PRD_002214   Click here for help

GtoPdb Ligand ID: 10716

Synonyms: inhibitor N3 | N-[(5-METHYLISOXAZOL-3-YL)CARBONYL]ALANYL-L-VALYL-N~1~-((1R,2Z)-4-(BENZYLOXY)-4-OXO-1-{[(3R)-2-OXOPYRROLIDIN-3-YL]METHYL}BUT-2-ENYL)-L-LEUCINAMIDE
Compound class: Synthetic organic
Comment: PRD_002214 is an irreversible peptide-like inhibitor of the main protease (MPRO) of SARS-CoV-2 [1]. The chemical structure was obtained from the RCSB Protein Data Bank entry 6LU7 which shows the ligand in complex with the protease. The article describing the work has not yet been published (March 12, 2020), but the inhibitor (also referred to as N3) has been deployed in other MPRO crystallisation studies [2]. The MPRO sequence is held in the NCBI record 'Chain A, SARS-CoV-2 main protease'.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 12
Hydrogen bond donors 5
Rotatable bonds 22
Topological polar surface area 197.83
Molecular weight 680.35
XLogP 3.31
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CC(C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)/C=C\C(=O)OCc1ccccc1)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)c1noc(c1)C)C)C
Isomeric SMILES CC(C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)/C=C\C(=O)OCc1ccccc1)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)c1noc(c1)C)C)C
InChI InChI=1S/C35H48N6O8/c1-20(2)16-27(39-35(47)30(21(3)4)40-31(43)23(6)37-34(46)28-17-22(5)49-41-28)33(45)38-26(18-25-14-15-36-32(25)44)12-13-29(42)48-19-24-10-8-7-9-11-24/h7-13,17,20-21,23,25-27,30H,14-16,18-19H2,1-6H3,(H,36,44)(H,37,46)(H,38,45)(H,39,47)(H,40,43)/b13-12-/t23-,25-,26+,27-,30-/m0/s1
InChI Key IDBWWEGDLCFCTD-NQJFWITJSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
benzyl (2Z,4S)-4-[(2S)-4-methyl-2-[(2S)-3-methyl-2-[(2S)-2-[(5-methyl-1,2-oxazol-3-yl)formamido]propanamido]butanamido]pentanamido]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate
Synonyms Click here for help
inhibitor N3 | N-[(5-METHYLISOXAZOL-3-YL)CARBONYL]ALANYL-L-VALYL-N~1~-((1R,2Z)-4-(BENZYLOXY)-4-OXO-1-{[(3R)-2-OXOPYRROLIDIN-3-YL]METHYL}BUT-2-ENYL)-L-LEUCINAMIDE
Database Links Click here for help
GtoPdb PubChem SID 405067310
PubChem CID 146025593
Search Google for chemical match using the InChIKey IDBWWEGDLCFCTD-NQJFWITJSA-N
Search Google for chemicals with the same backbone IDBWWEGDLCFCTD
Search UniChem for chemical match using the InChIKey IDBWWEGDLCFCTD-NQJFWITJSA-N
Search UniChem for chemicals with the same backbone IDBWWEGDLCFCTD