N-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-[(pyridin-4-ylmethyl)amino]pyridine-3-carboxamide

• ChemBase ID: 174775
• Molecular Formular: C22H23N5O
• Molecular Mass: 373.45092
• Monoisotopic Mass: 373.19026038
• SMILES: c1nc(c(cc1)C(=O)Nc1ccc2c(c1)NCC2(C)C)NCc1ccncc1
• Canonical SMILES: O=C(c1cccnc1NCc1ccncc1)Nc1ccc2c(c1)NCC2(C)C
• InChI: InChI=1S/C22H23N5O/c1-22(2)14-26-19-12-16(5-6-18(19)22)27-21(28)17-4-3-9-24-20(17)25-13-15-7-10-23-11-8-15/h3-12,26H,13-14H2,1-2H3,(H,24,25)(H,27,28)
• InChIKey: RAHBGWKEPAQNFF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-[(pyridin-4-ylmethyl)amino]pyridine-3-carboxamide
• IUPAC Traditional name: motesanib
• Synonyms: N-(2,3-Dihydro-3,3-dimethyl-1H-indol-6-yl)-2-[(4-pyridinylmethyl)amino]-3-pyridinecarboxamide; Motesanib

Database IDs

• CAS Number: 857876-30-3
• PubChem SID: 164230685
• PubChem CID: 11667893

CALCULATED PROPERTIES

• Acid pKa: 12.601569
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.0398972
• LogD (pH = 7.4): 3.322812
• Log P: 3.3271348
• Molar Refractivity: 114.7707 cm^3
• Polarizability: 41.41086 Å^3
• Polar Surface Area: 78.94 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M732500

Motesanib is an oral angiogenesis inhibitor, demonstrates clinical efficacy in advanced thymoma.

REFERENCES

• Rosen, L., et al.: J. Clin. Oncol., 25, 2369 (2007)
• Sherman, S., et al.: New Engl. J. Med., 359, 31 (2007)