swainsonine
CHEBI:9367 EXACT SEEDED cytotoxicenzyme inhibitor
An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.
Structure
| Standard InChIKey | FXUAIOOAOAVCGD-WCTZXXKLSA-N |
|---|---|
| SMILES | C1C[C@H]([C@@H]2[C@@H]([C@@H](CN2C1)O)O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:51683 |
Filing pathway
Alkaloids — 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 3
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 |
|---|---|---|---|
| Metarhizium robertsii ARSEF 23 NCBITaxon:655844 |
BGC_CHARACTERIZED | mibig:BGC0002270 | PMID:32786262 |
| Chaetothyriaceae sp. NCBITaxon:1963369 |
SOURCE_ASSERTION | mibig:BGC0001793 | DOI:10.7150/ijbs.3882 |
| Alternaria oxytropis NCBITaxon:570715 |
SOURCE_ASSERTION | mibig:BGC0001794 | PMID:28381497 |
Occurrences 25
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 |
|---|---|---|
| Slafractonia leguminicola NCBITaxon:1541393 |
LOTUS | DOI:10.1016/S0040-4020(01)97625-2 |
| Slafractonia leguminicola NCBITaxon:1541393 |
LOTUS | DOI:10.1021/JA00211A039 |
| Slafractonia leguminicola NCBITaxon:1541393 |
LOTUS | DOI:10.1021/JO00390A024 |
| Slafractonia leguminicola NCBITaxon:1541393 |
LOTUS | DOI:10.1128/AEM.48.2.386-388.1984 |
| Astragalus whitneyi NCBITaxon:1769941 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Oxytropis riparia NCBITaxon:1938221 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Astragalus flavus NCBITaxon:2014685 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Astragalus bisulcatus NCBITaxon:20406 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Astragalus hallii NCBITaxon:20413 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Astragalus lentiginosus NCBITaxon:20416 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Astragalus lentiginosus NCBITaxon:20416 |
LOTUS | DOI:10.1002/PCA.713 |
| Astragalus lentiginosus NCBITaxon:20416 |
LOTUS | DOI:10.1021/BI00459A032 |
| Astragalus purshii NCBITaxon:20422 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Oxytropis lambertii NCBITaxon:20805 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Oxytropis lambertii NCBITaxon:20805 |
LOTUS | DOI:10.1021/JF010596P |
| Castanospermum australe NCBITaxon:24962 |
LOTUS | DOI:10.1021/NP50069A011 |
| Ipomoea calobra NCBITaxon:2607090 |
LOTUS | DOI:10.1021/NP50120A009 |
| Astragalus pycnostachyus NCBITaxon:2897604 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Astragalus emoryanus NCBITaxon:3084112 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Astragalus emoryanus NCBITaxon:3084112 |
LOTUS | DOI:10.1104/PP.76.4.972 |
| Fabaceae NCBITaxon:3803 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Astragalus wootonii NCBITaxon:457888 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Astragalus falcatus NCBITaxon:47038 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Oxytropis glabra NCBITaxon:483874 |
LOTUS | DOI:10.1002/PCA.2800020307 |
| Swainsona canescens NCBITaxon:491199 |
LOTUS | DOI:10.1016/S0021-9258(18)32772-8 |
Biosynthetic gene clusters 3
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0002270 | Metarhizium robertsii ARSEF 23 NCBITaxon:655844 |
CLUSTER_DEMONSTRATED | genbank:ADNJ02000001.1 |
| mibig:BGC0001793 | Chaetothyriaceae sp. NCBITaxon:1963369 |
CLUSTER_UNSTATED | genbank:KY365740.1 |
| mibig:BGC0001794 | Alternaria oxytropis NCBITaxon:570715 |
CLUSTER_UNSTATED | genbank:KY365741.1 |
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.
Causal graph — bioactivity 2 nodes, 1 edges
Swainsonine inhibits Drosophila Golgi alpha-mannosidase II.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| swainsonine | inhibits | Drosophila Golgi alpha-mannosidase II | DOI:10.1002/cbic.200900750 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Bioactivities 9
| Assay | Result | Reference |
|---|---|---|
| Confirmatory qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay | 0.1 uM | PMID:33910017 |
| Confirmatory qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay | 31.6228 uM | PMID:33910017 |
| Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB | IC50 0.02 uM | PMID:11406577 |
| Golgi α-Mannosidase II (alpha-hGMII) and α-Mannosidase (alpha-hLM) Activity Assay from US Patent US20240190866: "POLYHYDROXYLATED INDOLIZIDINE AND PYRROLIZIDINE DERIVATIVES AND USES THEREOF" | IC50 0.08 uM | pubchem.aid:1964041 |
| Golgi α-Mannosidase II (alpha-hGMII) and α-Mannosidase (alpha-hLM) Activity Assay from US Patent US20240190866: "POLYHYDROXYLATED INDOLIZIDINE AND PYRROLIZIDINE DERIVATIVES AND USES THEREOF" | IC50 0.04 uM | pubchem.aid:1964041 |
| Inhibition Assay from Article 10.1002/cbic.200900750: "Structural investigation of the binding of 5-substituted swainsonine analogues to Golgi alpha-mannosidase II." | KI 0.003 uM | PMID:20209559 |
| Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation | 9.5283 uM | pubchem.aid:504834 |
| qHTS assay for identifying genotoxic compounds that show differential cytotoxicity against isogenic chicken DT40 cell lines with known DNA damage response pathways - Rev3 mutant cell line | 26.6032 uM | pubchem.aid:743014 |
| Experimentally measured binding affinity data derived from PDB | ACTIVE | PMID:11406577 |
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0001793, BGC0001794, BGC0002270. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0002270 | MIBIG | 2 |
| BGC0001793 | MIBIG | 4 |
| BGC0001794 | MIBIG | 4 |
| CHEBI:9367 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/swainsonine.yaml, which is generated from the committed inventories. Neither is edited by hand.