Securinine

CAS: 5610-40-2

Ref. 3D-FS27810

Product Information

• Name: Securinine
• Synonyms: (6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one1,2,3,4,10,10a-Hexahydro-10-hydroxy-6 ,10-methanopyrido [1,2-a]azepine-9(6H),a-acetic Acid ?-Lactone, (11aR,11bS)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, (6R,11aS,11bR)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, (6S,11aR)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, (6S,11aR,11bS)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, 6,10-Methanopyrido[1,2-a]azepine-Δ⁹⁽⁶^H^),α-acetic acid, 1,2,3,4,10,10a-hexahydro-10-hydroxy-, γ-lactone, 8H-6,11b-Methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, 9,10,11,11a-tetrahydro-, (6S,11aR,11bS)-, 9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, NSC 107413, Securinan-11-one, Securinin, l-Securinine, 6,10-Methanopyrido[1,2-a]azepine-Δ9(6H),α-acetic acid, 1,2,3,4,10,10a-hexahydro-10-hydroxy-, γ-lactone, Securinine, (-)-

Description

Securinine is a plant alkaloid that is structurally similar to the antibiotic rifampicin. Securinine inhibits bacterial growth by binding to RNA polymerase and preventing transcription and replication. The high frequency of human activity has been shown using a patch-clamp technique on human erythrocytes. This active form is metabolized through a number of metabolic transformations, including hydrolysis by esterases or glucuronidases, oxidation by cytochrome P450 enzymes, reduction by glutathione reductase, or conjugation with glucuronic acid. Securinine also specifically binds to markers expressed at high levels in Mycobacterium tuberculosis strains (e.g., ESX-1 secretion system protein) and inhibits cell growth in culture.

• Brand: Biosynth

Chemical properties

• Molecular weight: 217.26 g/mol
• Formula: C₁₃H₁₅NO₂
• Purity: Min. 95%
• 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
• InChI key: InChIKey=SWZMSZQQJRKFBP-WZRBSPASSA-N
• SMILES: O=C1C=C2C=C[C@@H]3C[C@@]2(O1)[C@H]1CCCCN31