methyl (3Z)-3-{[(4-{N-methyl-2-[4-(2H3)methylpiperazin-1-yl]acetamido}phenyl)amino](phenyl)methylidene}-2-oxo-2,3-dihydro-1H-indole-6-carboxylate

• ChemBase ID: 171656
• Molecular Formular: C31H33N5O4
• Molecular Mass: 539.62482
• Monoisotopic Mass: 539.25325456
• SMILES: c1(ccc2c(c1)NC(=O)/C/2=C(\Nc1ccc(cc1)N(C(=O)CN1CCN(CC1)C)C)/c1ccccc1)C(=O)OC
• Canonical SMILES: COC(=O)c1ccc2c(c1)NC(=O)/C/2=C(/c1ccccc1)\Nc1ccc(cc1)N(C(=O)CN1CCN(CC1)C)C
• InChI: InChI=1S/C31H33N5O4/c1-34-15-17-36(18-16-34)20-27(37)35(2)24-12-10-23(11-13-24)32-29(21-7-5-4-6-8-21)28-25-14-9-22(31(39)40-3)19-26(25)33-30(28)38/h4-14,19,32H,15-18,20H2,1-3H3,(H,33,38)/b29-28-
• InChIKey: XZXHXSATPCNXJR-ZIADKAODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3Z)-3-{[(4-{N-methyl-2-[4-(^2H₃)methylpiperazin-1-yl]acetamido}phenyl)amino](phenyl)methylidene}-2-oxo-2,3-dihydro-1H-indole-6-carboxylate
• IUPAC Traditional name: methyl (3Z)-3-{[(4-{N-methyl-2-[4-(^2H₃)methylpiperazin-1-yl]acetamido}phenyl)amino](phenyl)methylidene}-2-oxo-1H-indole-6-carboxylate
• Synonyms: (3Z)-2,3-Dihydro-3-[[[4-[methyl[2-(4-methyl-1-piperazinyl)acetyl]amino]phenyl]amino]phenylmethylene]-2-oxo-H-Indole-6-carboxylic Acid Methyl Ester; BIBF 1120; Intedanib-d3

Database IDs

• PubChem SID: 164227566
• PubChem CID: 71749506

CALCULATED PROPERTIES

• Acid pKa: 10.855381
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.6756415
• LogD (pH = 7.4): 2.3594947
• Log P: 2.7898567
• Molar Refractivity: 159.0974 cm^3
• Polarizability: 59.2078 Å^3
• Polar Surface Area: 94.22 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I666652

Labelled Intedanib (I666650). It is an indolinone derivative potently blocking VEGF-, PDGF-, and FGF-receptor kinases; an indolinone as triple angiokinase inhibitors. An antitumor agent.

REFERENCES

• Sun, L., et al.: J. Med. Chem., 41, 2588 (1998)
• Xie, H., et al.: J. Med. Chem., 50, 4898 (1998)
• Hilberg, F., et al.: Cancer Res., 68, 4774 (1998)