microcystin-LR
CHEBI:6925 EXACT SEEDED cytotoxic
A microcystin consisting of D-alanyl, L-leucyl, (3S)-3-methyl-D-β-aspartyl,L-arginyl, 2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl, D-γ-glutamyl, and 2,3-didehydro-N-methylalanyl residues joined into a 25-membered macrocycle. Produced by the cyanobacterium Microcystis aeruginosa, it is the most studied of the microcystins.
Structure
| Standard InChIKey | ZYZCGGRZINLQBL-GWRQVWKTSA-N |
|---|---|
| SMILES | C[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CCCN=C(N)N)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)/C |
| Stereochemistry | fully defined |
| Cross-references | pubchem:445434, chembl:CHEMBL444092, npatlas:NPA0593 |
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 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 |
|---|---|---|---|
| Microcystis aeruginosa PCC 7806 NCBITaxon:267872 |
BGC_CHARACTERIZED | mibig:BGC0001017 | PMID:11033079 |
| Anabaena sp. 90 NCBITaxon:46234 |
SOURCE_ASSERTION | mibig:BGC0001016 | PMID:14766543 |
| Fischerella sp. CENA161 NCBITaxon:548826 |
SOURCE_ASSERTION | mibig:BGC0001667 | PMID:29154789 |
Occurrences 24
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 |
|---|---|---|
| Microcystis NCBITaxon:1125 |
LOTUS | DOI:10.1016/0041-0101(94)90030-2 |
| Microcystis NCBITaxon:1125 |
LOTUS | DOI:10.1021/ES00050A024 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1016/0040-4020(96)00452-8 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1016/0041-0101(88)90200-0 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1016/0041-0101(95)00145-X |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1016/S0021-9673(01)84589-1 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1016/S1074-5521(00)00021-1 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1021/ACS.JNATPROD.7B00986 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1021/JA00013A066 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1021/JO00029A016 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1039/P19850002747 |
| Microcystis aeruginosa NCBITaxon:1126 |
CYANOMETDB | DOI:10.1039/p19850002747 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1073/PNAS.86.3.770 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1081/JLC-120003265 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.1515/BCHM3.1993.374.7-12.635 |
| Microcystis aeruginosa NCBITaxon:1126 |
LOTUS | DOI:10.5694/J.1326-5377.1983.TB136192.X |
| Anabaena NCBITaxon:1163 |
LOTUS | DOI:10.1128/AEM.70.2.686-692.2004 |
| Aphanizomenon flos-aquae NCBITaxon:1176 |
LOTUS | DOI:10.1016/0041-0101(92)90522-7 |
| Fischerella NCBITaxon:1190 |
LOTUS | DOI:10.1016/J.TOXICON.2017.10.021 |
| Romanoa NCBITaxon:316894 |
LOTUS | DOI:10.1128/AEM.70.2.686-692.2004 |
| Microcystis viridis NCBITaxon:44822 |
LOTUS | DOI:10.1016/0041-0101(88)90200-0 |
| Microcystis viridis NCBITaxon:44822 |
LOTUS | DOI:10.1016/0041-0101(90)90006-S |
| Microcystis viridis NCBITaxon:44822 |
LOTUS | DOI:10.1016/S0021-9673(01)84589-1 |
| Nodularia spumigena NCBITaxon:70799 |
LOTUS | DOI:10.1016/S0040-4039(00)61500-9 |
Biosynthetic gene clusters 3
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001017 | Microcystis aeruginosa PCC 7806 NCBITaxon:267872 |
CLUSTER_DEMONSTRATED | genbank:AF183408.1 |
| mibig:BGC0001016 | Anabaena sp. 90 NCBITaxon:46234 |
CLUSTER_UNSTATED | genbank:AY212249.1 |
| mibig:BGC0001667 | Fischerella sp. CENA161 NCBITaxon:548826 |
CLUSTER_UNSTATED | genbank:KX891213.1 |
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 1
| Assay | Result | Reference |
|---|---|---|
| NCI human tumor cell line growth inhibition assay. Data for the IGROV1 Ovarian cell line | ACTIVE | pubchem.aid:101 |
Open questions 2
name-disagreement — ChEBI calls this structure 'microcystin-LR' and MIBiG calls it 'microcystin LR'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
shared-structure — This structure is reported by more than one MIBiG entry: BGC0001016, BGC0001017, BGC0001667. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001017 | MIBIG | 5 |
| BGC0001016 | MIBIG | 5 |
| BGC0001667 | MIBIG | 4 |
| CHEBI:6925 | CHEBI | 3-star |
This page is generated from data/natural_products/amino_acids_and_peptides/microcystin-lr.yaml, which is generated from the committed inventories. Neither is edited by hand.