A macrolide antibiotic
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Virginiamycin S1

Item No. 17455

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal 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]oxa[4,7,10,13,16]pentaazacyclononadecin-9-yl)-3-hydroxypicolinamide
CAS Number
23152-29-6
Synonyms
  • Antibiotic 1754Z3B
  • Staphylomycin S1
Molecular Formula
C43H49N7O10
Formula Weight
823.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: SolubleWater: Slightly soluble
SMILES
O=C1C[C@](C(N[C@@H](C2=CC=CC=C2)C(O[C@H](C)[C@H](NC(C3=C(O)C=CC=N3)=O)C4=O)=O)=O)([H])N(C([C@@](CC5=CC=CC=C5)([H])N(C)C([C@]6([H])CCCN6C([C@H](N4)CC)=O)=O)=O)CC1
InChi Code
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
InChi Key
FEPMHVLSLDOMQC-IYPFLVAKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Virginiamycin S1 is a macrolide antibiotic that is a component of the virginiamycin complex (Item No. 14503), which also contains virginiamycin M1 (Item No. 9002172).1 It is a member of the streptogramin B group of antibiotics, which bind the 50S ribosomal subunit at the peptidyl transferase center to inhibit initiation and translocation.2 They show good bactericidal activity against methicillin-resistant S. aureus (MRSA), although resistance in MRSA is conferred by the cfr gene.2,3 Virginiamycin S1 acts synergistically with virginiamycin M1 to irreversibly inhibit protein synthesis in bacteria.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ningsih, F., Kitani, S., Fukushima, E., et al. VisG is essential for biosynthesis of virginiamycin S, a streptogramin type B antibiotic, as a provider of the nonproteinogenic amino acid phenylglycine. Microbiology 157(Pt. 11), 3213-3220 (2011).

    2. Fair, R.J., and Tor, Y. Antibiotics and bacterial resistance in the 21st century. Perspect. Medicin. Chem. 6, 25-64 (2014).

    3. Kehrenberg, C., Cuny, C., Strommenger, B., et al. Methicillin-resistant and -susceptible Staphylococcus aureus strains of clonal lineages ST398 and ST9 from swine carry the multidrug resistance gene cfr. Antimicrob. Agents Chemother. 53(2), 779-781 (2009).

    4. Parfait, R., and Cocito, C. Lasting damage to bacterial ribosomes by reversibly bound virginiamycin M. Proc. Natl. Acad. Sci. USA 77(9), 5492-5496 (1980).