Compound ID | 2742

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Staphylomycin S

Synonym(s): Virginiamycin S1  |  Virgimycin

Class: Streptogramin

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Protein synthesis inhibitor. Binds to the 50S ribosomal subunit
Target Pathogen: Active against Staphylococcus aureus
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):
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Molecular weight: 823.89
Iso. 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 Key: FEPMHVLSLDOMQC-UHFFFAOYSA-N
Can. 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
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)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/Staphylomycin-S
Guide to Pharmacology: virginiamycin S1
Citations:
  • https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1699-0463.1963.tb03437.x
  • https://pubs.acs.org/doi/10.1021/ja01501a070
  • https://pubs.acs.org/doi/abs/10.1021/bi00360a011

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