isomer #3CC1=CN=C(C(=NCCC2=CC=C(S(=O)(=O)N(C(O)=N[C@H]3CCC[C@@H](O[Si](C)(C)C(C)(C)C)C3)[Si](C)(C)C(C)(C)C)C=C2)O[Si](C)(C)C(C)(C)C)C=N14448.6Semi standard non polar33892256
3-cis-Hydroxyglipizide,3TBDMS,isomer #4CC1=CN=C(C(O)=NCCC2=CC=C(S(=O)(=O)N(C(=N[C@H]3CCC[C@@H](O[Si](C)(C)C(C)(C)C)C3)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=N14470.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-cis-Hydroxyglipizide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9614500000-64150592b72e8acb8c572017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-cis-Hydroxyglipizide GC-MS (3 TMS) - 70eV, Positivesplash10-03k9-5423429000-df478a70bf2a61f953392017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-cis-Hydroxyglipizide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 10V, Positive-QTOFsplash10-0006-2209600000-683041e6404b9a7874192017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 20V, Positive-QTOFsplash10-01oy-6904000000-ef9d26224001b5f3f91c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 40V, Positive-QTOFsplash10-01ox-9800000000-f60cca076e18f02c4d5a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 10V, Negative-QTOFsplash10-03di-1407900000-992c1bfeea2fffc14ebd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 20V, Negative-QTOFsplash10-014j-2519000000-56c5c8ff9d77d0391e672017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 40V, Negative-QTOFsplash10-0006-9711000000-7c13c92514adb010c5b52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 10V, Negative-QTOFsplash10-03di-0001900000-0da4d0865d55901550bc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 20V, Negative-QTOFsplash10-02tc-3209200000-0c81872be3bd0fe2a1392021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 40V, Negative-QTOFsplash10-0006-9222100000-eeac96b03bd481d93f222021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 10V, Positive-QTOFsplash10-03dl-0506900000-fb6e968fb17621ab2ec82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 20V, Positive-QTOFsplash10-0h94-3119300000-f3aed49fa38d62ada82f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-cis-Hydroxyglipizide 40V, Positive-QTOFsplash10-0uds-5942300000-73d6a2ed539f59356b952021-10-12Wishart LabView Spectrum
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 Compound131769998
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available