Glyceollin I

Glyceollin I is a glyceollin, a type of prenylated pterocarpan. It is a phytoalexin found in the soybean.

Glyceollin I
Names
Preferred IUPAC name
(6aS,11aS)-2,2-Dimethyl-2H,6H-[1]benzofuro[3,2-c]pyrano[2,3-h][1]benzopyran-6a,9(11aH)-diol
Other names
(−)-Glyceollin I
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.222.666
KEGG
PubChem CID
UNII
  • InChI=1S/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1 N
    Key: YIFYYPKWOQSCRI-AZUAARDMSA-N N
  • InChI=1/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1
    Key: YIFYYPKWOQSCRI-AZUAARDMBS
SMILES
  • CC1(C=Cc2c(ccc3c2OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O)O1)C
Properties
C20H18O5
Molar mass 338 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Glyceollin synthase is an enzyme responsible for the production of glyceollin. The five substrates of this enzyme are 2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, 4-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, NADPH, H+, and O2, whereas its three products are glyceollin, NADP+, and H2O.

In in vitro studies, this molecule has been shown to exhibit antiestrogenic properties.

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