Anisatin

Anisatin
Names

IUPAC name (1'S,2'R,3S,4'R,5'R,7'R,8'R,11'R)-4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-2,10'-dione
Identifiers
CAS Number	5230-87-5^N
3DMet	B05347
ChEMBL	ChEMBL517697^N
ChemSpider	103015^Y
Jmol interactive 3D	Image
KEGG	C09294^N
MeSH	Anisatin
PubChem	12306850
InChI 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
Chemical formula	C₁₅H₂₀O₈
Molar mass	328.32 g·mol⁻¹
log P	-1.894
Acidity (pK_a)	12.005
Basicity (pK_b)	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

Anisatin is an extremely toxic, insecticidally active component of the Shikimi plant.^[1] It is used in folk remedies topically in Japan. Lethal dose = 1 mg/kg (i.p.) in mice. ^[2] 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.^[3]

References

↑ Lane, John F.; Koch, Walter T.; Leeds, Norma S.; Gorin, George (1952). "The toxin of Illicium anisatum. I. The isolation and characterization of a convulsant principle: anisatin". Journal of the American Chemical Society 74 (13): 3211–2114. doi:10.1021/ja01133a002.
↑ Kouno, J Chem Soc Perkin Trans 1:1537 1988
↑ Naoru.com:シキミ(jpnese)

GABAergics

Receptor
(ligands)

GABA_A

Agonists	(+)-Catechin Bamaluzole Barbiturates (e.g., phenobarbital) BL-1020 DAVA Dihydromuscimol GABA Gabamide GABOB Gaboxadol (THIP) Homotaurine (tramiprosate, 3-APS) Ibotenic acid iso-THAZ iso-THIP Isoguvacine Isomuscimol Isonipecotic acid Kojic amine Lignans (e.g., honokiol) Monastrol Muscimol Neuroactive steroids (e.g., allopregnanolone) Org 20599 Phenibut Picamilon P4S Progabide Propofol Quisqualamine SL-75102 TACA TAMP Terpenoids (e.g., borneol) Thiomuscimol Tolgabide ZAPA

PAMs	(abridged; see here for a full list): α-EMTBL Alcohols (e.g., ethanol) Avermectins (e.g., ivermectin) Barbiturates (e.g., phenobarbital) Benzodiazepines (e.g., diazepam) Bromide compounds (e.g., potassium bromide) Carbamates (e.g., meprobamate) Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g., ergoloid (dihydroergotoxine)) Etazepine Etifoxine Fenamates (e.g., mefenamic acid) Flavonoids (e.g., apigenin, hispidulin) Fluoxetine Flupirtine Imidazoles (e.g., etomidate) Kava constituents (e.g., kavain) Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g., allopregnanolone, cholesterol) Niacin Nicotinamide (niacinamide) Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon)) Norfluoxetine Petrichloral Phenols (e.g., propofol) Phenytoin Piperidinediones (e.g., glutethimide) Propanidid Pyrazolopyridines (e.g., etazolate) Quinazolinones (e.g., methaqualone) Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g., baicalin) Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal)) Topiramate Valerian constituents (e.g., valerenic acid) Volatiles/gases (e.g., chloral hydrate, chloroform, diethyl ether, paraldehyde, sevoflurane)

Antagonists	Bicuculline Coriamyrtin Dihydrosecurinine Gabazine (SR-95531) Hydrastine Hyenachin (mellitoxin) PHP-501 Pitrazepin Securinine Sinomenine SR-42641 SR-95103 Thiocolchicoside Tutin

NAMs	1,3M1B 3M2B 17-Phenylandrostenol α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Amiloride Anisatin β-Lactams (e.g., penicillins, cephalosporins, carbapenems) Basmisanil Bemegride Bilobalide CHEB Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil) Flavonoids (e.g., amentoflavone, oroxylin A) Flumazenil Fluoroquinolones (e.g., ciprofloxacin) Flurothyl Furosemide Iomazenil (¹²³I) Isoallopregnanolone Isopregnanolone (sepranolone) L-655,708 Laudanosine Leptazol Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Non-steroidal antiandrogens (e.g., apalutamide, bicalutamide, enzalutamide, flutamide, nilutamide) Oenanthotoxin Pentetrazol (metrazol) Phenylsilatrane Picrotoxin (i.e., picrotin and picrotoxinin) Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426

GABA_A-ρ

Agonists	BL-1020 CACA CAMP Homohypotaurine GABA GABOB Ibotenic acid Isoguvacine Muscimol N⁴-Chloroacetylcytosine arabinoside Picamilon Progabide TACA TAMP Thiomuscimol Tolgabide

PAMs	Allopregnanolone Alphaxolone ATHDOC Lanthanides

Antagonists	(S)-2-MeGABA (S)-4-ACPBPA (S)-4-ACPCA 2-MeTACA 3-APMPA 4-ACPAM 4-GBA cis-3-ACPBPA CGP-36742 (SGS-742) DAVA Gabazine (SR-95531) Gaboxadol (THIP) I4AA Isonipecotic acid Loreclezole P4MPA P4S SKF-97541 SR-95318 SR-95813 TPMPA trans-3-ACPBPA ZAPA

NAMs	5α-Dihydroprogesterone Bilobalide Loreclezole Picrotoxin (picrotin, picrotoxinin) Pregnanolone ROD-188 THDOC Zinc

GABA_B

Agonists	1,4-Butanediol Aceburic acid Arbaclofen Arbaclofen placarbil Baclofen BL-1020 GABA Gabamide GABOB GBL GHB GHBAL GHV GVL Isovaline Lesogaberan Phenibut Picamilon Progabide Sodium oxybate SKF-97,541 SL 75102 Tolgabide

Antagonists	2-Hydroxysaclofen CGP-35348 CGP-46381 CGP-52432 CGP-54626 CGP-55845 CGP-64213 DAVA Homotaurine (tramiprosate, 3-APS) Phaclofen Saclofen SCH-50911 SKF-97541

NAMs	Compound 14

PAMs	ADX-71441 BHF-177 BHFF BSPP CGP-7930 CGP-13501 GS-39783 rac-BHFF

Transporter
(blockers)

GAT	4-Aminovaleric acid β-Alanine Arecaidine CI-966 DABA Deramciclane (EGIS-3886, EGYT-3886) EF-1502 Gabaculine Guvacine Ibotenic acid Muscimol Nipecotic acid NNC 05-2090 NO-711 Riluzole SKF-89976A SNAP-5114 TACA Tiagabine

VIAAT	β-Alanine Bafilomycin A1 Chicago sky blue 6B Evans blue GABA Glycine N-Butyric acid Nigericin Nipecotic acid Valinomycin Vigabatrin

Enzyme
(inhibitors)

GAD	3-Mercaptopropionic acid AAOA L-Allylglycine Semicarbazide

GABA-T	3-Hydrazinopropionic acid γ-Acetylenic-GABA AOAA EOS Gabaculine Isoniazid L-Cycloserine Phenelzine PEH Rosmarinic acid (lemon balm) Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium (divalproex sodium) Valproic acid Valpromide Vigabatrin

Others

Precursors	1,4-Butanediol GHB GHBAL Glutamate Glutamine

Analogues	Pregabalin 4-Methylpregabalin Atagabalin Gabapentin Gabapentin enacarbil Imagabalin Mirogabalin PD-200,347 PD-217,014 PD-299,685 Phenibut

Others	Vitamin B₆ GABA-T activators: 3-Methyl-GABA

See also: GHBergics • Glutamatergics • Glycinergics

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