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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:24:10 UTC
Update Date2019-07-23 07:14:40 UTC
HMDB IDHMDB0060595
Secondary Accession Numbers
  • HMDB60595
Metabolite Identification
Common NameOlopatadine n-oxide
DescriptionOlopatadine n-oxide is a metabolite of olopatadine. Olopatadine hydrochloride is an antihistamine (as well as anticholinergic) and mast cell stabilizer, sold as a prescription eye drop (0.2% solution, Pataday, manufactured by Alcon). It is used to treat itching associated with allergic conjunctivitis. Olopatadine hydrochloride 0.1% is sold as Patanol (or Opatanol in some countries). A nasal spray formulation is sold as Patanase, which was approved by the FDA on April 15, 2008. (Wikipedia)
Structure
Data?1563866080
Synonyms
ValueSource
Olsalazine-O-sulfuric acidGenerator
Olsalazine-O-sulphateGenerator
Olsalazine-O-sulphuric acidGenerator
Chemical FormulaC21H23NO4
Average Molecular Weight353.4116
Monoisotopic Molecular Weight353.162708229
IUPAC Name3-[(2Z)-5-(carboxymethyl)-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-ylidene]-N,N-dimethylpropanamine oxide
Traditional Name3-[(2Z)-5-(carboxymethyl)-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-ylidene]-N,N-dimethylpropanamine oxide
CAS Registry NumberNot Available
SMILES
C[N+](C)([O-])CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C2
InChI Identifier
InChI=1S/C21H23NO4/c1-22(2,25)11-5-8-18-17-7-4-3-6-16(17)14-26-20-10-9-15(12-19(18)20)13-21(23)24/h3-4,6-10,12H,5,11,13-14H2,1-2H3,(H,23,24)/b18-8-
InChI KeyTXKZPVWYFNGMCP-LSCVHKIXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentPhenylsulfates
Alternative Parents
Substituents
  • Phenylsulfate
  • Benzoic acid or derivatives
  • Benzoic acid
  • Phenoxy compound
  • Benzoyl
  • Phenylhydrazine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Benzenoid
  • Ketone
  • Cyclic ketone
  • Hydrazone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility0.0015 g/LALOGPS
logP0.95ALOGPS
logP1.89ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)4.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area73.41 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.6 m³·mol⁻¹ChemAxon
Polarizability38.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+176.24930932474
DeepCCS[M-H]-173.89130932474
DeepCCS[M-2H]-207.1630932474
DeepCCS[M+Na]+182.38930932474
AllCCS[M+H]+184.932859911
AllCCS[M+H-H2O]+181.932859911
AllCCS[M+NH4]+187.632859911
AllCCS[M+Na]+188.432859911
AllCCS[M-H]-191.032859911
AllCCS[M+Na-2H]-191.432859911
AllCCS[M+HCOO]-192.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Olopatadine n-oxideC[N+](C)([O-])CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C24305.9Standard polar33892256
Olopatadine n-oxideC[N+](C)([O-])CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C22251.7Standard non polar33892256
Olopatadine n-oxideC[N+](C)([O-])CC\C=C1\C2=CC=CC=C2COC2=C1C=C(CC(O)=O)C=C22803.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Olopatadine n-oxide,1TMS,isomer #1C[N+](C)([O-])CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C)C=C122945.3Semi standard non polar33892256
Olopatadine n-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C2OCC3=CC=CC=C3/C(=C/CC[N+](C)(C)[O-])C2=C13186.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Olopatadine n-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-002u-9088000000-09605686c9a9a2ae96982017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olopatadine n-oxide GC-MS (1 TMS) - 70eV, Positivesplash10-01w0-9025200000-857e9ff657420c499cd22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olopatadine n-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine n-oxide 10V, Positive-QTOFsplash10-000i-0019000000-bbdffd8ea9489b0bc0792017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine n-oxide 20V, Positive-QTOFsplash10-0a4u-0179000000-1ca95481277bf083f7272017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine n-oxide 40V, Positive-QTOFsplash10-0536-3290000000-5385f05604e0dbbc60722017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine n-oxide 10V, Negative-QTOFsplash10-0udi-0009000000-c3c627bed04156b8286c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine n-oxide 20V, Negative-QTOFsplash10-0udi-2009000000-34bc162820fdf64d4efe2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olopatadine n-oxide 40V, Negative-QTOFsplash10-0a4j-9460000000-5c85f356142b17bdbcfd2017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound9578291
PDB IDNot Available
ChEBI IDNot Available
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