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M  END
> <ID>
CHEBI:136462

> <NAME>
erucifoline

> <DEFINITION>
A pyrrolizine alkaloid that is produced by several Jacobaea species and displays toxicity towards insect herbivores.

> <STAR>
3

> <IUPAC_NAME>
(5aR,8Z,9aS,10aR,13bR)-8-ethylidene-9a-(hydroxymethyl)-10a-methyl-2,4,5,5a,8,9,9a,10a,13,13b-decahydrooxireno[8,9][1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-7,11-dione

> <FORMULA>
C18H23NO6

> <MASS>
349.379

> <MONOISOTOPIC_MASS>
349.15254

> <CHARGE>
0

> <SMILES>
C/1(\C[C@]2(O[C@]2(C(=O)OCC3=CCN4CC[C@@H](OC1=O)[C@@]34[H])C)CO)=C/C

> <INCHI>
InChI=1S/C18H23NO6/c1-3-11-8-18(10-20)17(2,25-18)16(22)23-9-12-4-6-19-7-5-13(14(12)19)24-15(11)21/h3-4,13-14,20H,5-10H2,1-2H3/b11-3-/t13-,14-,17+,18+/m1/s1

> <INCHIKEY>
NOQVBHHOUTTZGE-LUZNJDLOSA-N

> <CAS_REGISTRY_NUMBER>
40158-95-0

> <REAXYS_REGISTRY_NUMBER>
5456751

> <CHEMIDPLUS>
40158-95-0

> <AGRICOLA_CITATION>
IND22014228

> <PUBMED_CITATION>
11978435; 15081286; 21819407; 21969251; 24981118; 25607464; 28267991; 29377789

$$$$