(2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid

• ChemBase编号: 73040
• 分子式: C19H27NO3
• 平均质量: 317.42258
• 单一同位素质量: 317.19909373
• SMILES: C1[C@H](CC[C@@H](C1)C(=O)N[C@H](Cc1ccccc1)C(=O)O)C(C)C
• Canonical SMILES: CC([C@@H]1CC[C@H](CC1)C(=O)N[C@@H](C(=O)O)Cc1ccccc1)C
• InChI: InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1
• InChIKey: OELFLUMRDSZNSF-BRWVUGGUSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid
• IUPAC传统名: @nateglinide; nateglinide; (2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid
• 别名: N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-L-phenylalanine; L-Nateglinide; ent-Nateglinide; N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine; A 4166; AY 4166; D-Nateglinide; DJN 608; Glinate; Natelide; SDZ-DJN 608; Senaglinide; Starlix DS; Starlix; Nateglinide; Fastic; N-[(trans-4-isopropylcyclohexyl)carbonyl]-D-phenylalanine; Starsis; Nateglinide; (R)-2-((1r,4R)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoic acid

登记号

• CAS号: 105816-04-4; 105816-05-5
• MDL号: MFCD00875706
• PubChem SID: 162037960
• PubChem CID: 5311309

理论计算性质

• Acid pKa: 3.9972527
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 2.5164278
• LogD (pH = 7.4): 0.86791366
• Log P: 4.0285707
• 摩尔折射率: 89.4605 cm^3
• 极化性: 35.256687 Å^3
• 极化表面积: 66.4 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; DMSO: >5 mg/mL; H2O: insoluble; Methanol
• 外观: White Solid; white to off-white solid; White to Off-White Solid
• 熔点: 103-111°C; 129-130°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: SQ7318950
• 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: room temp

药理学性质

• 生物活性机理: Stimulats the release of insulin from the pancreas by closing ATP-dependent potassium channels in the membrane of the betta-cells

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• 应用领域: Antidiabetic agent; Oral hypoglycaemic agent
• Empirical Formula (Hill Notation): C19H27NO3

详细说明

Selleck Chemicals - S2489

Research Area: Endocrinology
Biological Activity:
Nateglinide(Starlix) is an insulin secretagog agent that lowers blood glucose levels by stimulating insulin secretion from the pancreas. It achieves this by closing ATP-dependent potassium channels in the membrane of the β cells. This depolarizes the β cells and causes voltage-gated calcium channels to open. The resulting calcium influx induces fusion of insulin-containing vesicles with the cell membrane, and insulin secretion occurs. [1][2]

Sigma Aldrich - N3538

Biochem/physiol Actions
Nateglinide is a Kir6.2/SUR1 channel inhibitor and antidiabetic. It is selective for the SUR1 subtype, which is found on pancreatic islet cells. Nateglinide evokes KATP channel-dependent insulin secretion (50-200 μM) in the absence and presence of insulin.

Toronto Research Chemicals - N379375

An amino-acid derivative that stimulates insulin secretion. Used as an antidiabetic.

Toronto Research Chemicals - N379365

An impurity found within the commercial pharmaceutical Nateglinide (N379375), a novel D-phenylalanine-derivative hypoglycemic agent.

参考文献

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