2-[(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]ethan-1-ol

• ChemBase ID: 175880
• Molecular Formular: C21H25NO2
• Molecular Mass: 323.4287
• Monoisotopic Mass: 323.18852905
• SMILES: C1Oc2c(/C(=C\CCN(C)C)/c3c1cccc3)cc(cc2)CCO
• Canonical SMILES: OCCc1ccc2c(c1)/C(=C\CCN(C)C)/c1ccccc1CO2
• InChI: InChI=1S/C21H25NO2/c1-22(2)12-5-8-19-18-7-4-3-6-17(18)15-24-21-10-9-16(11-13-23)14-20(19)21/h3-4,6-10,14,23H,5,11-13,15H2,1-2H3/b19-8-
• InChIKey: ZKOHNNRBHUBCOD-UWVJOHFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]ethan-1-ol
• IUPAC Traditional name: 2-[(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]ethanol
• Synonyms: (11Z)-11-[3-(Dimethylamino)propylidene]-6,11-dihydro-dibenz[b,e]oxepin-2-ethanol; Olopatadine Methanol

Database IDs

• CAS Number: 113835-76-0
• PubChem SID: 164231790
• PubChem CID: 15749405

CALCULATED PROPERTIES

• Acid pKa: 15.898385
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.07044791
• LogD (pH = 7.4): 1.0289891
• Log P: 3.3612854
• Molar Refractivity: 109.8157 cm^3
• Polarizability: 38.364662 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol

DETAILS

Toronto Research Chemicals - O575020

Olopatadine (O575000) derivative, with antiallergic activity.

REFERENCES

• Ohshima, E. et al.: J. Med. Chem. 35, 2074 (1992)