Asukamycin

• CAT Number: R003874
• CAS Number: 61116-33-4
• Molecular Formula: C31H34N2O7
• Molecular Weight: 546.62
• Purity: 95%
• Storage: -20°C
• Analysis method: HPLC
• IUPAC Name: (2E,4E,6E)-7-cyclohexyl-N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]hepta-2,4,6-trienamide
• InChI: InChI=1S/C31H34N2O7/c34-23-17-18-24(35)27(23)33-26(37)16-10-3-4-11-19-31(39)20-22(28(38)29-30(31)40-29)32-25(36)15-9-2-1-6-12-21-13-7-5-8-14-21/h1-4,6,9-12,15-16,19-21,29-30,34,39H,5,7-8,13-14,17-18H2,(H,32,36)(H,33,37)/b2-1+,4-3+,12-6+,15-9+,16-10+,19-11+/t29-,30-,31+/m1/s1
• InChIKey: SSHVAUUEPNULMP-JHWDTTIQSA-N
• SMILES: C1CCC(CC1)C=CC=CC=CC(=O)NC2=CC(C3C(C2=O)O3)(C=CC=CC=CC(=O)NC4=C(CCC4=O)O)O

Asukamycin is an unusual trienoic acid amide metabolite produced by Streptomyces nodosus, reported by Omura and
colleagues at the Kitasato Institute, Japan, in 1976. Asukamycin belongs to the manumycin class that comprises two trienoic
acid amides pivoted on a central cyclohexenone ring to give the molecule an unprecedented angular geometry. Asukamycin is
active against Gram positive bacteria, tumor cell lines and protozoans, notably coccidia. Asukamycin’s cell toxicity is
accompanied by activation of Caspases 3 and 8.

Reference

A new antibiotic, asukamycin, produced by Streptomyces. Omura S. et al. J. Antibiot. 1976, 29, 876.

The manumycin-group metabolites. Sattler I. et al. J. Antibiot. 2000, 53, 221.

Antitumor activity of asukamycin, a secondary metabolite from the actinomycete bacterium Streptomyces nodosus subspecies asukaensis. Shipley P.R. et al. Int. J. Mol. Med. 2009, 24, 711.