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

• ChemBase ID: 166544
• Molecular Formular: C20H21NO3
• Molecular Mass: 323.38564
• Monoisotopic Mass: 323.15214354
• SMILES: C1Oc2c(/C(=C\CCNC)/c3c1cccc3)cc(cc2)CC(=O)O
• Canonical SMILES: CNCC/C=C/1\c2cc(ccc2OCc2c1cccc2)CC(=O)O
• InChI: InChI=1S/C20H21NO3/c1-21-10-4-7-17-16-6-3-2-5-15(16)13-24-19-9-8-14(11-18(17)19)12-20(22)23/h2-3,5-9,11,21H,4,10,12-13H2,1H3,(H,22,23)/b17-7-
• InChIKey: VQMJUHOJPCPUAM-IDUWFGFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2Z)-2-[3-(methylamino)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: [(2Z)-2-[3-(methylamino)propylidene]-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]acetic acid
• Synonyms: (11Z)-6,11-Dihydro-11-[3-(methylamino)propylidene]dibenz[b,e]oxepin-2-acetic Acid; N-Mono-demethyl-KW-4679 (M1); N-Desmethyl Olopatadine

Database IDs

• CAS Number: 113835-92-0
• PubChem SID: 162260677
• PubChem CID: 14127209

CALCULATED PROPERTIES

• Acid pKa: 3.784032
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.6163486
• LogD (pH = 7.4): 0.6227885
• Log P: 0.6228587
• Molar Refractivity: 104.2577 cm^3
• Polarizability: 36.457016 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D292190

Olopatadine (O575000) metabolite.

REFERENCES

• Kajita, J., et al.: Drug Metab. Disposition, 30, 1504 (2002)