4-{[13-chloro-10-(2,6-difluorophenyl)-3,5,9-triazatricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,9,12,14-heptaen-4-yl]amino}(2H4)benzoic acid

• ChemBase ID: 174430
• Molecular Formular: C25H15ClF2N4O2
• Molecular Mass: 476.8620064
• Monoisotopic Mass: 476.08515986
• SMILES: c12c(C(=NCc3c1nc(nc3)Nc1ccc(cc1)C(=O)O)c1c(cccc1F)F)cc(cc2)Cl
• Canonical SMILES: Clc1ccc2c(c1)C(=NCc1c2nc(nc1)Nc1ccc(cc1)C(=O)O)c1c(F)cccc1F
• InChI: InChI=1S/C25H15ClF2N4O2/c26-15-6-9-17-18(10-15)23(21-19(27)2-1-3-20(21)28)29-11-14-12-30-25(32-22(14)17)31-16-7-4-13(5-8-16)24(33)34/h1-10,12H,11H2,(H,33,34)(H,30,31,32)
• InChIKey: HHFBDROWDBDFBR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[13-chloro-10-(2,6-difluorophenyl)-3,5,9-triazatricyclo[9.4.0.0^2,^7]pentadeca-1(11),2(7),3,5,9,12,14-heptaen-4-yl]amino}(^2H₄)benzoic acid
• IUPAC Traditional name: 4-{[13-chloro-10-(2,6-difluorophenyl)-3,5,9-triazatricyclo[9.4.0.0^2,^7]pentadeca-1(11),2(7),3,5,9,12,14-heptaen-4-yl]amino}(^2H₄)benzoic acid
• Synonyms: 4-[[9-Chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino]benzoic Acid-d4; MLN 8054-d4

Database IDs

• PubChem SID: 164230340
• PubChem CID: 71750643

CALCULATED PROPERTIES

• Acid pKa: 4.5909085
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 5.229278
• LogD (pH = 7.4): 3.4550352
• Log P: 6.06688
• Molar Refractivity: 124.4964 cm^3
• Polarizability: 47.03759 Å^3
• Polar Surface Area: 87.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M425127

Labelled MLN 8054 (M425125). An Aurora kinase inhibitor, used to treat patients with advanced solid tumors.

REFERENCES

• Kaestner, P., et al.: Mol. Cancer Ther., 8, 2046 (2009)
• Scutt, P., et al.: J. Biol. Chem., 284, 15880 (2009)
• Aliagas-Martin, I., et al.: J. Med. Chem., 52, 3300 (2009)