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

• ChemBase ID: 175877
• Molecular Formular: C21H23NO3
• Molecular Mass: 337.41222
• Monoisotopic Mass: 337.1677936
• SMILES: C1Oc2c(/C(=C/CCN(C)C)/c3c1cccc3)cc(cc2)CC(=O)O
• Canonical SMILES: CN(CC/C=C\1/c2cc(ccc2OCc2c1cccc2)CC(=O)O)C
• InChI: InChI=1S/C21H23NO3/c1-22(2)11-5-8-18-17-7-4-3-6-16(17)14-25-20-10-9-15(12-19(18)20)13-21(23)24/h3-4,6-10,12H,5,11,13-14H2,1-2H3,(H,23,24)/b18-8+
• InChIKey: JBIMVDZLSHOPLA-QGMBQPNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2E)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]acetic acid
• IUPAC Traditional name: olopatadine
• Synonyms: (11E)-11-[3-(Dimethylamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic Acid; (E)-Olopatadine

Database IDs

• CAS Number: 113806-06-7
• PubChem SID: 164231787
• PubChem CID: 5284599

CALCULATED PROPERTIES

• Acid pKa: 3.7840304
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.74022824
• LogD (pH = 7.4): 0.74543273
• Log P: 0.7462555
• Molar Refractivity: 109.5524 cm^3
• Polarizability: 38.300964 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O575005

The trans-isomeric impurity of antihistaminic Olopatadine (O575000).

REFERENCES

• Rele, R.V. et al.: Int. J. Chem. Sci., 9, 601 (2011)