CHEBI:46416 - virginiamycin S1

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ChEBI Name virginiamycin S1
ChEBI ID CHEBI:46416
ChEBI ASCII Name virginiamycin S1
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9998
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Formula C43H49N7O10
Net Charge 0
Average Mass 823.89010
Monoisotopic Mass 823.35409
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)/t25-,29-,30+,31+,32+,34+,35+/m1/s1
InChIKey FEPMHVLSLDOMQC-IYPFLVAKSA-N
SMILES CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]2CC(=O)CCN2C(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H]2CCCN2C1=O)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via macrolide antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
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-lactone ChemIDplus
N-(3-hydroxypicolinoyl)-L-threonyl-D-α-aminobutyryl-L-prolyl-N-methyl-L-phenylalanyl-4-oxo-L-pipecoloyl-L-2-phenylglycine ρ-lactone ChemIDplus
virginiamycin factor S ChemIDplus
Virginiamycin S1 KEGG COMPOUND
virginiamycin S1 ChemIDplus
Manual Xrefs Databases
C11269 KEGG COMPOUND
DB04805 DrugBank
Virginiamycin_S1 Wikipedia
VRS PDBeChem
View more database links
Registry Numbers Types Sources
23152-29-6 CAS Registry Number KEGG COMPOUND
23152-29-6 CAS Registry Number ChemIDplus
3647647 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1493906 PubMed citation Europe PMC
22934408 PubMed citation Europe PMC
3097264 PubMed citation Europe PMC
4142724 PubMed citation Europe PMC
Last Modified
03 August 2015