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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:25:15 UTC
Update Date2021-09-14 15:42:49 UTC
HMDB IDHMDB0060596
Secondary Accession Numbers
  • HMDB60596
Metabolite Identification
Common NameKetotifen-N-glucuronide
DescriptionKetotifen-N-glucuronide is a metabolite of ketotifen. Ketotifen is a second-generation H1-antihistamine and mast cell stabilizer. It is most commonly sold in as a salt of fumaric acid, ketotifen fumarate, and is available in two forms. In its ophthalmic form, it is used to treat allergic conjunctivitis, or the itchy red eyes caused by allergies. In its oral form, it is used to prevent asthma attacks. Side effects include drowsiness, weight gain, dry mouth, irritability, and increased nosebleeds. (Wikipedia)
Structure
Data?1563866080
SynonymsNot Available
Chemical FormulaC25H27NO7S
Average Molecular Weight485.549
Monoisotopic Molecular Weight485.150822913
IUPAC Name1-(6-carboxylato-3,4,5-trihydroxyoxan-2-yl)-1-methyl-4-{8-oxo-6-thiatricyclo[8.4.0.0³,⁷]tetradeca-1(10),3(7),4,11,13-pentaen-2-ylidene}piperidin-1-ium
Traditional Name1-(6-carboxylato-3,4,5-trihydroxyoxan-2-yl)-1-methyl-4-{8-oxo-6-thiatricyclo[8.4.0.0³,⁷]tetradeca-1(10),3(7),4,11,13-pentaen-2-ylidene}piperidin-1-ium
CAS Registry NumberNot Available
SMILES
C[N+]1(CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=C1C=CC=C2)C1OC(C(O)C(O)C1O)C([O-])=O
InChI Identifier
InChI=1S/C25H27NO7S/c1-26(24-21(30)19(28)20(29)22(33-24)25(31)32)9-6-13(7-10-26)18-15-5-3-2-4-14(15)12-17(27)23-16(18)8-11-34-23/h2-5,8,11,19-22,24,28-30H,6-7,9-10,12H2,1H3/b18-13-
InChI KeyWLTPAELNPGRIGG-AQTBWJFISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-glucuronides
Alternative Parents
Substituents
  • N-glucuronide
  • 1-n-glucuronide
  • Glycosyl compound
  • N-glycosyl compound
  • Cycloheptathiophene
  • Aryl ketone
  • Aryl alkyl ketone
  • Beta-hydroxy acid
  • Hydroxy acid
  • Oxane
  • Piperidine
  • Pyran
  • Benzenoid
  • Thiophene
  • Heteroaromatic compound
  • Tetraalkylammonium salt
  • Secondary alcohol
  • Carboxylic acid salt
  • Ketone
  • Hemiaminal
  • Organoheterocyclic compound
  • Polyol
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic salt
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.004 g/LALOGPS
logP1.41ALOGPS
logP-2.9ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area127.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity156.01 m³·mol⁻¹ChemAxon
Polarizability49.98 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+197.75330932474
DeepCCS[M-H]-195.35730932474
DeepCCS[M-2H]-228.23930932474
DeepCCS[M+Na]+203.66530932474
AllCCS[M+H]+210.432859911
AllCCS[M+H-H2O]+208.732859911
AllCCS[M+NH4]+212.032859911
AllCCS[M+Na]+212.432859911
AllCCS[M-H]-206.232859911
AllCCS[M+Na-2H]-207.132859911
AllCCS[M+HCOO]-208.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ketotifen-N-glucuronideC[N+]1(CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=C1C=CC=C2)C1OC(C(O)C(O)C1O)C([O-])=O4784.5Standard polar33892256
Ketotifen-N-glucuronideC[N+]1(CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=C1C=CC=C2)C1OC(C(O)C(O)C1O)C([O-])=O2933.6Standard non polar33892256
Ketotifen-N-glucuronideC[N+]1(CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=C1C=CC=C2)C1OC(C(O)C(O)C1O)C([O-])=O4433.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ketotifen-N-glucuronide,1TMS,isomer #1C[N+]1(C2OC(C(=O)[O-])C(O[Si](C)(C)C)C(O)C2O)CCC(=C2C3=CC=CC=C3CC(=O)C3=C2C=CS3)CC14123.4Semi standard non polar33892256
Ketotifen-N-glucuronide,1TMS,isomer #2C[N+]1(C2OC(C(=O)[O-])C(O)C(O[Si](C)(C)C)C2O)CCC(=C2C3=CC=CC=C3CC(=O)C3=C2C=CS3)CC14131.0Semi standard non polar33892256
Ketotifen-N-glucuronide,1TMS,isomer #3C[N+]1(C2OC(C(=O)[O-])C(O)C(O)C2O[Si](C)(C)C)CCC(=C2C3=CC=CC=C3CC(=O)C3=C2C=CS3)CC14124.5Semi standard non polar33892256
Ketotifen-N-glucuronide,2TMS,isomer #1C[N+]1(C2OC(C(=O)[O-])C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)CCC(=C2C3=CC=CC=C3CC(=O)C3=C2C=CS3)CC14050.0Semi standard non polar33892256
Ketotifen-N-glucuronide,2TMS,isomer #2C[N+]1(C2OC(C(=O)[O-])C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)CCC(=C2C3=CC=CC=C3CC(=O)C3=C2C=CS3)CC14056.4Semi standard non polar33892256
Ketotifen-N-glucuronide,2TMS,isomer #3C[N+]1(C2OC(C(=O)[O-])C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)CCC(=C2C3=CC=CC=C3CC(=O)C3=C2C=CS3)CC14058.0Semi standard non polar33892256
Ketotifen-N-glucuronide,3TMS,isomer #1C[N+]1(C2OC(C(=O)[O-])C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)CCC(=C2C3=CC=CC=C3CC(=O)C3=C2C=CS3)CC14025.8Semi standard non polar33892256
Ketotifen-N-glucuronide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C(C(=O)[O-])OC([N+]2(C)CCC(=C3C4=CC=CC=C4CC(=O)C4=C3C=CS4)CC2)C(O)C1O4346.5Semi standard non polar33892256
Ketotifen-N-glucuronide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1C(O)C(C(=O)[O-])OC([N+]2(C)CCC(=C3C4=CC=CC=C4CC(=O)C4=C3C=CS4)CC2)C1O4351.8Semi standard non polar33892256
Ketotifen-N-glucuronide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1C(O)C(O)C(C(=O)[O-])OC1[N+]1(C)CCC(=C2C3=CC=CC=C3CC(=O)C3=C2C=CS3)CC14339.5Semi standard non polar33892256
Ketotifen-N-glucuronide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C(C(=O)[O-])OC([N+]2(C)CCC(=C3C4=CC=CC=C4CC(=O)C4=C3C=CS4)CC2)C(O[Si](C)(C)C(C)(C)C)C1O4426.7Semi standard non polar33892256
Ketotifen-N-glucuronide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1C(C(=O)[O-])OC([N+]2(C)CCC(=C3C4=CC=CC=C4CC(=O)C4=C3C=CS4)CC2)C(O)C1O[Si](C)(C)C(C)(C)C4430.0Semi standard non polar33892256
Ketotifen-N-glucuronide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1C(O)C(C(=O)[O-])OC([N+]2(C)CCC(=C3C4=CC=CC=C4CC(=O)C4=C3C=CS4)CC2)C1O[Si](C)(C)C(C)(C)C4437.1Semi standard non polar33892256
Ketotifen-N-glucuronide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C(C(=O)[O-])OC([N+]2(C)CCC(=C3C4=CC=CC=C4CC(=O)C4=C3C=CS4)CC2)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C4549.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ketotifen-N-glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0009100000-c0938d2e54854ad13b9d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ketotifen-N-glucuronide GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1109000000-c729542c936a855d34572017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ketotifen-N-glucuronide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ketotifen-N-glucuronide 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 - Ketotifen-N-glucuronide 10V, Positive-QTOFsplash10-029i-0014900000-9aa1c93cf2f3efbd42972017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketotifen-N-glucuronide 20V, Positive-QTOFsplash10-03di-5159200000-2cb1fe671b060a36b61b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketotifen-N-glucuronide 40V, Positive-QTOFsplash10-03dl-2194000000-553dfa13dabc4f76f8a12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketotifen-N-glucuronide 10V, Negative-QTOFsplash10-001i-0100900000-e0c05a66ec2bcbd8e7882017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketotifen-N-glucuronide 20V, Negative-QTOFsplash10-0089-9800600000-2f373c371c240b5f2ba92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketotifen-N-glucuronide 40V, Negative-QTOFsplash10-0a5c-9300000000-087ab62e778f864695052017-10-06Wishart 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
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 CompoundNot Available
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