(8R)-2-oxa-9-azatetracyclo[6.5.1.01,5.09,13]tetradeca-4,6-dien-3-one

• ChemBase ID: 175713
• Molecular Formular: C12H13NO2
• Molecular Mass: 203.23712
• Monoisotopic Mass: 203.09462866
• SMILES: C12C34C[C@H](C=CC3=CC(=O)O4)N1CCC2
• Canonical SMILES: O=C1C=C2C3(O1)C[C@H](C=C2)N1C3CCC1
• InChI: InChI=1S/C12H13NO2/c14-11-6-8-3-4-9-7-12(8,15-11)10-2-1-5-13(9)10/h3-4,6,9-10H,1-2,5,7H2/t9-,10?,12?/m0/s1
• InChIKey: NBGOALXYAZVRPS-BMQDGWLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R)-2-oxa-9-azatetracyclo[6.5.1.0^1,^5.0^9,^1^3]tetradeca-4,6-dien-3-one
• IUPAC Traditional name: (8R)-2-oxa-9-azatetracyclo[6.5.1.0^1,^5.0^9,^1^3]tetradeca-4,6-dien-3-one
• Synonyms: (6S,10aR,10bS)-8,9,10,10a-Tetrahydro-6,10b-Methano-10bH-furo[2,3-c]pyrrolo[1,2-a]azepin-2(6H)-one; A-Norsecurinan-11-one; (-)-Norsecurinine; [6S-(6α,10aβ,10bα)]-8,9,10,10a-Tetrahydro-6,10b-methano-10bH-furo[2,3-c]pyrrolo[1,2-a]azepin-2(6H)-one; Nor Securinine

Database IDs

• CAS Number: 2650-35-3
• PubChem SID: 164231623
• PubChem CID: 365099

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.2615335
• LogD (pH = 7.4): -0.6892719
• Log P: 0.9609451
• Molar Refractivity: 56.7181 cm^3
• Polarizability: 21.728031 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N826000

A new alkaloid from Phyllanthus niruri. These alkaloids have found a sporadic use clinically for such diseases as poliomyelitis, ALS (amyotrophic lateral sclerosis) and chronic aplastic anemia.

REFERENCES

• Horii, Z., et al.: Chem. Pharm. Bull., 20, 1768 (1972)
• Rognan, D., et al.: J. Med. Chem., 35, 1969 (1972)
• Weenen, H., et al.: Planta Med., 56, 371 (1972)