(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one

• ChemBase ID: 155034
• Molecular Formular: C13H15NO2
• Molecular Mass: 217.2637
• Monoisotopic Mass: 217.11027873
• SMILES: C1CCN2[C@H](C1)[C@]13C[C@@H]2C=CC1=CC(=O)O3
• Canonical SMILES: O=C1C=C2[C@@]3(O1)C[C@H](C=C2)N1[C@@H]3CCCC1
• 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+/m1/s1
• InChIKey: SWZMSZQQJRKFBP-WZRBSPASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.0^1,^1^1.0^2,^7]pentadeca-9,11-dien-13-one
• IUPAC Traditional name: (-)-securinine
• Synonyms: Securinine

Database IDs

• CAS Number: 5610-40-2
• MDL Number: MFCD00078775
• PubChem SID: 162249172
• PubChem CID: 442872

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: DMSO: ≥25 mg/mL
• Apperance: yellow powder
• Optical Rotation: [α]/D -980 to -1015 ( C=1, MeOH)

Safety Information

• RTECS: VS4115000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H15NO2
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - SML0055

Biochem/physiol Actions
Securinine is an alkaloid widely in traditional folk medicine. Long known as a GABAA antagonist, securinine was recently found to up-regulate p53 protein and to modulate the related family member p73 protein in a p53-dependent fashion, inducing p73 in the HCT116 p53(-) cells and down-regulating it in the p53(+) cells. Induction of proapoptotic protein p73 only in p53 cells could be used to target cancer cells preferentially. Securinine has been found to induce p53-independent, p73-dependent apoptosis in RKO colon cancer cells.