(1R,3R,5S,8S,9R,12R,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

• ChemBase ID: 133486
• Molecular Formular: C15H16O6
• Molecular Mass: 292.28394
• Monoisotopic Mass: 292.09468823
• SMILES: CC(=C)[C@@H]1[C@@H]2[C@@H]3[C@@]4([C@]([C@@H]1C(=O)O2)(C[C@@H]1[C@]4(O1)C(=O)O3)O)C
• Canonical SMILES: CC(=C)[C@@H]1[C@H]2OC(=O)[C@H]1[C@]1([C@]3([C@@H]2OC(=O)[C@]23[C@@H](C1)O2)C)O
• InChI: InChI=1S/C15H16O6/c1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h6-10,18H,1,4H2,2-3H3/t6-,7+,8+,9-,10-,13-,14-,15+/m1/s1
• InChIKey: PIMZUZSSNYHVCU-KBLUICEQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5S,8S,9R,12R,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1^9,^1^2.0^3,^5.0^5,^1^3]tetradecane-6,11-dione
• IUPAC Traditional name: (1R,3R,5S,8S,9R,12R,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1^9,^1^2.0^3,^5.0^5,^1^3]tetradecane-6,11-dione
• Synonyms: Picrotoxinin

Database IDs

• CAS Number: 17617-45-7
• MDL Number: MFCD00078765
• PubChem SID: 24898746; 162227763
• PubChem CID: 7098683

CALCULATED PROPERTIES

• Acid pKa: 13.610567
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.0031599717
• LogD (pH = 7.4): 0.0031597079
• Log P: 0.003159975
• Molar Refractivity: 66.3301 cm^3
• Polarizability: 27.47222 Å^3
• Polar Surface Area: 85.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: PC5150000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

DETAILS

Sigma Aldrich - P8390

Biochem/physiol Actions
GABAA receptor antagonist; binds to the GABA receptor-linked Cl- channel.
Other Notes
Active component of picrotoxin