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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:08:25 UTC
Update Date2018-05-20 20:31:46 UTC
HMDB IDHMDB0060938
Secondary Accession Numbers
  • HMDB60938
Metabolite Identification
Common Name4-trans-Hydroxycyclohexyl glyburide
Description4-trans-Hydroxycyclohexyl glyburide is a metabolite of glyburide. Glibenclamide, also known as glyburide (USAN), is an antidiabetic drug in a class of medications known as sulfonylureas, closely related to sulfa drugs. It was developed in 1966 in a cooperative study between Boehringer Mannheim (now part of Roche) and Hoechst (now part of Sanofi-Aventis). (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H28ClN3O6S
Average Molecular Weight510.003
Monoisotopic Molecular Weight509.13873404
IUPAC Name5-chloro-2-methoxy-N-(2-{4-[({[(1r,4r)-4-hydroxycyclohexyl]-C-hydroxycarbonimidoyl}amino)sulfonyl]phenyl}ethyl)benzene-1-carboximidic acid
Traditional Name5-chloro-2-methoxy-N-{2-[4-({[(1r,4r)-4-hydroxycyclohexyl]-C-hydroxycarbonimidoyl}aminosulfonyl)phenyl]ethyl}benzenecarboximidic acid
CAS Registry NumberNot Available
SMILES
COC1=C(C=C(Cl)C=C1)C(O)=NCCC1=CC=C(C=C1)S(=O)(=O)NC(O)=N[C@H]1CC[C@H](O)CC1
InChI Identifier
InChI=1S/C23H28ClN3O6S/c1-33-21-11-4-16(24)14-20(21)22(29)25-13-12-15-2-9-19(10-3-15)34(31,32)27-23(30)26-17-5-7-18(28)8-6-17/h2-4,9-11,14,17-18,28H,5-8,12-13H2,1H3,(H,25,29)(H2,26,27,30)/t17-,18-
InChI KeyIUWSGCQEWOOQDN-IYARVYRRSA-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
  • Halobenzoic acid or derivatives
  • 3-halobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzenesulfonyl group
  • Benzamide
  • Phenol ether
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Alkyl aryl ether
  • Chlorobenzene
  • Sulfonylurea
  • Cyclohexanol
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Aminosulfonyl compound
  • Cyclic alcohol
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Carbonic acid derivative
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Ether
  • Alcohol
  • Organohalogen compound
  • Organochloride
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.012 g/LALOGPS
logP3.17ALOGPS
logP4.04ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)5.62ChemAxon
pKa (Strongest Basic)3.35ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area140.81 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.69 m³·mol⁻¹ChemAxon
Polarizability52.2 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, Positivesplash10-02ft-4924400000-90a8e5dc396e959f59abView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0080-9156028000-fe327f0e1453a6045154View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0296-1309640000-97375dcd567f4de68926View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ta-2903000000-d410a625e6858eae8864View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-4900000000-e1c76b297b9faca52becView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0509380000-fe7224f31cc73db1b958View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1419000000-a6c648e83c7ba4ae0d80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01po-4903000000-c71a862c4deac31558e3View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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