CHEBI:82621 - monascin

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ChEBI Name monascin
ChEBI ID CHEBI:82621
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
InChIKey XXKNHBAFFJINCK-RVEJDSBJSA-N
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)
IUPAC Name
(3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-[(1E)-prop-1-en-1-yl]-3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione
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
21777645 PubMed citation Europe PMC
22041455 PubMed citation Europe PMC
23237237 PubMed citation Europe PMC
23360447 PubMed citation Europe PMC
23673903 PubMed citation Europe PMC
23848565 PubMed citation Europe PMC
23954466 PubMed citation Europe PMC
24275089 PubMed citation Europe PMC
24865672 PubMed citation Europe PMC
Last Modified
05 August 2014