6-(2-{4-[(4-fluorophenyl)(phenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

• ChemBase ID: 103603
• Molecular Formular: C27H26FN3OS
• Molecular Mass: 459.5782432
• Monoisotopic Mass: 459.17806169
• SMILES: Cc1c(CCN2CC/C(=C(/c3ccccc3)\c3ccc(F)cc3)/CC2)c(=O)n2ccsc2n1
• Canonical SMILES: Fc1ccc(cc1)/C(=C/1\CCN(CC1)CCc1c(C)nc2n(c1=O)ccs2)/c1ccccc1
• InChI: InChI=1S/C27H26FN3OS/c1-19-24(26(32)31-17-18-33-27(31)29-19)13-16-30-14-11-22(12-15-30)25(20-5-3-2-4-6-20)21-7-9-23(28)10-8-21/h2-10,17-18H,11-16H2,1H3
• InChIKey: MFVJXLPANKSLLD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(2-{4-[(4-fluorophenyl)(phenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
• IUPAC Traditional name: 6-(2-{4-[(4-fluorophenyl)(phenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one
• Synonyms: R59022; 6-[2-[4-[(4-fluorophenyl)phenyl-methylene]-1-piperidinyl]ethyl]-7-methyl-5H-thiazolo-[3,2-a]pyrimidin-5-one; DKI; DIACYLGLYCEROL KINASE INHIBITOR I

Database IDs

• CAS Number: 93076-89-2
• PubChem SID: 162090924
• PubChem CID: 3012

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.6849563
• LogD (pH = 7.4): 4.4510875
• Log P: 5.1702523
• Molar Refractivity: 144.2537 cm^3
• Polarizability: 50.906414 Å^3
• Polar Surface Area: 35.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)

DETAILS

MP Biomedicals - 02152409

The elevation of diacylglycerol became of major importance when diacylglycerol was shown to stimulate protein kinase C, making this lipid candidate for a second messenger function in the signal transduction system. In intact cells, diacylglycerol is rapidly phosphorylated into phosphatidic acid by diacylglycerol kinase and reverses the protein kinase C activity.
DKI was found to inhibit diacylglycerol kinase. In human red blood cell membranes and in intact platelets, the concentrations needed for half maximal inhibition ranged from 2 to 4x10^-6M.