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

• ChemBase编号: 131029
• 分子式: C30H34O13
• 平均质量: 602.58316
• 单一同位素质量: 602.19994115
• 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.C[C@@]12[C@H]3[C@@H]4[C@H]([C@H]([C@@]1(C[C@@H]1[C@]2(O1)C(=O)O3)O)C(=O)O4)C(C)(C)O
• 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-NGKRNLQBSA-N

名称和登记号

名称

• IUPAC标准名: (1R,3R,5S,8S,9S,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; (1R,3R,5S,8S,9S,12R,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^9,^1^2.0^3,^5.0^5,^1^3]tetradecane-6,11-dione
• IUPAC传统名: (1R,3R,5S,8S,9S,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; (1R,3R,5S,8S,9S,12R,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^9,^1^2.0^3,^5.0^5,^1^3]tetradecane-6,11-dione
• 别名: Cocculin; Picrotoxin

登记号

• CAS号: 124-87-8
• EC号: 204-716-6
• MDL号: MFCD00074824
• Beilstein号: 3894406
• PubChem SID: 24278188; 24887544; 162225307
• PubChem CID: 5311359

理论计算性质

• Acid pKa: 13.596322
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): -1.0787522
• LogD (pH = 7.4): -1.0787524
• Log P: -1.0787522
• 摩尔折射率: 68.2899 cm^3
• 极化性: 28.414474 Å^3
• 极化表面积: 105.59 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: ethanol: soluble50 mg/mL, clear to slightly hazy
• 外观: white to light yellow powder
• 熔点: 203 °C(lit.)

安全信息

• RTECS编号: TJ9100000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 3462
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 28
• 安全公开号: 28-36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300
• GHS警示性声明: P264-P301 + P310
• 个人保护装置: 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 3462 6.1/PG 2

药理学性质

• 相关基因信息: human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)

产品相关信息

• 纯度: 98.0% (TLC)
• Empirical Formula (Hill Notation): C30H34O13

详细说明

Sigma Aldrich - P1675

Biochem/physiol Actions
GABAA receptor antagonist; binds to the GABA receptor-linked Cl- channel.
Other Notes
Molecular complex (1:1) of picrotin and picrotoxinin.

Sigma Aldrich - 80410

Biochem/physiol Actions
GABAA receptor antagonist; binds to the GABA receptor-linked Cl- channel.
Other Notes
GABA receptor antagonist1