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Record Information
Version4.0
Creation Date2013-07-09 16:17:42 UTC
Update Date2017-09-27 08:44:01 UTC
HMDB IDHMDB0061091
Secondary Accession Numbers
  • HMDB61091
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
5-Hydroxy omeprazoleMeSH
5-HydroxymethylomeprazoleMeSH
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=1S/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 KeyCMZHQFXXAAIBKE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzimidazoles
Direct ParentSulfinylbenzimidazoles
Alternative Parents
Substituents
  • Sulfinylbenzimidazole
  • Anisole
  • Alkyl aryl ether
  • Methylpyridine
  • Pyridine
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Sulfoxide
  • Sulfinyl compound
  • Ether
  • Azacycle
  • Aromatic alcohol
  • Organic oxide
  • Organopnictogen compound
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

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 Solubility0.75 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.44 m³·mol⁻¹ChemAxon
Polarizability38.43 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0129000000-63b3da2a877ed49bac04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-0938000000-921769315297d14c7ef9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-464e1df97777a9c0f193View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0609000000-347b6db613e118706276View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0901000000-62a5cbcb1ba7d17112caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-0901000000-364ea8566e3d1bc71711View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
      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
      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