compound 11r [PMID: 32045235]   

GtoPdb Ligand ID: 10705

Synonyms: Cinnamoyl-cyclopropylalanine-GlnLactam-CO-CO-NH-benzyl
Compound class: Synthetic organic
Comment: Compound 11r is a peptidomimetic α-ketoamide that was designed for antiviral activity against corona- and enteroviruses [2]. This study was posted to the BioRxiv preprint server [1] prior to certification by peer review and publication in J. Med. Chem. The proteases that are essential for viral polyprotein processing by the corona- and enteroviruses exhibit a strong preference for substrates containing Gln at P1 position, and share an active-site conformation that engages the substrate's P1 residue. Compound 11r targets this unique P1-binding position within the active-sites of the main coronavirus protease and the enterovirus 3C protease.
A crystal structure of 11r bound to the human SARS-CoV main protease has been submitted to the RSCB Protein Data Bank with accession ID 5N5O. UniProt P0C6X7 provides details of SARS-CoV proteins.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 16
Topological polar surface area 133.47
Molecular weight 572.3
XLogP 4.54
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C(N[C@H](C(=O)N[C@H](C(=O)C(=O)NCc1ccccc1)C[C@@H]1CCNC1=O)CC1CCCCC1)/C=C/c1ccccc1
Isomeric SMILES O=C(N[C@H](C(=O)N[C@H](C(=O)C(=O)NCc1ccccc1)C[C@@H]1CCNC1=O)CC1CCCCC1)/C=C/c1ccccc1
InChI InChI=1S/C33H40N4O5/c38-29(17-16-23-10-4-1-5-11-23)36-28(20-24-12-6-2-7-13-24)32(41)37-27(21-26-18-19-34-31(26)40)30(39)33(42)35-22-25-14-8-3-9-15-25/h1,3-5,8-11,14-17,24,26-28H,2,6-7,12-13,18-22H2,(H,34,40)(H,35,42)(H,36,38)(H,37,41)/b17-16+/t26-,27-,28-/m0/s1
InChI Key QTGORSKTHIBLJT-FIVJMQNTSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(S)-N-Benzyl-3-((S)-2-cinnamamido-3-cyclohexylpropanamido)-2-oxo-4-((S)-2-oxopyrrolidin-3-yl)butanamide
Synonyms
Cinnamoyl-cyclopropylalanine-GlnLactam-CO-CO-NH-benzyl
Database Links
GtoPdb PubChem SID 404859152
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