MLN-8054   Click here for help

GtoPdb Ligand ID: 5696

Synonyms: MLN 8054 | MLN8054
PDB Ligand
Compound class: Synthetic organic
Comment: MLN-8054 is an ATP-competitive (Type I), reversible inhibitor of Aurora kinases A, B and C with limited selectivity for A [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 87.47
Molecular weight 476.09
XLogP 5.36
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES Clc1ccc2c(c1)C(=NCc1c2nc(nc1)Nc1ccc(cc1)C(=O)O)c1c(F)cccc1F
Isomeric 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)
InChI Key HHFBDROWDBDFBR-UHFFFAOYSA-N
References
1. Aliagas-Martin I, Burdick D, Corson L, Dotson J, Drummond J, Fields C, Huang OW, Hunsaker T, Kleinheinz T, Krueger E et al.. (2009)
A class of 2,4-bisanilinopyrimidine Aurora A inhibitors with unusually high selectivity against Aurora B.
J Med Chem, 52 (10): 3300-7. [PMID:19402633]
2. Davis MI, Hunt JP, Herrgard S, Ciceri P, Wodicka LM, Pallares G, Hocker M, Treiber DK, Zarrinkar PP. (2011)
Comprehensive analysis of kinase inhibitor selectivity.
Nat Biotechnol, 29 (11): 1046-51. [PMID:22037378]
3. Manfredi MG, Ecsedy JA, Meetze KA, Balani SK, Burenkova O, Chen W, Galvin KM, Hoar KM, Huck JJ, LeRoy PJ et al.. (2007)
Antitumor activity of MLN8054, an orally active small-molecule inhibitor of Aurora A kinase.
Proc Natl Acad Sci USA, 104 (10): 4106-11. [PMID:17360485]
4. Willemsen-Seegers N, Uitdehaag JCM, Prinsen MBW, de Vetter JRF, de Man J, Sawa M, Kawase Y, Buijsman RC, Zaman GJR. (2017)
Compound Selectivity and Target Residence Time of Kinase Inhibitors Studied with Surface Plasmon Resonance.
J Mol Biol, 429 (4): 574-586. [PMID:28043854]
5. Wodicka LM, Ciceri P, Davis MI, Hunt JP, Floyd M, Salerno S, Hua XH, Ford JM, Armstrong RC, Zarrinkar PP et al.. (2010)
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.
Chem Biol, 17 (11): 1241-9. [PMID:21095574]