(1R,2R,9R,17S)-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one

• ChemBase ID: 119455
• Molecular Formular: C15H24N2O
• Molecular Mass: 248.36386
• Monoisotopic Mass: 248.1888634
• SMILES: N12[C@@H]([C@@H]3[C@@H]4[C@@H](C1)CCCN4CCC3)CCCC2=O
• Canonical SMILES: O=C1CCC[C@H]2N1C[C@H]1CCCN3[C@@H]1[C@@H]2CCC3
• InChI: InChI=1S/C15H24N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h11-13,15H,1-10H2/t11-,12-,13-,15+/m1/s1
• InChIKey: ZSBXGIUJOOQZMP-BHPKHCPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,9R,17S)-7,13-diazatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadecan-6-one
• IUPAC Traditional name: (1R,2R,9R,17S)-7,13-diazatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadecan-6-one
• Synonyms: (4(1)S,7aR,13aR,13bR)-dodecahydro-1H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10(4(1)H)-one; Sophoridine

Database IDs

• CAS Number: 6882-68-4
• PubChem SID: 162107974
• PubChem CID: 165549

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.3545308
• LogD (pH = 7.4): -1.248441
• Log P: 1.0759273
• Molar Refractivity: 71.4485 cm^3
• Polarizability: 28.175423 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Oil

Pharmacology Properties

• Mechanism of Action: Antioxidant; Enhancer of sodium and calcium channels blocking

Product Information

• Biological Source: Alkaloid from roots of Sophora flavescens (Leguminosae)
• Application(s): Antiarrhythmic; Antioxidant

REFERENCES

• Kamalitdinov, D. et al., Khim. Prir. Soedin., 1967, 3, 352; Chem. Nat. Compd. (Engl. Transl.), 1967, 3, 297, (isol)
• Yunusov, T.K. et al., Khim. Prir. Soedin., 1972, 8, 200; Chem. Nat. Compd. (Engl. Transl.), 1972, 8, 201, (ir)
• Monakhova, T.E. et al., Khim. Prir. Soedin., 1973, 9, 59; Chem. Nat. Compd. (Engl. Transl.), 1973, 9, 52, (deriv)
• Vul'fson, N.S. et al., Khim. Geterotsikl. Soedin., 1974, 10, 251; Chem. Heterocycl. Compd. (Engl. Transl.), 1974, 10, 221, (ms)
• Kamaev, F.G. et al., Khim. Prir. Soedin., 1974, 10, 744; Chem. Nat. Compd. (Engl. Transl.), 1974, 10, 765, (pmr, struct)
• Morinaga, K. et al., Chem. Pharm. Bull., 1978, 26, 2483, (pmr)
• Kuchkarov, S. et al., Khim. Prir. Soedin., 1979, 15, 364; Chem. Nat. Compd. (Engl. Transl.), 1979, 15, 364, (isol)
• Ibragimov, B.T. et al., Khim. Prir. Soedin., 1982, 18, 71; Chem. Nat. Compd. (Engl. Transl.), 1982, 18, 66, (rev, stereochem)