(1R,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

• ChemBase ID: 129440
• Molecular Formular: C18H25NO5
• Molecular Mass: 335.3948
• Monoisotopic Mass: 335.17327291
• SMILES: O=C1O[C@@H]2CCN3CC=C(COC(=O)[C@](C)(O)[C@H](C)C/C/1=C/C)[C@H]23
• Canonical SMILES: C/C=C\1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
• InChI: InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/t11-,14-,15-,18-/m1/s1
• InChIKey: HKODIGSRFALUTA-XKLVTHTNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^1^4,^1^7]heptadec-11-ene-3,8-dione
• IUPAC Traditional name: senecionine
• Synonyms: Aureine; Senecionine

Database IDs

• PubChem SID: 162223734
• PubChem CID: 5280906
• CHEBI ID: 9107
• CHEMBL: 362153
• Chemspider ID: 10254883
• KEGG ID: C06176
• Wikipedia Title: Senecionine

CALCULATED PROPERTIES

• Acid pKa: 12.370886
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.9376966
• LogD (pH = 7.4): 0.8353181
• Log P: 1.6438626
• Molar Refractivity: 89.4066 cm^3
• Polarizability: 34.92372 Å^3
• Polar Surface Area: 76.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Density: 1.25 g/cm^3