Narciclasine

Narciclasine is a toxic alkaloid found in various Amaryllidaceae species.[1]

Narciclasine

Names
IUPAC name (2S-(2α,3β,4β,4aβ))-3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one
Other names BRN 1087400, Lycoricidin-A, Lycoricidinol, NSC 266535
Identifiers
CAS Number	29477-83-6^N
3D model (JSmol)	Interactive image
ChemSpider	65310^Y
ECHA InfoCard	100.214.093
KEGG	C08533
PubChem CID	72376
CompTox Dashboard (EPA)	DTXSID70183677
InChI InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1 Key: LZAZURSABQIKGB-AEKGRLRDSA-N InChI=1/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1 Key: LZAZURSABQIKGB-AEKGRLRDBO
SMILES C1OC2=C(O1)C(=C3C(=C2)C4=C[C@@H]([C@H]([C@H]([C@@H]4NC3=O)O)O)O)O
Properties
Chemical formula	C14H13NO7
Molar mass	307.258 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

References

1. Kornienko A, Evidente A (2008). "Chemistry, biology, and medicinal potential of narciclasine and its congeners". Chem Rev. 108 (6): 1982–2014. doi:10.1021/cr078198u. PMC 2856661. PMID 18489166.

Bibliography

• Gwendoline Van Goietsenoven; Véronique Mathieu; Florence Lefranc; Alexander Kornienko; Antonio Evidente; Robert Kiss (March 2013). "Narciclasine as well as other Amaryllidaceae Isocarbostyrils are Promising GTP-ase Targeting Agents against Brain Cancers". Medicinal Research Reviews. 33 (2): 439–455. doi:10.1002/med.21253.