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-pentaazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide

• ChemBase ID: 154593
• Molecular Formular: C43H49N7O10
• Molecular Mass: 823.89006
• Monoisotopic Mass: 823.3540908
• SMILES: CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@@H](C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)c1c(cccn1)O)C)c1ccccc1)Cc1ccccc1)C
• Canonical SMILES: CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@H](N(C(=O)[C@H]3N(C1=O)CCC3)C)Cc1ccccc1)CCC(=O)C2)c1ccccc1
• 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

NAMES AND DATABASE IDS

Names

• 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-pentaazatricyclo[20.4.0.0^6,^1^0]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
• IUPAC Traditional name: virginiamycin S1
• Synonyms: Antibiotic 899; Staphylomycin S; Virginiamycin S1

Database IDs

• CAS Number: 23152-29-6
• EC Number: 245-462-6
• PubChem SID: 162248731
• PubChem CID: 5388936

CALCULATED PROPERTIES

• Acid pKa: 7.529842
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 1.8491545
• LogD (pH = 7.4): 1.6192802
• Log P: 1.8531505
• Molar Refractivity: 213.2372 cm^3
• Polarizability: 82.944954 Å^3
• Polar Surface Area: 224.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white powder

Safety Information

• Storage Temperature: -20°C

Product Information

• Purity: ≥99% (HPLC)
• Empirical Formula (Hill Notation): C43H49N7O10

DETAILS

Sigma Aldrich - V4140

Biochem/physiol Actions
Cyclic polypeptide antibiotic from Streptomyces sp. Acts as a synergist binding to the conformational change in the peptidyl transferase center fo the 50S ribosome.
Virginiamycin S inhibits bacterial protein synthesis at the level of aminoacyl-tRNA binding and peptide bond formation. It inactivates the 50S ribosome. VS is a cyclic hexadepsipeptide containing a nonproteinogenic amino acid, Lphenylglycine (L-pheGly), in its core structure. The visG gene is required for VS biosynthesis. Nonribosomal peptide synthetase (NRPS) may be involved in VS biosynthesis. Virginiamycin S is active against Gram-positive bacteria1.
Application
The antibiotic virginiamycin is produced by Streptomyces virginiae and is a member of the virginiamycin family. Each member is produced as a mixture of two structurally different compounds that exhibit synergistic antibacterial activity. There are two groups: virginiamycin M1 (VM1) and virginiamycin S (VS). VS is a cyclic hexadepsipeptide. VS and VM1 are both used to inhibit protein synthesis since they are bacteriostatic. When used in combination they are more effective. Virginiamycin is used as a performance promoter in animal husbandry. It is chemically modified to make therapeutic drugs such as quinupristin and dalfopristin1,2.