Cyclopenin

• CAT Number: M137335
• CAS Number: 19553-26-5
• Molecular Formula: C17H14N2O3
• Molecular Weight: 294.3
• Purity: 98%
• Storage: -20°C
• Analysis method: HPLC
• IUPAC Name: (3S,3'S)-4-methyl-3'-phenylspiro[1H-1,4-benzodiazepine-3,2'-oxirane]-2,5-dione
• InChI: InChI=1S/C17H14N2O3/c1-19-15(20)12-9-5-6-10-13(12)18-16(21)17(19)14(22-17)11-7-3-2-4-8-11/h2-10,14H,1H3,(H,18,21)/t14-,17-/m0/s1
• InChIKey: APLKWZASYUZSBL-YOEHRIQHSA-N
• SMILES: CN1C(=O)C2=CC=CC=C2NC(=O)C13C(O3)C4=CC=CC=C4

Cyclopenin is one of an unusual family of benzodiazepine metabolites produced by a number of Penicillium species. Often
mistakenly referred to as a mycotoxin, cyclopenin shows little toxicity against mammalian cells, bacteria or fungi in vitro.
Cyclopenin is an intermediate in the biosynthesis of 3-O-methyl viridicatin, a strong inhibitor of TNFα-induced replication HIV.
Lack of availability has hitherto restricted a more intensive investigation of this interesting metabolite.

Reference

Studies in the biochemistry of microorganisms. 93. Cyclopenin, a nitrogen-containing metabolic product of Penicillium cyclopium Westling. Bracken A. et al. Biochem J. 1954, 57, 587. 

Isolation and characterization of the fungal metabolite 3-O-methylviridicatin as an inhibitor of tumor necrosis factor alpha-induced human immunodeficiency virus replication. Heguy A. et al. Antivir. Chem. Chemother. 1998, 9, 149.