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MDL-28170   Click here for help

GtoPdb Ligand ID: 10745

Synonyms: calpain inhibitor III | MDL28170 | N-benzyloxycarbonyl-L-valyl-L-phenylalaninal | N-CBZ-Val-Phe-al
Compound class: Synthetic organic
Comment: MDL-28170 is a calpain and cathepsin B inhibitor [1]. It impairs infection by SARS-CoV and Ebola virus (EBOV). MDL-28170 has some antiviral activity against SARS-CoV-2, and antagonises viral replication in human iPSC-derived pneumocyte-like cells [2].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 84.5
Molecular weight 382.19
XLogP 3.71
No. Lipinski's rules broken 0

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/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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Canonical SMILES O=C[C@@H](NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1)Cc1ccccc1
Isomeric SMILES O=C[C@@H](NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1)Cc1ccccc1
InChI InChI=1S/C22H26N2O4/c1-16(2)20(24-22(27)28-15-18-11-7-4-8-12-18)21(26)23-19(14-25)13-17-9-5-3-6-10-17/h3-12,14,16,19-20H,13,15H2,1-2H3,(H,23,26)(H,24,27)/t19-,20-/m0/s1
InChI Key NGBKFLTYGSREKK-PMACEKPBSA-N

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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
benzyl N-[(2S)-3-methyl-1-oxo-1-[[(2S)-1-oxo-3-phenylpropan-2-yl]amino]butan-2-yl]carbamate
Synonyms Click here for help
calpain inhibitor III | MDL28170 | N-benzyloxycarbonyl-L-valyl-L-phenylalaninal | N-CBZ-Val-Phe-al
Database Links Click here for help
CAS Registry No. 88191-84-8 (source: PubChem)
GtoPdb PubChem SID 405560188
PubChem CID 72430
Search Google for chemical match using the InChIKey NGBKFLTYGSREKK-PMACEKPBSA-N
Search Google for chemicals with the same backbone NGBKFLTYGSREKK
UniChem Compound Search for chemical match using the InChIKey NGBKFLTYGSREKK-PMACEKPBSA-N
UniChem Connectivity Search for chemical match using the InChIKey NGBKFLTYGSREKK-PMACEKPBSA-N