ERD-308   Click here for help

GtoPdb Ligand ID: 10565

Synonyms: compound 32 [PMID: 30990042] | ERD308
Compound class: Synthetic organic
Comment: ERD-308 is a small-molecule ERα degrader that was designed using the proteolysis targeting chimeras (PROTAC) model [1]. It is a hybrid molecule that links together an ERα antagonist (a derivative of raloxifene) and a VHL ligand that engages the VHL E3 ligase to direct ERα receptors for ubiquitination and proteasomal degradation.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 5
Rotatable bonds 26
Topological polar surface area 247.34
Molecular weight 1003.42
XLogP 7.84
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CCN(CCOc1ccc(cc1)C(=O)c1c(sc2c1ccc(c2)O)c1ccc(cc1)O)CCCCCOCC(=O)NC(C(C)(C)C)C(=O)N1CC(CC1C(=O)NC(c1ccc(cc1)c1scnc1C)C)O
Isomeric SMILES CCN(CCOc1ccc(cc1)C(=O)c1c(sc2c1ccc(c2)O)c1ccc(cc1)O)CCCCCOCC(=O)N[C@@H](C(C)(C)C)C(=O)N1C[C@@H](C[C@H]1C(=O)N[C@H](c1ccc(cc1)c1scnc1C)C)O
InChI InChI=1S/C55H65N5O9S2/c1-7-59(26-28-69-43-22-17-37(18-23-43)49(65)48-44-24-21-41(62)30-46(44)71-51(48)39-15-19-40(61)20-16-39)25-9-8-10-27-68-32-47(64)58-52(55(4,5)6)54(67)60-31-42(63)29-45(60)53(66)57-34(2)36-11-13-38(14-12-36)50-35(3)56-33-70-50/h11-24,30,33-34,42,45,52,61-63H,7-10,25-29,31-32H2,1-6H3,(H,57,66)(H,58,64)/t34-,42+,45-,52+/m0/s1
InChI Key BQXUPNKLZNSUMC-YUQWMIPFSA-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
(2S,4R)-1-[(2S)-2-[[2-[5-[ethyl-[2-[4-[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophene-3-carbonyl]phenoxy]ethyl]amino]pentoxy]acetyl]amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[(1S)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]ethyl]pyrrolidine-2-carboxamide
Synonyms Click here for help
compound 32 [PMID: 30990042] | ERD308
Database Links Click here for help
GtoPdb PubChem SID 404859012
PubChem CID 138454799
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