Mrv0541 08051413322D          

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M  END
> <ID>
CHEBI:82621

> <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.

> <STAR>
3

> <SYNONYM>
monascusone B

> <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

> <FORMULA>
C21H26O5

> <MASS>
358.42810

> <MONOISOTOPIC_MASS>
358.17802

> <CHARGE>
0

> <SMILES>
CCCCCC(=O)[C@@H]1[C@H]2CC3=C(COC(\C=C\C)=C3)C(=O)[C@]2(C)OC1=O

> <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

> <CAS_REGISTRY_NUMBER>
21516-68-7

> <REAXYS_REGISTRY_NUMBER>
51355

> <CHEMIDPLUS>
21516-68-7

> <PUBMED_CITATION>
17191930; 20666456; 21080714; 21777645; 22041455; 23237237; 23360447; 23673903; 23848565; 23954466; 24275089; 24865672

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