(1R,3R,5S,8S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione; (1R,5S,8S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione

• ChemBase ID: 349
• Molecular Formular: C30H34O13
• Molecular Mass: 602.58316
• Monoisotopic Mass: 602.19994115
• SMILES: O1[C@@]23[C@]4([C@@](O)(C[C@@H]12)C1[C@@H](C(OC1=O)[C@H]4OC3=O)C(O)(C)C)C.O1[C@@]23[C@]4([C@@](O)(CC12)C1[C@@H](C(OC1=O)[C@H]4OC3=O)C(=C)C)C
• Canonical SMILES: CC(=C)[C@@H]1C2OC(=O)C1[C@]1([C@]3([C@@H]2OC(=O)[C@]23C(C1)O2)C)O.O=C1OC2[C@H](C1[C@]1(O)C[C@@H]3[C@]4([C@@]1([C@@H]2OC4=O)C)O3)C(O)(C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5S,8S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione; (1R,5S,8S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione
• IUPAC Traditional name: (1R,3R,5S,8S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione; (1R,5S,8S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione
• Brand Name: Cocculin; Cocculine; Cocculus; Coques du levant; Fish berry; Indian berry; Oriental berry
• Synonyms: Picrotoxin

Database IDs

• CAS Number: 124-87-8
• PubChem SID: 46506796; 160963812
• PubChem CID: 31304

CALCULATED PROPERTIES

• Acid pKa: 13.596322
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.0787522
• LogD (pH = 7.4): -1.0787524
• Log P: -1.0787522
• Molar Refractivity: 68.2899 cm^3
• Polarizability: 28.414474 Å^3
• Polar Surface Area: 105.59 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 4100 mg/L
• Hydrophobicity(logP): -2.229

DETAILS

DrugBank - DB00466

• Drug Groups: approved
• Description: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the gamma-aminobutyric acid-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates. [PubChem]
• Indication: Used internally for relieving respiratory distress. Also for use as an antidote in poisoning by CNS depressants, especially barbiturates.
• Pharmacology: Picrotoxin is a toxin obtained from the seeds of the shrub Anamirta cocculus. It is used as a central nervous system stimulant, antidote, convulsant, and GABA (gamma aminobutyric acid) antagonist. It is a noncompetitive antagonist at GABA_A receptors and thus a convulsant. Picrotoxin blocks the GABA_Activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially barbiturates.
• Toxicity: Oral, mouse: LD₅₀ = 15 mg/kg. In large doses it is a powerful poison, causing unconsciousness, delirium, convulsions, gastro-enteritis and stimulation of the respiratory centre followed by paralysis, from which death sometimes results.
• Affected Organisms: Humans and other mammals
• References: [Link] ; Ehrenberger K, Benkoe E, Felix D: Suppressive action of picrotoxin, a GABA antagonist, on labyrinthine spontaneous nystagmus and vertigo in man. Acta Otolaryngol. 1982 Mar-Apr;93(3-4):269-73. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Link
• Ehrenberger K, Benkoe E, Felix D: Suppressive action of picrotoxin, a GABA antagonist, on labyrinthine spontaneous nystagmus and vertigo in man. Acta Otolaryngol. 1982 Mar-Apr;93(3-4):269-73. Pubmed