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epoxomicin

CHEBI:42265 EXACT SEEDED cytotoxicenzyme inhibitor

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

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 InChIKeyDOGIDQKFVLKMLQ-JTHVHQAWSA-N
SMILESCC[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
Stereochemistryfully defined
Cross-referencespubchem: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.

TaxonBasisClusterEvidence
Goodfellowiella coeruleoviolacea
NCBITaxon:334858		 SOURCE_ASSERTION mibig:BGC0000346 PMID:24168704

Occurrences 0

None cited.

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
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.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (0 causal) 0 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 0 curated pathway steps NATURAL PRODUCT epoxomicin CHEBI:42265 Amino acids and peptides TARGETS & BIOACTIVITY 0 molecular targets 22 bioactivities · 1 graph

Causal graph — bioactivity 2 nodes, 1 edge

Epoxomicin covalently binds the Saccharomyces cerevisiae 20S proteasome beta type-5 active subunit.

SubjectPredicateObjectNotesEvidence
epoxomicin binds yeast proteasome subunit beta type-5 PDB 1G65 models epoxomicin as peptide-inhibitor chains 3 and 4, each covalently linked through the terminal 04D residue to Thr1 of yeast PRE2 chains K and Y, both mapped to UniProtKB:P30656.
DOI:10.1021/ja993588m
  • reference
    DOI:10.1021/ja993588m
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Crystal Structure of Epoxomicin:20S Proteasome reveals a molecular basis for selectivity of alpha,beta-Epoxyketone Proteasome Inhibitors
    notes
    Groll et al. solved PDB 1G65 as a yeast 20S proteasome structure with two epoxomicin peptide-inhibitor chains covalently bound to PRE2.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Bioactivities 22

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

AssayResultTarget enzymeSource detail
Constitutive androstane receptor (CAR) small molecule agonists, cell-based qHTS assay in HepG2 cellsOTHER 0.0651 uM; INACTIVENot recorded
pubchem.aid:2202728
assay
Constitutive androstane receptor (CAR) small molecule agonists, cell-based qHTS assay in HepG2 cells
evidence
  • reference
    pubchem.aid:2202728
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202728, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
INACTIVE
measurement type
OTHER
value
0.0651
units
uM
Constitutive androstane receptor (CAR) small molecule agonists, cell-based qHTS assay in HepG2 cellsOTHER 0.0651 uM; INACTIVENot recorded
pubchem.aid:2202728
assay
Constitutive androstane receptor (CAR) small molecule agonists, cell-based qHTS assay in HepG2 cells
evidence
  • reference
    pubchem.aid:2202728
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202728, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. Target accession ADZ17385 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
INACTIVE
measurement type
OTHER
value
0.0651
units
uM
GF-AFC viability counterscreen for inhibitors of alpha-synuclein gene (SNCA) expressionOTHER 0.0238 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1671193
assay
GF-AFC viability counterscreen for inhibitors of alpha-synuclein gene (SNCA) expression
evidence
  • reference
    pubchem.aid:1671193
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1671193, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
0.0238
units
uM
NCATS anti-infectives library activity on the primary C. elegans qHTS viability assayOTHER 0.1028 uM; INACTIVENot recorded
PMID:36786055
assay
NCATS anti-infectives library activity on the primary C. elegans qHTS viability assay
evidence
  • reference
    PMID:36786055
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1745855, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
INACTIVE
measurement type
OTHER
value
0.1028
units
uM
P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screenOTHER 2.5929 uM; ACTIVENot recorded
PMID:31515284
assay
P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen
evidence
  • reference
    PMID:31515284
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346987, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
2.5929
units
uM
Primary fluorescence-based thiol-reactive (MSTI) qHTS assay for identification of artifact compounds.OTHER 1.8888 uM; INACTIVENot recorded
pubchem.aid:1845221
assay
Primary fluorescence-based thiol-reactive (MSTI) qHTS assay for identification of artifact compounds.
evidence
  • reference
    pubchem.aid:1845221
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1845221, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
INACTIVE
measurement type
OTHER
value
1.8888
units
uM
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C)OTHER 0.0073 uM; ACTIVENot recorded
pubchem.aid:1645877
assay
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C)
evidence
  • reference
    pubchem.aid:1645877
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645877, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0073
units
uM
activity class
ENZYME_INHIBITOR
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C)OTHER 0.0073 uM; ACTIVEUniProtKB:O96028
pubchem.aid:1645877
assay
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an RCH-ACV wild type WT cells (2C)
evidence
  • reference
    pubchem.aid:1645877
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645877, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0073
units
uM
target enzyme
UniProtKB:O96028
activity class
ENZYME_INHIBITOR
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B)OTHER 0.0129 uM; ACTIVENot recorded
pubchem.aid:1645876
assay
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B)
evidence
  • reference
    pubchem.aid:1645876
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645876, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0129
units
uM
activity class
ENZYME_INHIBITOR
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B)OTHER 0.0129 uM; ACTIVEUniProtKB:O96028
pubchem.aid:1645876
assay
Primary qHTS for inhibitors of nuclear receptor binding SET domain protein 2 (NSD2) in an isogenic RCH-ACV NSD2 p.E1099K mutant (9B)
evidence
  • reference
    pubchem.aid:1645876
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645876, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0129
units
uM
target enzyme
UniProtKB:O96028
activity class
ENZYME_INHIBITOR
Primary qHTS for small molecule compounds that upregulate eGFP-tagged delta133p53alpha (in N-terminal) cells.OTHER 0.0757 uM; NOT_DETERMINEDNot recorded
pubchem.aid:2060322
assay
Primary qHTS for small molecule compounds that upregulate eGFP-tagged delta133p53alpha (in N-terminal) cells.
evidence
  • reference
    pubchem.aid:2060322
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2060322, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
0.0757
units
uM
Primary qHTS for small molecule compounds that upregulate eGFP-tagged delta133p53alpha (in N-terminal) cells.OTHER 0.0757 uM; NOT_DETERMINEDNot recorded
pubchem.aid:2060322
assay
Primary qHTS for small molecule compounds that upregulate eGFP-tagged delta133p53alpha (in N-terminal) cells.
evidence
  • reference
    pubchem.aid:2060322
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2060322, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_001119587 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
0.0757
units
uM
Primary qHTS to identify anti-liver cancer compounds using libraries of approved drugs and bioactive compoundsOTHER 1.122 uM; NOT_DETERMINEDNot recorded
pubchem.aid:2202548
assay
Primary qHTS to identify anti-liver cancer compounds using libraries of approved drugs and bioactive compounds
evidence
  • reference
    pubchem.aid:2202548
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2202548, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
1.122
units
uM
Primary redox qHTS assay for identification of artifact compounds.OTHER 6.7016 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1845223
assay
Primary redox qHTS assay for identification of artifact compounds.
evidence
  • reference
    pubchem.aid:1845223
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1845223, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
6.7016
units
uM
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cellsOTHER 0.0073 uM; ACTIVENot recorded
pubchem.aid:1963824
assay
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells
evidence
  • reference
    pubchem.aid:1963824
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963824, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0073
units
uM
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cellsOTHER 0.0073 uM; ACTIVEUniProtKB:P43405
pubchem.aid:1963824
assay
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) drug resistant MV4-11 cells
evidence
  • reference
    pubchem.aid:1963824
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963824, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0073
units
uM
target enzyme
UniProtKB:P43405
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cellsOTHER 0.0058 uM; ACTIVENot recorded
pubchem.aid:1963823
assay
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells
evidence
  • reference
    pubchem.aid:1963823
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963823, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0058
units
uM
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cellsOTHER 0.0058 uM; ACTIVEUniProtKB:P43405
pubchem.aid:1963823
assay
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells
evidence
  • reference
    pubchem.aid:1963823
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963823, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0058
units
uM
target enzyme
UniProtKB:P43405
Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput ScreeningACTIVENot recorded
PMID:31498718
assay
Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening
evidence
  • reference
    PMID:31498718
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1296008, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
activity class
CYTOTOXIC
P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screenACTIVENot recorded
PMID:31515284
assay
P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen
evidence
  • reference
    PMID:31515284
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346986, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
Primary qHTS to identify gynecologic anti-cancer compounds using libraries of approved drugs and bioactive compoundsACTIVENot recorded
pubchem.aid:1345084
assay
Primary qHTS to identify gynecologic anti-cancer compounds using libraries of approved drugs and bioactive compounds
evidence
  • reference
    pubchem.aid:1345084
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1345084, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
activity class
CYTOTOXIC
qHTS assay to identify novel small-molecules to repurpose for Merkel cell carcinoma treatmentACTIVENot recorded
pubchem.aid:1296009
assay
qHTS assay to identify novel small-molecules to repurpose for Merkel cell carcinoma treatment
evidence
  • reference
    pubchem.aid:1296009
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1296009, deposited by NCGC; assay type Confirmatory.
call
ACTIVE

Explore across X-Mech

AntibioticMech (epoxomicin) ↗ MediaIngredientMech (CHEBI:42265) ↗ TaxonMech: Goodfellowiella coeruleoviolacea (NCBITaxon:334858) ↗ PathwayMech (mibig:BGC0000346) ↗

Provenance

Source conceptSourceVersion
BGC0000346MIBIG5
CHEBI:42265CHEBI3-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.