5-fluoro-N-{2-[4-(2-oxo-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]ethyl}-1H-indole-2-carboxamide hydrate hydrochloride

• ChemBase编号: 154463
• 分子式: C23H27ClFN5O3
• 平均质量: 475.9435832
• 单一同位素质量: 475.17864565
• SMILES: c1ccc2c(c1)[nH]c(=O)n2C1CCN(CC1)CCNC(=O)c1cc2cc(ccc2[nH]1)F.O.Cl
• Canonical SMILES: Fc1ccc2c(c1)cc([nH]2)C(=O)NCCN1CCC(CC1)n1c(=O)[nH]c2c1cccc2.O.Cl
• InChI: InChI=1S/C23H24FN5O2.ClH.H2O/c24-16-5-6-18-15(13-16)14-20(26-18)22(30)25-9-12-28-10-7-17(8-11-28)29-21-4-2-1-3-19(21)27-23(29)31;;/h1-6,13-14,17,26H,7-12H2,(H,25,30)(H,27,31);1H;1H2
• InChIKey: ZORDQKCXPCXYKL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-fluoro-N-{2-[4-(2-oxo-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl]ethyl}-1H-indole-2-carboxamide hydrate hydrochloride
• IUPAC传统名: 5-fluoro-N-{2-[4-(2-oxo-3H-1,3-benzodiazol-1-yl)piperidin-1-yl]ethyl}-1H-indole-2-carboxamide hydrate hydrochloride
• 别名: 4-Fluoro-N-(2-(4-(5-fluoro-1H-indol-1-yl)piperidin-1-yl)ethyl)benzamide; 5-Fluoro-2-indolyl des-chlorohalopemide hydrochloride hydrate; FIPI hydrochloride hydrate

登记号

• MDL号: MFCD12912411
• PubChem SID: 162248602
• PubChem CID: 57347524

理论计算性质

• Acid pKa: 12.311011
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 0.8996737
• LogD (pH = 7.4): 2.1494098
• Log P: 2.254717
• 摩尔折射率: 117.8063 cm^3
• 极化性: 44.74031 Å^3
• 极化表面积: 80.47 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >20 mg/mL
• 外观: off-white powder

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H24FN5O2·HCl · xH2O

详细说明

Sigma Aldrich - F5807

Biochem/physiol Actions
FIPI is a potent Phospholipase D (PLD) inhibitor. The signaling enzyme Phospholipase D (PLD) and the lipid second messenger phosphatidic acid (PA) generated by PLD are implicated in many cell biological processes including Ras activation, cell spreading, stress fiber formation, chemotaxis, and membrane vesicle trafficking. FIPI is a potent in vivo inhibitor of both PLD1 and PLD2, setting the stage for a new era of exploration and validation of cell biological roles for mammalian PLD. It rapidly blocks in vivo PA production with sub-nM potency. FIPI inhibits PLD regulation of F-actin cytoskeleton reorganization, cell spreading, and chemotaxis, indicating potential utility for it as a therapeutic for autoimmunity and cancer metastasis. It does not affect PLD subcellular localization, PIP2 availability, the actin stress fiber network in resting CHO cells, or selected signaling events proximal to PLD activation.
FIPI is a potent phospholipase D (PLD) inhibitor effective at sub-nM levels. Phospholipase D (PLD) and the lipid second messenger phosphatidic acid (PA) generated by PLD are implicated in many cell biological processes including Ras activation, cell spreading, stress fiber formation, chemotaxis, and membrane vesicle trafficking. FIPI inhibits both PLD1 and PLD2, rapidly blocking in vivo PA production. FIPI inhibits PLD regulation of F-actin cytoskeleton reorganization, cell spreading, and chemotaxis, suggesting potential as a therapeutic for autoimmune diseases and cancer metastasis.