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 ID: 154463
• Molecular Formular: C23H27ClFN5O3
• Molecular Mass: 475.9435832
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: 5-fluoro-N-{2-[4-(2-oxo-3H-1,3-benzodiazol-1-yl)piperidin-1-yl]ethyl}-1H-indole-2-carboxamide hydrate hydrochloride
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 12.311011
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.8996737
• LogD (pH = 7.4): 2.1494098
• Log P: 2.254717
• Molar Refractivity: 117.8063 cm^3
• Polarizability: 44.74031 Å^3
• Polar Surface Area: 80.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

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

DETAILS

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.