AK-2292   Click here for help

GtoPdb Ligand ID: 12409

Synonyms: AK2292
Compound class: Synthetic organic
Comment: AK-2292 is a PROTAC that mediates degradation of the STAT5A/B transcription factors [1]. It contains a STAT5-binding ligand (AK-305; PubChem CID 166594169) linked to lenalidomide moeity that mediates cereblon binding, and directs the STAT5 proteins for ubiquitination and proteosomal degradation. AK-2292 was designed to evaluate STAT5 degradation as a therapeutic strategy for haematologic malignancies such as acute myeloid leukemia (AML). The PROTAC selectively inhibits phosphorylation and transcriptional activity of STAT5 in vitro and in vivo.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 17
Hydrogen bond donors 4
Rotatable bonds 20
Topological polar surface area 286.81
Molecular weight 1070.13
XLogP 0.23
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CC(C)(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)N(CCC(=O)N(C)CCCC#CC2=CC=CC3=C2CN(C4CCC(=O)NC4=O)C3=O)C5=CC=C(C=C5)C6=NC=CS6)NC(=O)C7=CC8=C(C=CC(=C8)C(F)(F)P(=O)(O)O)S7
Isomeric SMILES O=C1NC(CCC1N2C(C3=CC=CC(=C3C2)C#CCCCN(C(CCN(C(=O)[C@H]4N(CCC4)C([C@H](C(C)(C)C)NC(=O)C5=CC6=C(S5)C=CC(=C6)C(F)(F)P(O)(O)=O)=O)C7=CC=C(C=C7)C=8SC=CN8)=O)C)=O)=O
InChI InChI=1S/C52H54F2N7O10PS2/c1-51(2,3)44(57-46(65)41-29-33-28-34(16-20-40(33)74-41)52(53,54)72(69,70)71)50(68)60-25-9-13-39(60)49(67)59(35-17-14-32(15-18-35)47-55-23-27-73-47)26-22-43(63)58(4)24-7-5-6-10-31-11-8-12-36-37(31)30-61(48(36)66)38-19-21-42(62)56-45(38)64/h8,11-12,14-18,20,23,27-29,38-39,44H,5,7,9,13,19,21-22,24-26,30H2,1-4H3,(H,57,65)(H,56,62,64)(H2,69,70,71)/t38?,39-,44+/m0/s1
InChI Key LOPYPDQOHNOVBM-QOIUHGAOSA-N
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InChI standard key Download

Molecular structure representations generated using Open Babel