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(−)-anisatin
Sign in to saveAnisatin 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.
In the Vinony graph
Within Vinony's link graph, (−)-anisatin is referenced by 354 other articles, and connects out to picrotoxin, tetrahydrodeoxycorticosterone and (RS)-baclofen.
It is catalogued under topics including Chembox image size set, ECHA InfoCard ID from Wikidata and GABAA receptor negative allosteric modulators.
Its subject is documented across 13 Wikipedia language editions.
Chemical data
- Formula
- C15H20O8
- Molecular weight
- 328.31 g/mol
- IUPAC name
- (1S,2R,4R,5R,6S,7R,8R,11R)-4,5,7,11-tetrahydroxy-2,7-dimethylspiro[9-oxatricyclo[6.3.1.01,5]dodecane-6,3'-oxetane]-2',10-dione
- SMILES
- C[C@@H]1C[C@H]([C@]2([C@@]13C[C@H]([C@]([C@@]24COC4=O)(C)O)OC(=O)[C@@H]3O)O)O
- InChIKey
- GEVWHIDSUOMVRI-QWNPAUMXSA-N
- XLogP
- -1.9
- Polar surface area
- 134 Ų
- H-bond donors
- 4
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 328.1158176
Show 5 more facts
- canonical SMILES
- O=C1OC2CC3(C1O)C(C)CC(O)C3(O)C4(C(=O)OC4)C2(O)C
- isomeric SMILES
- C[C@@H]1C[C@@H](O)[C@@]2(O)[C@@]13C[C@@H](OC(=O)[C@@H]3O)[C@](C)(O)[C@@]21COC1=O
- chemical formula
- C₁₅H₂₀O₈
- found in taxon
- Illicium verum
- Commons category
- Anisatin
Sources (1)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Role in the GABA system
- Synthesis
- References
- External links
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.
== Role in the GABA system == The GABA system is an important site of action by a variety of chemicals, including alcohols, heavy metals, and insecticides. A study conducted on frog spinal cords and rat brains indicated that anisatin was a strong non-competitive GABA antagonist. Anisatin was shown to suppress GABA-induced signals, but when anisatin was added without GABA, there was no change in the signal. Anisatin was also found to share the same binding site as picrotoxinin, and did not cause additional suppression of GABA-induced signals in the presence of high concentrations of picrotoxinin.
Excerpted from Wikipedia’s “(−)-anisatin” article, available under the CC BY-SA 4.0 licence.
Available in 13 languages
via Wikidata sitelinks · CC0