virginiamycin S1

CHEBI:46416 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:25105 CHEBI:25105
CHEBI:35213 CHEBI:35213

Chemical structure

Computed structure properties
Molecular formula	C43H49N7O10
Charge	0
Average mass	823.904 Da
Monoisotopic mass	823.35409 Da
Source	ChEBI
InChIKey	FEPMHVLSLDOMQC-IYPFLVAKSA-N

SMILES

[H][C@]1(Cc2ccccc2)C(=O)N2CCC(=O)C[C@@]2([H])C(=O)N[C@@H](c2ccccc2)C(=O)O[C@H](C)[C@H](NC(=O)c2ncccc2O)C(=O)N[C@H](CC)C(=O)N2CCC[C@@]2([H])C(=O)N1C

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

Also called

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 (EXACT_SYNONYM)— chebi
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 (EXACT_SYNONYM)— chebi
N-(3-hydroxypicolinoyl)-L-threonyl-D-α-aminobutyryl-L-prolyl-N-methyl-L-phenylalanyl-4-oxo-L-pipecoloyl-L-2-phenylglycine ρ-lactone (EXACT_SYNONYM)— chebi
Virginiamycin S1 (EXACT_SYNONYM)— chebi
virginiamycin factor S (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:23152-29-6
drugbank:DB04805
kegg.compound:C11269
pdb-ccd:VRS
reaxys:3647647
wikipedia.en:Virginiamycin_S1

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:46416`	virginiamycin S1	`antibioticmech:chebi-28279e2ba4`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.