Picrotoxin, GABAA antagonist

Key facts

CAS number

124-87-8

Purity

>98%

Form

Solid

form

Source

Anamirta cocculus

Molecular weight

602.6 Da

Molecular formula

C₁₅H₁₈O₇.C₁₅H₁₆O₆

PubChem

31304

Nature

Native

Solubility

For more Solubility (Complete) data for PICROTOXIN (7 total), please visit the HSDB record page.

Soluble in DMSO to 100 mM

Soluble in ethanol to 50 mM (with heating)

Biochemical name

Picrotoxin

Biological description

Plant alkaloid. Non-competitive GABAA antagonist. Also inhibits homomeric glycine receptor. Convulsant *in vivo*.

Canonical smiles

CC(=C)C1C2C3C4(C(C1C(=O)O2)(CC5C4(O5)C(=O)O3)O)C.CC12C3C4C(C(C1(CC5C2(O5)C(=O)O3)O)C(=O)O4)C(C)(C)O

Isomeric smiles

CC(=C)[C@@H]1C2[C@@H]3[C@@]4([C@](C1C(=O)O2)(CC5[C@]4(O5)C(=O)O3)O)C.C[C@@]12[C@H]3C4[C@H](C([C@@]1(C[C@@H]5[C@]2(O5)C(=O)O3)O)C(=O)O4)C(C)(C)O

InChi

InChI=1S/C15H18O7.C15H16O6/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9;1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h5-9,18-19H,4H2,1-3H3;6-10,18H,1,4H2,2-3H3/t5-,6+,7?,8?,9-,13-,14-,15+;6?,7-,8?,9?,10+,13+,14+,15-/m10/s1

InChiKey

VJKUPQSHOVKBCO-ZTYBEOBUSA-N

IUPAC Name

(1R,3R,5S,8S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione;(1R,5S,8S,13R,14R)-1-hydroxy-13-methyl-14-prop-1-en-2-yl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione