epoxomicin
CHEBI:42265 EXACT SEEDED cytotoxicenzyme inhibitor
A tripeptide consisting of an Ile-Ile-Thr-NH2 sequence N-substituted on the threonamide amidic nitrogen with a (2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl group and with acetyl and methyl groups on the nitrogen of the isoleucine residue distal to the threonamide; a naturally occurring selective proteasome inhibitor with anti-inflammatory activity.
Structure
| Standard InChIKey | DOGIDQKFVLKMLQ-JTHVHQAWSA-N |
|---|---|
| SMILES | CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(CO1)C)NC(=O)[C@H]([C@@H](C)CC)N(C)C(=O)C |
| Stereochemistry | fully defined |
| Cross-references | pubchem:11226684, pubchem:9915668 |
Filing pathway
Amino acids and peptides — 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 |
|---|---|---|---|
| Goodfellowiella coeruleoviolacea NCBITaxon:334858 |
SOURCE_ASSERTION | mibig:BGC0000346 | PMID:24168704 |
Occurrences 0
None cited.
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000346 | Goodfellowiella coeruleoviolacea NCBITaxon:334858 |
CLUSTER_DEMONSTRATED | genbank:KF647219.1 |
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.
Bioactivities 22
| Assay | Result | Reference |
|---|---|---|
| Constitutive androstane receptor (CAR) small molecule agonists, cell-based qHTS assay in HepG2 cells | 0.0651 uM | pubchem.aid:2202728 |
| Constitutive androstane receptor (CAR) small molecule agonists, cell-based qHTS assay in HepG2 cells | 0.0651 uM | pubchem.aid:2202728 |
| GF-AFC viability counterscreen for inhibitors of alpha-synuclein gene (SNCA) expression | 0.0238 uM | pubchem.aid:1671193 |
| NCATS anti-infectives library activity on the primary C. elegans qHTS viability assay | 0.1028 uM | PMID:36786055 |
| P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2.5929 uM | PMID:31515284 |
| Primary fluorescence-based thiol-reactive (MSTI) qHTS assay for identification of artifact compounds. | 1.8888 uM | pubchem.aid:1845221 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 0.0073 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C) | 0.0073 uM | pubchem.aid:1645877 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 0.0129 uM | pubchem.aid:1645876 |
| Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B) | 0.0129 uM | pubchem.aid:1645876 |
| Primary qHTS for small molecule compounds that upregulate eGFP-tagged delta133p53alpha (in N-terminal) cells. | 0.0757 uM | pubchem.aid:2060322 |
| Primary qHTS for small molecule compounds that upregulate eGFP-tagged delta133p53alpha (in N-terminal) cells. | 0.0757 uM | pubchem.aid:2060322 |
| Primary qHTS to identify anti-liver cancer compounds using libraries of approved drugs and bioactive compounds | 1.122 uM | pubchem.aid:2202548 |
| Primary redox qHTS assay for identification of artifact compounds. | 6.7016 uM | pubchem.aid:1845223 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 0.0073 uM | pubchem.aid:1963824 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells | 0.0073 uM | pubchem.aid:1963824 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells | 0.0058 uM | pubchem.aid:1963823 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells | 0.0058 uM | pubchem.aid:1963823 |
| Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | ACTIVE | PMID:31498718 |
| P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | ACTIVE | PMID:31515284 |
| Primary qHTS to identify gynecologic anti-cancer compounds using libraries of approved drugs and bioactive compounds | ACTIVE | pubchem.aid:1345084 |
| qHTS assay to identify novel small-molecules to repurpose for Merkel cell carcinoma treatment | ACTIVE | pubchem.aid:1296009 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000346 | MIBIG | 5 |
| CHEBI:42265 | CHEBI | 3-star |
This page is generated from data/natural_products/amino_acids_and_peptides/epoxomicin.yaml, which is generated from the committed inventories. Neither is edited by hand.