Homolycorine

Homolycorine is one of a number of toxic alkaloids found in various Amaryllidaceae species such as daffodils (Narcissus).

Homolycorine

Names
IUPAC name (5aR,11bS,11cS)-9,10-Dimethoxy-1-methyl-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-7-one
Other names 9,10-Dimethoxy-1-methyllycorenan-7-one
Identifiers
CAS Number	477-20-3^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1221973^Y
ChemSpider	141017^Y
PubChem CID	160473
CompTox Dashboard (EPA)	DTXSID80963902
InChI InChI=1S/C18H21NO4/c1-19-7-6-10-4-5-13-16(17(10)19)11-8-14(21-2)15(22-3)9-12(11)18(20)23-13/h4,8-9,13,16-17H,5-7H2,1-3H3/t13-,16-,17-/m1/s1^Y Key: WXZAKVLYZHWSNF-KBRIMQKVSA-N^Y
SMILES COc1cc2[C@@H]3[C@@H](CC=C4CCN(C)[C@@H]34)OC(=O)c2cc1OC
Properties
Chemical formula	C18H21NO4
Molar mass	315.369 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Sources

• Four new Amaryllidaceae alkaloids from Zephyranthes candida. Shitara N, Hirasawa Y, Hasumi S, Sasaki T, Matsumoto M, Wong CP, Kaneda T, Asakawa Y, Morita H (2014 Jul) Journal of natural medicines, 68(3):610-4
• Acta Crystallographica
• T. Kitagawa, W. I. Taylor, S. Uyeo and H. Yajima. The constitution of homolycorine and lycorenine J. Chem. Soc., 1955, 1066-1068 DOI: 10.1039/JR9550001066
• Bastida, Jaume, Rodolfo Lavilla, and Francesc Viladomat. "CHEMICAL AND BIOLOGICAL ASPECTS OF Narcissus ALKALOIDS", in “The Alkaloids: Chemistry and Biology” (G. A. Cordell, ed.), Vol. 63 pp. 87-179 (2006). Elsevier Inc. Amsterdam. DOI: 10.1016/S1099-4831(06)63003-4