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CHEBI:46416 - virginiamycin S1

ChEBI IDCHEBI:46416
ChEBI Namevirginiamycin S1
Stars
ASCII Namevirginiamycin S1
DefinitionA cyclodepsipeptide that is N-(3-hydroxypicolinoyl)-L-threonyl-D-α-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.
Secondary ChEBI IDCHEBI:9998
Last Modified3 August 2015
DownloadsMolfile
FormulaC43H49N7O10
Net Charge0
Average Mass823.904
Monoisotopic Mass823.35409
SMILES[H][C@]1(Cc2ccccc2)C(=O)N2CCC(=O)C[C@@]2([H])C(=O)N[C@@H](c2ccccc2)C(=O)O[C@H](C)[C@H](NC(=O)c2ncccc2O)C(=O)N[C@H](CC)C(=O)N2CCC[C@@]2([H])C(=O)N1C
InChIInChI=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)/t25-,29-,30+,31+,32+,34+,35+/m1/s1
InChIKeyFEPMHVLSLDOMQC-IYPFLVAKSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antibacterial drug  A drug used to treat or prevent bacterial infections.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
virginiamycin S1 (CHEBI:46416) has role antibacterial drug (CHEBI:36047)
virginiamycin S1 (CHEBI:46416) has role bacterial metabolite (CHEBI:76969)
virginiamycin S1 (CHEBI:46416) is a cyclodepsipeptide (CHEBI:35213)
virginiamycin S1 (CHEBI:46416) is a macrolide antibiotic (CHEBI:25105)
Incoming Relation(s)
virginiamycin (CHEBI:87209) has part virginiamycin S1 (CHEBI:46416)
IUPAC Name 
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
Synonyms  Source
Virginiamycin S1KEGG COMPOUND
virginiamycin S1ChemIDplus
N-(3-hydroxypicolinoyl)-L-threonyl-D-α-aminobutyryl-L-prolyl-N-methyl-L-phenylalanyl-4-oxo-L-pipecoloyl-L-2-phenylglycine ρ-lactoneChemIDplus
N-((3-hydroxy-2-pyridinyl)carbonyl)-L-threonyl-D-α-aminobutyryl-L-prolyl-N-methyl-L-phenylalanyl-4-oxo-L-pipecoloyl-L-2-phenylglycine ρ-lactoneChemIDplus
virginiamycin factor SChemIDplus
Manual XrefsDatabases
C11269KEGG COMPOUND
VRSPDBeChem
DB04805DrugBank
Virginiamycin_S1Wikipedia
Registry NumbersSources
Reaxys:3647647Reaxys
CAS:23152-29-6KEGG COMPOUND
CAS:23152-29-6ChemIDplus
Citations