monascin
CHEBI:82621 EXACT SEEDED
An organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours.
Structure
| Standard InChIKey | XXKNHBAFFJINCK-RVEJDSBJSA-N |
|---|---|
| SMILES | [H]\C(C)=C(\[H])C1=CC2=C(CO1)C(=O)[C@]1(C)OC(=O)[C@H](C(=O)CCCCC)[C@@]1([H])C2 |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA09686, pubchem:12118082 |
Filing pathway
Polyketides — 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 |
|---|---|---|---|
| Monascus pilosus NCBITaxon:89488 |
SOURCE_ASSERTION | mibig:BGC0000027 | DOI:10.1021/jf040199p |
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 |
|---|---|---|
| Monascus kaoliang NCBITaxon:180403 |
LOTUS | DOI:10.1002/CHIN.200508186 |
| Monascus kaoliang NCBITaxon:180403 |
LOTUS | DOI:10.1016/J.PHYTOCHEM.2004.08.032 |
| Monascus NCBITaxon:5097 |
LOTUS | DOI:10.1039/JR9610004579 |
| Monascus purpureus NCBITaxon:5098 |
LOTUS | DOI:10.1016/J.PHYTOL.2011.08.003 |
| Monascus purpureus NCBITaxon:5098 |
LOTUS | DOI:10.1021/JF020023S |
| Monascus pilosus NCBITaxon:89488 |
LOTUS | DOI:10.1016/J.PHYTOL.2011.09.008 |
| Monascus pilosus NCBITaxon:89488 |
LOTUS | DOI:10.1021/JF040199P |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000027 | Monascus pilosus NCBITaxon:89488 |
CLUSTER_UNSTATED | genbank:KC148521.1 |
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 |
|---|---|---|
| BGC0000027 | MIBIG | 4 |
| CHEBI:82621 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/monascin.yaml, which is generated from the committed inventories. Neither is edited by hand.