phevalin
CHEBI:167320 EXACT SEEDED
A member of the class of pyrazinones that is pyrazin-2(1H)-one substituted by an isopropyl and benzyl groups at position 3 and 6, respectively. It is a natural product found in Staphylococcus aureus that inhibits calpain in a casein hydrolysis assay (IC50 = 1.3 μM), contributes to S. aureus infection in mice, and alters human keratinocyte gene expression.
Structure
| Standard InChIKey | CZUORGWXUVRUMV-UHFFFAOYSA-N |
|---|---|
| SMILES | CC(C)C1=NC=C(NC1=O)CC2=CC=CC=C2 |
| Stereochemistry | fully defined |
| Cross-references | pubchem:10376483 |
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, 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 |
|---|---|---|---|
| Staphylococcus aureus subsp. aureus str. JKD6008 NCBITaxon:546342 |
SOURCE_ASSERTION | mibig:BGC0000308 | PMID:23302043 |
Occurrences 5
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 |
|---|---|---|
| Staphylococcus aureus NCBITaxon:1280 |
CHEBI | PMID:23302043 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.7164/ANTIBIOTICS.48.1165 |
| Streptomyces griseus NCBITaxon:1911 |
LOTUS | DOI:10.1016/S0960-894X(01)00524-8 |
| Streptomyces sp. NCBITaxon:1931 |
CHEBI | 10.7164/antibiotics.48.1165 |
| Escherichia coli NCBITaxon:562 |
CHEBI | PMID:28111075 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000308 | Staphylococcus aureus subsp. aureus str. JKD6008 NCBITaxon:546342 |
CLUSTER_UNSTATED | genbank:CP002120.1 |
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.
Open questions 1
name-disagreement — ChEBI calls this structure 'phevalin' and MIBiG calls it 'aureusimine B'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000308 | MIBIG | 5 |
| CHEBI:167320 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/phevalin.yaml, which is generated from the committed inventories. Neither is edited by hand.