Staphylomycin S

Synonym(s): Virginiamycin S1  |  Virgimycin

Class: Streptogramin

Spectrum of activity:	Gram-positive
Details of activity:	Active against Staphylococcus aureus; protein synthesis inhibitor (binds to the 50S ribosomal subunit)
Description:	Natural product from Streptomyces sp. (closely related to S. virginiae); isolated as part of staphylomycin complex containing M1, M2, and S; has poor water solubility; currently used in animal husbandry as growth promoter
Year first mentioned:	1954
Development status:	Experimental

Chemical structure(s):
Canonical SMILES:	CCC1C(=O)N2CCCC2C(=O)N(C)C(CC3=CC=CC=C3)C(=O)N4CCC(=O)CC4C(=O)NC(C5=CC=CC=C5)C(=O)OC(C)C(C(=O)N1)NC(=O)C6=NC=CC=C6O
Isomeric SMILES:	CCC1C(=O)N2CCCC2C(=O)N(C(C(=O)N3CCC(=O)CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CC6=CC=CC=C6)C
InChI:	InChI=1S/C43H49N7O10/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53)
InChI Key:	FEPMHVLSLDOMQC-UHFFFAOYSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/Staphylomycin-S

External links:
Main Source:	https://pubs.acs.org/doi/abs/10.1021/bi00360a011
Citations:	https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1699-0463.1963.tb03437.x https://pubs.acs.org/doi/10.1021/ja01501a070