4-nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate hydrate

• ChemBase编号: 155790
• 分子式: C27H26N2O10
• 平均质量: 538.50274
• 单一同位素质量: 538.15874504
• SMILES: c1cc(ccc1[N+](=O)[O-])OC(=O)N1CCC(CC1)C(c1ccc2c(c1)OCO2)(c1ccc2c(c1)OCO2)O.O
• Canonical SMILES: O=C(N1CCC(CC1)C(c1ccc2c(c1)OCO2)(c1ccc2c(c1)OCO2)O)Oc1ccc(cc1)[N+](=O)[O-].O
• InChI: InChI=1S/C27H24N2O9.H2O/c30-26(38-21-5-3-20(4-6-21)29(32)33)28-11-9-17(10-12-28)27(31,18-1-7-22-24(13-18)36-15-34-22)19-2-8-23-25(14-19)37-16-35-23;/h1-8,13-14,17,31H,9-12,15-16H2;1H2
• InChIKey: HNSBVGMOKGQJLT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate hydrate
• IUPAC传统名: 4-nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate hydrate
• 别名: JZL 184 hydrate; JZL184 hydrate

登记号

• MDL号: MFCD12912421
• PubChem SID: 162249928
• PubChem CID: 71312223

理论计算性质

• Acid pKa: 13.1246605
• 质子受体: 8
• 质子供体: 1
• LogD (pH = 5.5): 3.9531872
• LogD (pH = 7.4): 3.9531865
• Log P: 3.9531872
• 摩尔折射率: 132.0473 cm^3
• 极化性: 51.068157 Å^3
• 极化表面积: 132.51 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: >20 mg/mL
• 外观: light yellow powder

安全信息

• 保存条件: desiccated
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 25
• 安全公开号: 45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C27H24N2O9 · xH2O

详细说明

Sigma Aldrich - J3455

Biochem/physiol Actions
JZL184 selectively inhibits MAGL, the enzyme predominantly responsible for the degradation of the endocannabinoid 2-arachidonoylglycerol (2-AG). Anandamide and 2-AG are the two endogenous endocannabinoids that activate the cannabinoid receptors CB1 and CB2. Anandamide is predominantly metabolized by fatty acid amide hydrolase (FAAH), whereas monoacylglycerol lipase (MAGL) is thought to be the enzyme primarily responsible for the degradation of 2-AG. It is difficult to separate the activities of the two because most currently available inhibitors of MAGL are not selective, and also inhibit FAAH or other enzymes. JZL 184 is the first selective inhibitor of MAGL with nanomolar portency and over 200-fold selectivity for MAGL vs FAAH. When administered to mice, JZL184 increased levels of 2-arachidonoylglycerol in the brain by about 8-fold, with no effect on levels of anandamide.