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Record Information
Version3.6
Creation Date2013-07-09 16:08:25 UTC
Update Date2016-02-11 08:15:44 UTC
HMDB IDHMDB60938
Secondary Accession NumbersNone
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=1/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 KeyInChIKey=IUWSGCQEWOOQDN-IYARVYRRNA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.69 m3·mol-1ChemAxon
Polarizability52.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDDBMET00209
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 LinkHMDB60938
Metagene LinkHMDB60938
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