virginiamycin S1
CHEBI:46416 EXACT SEEDED antibacterial
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.
Structure
| Standard InChIKey | FEPMHVLSLDOMQC-IYPFLVAKSA-N |
|---|---|
| SMILES | [H][C@@]12CCCN1C(=O)[C@@]([H])(CC)NC(=O)[C@@]([H])(NC(=O)C1=C(O)C=CC=N1)[C@@]([H])(C)OC(=O)[C@@]([H])(NC(=O)[C@]1([H])CC(=O)CCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N(C)C2=O)C1=CC=CC=C1 |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA09403 |
Filing pathway
Unclassified — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is nrps, pks, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Streptomyces virginiae NCBITaxon:1961 |
SOURCE_ASSERTION | mibig:BGC0001116 | PMID:17350183 |
Occurrences 2
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Streptomyces virginiae NCBITaxon:1961 |
LOTUS | DOI:10.1016/J.GENE.2006.12.035 |
| Streptomyces virginiae NCBITaxon:1961 |
LOTUS | DOI:10.1021/JA01501A070 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001116 | Streptomyces virginiae NCBITaxon:1961 |
CLUSTER_UNSTATED | genbank:AB283030.2 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Elsewhere in the fleet
- AntibioticMech — CHEBI:46416 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001116 | MIBIG | 5 |
| CHEBI:46416 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/virginiamycin-s1.yaml, which is generated from the committed inventories. Neither is edited by hand.