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

• ChemBase ID: 75736
• Molecular Formular: C30H34O13
• Molecular Mass: 602.58316
• Monoisotopic Mass: 602.19994115
• SMILES: CC(=C)[C@H]1[C@H]2OC(=O)[C@@H]1[C@]1(O)C[C@H]3O[C@@]43C(=O)O[C@H]2[C@]14C.CC(C)(O)[C@H]1[C@H]2OC(=O)[C@@H]1[C@]1(O)C[C@H]3O[C@@]43C(=O)O[C@H]2[C@]14C
• 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.O=C1O[C@@H]2[C@@H]([C@H]1[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+/m11/s1
• InChIKey: VJKUPQSHOVKBCO-AHMKVGDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5S,8S,9R,12S,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; (1R,3R,5S,8S,9R,12S,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
• IUPAC Traditional name: picrotin; picrotoxinin
• Synonyms: Picrotoxin

Database IDs

• CAS Number: 124-87-8
• MDL Number: MFCD00074824
• PubChem SID: 162040654
• PubChem CID: 6473767

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

• Melting Point: 200-202°C

Safety Information

• Storage Warning: Very Toxic

DETAILS

Apollo Scientific Ltd - OR1176

Antagonist of GABA receptors