cenisertib   Click here for help

GtoPdb Ligand ID: 9927

Synonyms: AS-703569 | AS703569 [1] | compound 2 [PMID: 22695126] | compound 60a [WO2005118544A2] | enantiomer E1 [WO2005118544A2] | R-763 | R763
Compound class: Synthetic organic
Comment: Cenisertib is an Aurora kinase A/B inhibitor that was developed for anti-cancer potential [1]. We show the compound with chirality as specified by the IUPAC name submitted to the WHO for INN registration. It is compound 60a as claimed in patent WO2005118544A2 [3].
Cenisertib has improved aqueous solubility compared to the dual inhibitor ABT-348 (ilorasertib). Preclinical anti-proliferative efficacy of cenisertib has been demonstrated in a wide range of xenograft models [4] and cell lines [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 99.41
Molecular weight 451.25
XLogP 2.35
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN1CCN(CC1)c1ccc(cc1C)Nc1ncc(c(n1)NC1C2C=CC(C1C(=O)N)C2)F
Isomeric SMILES CN1CCN(CC1)c1ccc(cc1C)Nc1ncc(c(n1)N[C@@H]1[C@H]2C=C[C@@H]([C@@H]1C(=O)N)C2)F
InChI InChI=1S/C24H30FN7O/c1-14-11-17(5-6-19(14)32-9-7-31(2)8-10-32)28-24-27-13-18(25)23(30-24)29-21-16-4-3-15(12-16)20(21)22(26)33/h3-6,11,13,15-16,20-21H,7-10,12H2,1-2H3,(H2,26,33)(H2,27,28,29,30)/t15-,16+,20+,21-/m1/s1
InChI Key KSOVGRCOLZZTPF-QMKUDKLTSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(1S,2S,3R,4R)-3-[[5-fluoro-2-[3-methyl-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
9355 cenisertib
Synonyms Click here for help
AS-703569 | AS703569 [1] | compound 2 [PMID: 22695126] | compound 60a [WO2005118544A2] | enantiomer E1 [WO2005118544A2] | R-763 | R763
Database Links Click here for help
BindingDB Ligand 50389967
CAS Registry No. 871357-89-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL1614709
GtoPdb PubChem SID 363894221
PubChem CID 11569967
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