peptide 22d   Click here for help

GtoPdb Ligand ID: 12063

Compound class: Synthetic organic
Comment: This is a macrocyclic peptide that targets the STUB1 E3 ubiquitin ligase [1]. 22d was developed from a short linear peptide (LWWPD) that binds STUB1 [2], to guide the design of more selective pharmacological inhibitors as tool compounds for target validation. Although 22d retains the binding affinity for STUB1 of the linear peptide, suboptimal cellular permeability means that this construct is not suitable for experiments in cells or in vivo.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 18
Hydrogen bond donors 9
Rotatable bonds 13
Topological polar surface area 333.91
Molecular weight 930.42
XLogP 3.54
No. Lipinski's rules broken 3
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Canonical SMILES CC[C@@H]([C@@H]1NC(=O)[C@H](CO)NC(=O)CCCOc2ccccc2CCSC[C@H](NC(=O)[C@@H](NC1=O)Cc1c[nH]c2c1cccc2)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N)Cc1nnn[nH]1)C
Isomeric SMILES OC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2[C@H](C(=O)N[C@@H](Cc3nnn[nH]3)C(=O)N)CCC2)CSCCc2ccccc2OCCCC(=O)N1)Cc1c[nH]c2c1cccc2)[C@@H](C)CC
InChI InChI=1S/C44H58N12O9S/c1-3-25(2)38-43(63)49-31(20-27-22-46-29-12-6-5-11-28(27)29)40(60)50-33(44(64)56-17-8-13-34(56)42(62)48-30(39(45)59)21-36-52-54-55-53-36)24-66-19-16-26-10-4-7-14-35(26)65-18-9-15-37(58)47-32(23-57)41(61)51-38/h4-7,10-12,14,22,25,30-34,38,46,57H,3,8-9,13,15-21,23-24H2,1-2H3,(H2,45,59)(H,47,58)(H,48,62)(H,49,63)(H,50,60)(H,51,61)(H,52,53,54,55)/t25-,30-,31-,32-,33-,34-,38-/m0/s1