methyl 4-[6-(4-{[(2H3)methoxycarbonyl]amino}phenyl)-4-(morpholin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate

• ChemBase ID: 179590
• Molecular Formular: C24H29N7O5
• Molecular Mass: 495.53096
• Monoisotopic Mass: 495.22301706
• SMILES: n1c(nc2c(c1N1CCOCC1)cnn2C1CCN(CC1)C(=O)OC)c1ccc(cc1)NC(=O)OC
• Canonical SMILES: COC(=O)Nc1ccc(cc1)c1nc(N2CCOCC2)c2c(n1)n(nc2)C1CCN(CC1)C(=O)OC
• InChI: InChI=1S/C24H29N7O5/c1-34-23(32)26-17-5-3-16(4-6-17)20-27-21(29-11-13-36-14-12-29)19-15-25-31(22(19)28-20)18-7-9-30(10-8-18)24(33)35-2/h3-6,15,18H,7-14H2,1-2H3,(H,26,32)
• InChIKey: IMXHGCRIEAKIBU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 4-[6-(4-{[(^2H₃)methoxycarbonyl]amino}phenyl)-4-(morpholin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate
• IUPAC Traditional name: methyl 4-[6-(4-{[(^2H₃)methoxycarbonyl]amino}phenyl)-4-(morpholin-4-yl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate
• Synonyms: 4-[6-[4-[[(Methoxy-d3)carbonyl]amino]phenyl]-4-(4-morpholinyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylic Acid Methyl Ester; WYE-354-d3; WYE 354-d3

Database IDs

• PubChem SID: 164235500
• PubChem CID: 71752999

CALCULATED PROPERTIES

• Acid pKa: 12.800424
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 2.6181035
• LogD (pH = 7.4): 2.6181347
• Log P: 2.618137
• Molar Refractivity: 154.9662 cm^3
• Polarizability: 50.622997 Å^3
• Polar Surface Area: 123.94 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - W950002

A labelled pyrazolopyrimidines derivative that is a potent and ATP-competitive mTOR inhibitor with much reduced activity against PI 3-Kα or PI 3-Kγ. WYE-354 is equally potent against mTORC1 and mTORC2 activities in HEK293 immune complex kinase assays usin

REFERENCES

• Yu, K. et al.: Cancer Res., 69, 6232 (2009)
• Zask, A. et al.: J. Med. Chem., 52, 5-13 (2009)
• Dormind-Meuwly, A. et al.: Biochem. Biophys. Res. Comm., 407, 714 (2009)