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CHEBI:82621 - monascin

ChEBI IDCHEBI:82621
ChEBI Namemonascin
Stars
DefinitionAn 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.
Last Modified5 August 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC21H26O5
Net Charge0
Average Mass358.434
Monoisotopic Mass358.17802
SMILES[H][C@]1(C(=O)CCCCC)C(=O)O[C@@]2(C)C(=O)C3=C(C=C(/C=C/C)OC3)C[C@]12[H]
InChIInChI=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
InChIKeyXXKNHBAFFJINCK-RVEJDSBJSA-N
Roles Classification
Biological Roles:
PPARgamma agonist  A PPAR modulator which activates the peroxisome proliferator-activated receptor-γ.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Applications:
antilipemic drug  A substance used to treat hyperlipidemia (an excess of lipids in the blood).
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 organic heterotricyclic compound (CHEBI:26979)
monascin (CHEBI:82621) is a polyketide (CHEBI:26188)
monascin (CHEBI:82621) is a α,β-unsaturated ketone (CHEBI:51721)
monascin (CHEBI:82621) is a γ-lactone (CHEBI:37581)
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 BChEBI
Registry NumbersSources
Reaxys:51355Reaxys
CAS:21516-68-7ChemIDplus
Citations