virginiamycin S1

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Ligands
virginiamycin S1

GtoPdb Ligand ID: 13755

Synonyms: staphylomycin S | virgimycin

Comment: Virginiamycin S1 is a streptogramin antibacterial produced by a Streptomyces sp. related to S. virginiae [5]. It is isolated as part of a virginiamycin complex containing M components (M1 and M2) and S components (S1-S4)(reviewed in [1]). Virginiamycin S1 and pristinamycin IIA (virginiamycin M1) are the major components of virginiamycin [2], an antibacterial used in veterinary medicine and also in animal husbandry as a growth promoter.

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	17
Hydrogen bond donors	4
Rotatable bonds	7
Topological polar surface area	224.19
Molecular weight	823.89
XLogP	1.42
No. Lipinski's rules broken	2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey

Canonical SMILES	CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N(C)[C@@H](CC3=CC=CC=C3)C(=O)N4CCC(=O)C[C@H]4C(=O)N[C@@H](C5=CC=CC=C5)C(=O)O[C@H](C)[C@@H](C(=O)N1)NC(=O)C6=NC=CC=C6O
Isomeric SMILES	CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3CCC(=O)C[C@H]3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CC6=CC=CC=C6)C
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
InChI Key	FEPMHVLSLDOMQC-IYPFLVAKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)