7-epi-cylindrospermopsin
CHEBI:88049 EXACT SEEDED
A triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(hydroxy)methyl groups, respectively (the 2aS,3R,4S,5aS,7R stereoisomer in which the carbon bearing the hydroxy group has S configuration). It is a cyanotoxin produced by several species of freshwater cyanobacteria, such as Aphanizomenon ovalisporum.
Structure
| Standard InChIKey | LHJPHMKIGRLKDR-YUQKHPEDSA-N |
|---|---|
| SMILES | C[C@H]1[C@H](C[C@@H]2C[C@@H](NC3=NC[C@H]1N23)[C@@H](C4=CC(=O)NC(=O)N4)O)OS(=O)(=O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:115005 |
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, other, from MIBiG.
Producer organisms 4
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 |
|---|---|---|---|
| Cylindrospermopsis raciborskii AWT205 NCBITaxon:478021 |
SOURCE_ASSERTION | mibig:BGC0000978 | PMID:18065631 |
| Aphanizomenon sp. 10E9 NCBITaxon:459665 |
SOURCE_ASSERTION | mibig:BGC0000979 | PMID:20430808 |
| Aphanizomenon sp. 22D11 NCBITaxon:459668 |
SOURCE_ASSERTION | mibig:BGC0000980 | PMID:20430808 |
| Aphanizomenon sp. 10E6 NCBITaxon:459664 |
SOURCE_ASSERTION | mibig:BGC0000981 | PMID:20430808 |
Occurrences 12
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 |
|---|---|---|
| Oscillatoria NCBITaxon:1158 |
LOTUS | DOI:10.1128/AEM.00717-10 |
| Oscillatoria sp. NCBITaxon:1159 |
CHEBI | PMID:20525864 |
| Aphanizomenon NCBITaxon:1175 |
LOTUS | DOI:10.1099/MIC.0.036988-0 |
| Umezakia natans NCBITaxon:198593 |
LOTUS | DOI:10.1016/0041-0101(94)90008-6 |
| Chrysosporum ovalisporum NCBITaxon:75695 |
LOTUS | DOI:10.1021/NP990498M |
| Aphanizomenon ovalisporum NCBITaxon:75695 |
CHEBI | PMID:10757726 |
| Cylindrospermopsis raciborskii NCBITaxon:77022 |
LOTUS | DOI:10.1006/BBRC.1994.1694 |
| Cylindrospermopsis raciborskii NCBITaxon:77022 |
LOTUS | DOI:10.1016/S0041-0101(00)00236-1 |
| Cylindrospermopsis raciborskii NCBITaxon:77022 |
LOTUS | DOI:10.1021/JA00046A067 |
| Cylindrospermopsis raciborskii NCBITaxon:77022 |
LOTUS | DOI:10.1021/JO0486387 |
| Cylindrospermopsis raciborskii NCBITaxon:77022 |
LOTUS | DOI:10.1021/JO991257M |
| Cylindrospermopsis raciborskii NCBITaxon:77022 |
CYANOMETDB | DOI:10.1021/ja00046a067 |
Biosynthetic gene clusters 4
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000978 | Cylindrospermopsis raciborskii AWT205 NCBITaxon:478021 |
CLUSTER_UNSTATED | genbank:EU140798.1 |
| mibig:BGC0000979 | Aphanizomenon sp. 10E9 NCBITaxon:459665 |
CLUSTER_UNSTATED | genbank:GQ385959.1 |
| mibig:BGC0000980 | Aphanizomenon sp. 22D11 NCBITaxon:459668 |
CLUSTER_UNSTATED | genbank:GQ385960.1 |
| mibig:BGC0000981 | Aphanizomenon sp. 10E6 NCBITaxon:459664 |
CLUSTER_UNSTATED | genbank:GQ385961.1 |
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.
Open questions 2
name-disagreement — ChEBI calls this structure '7-epi-cylindrospermopsin' and MIBiG calls it 'cylindrospermopsin'. 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: BGC0000978, BGC0000979, BGC0000980, BGC0000981. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000978 | MIBIG | 5 |
| BGC0000979 | MIBIG | 3 |
| BGC0000980 | MIBIG | 3 |
| BGC0000981 | MIBIG | 3 |
| CHEBI:88049 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/7-epi-cylindrospermopsin.yaml, which is generated from the committed inventories. Neither is edited by hand.