WWL0245   Click here for help

GtoPdb Ligand ID: 12142

Synonyms: BRD4-PROTAC 12a | WWL-0245
Compound class: Synthetic organic
Comment: WWL0245 is a bifunctional cereblon-based PROTAC molecule that promotes ubiquitin-proteasomal degradation of BRD4 protein [1]. The BET domain-binding region is based on the dual BET/PLK1 inhibitor WNY0824. Cereblon binding is mediated via a modified thalidomide moiety. WWL0245 exhibits selective cytotoxicity in BET inhibitor sensitive cancer cell lines such as androgen receptor (AR)-positive prostate cancer cell lines, and it promotes a more potent anti-proliferative effect than the parent BET inhibitor.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 16
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 222.66
Molecular weight 873.39
XLogP 6.63
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES COc1cc(ccc1Nc1ncc2c(n1)N(CC1CCCCC1)[C@@H](c1n2c(C)nn1)CC)C(=O)NC1CCN(CC1)C(=O)COc1cccc2c1C(=O)N(C2=O)C1CCC(=O)NC1=O
Isomeric SMILES C1(CCCCC1)CN1[C@@H](c2n(c3cnc(nc13)Nc1c(cc(C(=O)NC3CCN(CC3)C(=O)COc3c4C(=O)N(C(=O)c4ccc3)C3C(=O)NC(=O)CC3)cc1)OC)c(nn2)C)CC
InChI InChI=1S/C45H51N11O8/c1-4-31-40-52-51-25(2)55(40)33-22-46-45(50-39(33)54(31)23-26-9-6-5-7-10-26)48-30-14-13-27(21-35(30)63-3)41(59)47-28-17-19-53(20-18-28)37(58)24-64-34-12-8-11-29-38(34)44(62)56(43(29)61)32-15-16-36(57)49-42(32)60/h8,11-14,21-22,26,28,31-32H,4-7,9-10,15-20,23-24H2,1-3H3,(H,47,59)(H,46,48,50)(H,49,57,60)/t31-,32?/m1/s1
InChI Key AORZPRLVKUMTOJ-XGDNGBMYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
Synonyms Click here for help
BRD4-PROTAC 12a | WWL-0245
Database Links Click here for help
GtoPdb PubChem SID 472319264
Search Google for chemical match using the InChIKey AORZPRLVKUMTOJ-XGDNGBMYSA-N
Search Google for chemicals with the same backbone AORZPRLVKUMTOJ
UniChem Compound Search for chemical match using the InChIKey AORZPRLVKUMTOJ-XGDNGBMYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AORZPRLVKUMTOJ-XGDNGBMYSA-N