BIRD-PRD_000235: N-acetyl-L-leucyl-L-alanyl-N-[(1R,2R)-2-hydroxy-1-{[(3S)-2-oxopyr...

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000235
• Status: Status: REF ONLY
• Name: N-acetyl-L-leucyl-L-alanyl-N-[(1R,2R)-2-hydroxy-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl]-L-alaninamide

BIRD information

• Type: Peptide-like / Inhibitor
• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• Ac-LAAQcmph (PMID:17599357)
• acetyl-leucyl-alanyl-alanyl-ketomethyl(cycloglutamine)-phthalhydrazide (PMID:17599357)

Annotation

• Function: inhibitor of Replicase polyprotein 1ab (pp1ab), EC: 3.4.22.-,EC: inhibitor of Replicase polyprotein 1ab (pp1ab), EC: 3.4.22.-, / Info source: PubMed: 17599357
• Mechanism of action: form an unusual thiiranium ring with the nucleophilic sulfur atom of Cys145, trapping the enzyme's catalytic residues in configurations similar to the intermediate states / Info source: PubMed: 17599357

External info

• PubChem: 70698670

Family

Ac-LAAQcmph inhibitor

N-acetyl-L-leucyl-L-alanyl-N-[(1R,2R)-2-hydroxy-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl]-L-alaninamide

Chemical information

Composition

Formula: C₂₂H₃₉N₅O₆ / Formula weight: 469.575

• Others: Type: peptide-like

History

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C(NC(C(=O)NC(C(=O)NC(C(=O)NC(CC1C(=O)NCC1)C(O)C)C)C)CC(C)C)C
• CACTVS 3.370: CC(C)C[CH](NC(C)=O)C(=O)N[CH](C)C(=O)N[CH](C)C(=O)N[CH](C[CH]1CCNC1=O)[CH](C)O
• OpenEye OEToolkits 1.7.6: CC(C)CC(C(=O)NC(C)C(=O)NC(C)C(=O)NC(CC1CCNC1=O)C(C)O)NC(=O)C

SMILES CANONICAL

• CACTVS 3.370: CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C[C@@H]1CCNC1=O)[C@@H](C)O
• OpenEye OEToolkits 1.7.6: C[C@H]([C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)C)O

InChI

• InChI 1.03: InChI=1S/C22H39N5O6/c1-11(2)9-18(26-15(6)29)22(33)25-12(3)19(30)24-13(4)20(31)27-17(14(5)28)10-16-7-8-23-21(16)32/h11-14,16-18,28H,7-10H2,1-6H3,(H,23,32)(H,24,30)(H,25,33)(H,26,29)(H,27,31)/t12-,13+,14?,16+,17+,18+/m1/s1

InChIKey

• InChI 1.03: FAPGNOPTOGGBFK-BWEDKLARSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N-acetyl-L-leucyl-L-alanyl-N-{(2R,3R)-3-hydroxy-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl}-L-alaninamide
• OpenEye OEToolkits 1.7.6: (2S)-2-acetamido-4-methyl-N-[(2S)-1-oxidanylidene-1-[[(2S)-1-oxidanylidene-1-[[(2S,3R)-3-oxidanyl-1-[(3S)-2-oxidanylidenepyrrolidin-3-yl]butan-2-yl]amino]propan-2-yl]amino]propan-2-yl]pentanamide

PDB entries

Showing all 1 items

PDB-2z3d:
A Mechanistic view of Enzyme Inhibition and Peptide Hydrolysis in the Active Site of the SARS-CoV 3C-Like peptidase