Virginiamycin S1

Chemical Information
Virginiamycin S1 is 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. It has a role as an antibacterial drug and a bacterial metabolite. It is a macrolide antibiotic and a cyclodepsipeptide.
| CAS Number | 23152-29-6 |
| PubChem CID | 5388936 |
| IUPAC Name | N-[(3S,6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide |
| Molecular Formula | C43H49N7O10 |
| Molecular Weight | 823.9 |
| XLogP | 2.7 |
| Topological Polar Surface Area | 225 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 60 |
| Formal Charge | 0 |
| Complexity | 1620 |
| Property | Value |
|---|---|
| Molecular Weight | 823.9 |
| XLogP3 | 2.7 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 6 |
| Exact Mass | 823.35409079 |
| Monoisotopic Mass | 823.35409079 |
| Topological Polar Surface Area | 225 Ų |
| Heavy Atom Count | 60 |
| Formal Charge | 0 |
| Complexity | 1620 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 7 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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