DD-03-171   Click here for help

GtoPdb Ligand ID: 10535

Compound class: Synthetic organic
Comment: DD-03-171 is a cereblon (CRBN)-engaging degrader (or PROTAC; proteolysis targeting chimera) of BTK protein [1]. The BTK inhibitor portion of DD-03-171 is derived from CGI1746, and this is conjugated to thalidomide using a saturated hydrocarbon linker to create the hybrid molecule. DD-03-171 produces potent antiproliferative effects on lymphoma cells in vitro and on patient-derived xenografts in vivo. It is suggested that DD-03-171's mechanism of action may be able to overcome tumour resistance to ibrutinib therapy.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 5
Rotatable bonds 21
Topological polar surface area 224.25
Molecular weight 990.48
XLogP 7.17
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES O=C(CNc1cccc2c1C(=O)N(C2=O)C1CCC(=O)NC1=O)NCCCCCCN1CCN(CC1)C(=O)c1ccc(cc1)Nc1nc(cn(c1=O)C)c1cccc(c1C)NC(=O)c1ccc(cc1)C(C)(C)C
Isomeric SMILES O=C(CNc1cccc2c1C(=O)N(C2=O)C1CCC(=O)NC1=O)NCCCCCCN1CCN(CC1)C(=O)c1ccc(cc1)Nc1nc(cn(c1=O)C)c1cccc(c1C)NC(=O)c1ccc(cc1)C(C)(C)C
InChI InChI=1S/C55H62N10O8/c1-34-39(12-10-14-41(34)60-49(68)35-16-20-37(21-17-35)55(2,3)4)43-33-62(5)54(73)48(59-43)58-38-22-18-36(19-23-38)51(70)64-30-28-63(29-31-64)27-9-7-6-8-26-56-46(67)32-57-42-15-11-13-40-47(42)53(72)65(52(40)71)44-24-25-45(66)61-50(44)69/h10-23,33,44,57H,6-9,24-32H2,1-5H3,(H,56,67)(H,58,59)(H,60,68)(H,61,66,69)
InChI Key QBPVFCNYKUENHU-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
IUPAC Name Click here for help
4-tert-butyl-N-[3-[6-[4-[4-[6-[[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]acetyl]amino]hexyl]piperazine-1-carbonyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]benzamide
Database Links Click here for help
GtoPdb PubChem SID 387065617
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