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Record Information
Version3.6
Creation Date2013-07-09 16:17:42 UTC
Update Date2016-02-11 08:18:23 UTC
HMDB IDHMDB61091
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-hydroxyesomeprazole
Description5-hydroxyesomeprazole is a metabolite of esomeprazole. Esomeprazole is a proton pump inhibitor (brand name Nexium) developed and marketed by AstraZeneca which is used in the treatment of dyspepsia, peptic ulcer disease (PUD), gastroesophageal reflux disease (GORD/GERD) and Zollinger-Ellison syndrome. Esomeprazole is the S-enantiomer of omeprazole (marketed as Losec/Prilosec), and AstraZeneca claims improved efficacy of this single enantiomer product over the racemic mixture of omeprazole. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
5-Methoxy-2-(((4-methoxy-3-methyl-5-hydroxymethyl-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazoleChEBI
HydroxyomeprazoleChEBI
5-Methoxy-2-(((4-methoxy-3-methyl-5-hydroxymethyl-2-pyridinyl)methyl)sulphinyl)-1H-benzimidazoleGenerator
Chemical FormulaC17H19N3O4S
Average Molecular Weight361.415
Monoisotopic Molecular Weight361.109626801
IUPAC Name(4-methoxy-6-{[(6-methoxy-1H-1,3-benzodiazol-2-yl)sulfinyl]methyl}-5-methylpyridin-3-yl)methanol
Traditional Name{4-methoxy-6-[(5-methoxy-3H-1,3-benzodiazol-2-ylsulfinyl)methyl]-5-methylpyridin-3-yl}methanol
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(CO)C(OC)=C1C
InChI Identifier
InChI=1/C17H19N3O4S/c1-10-15(18-7-11(8-21)16(10)24-3)9-25(22)17-19-13-5-4-12(23-2)6-14(13)20-17/h4-7,21H,8-9H2,1-3H3,(H,19,20)
InChI KeyInChIKey=CMZHQFXXAAIBKE-UHFFFAOYNA-N
Chemical Taxonomy
ClassificationNot classified
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 Solubility0.75 mg/mLALOGPS
logP1.05ALOGPS
logP1.15ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)3.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.33 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.44 m3·mol-1ChemAxon
Polarizability38.43 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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 IDDBMET00448
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 LinkHMDB61091
Metagene LinkHMDB61091
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