Anisatin

Anisatin is an extremely toxic, insecticidally active component of the shikimi plant. The lethal dose is 1 mg/kg (i.p.) in mice. Symptoms begin to appear about 1–6 hours after ingestion, beginning with gastrointestinal ailments, such as diarrhea, vomiting, and stomach pain, followed by nervous system excitation, seizures, loss of consciousness, and respiratory paralysis, which is the ultimate cause of death.

Anisatin
Names
Preferred IUPAC name
(1R,4S,5R,6S,6aR,7R,9R,9aS)-1,5,6a,7-Tetrahydroxy-5,9-dimethylhexahydrospiro[[4,9a]methanocyclopenta[d]oxocine-6,3′-oxetane]-2,2′(1H)-dione
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.208.646
KEGG
MeSH Anisatin
PubChem CID
UNII
  • InChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8-,9+,12+,13+,14+,15-/m1/s1 N
    Key: GEVWHIDSUOMVRI-QWNPAUMXSA-N Y
SMILES
  • O=C1OC[C@]14[C@@]2(O)[C@H](O)C[C@H]([C@]23C[C@@H](OC(=O)[C@@H]3O)[C@@]4(O)C)C
Properties
C15H20O8
Molar mass 328.317 g·mol−1
log P -1.894
Acidity (pKa) 12.005
Basicity (pKb) 1.992
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
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