(8R)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one

• ChemBase ID: 177729
• Molecular Formular: C13H15NO2
• Molecular Mass: 217.2637
• Monoisotopic Mass: 217.11027873
• SMILES: C1CCC2C34C[C@H](C=CC3=CC(=O)O4)N2C1
• Canonical SMILES: O=C1C=C2C3(O1)C[C@H](C=C2)N1C3CCCC1
• InChI: InChI=1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11?,13?/m0/s1
• InChIKey: SWZMSZQQJRKFBP-ZBOXLXRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R)-14-oxa-7-azatetracyclo[6.6.1.0^1,^1^1.0^2,^7]pentadeca-9,11-dien-13-one
• IUPAC Traditional name: (8R)-14-oxa-7-azatetracyclo[6.6.1.0^1,^1^1.0^2,^7]pentadeca-9,11-dien-13-one
• Synonyms: (6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one; 1,2,3,4,10,10a-Hexahydro-10-hydroxy-6,10-methanopyrido[1,2-a]azepine-9(6H),α-acetic Acid γ-Lactone; Securinan-11-one; (-)-Securinine; NSC 107413; Securinin; l-Securinine; Securinine

Database IDs

• CAS Number: 5610-40-2
• PubChem SID: 164233639
• PubChem CID: 71752176

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.9773666
• LogD (pH = 7.4): -0.68543625
• Log P: 1.4055138
• Molar Refractivity: 61.3191 cm^3
• Polarizability: 23.567463 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Alcohol
• Apperance: Yellow Solid
• Melting Point: 140-142°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S241000

Extracted from leaves and roots of Securinega suffruticosa Rehder. The most widely studied of these alkaloids, Securinine, is a specific GABA receptor antagonist and has been found to have significant in vivo CNS activity.

REFERENCES

• Friess, S.L., et al.: Toxicol. Appl. Pharmacol., 3, 347 (1961)