antimycin A
CHEBI:2762 EXACT SEEDED antifungalcytotoxicenzyme inhibitor
A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.
Structure
| Standard InChIKey | UIFFUZWRFRDZJC-SBOOETFBSA-N |
|---|---|
| SMILES | CCCCCC[C@@H]1[C@H]([C@@H](OC(=O)[C@H]([C@H](OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)CC(C)C |
| Stereochemistry | fully defined |
| Cross-references | pubchem:14957 |
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 sp. S4 NCBITaxon:889487 |
BGC_CHARACTERIZED | mibig:BGC0000958 | PMID:21857911 |
Occurrences 7
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 wadayamensis NCBITaxon:141454 |
LOTUS | DOI:10.1128/GENOMEA.00625-14 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1021/NP0001676 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1371/JOURNAL.PONE.0022028 |
| Streptomyces antibioticus NCBITaxon:1890 |
LOTUS | DOI:10.3390/MOLECULES22040557 |
| Streptomyces setonii NCBITaxon:1911 |
LOTUS | DOI:10.1007/BF01027810 |
| Streptomyces argillaceus NCBITaxon:41951 |
LOTUS | DOI:10.1371/JOURNAL.PONE.0198145 |
| Streptomyces baarnensis NCBITaxon:66872 |
LOTUS | DOI:10.1007/BF01027810 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000958 | Streptomyces sp. S4 NCBITaxon:889487 |
CLUSTER_DEMONSTRATED | genbank:NZ_FR873698.1 |
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 25
| Assay | Result | Reference |
|---|---|---|
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line | 0.2633 uM | pubchem.aid:2202236 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line | 7.4219 uM | pubchem.aid:2202234 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell line | 1.3198 uM | pubchem.aid:2202233 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line | 0.132 uM | pubchem.aid:2202232 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell line | 0.0934 uM | pubchem.aid:2202231 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 1.9953 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 | 0.7943 uM | pubchem.aid:1963989 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line 8505C | 0.5506 uM | pubchem.aid:2202553 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-11T | 0.0778 uM | pubchem.aid:2202552 |
| Cellular viability qHTS for anaplastic thyroid cancer (ATC) cell line THJ-16T | 0.3474 uM | pubchem.aid:2202551 |
| Counterscreen qHTS for Inhibitors of Tau Fibril Formation, Fluorescence Polarization | 12.5893 uM | pubchem.aid:1463 |
| High-throughput drug toxicity screening in the BPDCN cell line Cal-1 | 0.0935 uM | pubchem.aid:1224825 |
| High-throughput drug toxicity screening in the BPDCN cell line Gen2.2 | 0.0132 uM | pubchem.aid:1224824 |
| NCATS anti-infectives library activity on the primary C. elegans qHTS viability assay | 7.2747 uM | PMID:36786055 |
| NS1 protein of Zika virus - qHTS assay to identify small molecule inhibitors in human HEK 293 cells | 2.9566 uM | pubchem.aid:1347053 |
| P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 0.4176 uM | PMID:31515284 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) | 25.4789 uM | pubchem.aid:1845192 |
| Primary qHTS Assay for Inhibitors of Recombinant Selenoprotein Glutathione Peroxidase 4 (GPX4) | 25.4789 uM | pubchem.aid:1845192 |
| Primary qHTS for Identification of Small Molecule Activators of Huntingtin-Antisense Promoter Activity | 0.1086 uM | pubchem.aid:1508624 |
| Primary qHTS for Identification of Small Molecule Activators of Huntingtin-Antisense Promoter Activity | 0.1086 uM | pubchem.aid:1508624 |
| Primary qHTS for Identification of Small Molecule Inhibitors of Huntingtin Promoter Activity | 0.0863 uM | pubchem.aid:1508623 |
| Primary qHTS for Identification of Small Molecule Inhibitors of Huntingtin Promoter Activity | 0.0863 uM | pubchem.aid:1508623 |
| Primary qHTS for Inhibitors of ATXN expression | 30.6114 uM | PMID:35787375 |
| Primary qHTS for Inhibitors of ATXN expression | 30.6114 uM | PMID:35787375 |
| Primary qHTS for Inhibitors of N-terminal methyltransferase 1 (NTMT1): MTaseGlo Assay | 15.2369 uM | pubchem.aid:1645870 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:2762 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000958 | MIBIG | 5 |
| CHEBI:2762 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/antimycin-a.yaml, which is generated from the committed inventories. Neither is edited by hand.