(2E)-but-2-enedioic acid; 13-chloro-2-{1-[(5-methylpyridin-3-yl)methyl](2,2,6,6-2H4)piperidin-4-ylidene}-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene

• ChemBase ID: 177655
• Molecular Formular: C30H30ClN3O4
• Molecular Mass: 532.0299
• Monoisotopic Mass: 531.19248414
• SMILES: C1Cc2c(/C(=C/3\CCN(CC3)Cc3cncc(c3)C)/c3c1cc(cc3)Cl)nccc2.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: Cc1cncc(c1)CN1CC/C(=C/2\c3ccc(cc3CCc3c2nccc3)Cl)/CC1.OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C26H26ClN3.C4H4O4/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;5-3(6)1-2-4(7)8/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
• InChIKey: JYBLCDXVHQWMSU-WLHGVMLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; 13-chloro-2-{1-[(5-methylpyridin-3-yl)methyl](2,2,6,6-^2H₄)piperidin-4-ylidene}-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene
• IUPAC Traditional name: 13-chloro-2-{1-[(5-methylpyridin-3-yl)methyl](2,2,6,6-^2H₄)piperidin-4-ylidene}-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene; fumaric acid
• Synonyms: 8-Chloro-6,11-dihydro-11-[1-[(5-methyl-3-pyridinyl)methyl]-4-piperidinylidene-d4]- 5H-benzo[5,6]cyclohepta[1,2-b]pyridine (2E)-2-Butenedioate; Rupafin-d4 Fumarate; Rupatadine-d4 Fumarate

Database IDs

• PubChem SID: 164233565
• PubChem CID: 71752142

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.3898315
• LogD (pH = 7.4): 5.0328426
• Log P: 5.371808
• Molar Refractivity: 133.8304 cm^3
• Polarizability: 47.6801 Å^3
• Polar Surface Area: 29.02 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R701652

Labelled Rupatadine (R701650). Rupatadine is a dual antagonist of histamine H1 and platelet-activating factor receptors. Rupatadine is used as an antihistaminic.

REFERENCES

• Merlos, M., et al.: J. Pharmacol. Exp. Ther., 280, 114 (1997)
• Guadano, E.M., et al.: Allergy, 59, 766 (1997)