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
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18
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Hydrogen bond donors
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9
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Rotatable bonds
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13
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Topological polar surface area
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333.91
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Molecular weight
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930.42
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XLogP
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3.54
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No. Lipinski's rules broken
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3
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Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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SMILES / InChI / InChIKey
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Canonical SMILES
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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
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Isomeric SMILES
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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
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InChI
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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
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InChI Key
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CPNJMMBLVDNJTP-GQUKTMJCSA-N
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Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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