cyclohexyl N-(3-phenylphenyl)carbamate

• ChemBase编号: 130096
• 分子式: C19H21NO2
• 平均质量: 295.37554
• 单一同位素质量: 295.15722892
• SMILES: O=C(OC1CCCCC1)Nc1cccc(c1)c1ccccc1
• Canonical SMILES: O=C(Nc1cccc(c1)c1ccccc1)OC1CCCCC1
• InChI: InChI=1S/C19H21NO2/c21-19(22-18-12-5-2-6-13-18)20-17-11-7-10-16(14-17)15-8-3-1-4-9-15/h1,3-4,7-11,14,18H,2,5-6,12-13H2,(H,20,21)
• InChIKey: HHVUFQYJOSFTEH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: cyclohexyl N-(3-phenylphenyl)carbamate
• IUPAC传统名: cyclohexyl N-(3-phenylphenyl)carbamate
• 别名: Biphenyl-3-yl Carbamic Acid, Cyclohexyl Ester; N-[1,1'-Biphenyl]-3-yl-carbamic Acid Cyclohexyl Ester; [1,1'-Biphenyl]-3-yl-carbamic acid; cyclohexyl ester; URB602; [1,1’-Biphenyl]-3-yl-carbamic acid cyclohexyl ester; URB602

登记号

• CAS号: 565460-15-3
• MDL号: MFCD08457914
• PubChem SID: 162224381
• PubChem CID: 10979337
• CHEMBL: 77767
• Chemspider ID: 9154538
• 维基百科标题: URB602

理论计算性质

• Acid pKa: 12.972227
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 5.2767434
• LogD (pH = 7.4): 5.276742
• Log P: 5.2767434
• 摩尔折射率: 88.695 cm^3
• 极化性: 35.370617 Å^3
• 极化表面积: 38.33 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; DMSO: >10 mg/mL
• 外观: Crystalline solid; Off-White Solid; white to off-white powder
• 熔点: 122-123°C

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H21NO2

详细说明

Sigma Aldrich - U3010

Biochem/physiol Actions
URB602 is an inhibitor of monoacylglycerol lipase (MGL). The IC50 = 28 μM and Km = 20 μM. URB602 increases 2-arachidonoylglycerol (2-AG) concentrations. When URB602 is injected into the periaqueductal grey matter, it enhances stress-induced analgesia (tail-flick test) in a CB1-dependent manner. An effect that is prevented by a CB1 cannabinoid receptor antagonist, Rimonabant (SR141716). URB602 is not suitable for systemic administration due to relatively low potency, but useful for research of pain and stress-related disorders, which identifies MGL as a previously unrecognized therapeutic target (highlighted in Chemical Engineering News, June 27, 2005).

Toronto Research Chemicals - U821925

URB602 is a selective inhibitor of MGL, exhibiting an IC50 of 28 μM for the rat brain enzyme. It does not inhibit fatty acid amide hydrolase (FAAH) at concentrations up to 100 μM, or other lipid metabolizing enzymes such as diacylglycerol lipase or cyclooxygenase-2.5 6 Inhibition of 2-AG hydrolysis is associated with enhanced stress-induced analgesia and may represent a novel drug target in pain and stress management.

参考文献

• Hohmann, A.G., et al.: Nature, 435, 1108 (2005)
• Suplita, R.L., et al.: Neuropharmacol., Nov. 25 (epub), (2005)