6-(2-{4-[(4-fluorophenyl)(phenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one

• ChemBase ID: 134394
• Molecular Formular: C27H27FN4O
• Molecular Mass: 442.5278832
• Monoisotopic Mass: 442.21688972
• SMILES: Cc1c(c(=O)n2cc[nH]c2n1)CCN1CC/C(=C(/c2ccccc2)\c2ccc(cc2)F)/CC1
• Canonical SMILES: Fc1ccc(cc1)/C(=C/1\CCN(CC1)CCc1c(C)nc2n(c1=O)cc[nH]2)/c1ccccc1
• InChI: InChI=1S/C27H27FN4O/c1-19-24(26(33)32-18-14-29-27(32)30-19)13-17-31-15-11-22(12-16-31)25(20-5-3-2-4-6-20)21-7-9-23(28)10-8-21/h2-10,14,18H,11-13,15-17H2,1H3,(H,29,30)
• InChIKey: AYKNTNIBYFCKIM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(2-{4-[(4-fluorophenyl)(phenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one
• IUPAC Traditional name: 6-(2-{4-[(4-fluorophenyl)(phenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-1H-imidazo[1,2-a]pyrimidin-5-one
• Synonyms: 6-[2-[4-[(4-Fluorophenyl)phenylmethylene]-1-piperidin-yl]ethyl]-7-methyl-5H-thiazolo-[3,2-a]-pyrimidin-5-one; R59022; Diacylglycerol Kinase Inhibitor I

Database IDs

• CAS Number: 93076-89-2
• MDL Number: MFCD00055114
• PubChem SID: 24893986; 162228670
• PubChem CID: 71308799

CALCULATED PROPERTIES

• Acid pKa: 12.203921
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.6968848
• LogD (pH = 7.4): 3.4663887
• Log P: 4.185601
• Molar Refractivity: 139.6668 cm^3
• Polarizability: 48.948963 Å^3
• Polar Surface Area: 47.94 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: slightly soluble; 0.1 M NaOH: slightly soluble; DMSO: soluble; ethanol: soluble; ethyl acetate: soluble; H2O: insoluble
• Apperance: pale yellow solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - D5919

Biochem/physiol Actions
Diacylglycerol kinase inhibitor. Inhibits formation of [38P]1-Oleoxyl-2-acetylglyceryl-3-phosphoric acid (OAPA) in red blood cell membranes: IC50 = 3.3 μM.