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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:40:04 UTC
Update Date2019-07-23 14:38:54 UTC
HMDB IDHMDB0240234
Secondary Accession NumbersNone
Metabolite Identification
Common NameRupatadine
DescriptionRupatadine belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle. Rupatadine is a drug which is used for the symptomatic relief of nasal and non-nasal symptoms of seasonal allergic rhinitis and perennial allergic rhinitis in patients 2 years of age and older [fda label]. also used for the symptomatic relief of chronic spontaneous urticaria in patients 2 years of age and older. In humans, rupatadine is involved in the rupatadine h1-antihistamine action pathway. Rupatadine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Rupatadine.
Structure
Data?1563892734
Synonyms
ValueSource
AlergoliberHMDB
PafinurHMDB
RinialerHMDB
RupafinHMDB
RupaxHMDB
RupatadineHMDB
8-chloro-6,11-dihydro-11-(1-((5-Methyl-3-pyridinyl)methyl)-4-piperidinylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridineMeSH, HMDB
Chemical FormulaC26H26ClN3
Average Molecular Weight415.97
Monoisotopic Molecular Weight415.1815255
IUPAC Name13-chloro-2-{1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene}-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene
Traditional Name13-chloro-2-{1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene}-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene
CAS Registry Number158876-82-5
SMILES
CC1=CC(CN2CCC(CC2)=C2C3=CC=C(Cl)C=C3CCC3=C2N=CC=C3)=CN=C1
InChI Identifier
InChI=1S/C26H26ClN3/c1-18-13-19(16-28-15-18)17-30-11-8-20(9-12-30)25-24-7-6-23(27)14-22(24)5-4-21-3-2-10-29-26(21)25/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3
InChI KeyWUZYKBABMWJHDL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzocycloheptapyridines
Sub ClassNot Available
Direct ParentBenzocycloheptapyridines
Alternative Parents
Substituents
  • Benzocycloheptapyridine
  • Methylpyridine
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Piperidine
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(4.82) g/LALOGPS
logP10(5.37) g/LChemAxon
logS10(-4.9) g/LALOGPS
pKa (Strongest Basic)7.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity133.83 m³·mol⁻¹ChemAxon
Polarizability46.98 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+202.77631661259
AllCCS[M-H]-200.84131661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rupatadine 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 - Rupatadine 10V, Positive-QTOFsplash10-014i-0001900000-50ad6856523ebb65d61c2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 20V, Positive-QTOFsplash10-014r-1459800000-b77f7dd4eb9730e8a3f92017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 40V, Positive-QTOFsplash10-0006-9122100000-8b1654433eb949efa7e22017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 10V, Negative-QTOFsplash10-03di-0000900000-049e64830c3bc2a7ceb92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 20V, Negative-QTOFsplash10-03di-0112900000-355dcca35f8056d1382d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 40V, Negative-QTOFsplash10-0006-9104000000-16b70b4af0fce61811cf2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 10V, Positive-QTOFsplash10-014i-0000900000-39a07ac15a39a39804f82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 20V, Positive-QTOFsplash10-014i-0000900000-8c62478012de9a9609872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 40V, Positive-QTOFsplash10-000i-1129100000-990e448a6b9a422bed832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 10V, Negative-QTOFsplash10-03di-0000900000-22cba1cd3e775618af752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 20V, Negative-QTOFsplash10-01q9-9000700000-4804c39f6d9203d5956e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rupatadine 40V, Negative-QTOFsplash10-001i-9112100000-0baea998b23df99668002021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDDB11614
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID117388
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRupatadine
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 References
  1. Picado C: Rupatadine: pharmacological profile and its use in the treatment of allergic disorders. Expert Opin Pharmacother. 2006 Oct;7(14):1989-2001. [PubMed:17020424 ]