AMORPHIGENIN

Structure

2D structure of AMORPHIGENIN
2D structure
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3D model

Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 92207

Names and identifiers

Name

AMORPHIGENIN

IUPAC name

(2R,6aS,12aS)-2-(3-hydroxyprop-1-en-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

SMILES

COC1=C(C=C2C(=C1)[C@H]3[C@@H](CO2)OC4=C(C3=O)C=CC5=C4C[C@@H](O5)C(=C)CO)OC

General information

Molecular formula

C23H22O7

Molecular weight

410.42 g/mol

Monoisotopic mass

410.1366 Da

Classification

Pathway:
Superclass:
Class:
Glycoside:
No

Chemical classification: NPClassifier (Kim et al., 2021)

Plants with the compound

Plant Plant part Amount Reference
Amorpha fruticosa L. aerial parts -
Li, L.P., Wang, H.K., Chang, J.J., Mcphail, A.T., Mcphaildr, Terada, H., Konoshima, T., Kokumai, M., Kozuka, M., Estes, J.R., Lee, K.H. (1993). Antitumor agents, 138. rotenoids and isoflavones as cytotoxic constituents from Amorpha fruticosa. J Nat Prod, 56(5), 690-698 doi:10.1021/np50095a005
Amorpha fruticosa L. leaf -
Terada, H., Kokumai, M., Konoshima, T., Kozuka, M., Haruna, M., Ito, K., Lee, K.H., Li, L.P., Wang, H.K. (1992). A novel rotenoid from Amorpha fruticosa. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 34, 502-509
Amorpha fruticosa L. root -
Hohmann, J., Rozsa, Z., Reisch, J., Szendrei, K. (1982). Flavonoids of root-bark of Amorpha fruticosa L. Herba Hung, 21(2/3), 179-183
Amorpha fruticosa L. root -
Shibata, H., Shimizu, S. (1978). Amorphaquinone, a new isoflavanquinone from Amorpha fruticosa L. Heterocycles, 10, 85-86 doi:10.3987/s-1978-01-0085
Amorpha fruticosa L. seed -
Bhandari, P., Cormbie, L., Daniels, P., Holden, I., Vanbruggen, N., Whiting, D.A. (1992). Biosynthesis of the a/b/c/d/-ring system of the rotenoid amorphigenin by Amorpha fruticosa seedlings. J Chem Soc Perkin Trans I, (7), 839-849 doi:10.1039/p19920000839
Amorpha fruticosa L. seed -
Crombie, L., Green, C.L., Whiting, D.A. (1968). Biosynthesis of rotenoids, the origin of c-6a and the extra methylene at c-6. Chem Commun, 234 doi:10.1039/c19680000234
Amorpha fruticosa L. seed -
Klouchek, E., Popov, A., Drenska, D., Usunov, P. (1985). Experimental studies on the hepatoprotective activity of isolated Amorpha fruticosa flavonoids. Eksp Med Morfol, 24(2), 50-54
Amorpha fruticosa L. seedling -
Crombie, L., Holden, I., Kilbee, G.W., Whiting, D.A. (1982). Biosynthesis of rotenoids by Amorpha fruticosa: sequence, specificity, and stereochemistry in the development of the hemiterpenoid segment. J Chem Soc Perkin Trans I, 789-797 doi:10.1039/p19820000789