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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2022-03-07 03:17:33 UTC
HMDB IDHMDB0059609
Secondary Accession Numbers
  • HMDB59609
Metabolite Identification
Common Namealbendazole S-oxide
Descriptionalbendazole S-oxide, also known as ricobendazole, belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds). Albendazole s-oxide is part of the Steroid hormone biosynthesis, Linoleic acid metabolism, Retinol metabolism, and Bile secretion pathways. albendazole S-oxide is a moderately basic compound (based on its pKa).
Structure
Data?1563865954
Synonyms
ValueSource
(+-)-Albendazole sulfoxideChEBI
Albendazole oxideChEBI
Albendazole sulfoxideChEBI
RicobendazoleChEBI
RycobendazoleChEBI
(+-)-Albendazole sulphoxideGenerator
Albendazole sulphoxideGenerator
Albendazole sulfoxide, monohydrochlorideHMDB
Chemical FormulaC12H15N3O3S
Average Molecular Weight281.331
Monoisotopic Molecular Weight281.083412051
IUPAC NameN-[6-(propane-1-sulfinyl)-1H-1,3-benzodiazol-2-yl]methoxycarboximidic acid
Traditional NameN-[5-(propane-1-sulfinyl)-3H-1,3-benzodiazol-2-yl]methoxycarboximidic acid
CAS Registry NumberNot Available
SMILES
CCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC
InChI Identifier
InChI=1S/C12H15N3O3S/c1-3-6-19(17)8-4-5-9-10(7-8)14-11(13-9)15-12(16)18-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
InChI KeyVXTGHWHFYNYFFV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Sulfoxide
  • Carboximidic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfinyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.45 g/LALOGPS
logP1.17ALOGPS
logP2.26ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.07ChemAxon
pKa (Strongest Basic)1.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.56 m³·mol⁻¹ChemAxon
Polarizability29.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.89731661259
DarkChem[M-H]-166.10731661259
DeepCCS[M+H]+171.1630932474
DeepCCS[M-H]-168.80230932474
DeepCCS[M-2H]-201.68830932474
DeepCCS[M+Na]+177.25330932474
AllCCS[M+H]+163.332859911
AllCCS[M+H-H2O]+160.032859911
AllCCS[M+NH4]+166.332859911
AllCCS[M+Na]+167.132859911
AllCCS[M-H]-163.632859911
AllCCS[M+Na-2H]-163.732859911
AllCCS[M+HCOO]-164.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
albendazole S-oxideCCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC3748.7Standard polar33892256
albendazole S-oxideCCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC2459.7Standard non polar33892256
albendazole S-oxideCCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC2799.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
albendazole S-oxide,1TMS,isomer #1CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C)[NH]C2=C12497.8Semi standard non polar33892256
albendazole S-oxide,1TMS,isomer #1CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C)[NH]C2=C12497.8Semi standard non polar33892256
albendazole S-oxide,1TMS,isomer #2CCCS(=O)C1=CC=C2N=C(N=C(O)OC)N([Si](C)(C)C)C2=C12581.0Semi standard non polar33892256
albendazole S-oxide,1TMS,isomer #2CCCS(=O)C1=CC=C2N=C(N=C(O)OC)N([Si](C)(C)C)C2=C12581.0Semi standard non polar33892256
albendazole S-oxide,2TMS,isomer #1CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C)N([Si](C)(C)C)C2=C12534.5Semi standard non polar33892256
albendazole S-oxide,2TMS,isomer #1CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C)N([Si](C)(C)C)C2=C12762.0Standard non polar33892256
albendazole S-oxide,1TBDMS,isomer #1CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C(C)(C)C)[NH]C2=C12701.8Semi standard non polar33892256
albendazole S-oxide,1TBDMS,isomer #1CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C(C)(C)C)[NH]C2=C12701.8Semi standard non polar33892256
albendazole S-oxide,1TBDMS,isomer #2CCCS(=O)C1=CC=C2N=C(N=C(O)OC)N([Si](C)(C)C(C)(C)C)C2=C12752.4Semi standard non polar33892256
albendazole S-oxide,1TBDMS,isomer #2CCCS(=O)C1=CC=C2N=C(N=C(O)OC)N([Si](C)(C)C(C)(C)C)C2=C12752.4Semi standard non polar33892256
albendazole S-oxide,2TBDMS,isomer #1CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=C12876.2Semi standard non polar33892256
albendazole S-oxide,2TBDMS,isomer #1CCCS(=O)C1=CC=C2N=C(N=C(OC)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C2=C13167.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - albendazole S-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7690000000-21e36ddf2465905dc7552017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - albendazole S-oxide GC-MS (1 TMS) - 70eV, Positivesplash10-0084-9344000000-708b54c2fe0b2ab0f4d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - albendazole S-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - albendazole S-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - albendazole S-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide LC-ESI-QTOF , positive-QTOFsplash10-001i-0090000000-4f8faf80d5525c831f612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide LC-ESI-QTOF , positive-QTOFsplash10-0006-0090000000-e552a43e2f05f7fd3a522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0390000000-4daf753348e11cbca5d92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0940000000-be363233970a009f5c672017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0900000000-19ee9c1374c824bdde532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOFsplash10-0a4i-0940000000-d0f2d647b9566b3d54712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide 30V, Positive-QTOFsplash10-0a4i-0390000000-c5c2b369163baa89e8942021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide 10V, Positive-QTOFsplash10-001i-0090000000-c50a14c071083e785b902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide 50V, Positive-QTOFsplash10-0a4i-0900000000-17ddc6573026b461668c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide 20V, Positive-QTOFsplash10-0006-0090000000-2ddcbc6be8944aa702422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide 30V, Positive-QTOFsplash10-0a4i-0390000000-0f0e9cf17b08dacc147e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOFsplash10-0a4i-0940000000-4a544a55485d72dcc2322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide 50V, Positive-QTOFsplash10-0a4i-0900000000-302cd5c535d552fe5fdc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOFsplash10-0a4i-0940000000-5a13db941efced21b9d72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 10V, Positive-QTOFsplash10-00e9-1090000000-e150095a8f96d26a5f0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 20V, Positive-QTOFsplash10-00di-2190000000-95bc61e0d527da36378f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOFsplash10-0006-9450000000-880977de0008e20d58832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 10V, Negative-QTOFsplash10-0532-3090000000-8b0222ac217c5e4b2b612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 20V, Negative-QTOFsplash10-0a4i-2190000000-a555b482ba6eed51876f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 40V, Negative-QTOFsplash10-0a6u-9680000000-b24eefc0024e732c7ed62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 10V, Positive-QTOFsplash10-001i-0090000000-a179b59f66fecad942722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 20V, Positive-QTOFsplash10-0f89-0090000000-4e8a2af4bd5b530c02912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 40V, Positive-QTOFsplash10-0ab9-0390000000-5eef2c7c5b772cf0e81b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 10V, Negative-QTOFsplash10-007k-0090000000-cb9845674928abb020ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - albendazole S-oxide 20V, Negative-QTOFsplash10-053s-0390000000-389222650909bec431c32021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13871
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02809
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlbendazole
METLIN IDNot Available
PubChem Compound83969
PDB IDNot Available
ChEBI ID16959
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
Reactions
Albendazole + NADPH + Oxygen → albendazole S-oxide + NADP + Waterdetails