cichorine
CHEBI:64977 EXACT SEEDED
A member of the class of isoindoles that is 6-hydroxy-4-methoxy-5-methyl-2,3-dihydro-1H-isoindol-1-one which is substituted at position 4, 5, and 6 by methoxy, methyl, and hydroxy groups, respectively. A secondary metabolite found in Aspergillus silvativus, Aspergillus nidulans and Alternaria cichorii, it is poisonous to Russian knapweed (Acroptilon repens).
Structure
| Standard InChIKey | ICZVDXDXJQCDOJ-UHFFFAOYSA-N |
|---|---|
| SMILES | CC1=C(C=C2C(=C1OC)CNC2=O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:442849 |
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 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 |
|---|---|---|---|
| Aspergillus nidulans FGSC A4 NCBITaxon:227321 |
SOURCE_ASSERTION | mibig:BGC0000037 | PMID:22510154 |
Occurrences 6
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 |
|---|---|---|
| Althaea officinalis NCBITaxon:145745 |
LOTUS | DOI:10.1007/BF00630189 |
| Aspergillus nidulans NCBITaxon:162425 |
LOTUS | DOI:10.1021/JA3016395 |
| Alternaria cichorii NCBITaxon:378258 |
LOTUS | DOI:10.1016/S0031-9422(00)95080-5 |
| Althaea armeniaca NCBITaxon:446321 |
LOTUS | DOI:10.1007/BF00630189 |
| Sonchus asper NCBITaxon:50193 |
LOTUS | DOI:10.1016/0305-1978(93)90062-V |
| Sonchus maritimus NCBITaxon:50206 |
LOTUS | DOI:10.1016/0305-1978(93)90062-V |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000037 | Aspergillus nidulans FGSC A4 NCBITaxon:227321 |
CLUSTER_UNSTATED | genbank:BN001301.1 |
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.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000037 | MIBIG | 4 |
| CHEBI:64977 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/cichorine.yaml, which is generated from the committed inventories. Neither is edited by hand.