CHEBI:82621 - monascin

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ChEBI Name monascin
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H26O5
Net Charge 0
Average Mass 358.42810
Monoisotopic Mass 358.17802
InChI InChI=1S/C21H26O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10,16,18H,4,6-7,9,11-12H2,1-3H3/b8-5+/t16-,18+,21-/m1/s1
SMILES CCCCCC(=O)[C@@H]1[C@H]2CC3=C(COC(\C=C\C)=C3)C(=O)[C@]2(C)OC1=O
Roles Classification
Biological Role(s): PPARgamma agonist
A PPAR modulator which activates the peroxisome proliferator-activated receptor-gamma.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing monascin (CHEBI:82621) has role antilipemic drug (CHEBI:35679)
monascin (CHEBI:82621) has role antineoplastic agent (CHEBI:35610)
monascin (CHEBI:82621) has role fungal metabolite (CHEBI:76946)
monascin (CHEBI:82621) has role PPARγ agonist (CHEBI:71554)
monascin (CHEBI:82621) is a α,β-unsaturated ketone (CHEBI:51721)
monascin (CHEBI:82621) is a γ-lactone (CHEBI:37581)
monascin (CHEBI:82621) is a organic heterotricyclic compound (CHEBI:26979)
monascin (CHEBI:82621) is a polyketide (CHEBI:26188)
Synonym Source
monascusone B ChEBI
Registry Numbers Types Sources
21516-68-7 CAS Registry Number ChemIDplus
51355 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17191930 PubMed citation Europe PMC
20666456 PubMed citation Europe PMC
21080714 PubMed citation Europe PMC
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Last Modified
05 August 2014