LIPID MAPS

Structure Database (LMSD)

Common Name

asukamycin

Systematic Name

(2E,4E,6E)-7-cyclohexyl-N-[(1S,5S,6R)-5-hydroxy-5-{(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)amino]-7-oxohepta-1,3,5-trien-1-yl}-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]hepta-2,4,6-trienamide

Synonyms

AM 1042
Asukamycin
asukamycin A1

LM ID

LMFA08020166

Formula

C₃₁H₃₄N₂O₇

Exact Mass

Calculate m/z

546.236603

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Asukamycin is polyketide isolated from the S. nodosus subspecies asukaensis that demonstrates a broad range of antibiotic functions. It has been shown to inhibit growth of various tumor cell lines (IC50s = 1-5 µM) by activating caspases 8 and 3.1

This information has been provided by Cayman Chemical

References

1. Shipley, P.R., Donnelly, C.C.A., Le, C.H., et al. Antitumor activity of asukamycin, a secondary metabolite from the actinomycete bacterium Streptomyces nodosus subspecies asukaensis. Int. J. Mol. Med. 24(5), 711-715 (2009).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Streptomyces nodosus subsp. asukaensis (#222892)

Actinomycetes (#1760)

Antitumor activity of asukamycin, a secondary metabolite from the actinomycete bacterium Streptomyces nodosus subspecies asukaensis.,
Int J Mol Med, 2009

Pubmed ID: 19787206

String Representations

InChiKey (Click to copy)

SSHVAUUEPNULMP-JHWDTTIQSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1(=O)C(NC(=O)/C=C/C=C/C=C/C2CCCCC2)=C[C@@](O)(/C=C/C=C/C=C/C(=O)NC2C(=O)CCC=2O)[C@@H]2O[C@H]12