virginiamycin S1

Term ID

CHEBI:46416

Synonyms

• N-((3-hydroxy-2-pyridinyl)carbonyl)-L-threonyl-D-alpha-aminobutyryl-L-prolyl-N-methyl-L-phenylalanyl-4-oxo-L-pipecoloyl-L-2-phenylglycine rho-lactone
• N-(3-hydroxypicolinoyl)-L-threonyl-D-alpha-aminobutyryl-L-prolyl-N-methyl-L-phenylalanyl-4-oxo-L-pipecoloyl-L-2-phenylglycine rho-lactone
• N-[(6R,9S,10R,13S,15aS,22S,24aS)-22-benzyl-6-ethyl-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyldocosahydro-12H-pyrido[2,1-f]pyrrolo[2,1-l][1,4,7,10,13,16]oxapentaazacyclononadecin-9-yl]-3-hydroxypyridine-2-carboxamide
• virginiamycin factor S
• virginiamycin S1

Definition

A cyclodepsipeptide that is N-(3-hydroxypicolinoyl)-L-threonyl-D-alpha-aminobutyryl-L-prolyl-N-methyl-L-phenylalanyl-4-oxo-L-pipecoloyl-L-2-phenylglycine in which the carboxy group of the 2-phenylglycine moiety has undergone formal intramolecular condensation with the hydroxy group of the N-(3-hydroxypicolinoyl)-L-threonyl to give the corresponding 19-membered ring lactone. It is one of the two major components of the antibacterial drug virginiamycin, produced by Streptomyces virginiae, S. loidensis, S. mitakaensis, S. pristina-spiralis, S. ostreogriseus, and others.

References

• CAS:23152-29-6
• DrugBank:DB04805
• KEGG:C11269
• PDBeChem:VRS
• PMID:1493906
• PMID:22934408
• PMID:3097264
• PMID:4142724
• Reaxys:3647647
• Wikipedia:Virginiamycin_S1

Ontology

ChEBI  ( EBI )