(1'R,2'S,3S,6'S,8'R)-2'-ethenyl-4'-methyl-1,2-dihydro-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.02,6.05,11]dodecane]-2-one

• ChemBase ID: 127540
• Molecular Formular: C20H22N2O2
• Molecular Mass: 322.40088
• Monoisotopic Mass: 322.16812795
• SMILES: CN1C2C3CO[C@H]4[C@]5([C@@H]2[C@@]([C@@H]3C4)(C=C)C1)c1ccccc1NC5=O
• Canonical SMILES: C=C[C@]12CN(C3[C@@H]2[C@]2([C@H]4C[C@@H]1C3CO4)C(=O)Nc1c2cccc1)C
• InChI: InChI=1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11?,13-,15-,16?,17+,19+,20+/m1/s1
• InChIKey: NFYYATWFXNPTRM-WKRGLROPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,2'S,3S,6'S,8'R)-2'-ethenyl-4'-methyl-1,2-dihydro-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^2,^6.0^5,^1^1]dodecane]-2-one
• IUPAC Traditional name: (1'R,2'S,3S,6'S,8'R)-2'-ethenyl-4'-methyl-1H-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^2,^6.0^5,^1^1]dodecane]-2-one
• Synonyms: Gelsemine

Database IDs

• CAS Number: 509-15-9
• PubChem SID: 162221859
• PubChem CID: 279057; 71308207
• Wikipedia Title: Gelsemine

CALCULATED PROPERTIES

• Acid pKa: 13.101784
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.0188797
• LogD (pH = 7.4): -0.94488364
• Log P: 1.4175211
• Molar Refractivity: 92.7646 cm^3
• Polarizability: 35.634853 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true