Showing metabocard for Rabeprazole (BMDB0005026)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:46 UTC
Update Date2020-04-22 15:15:09 UTC
BMDB IDBMDB0005026
Secondary Accession Numbers
  • BMDB05026
Metabolite Identification
Common NameRabeprazole
DescriptionRabeprazole, also known as clofezone or eraloc, belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety. Rabeprazole is a drug which is used for the treatment of acid-reflux disorders (gerd), peptic ulcer disease, h. pylori eradication, and prevention of gastroinetestinal bleeds with nsaid use. Based on a literature review a significant number of articles have been published on Rabeprazole.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ClofezoneChEBI
EralocKegg
AciphexHMDB, MeSH
HabeprazoleHMDB
ParietHMDB, MeSH
ParietsHMDB
Rabeprazole sodiumHMDB, MeSH
Sodium rabeprazoleHMDB
DexrabeprazoleMeSH, HMDB
1H-Benzimidazole, 2-(((4-(3-methoxypropoxy)-3-methyl-2-pyridinyl)methyl)sulfinyl)-, sodium saltMeSH, HMDB
2-((4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methylsulfinyl)-1H-benzimidazoleMeSH, HMDB
Sodium, rabeprazoleMeSH, HMDB
Chemical FormulaC18H21N3O3S
Average Molecular Weight359.443
Monoisotopic Molecular Weight359.130362243
IUPAC Name2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
Traditional Namerabeprazole
CAS Registry Number117976-89-3
SMILES
COCCCOC1=C(C)C(CS(=O)C2=NC3=CC=CC=C3N2)=NC=C1
InChI Identifier
InChI=1S/C18H21N3O3S/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)
InChI KeyYREYEVIYCVEVJK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassSulfinylbenzimidazoles
Direct ParentSulfinylbenzimidazoles
Alternative Parents
Substituents
  • Sulfinylbenzimidazole
  • Alkyl aryl ether
  • Methylpyridine
  • Pyridine
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Sulfoxide
  • Sulfinyl compound
  • Ether
  • Dialkyl ether
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point101.7 - 103.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.04ALOGPS
logP2.09ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)4.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.1 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity98.07 m³·mol⁻¹ChemAxon
Polarizability39.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-009e-9843000000-7b2764dc90023b55c85cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-2159000000-f97510bdc8045ab08ca6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-5792000000-af268bb77b35247f0f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9800000000-6bea6647768de1869c4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-1938000000-25678fb8a17be5befc29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-c503bc067607aca1451eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2910000000-aa7552fe843abc4a67e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0119000000-c5f221b3ffcf7b5cc55cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-3214248b0f4d9b60f153View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-9c4b8759dd61ba097216View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0093000000-14b0419adbad3c76149eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-1950000000-ce8b99f657880db6f1d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08ml-2910000000-2fbee5190b8417e0ac8aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0251094
DrugBank IDDB01129
Phenol Explorer Compound IDNot Available
FooDB IDFDB023595
KNApSAcK IDNot Available
Chemspider ID4853
KEGG Compound IDC07864
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRabeprazole
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID8768
References
Synthesis ReferenceSouda, Shigeru; Ueda, Norihiro; Miyazawa, Shuhei; Tagami, Katsuya; Nomoto, Seiichiro; Okita, Makoto; Shimomura, Naoyuki; Kaneko, Toshihiko; Fujimoto, Masatoshi; et al. Preparation of 2-[(4-alkoxypyrid-2-yl)methylthio]benzimidazoles, -benzothiazoles, and -benzoxazoles as ulcer inhibitors. Eur. Pat. Appl. (1988), 96 pp. CODEN: EPXXDW EP 268956 A2 19880601 CAN 110:23889 AN 1989:23889
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available