BIRD-PRD_000250: N-acetyl-L-valyl-O-benzyl-L-threonyl-N-[(1R,2R)-2-hydroxy-1-{[(3R...

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000250
• Status: Status: REF ONLY
• Name: N-acetyl-L-valyl-O-benzyl-L-threonyl-N-[(1R,2R)-2-hydroxy-1-{[(3R)-2-oxopyrrolidin-3-yl]methyl}propyl]-L-leucinamide

BIRD information

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

Synonyms

• Ac-VTbLQcmph (PDB)
• acetyl-valyl-(O-benzyloxy)threonyl-leucyl-ketomethyl(cycloglutamine)-phthalhydrazide (PDB)

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

Family

Ac-VTbLQcmph inhibitor

N-acetyl-L-valyl-O-benzyl-L-threonyl-N-[(1R,2R)-2-hydroxy-1-{[(3R)-2-oxopyrrolidin-3-yl]methyl}propyl]-L-leucinamide

Chemical information

Composition

Formula: C₃₂H₅₁N₅O₇ / Formula weight: 617.777

• 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)CC(C)C)C(OCc2ccccc2)C)C(C)C)C
• CACTVS 3.370: CC(C)C[CH](NC(=O)[CH](NC(=O)[CH](NC(C)=O)C(C)C)[CH](C)OCc1ccccc1)C(=O)N[CH](C[CH]2CCNC2=O)[CH](C)O
• OpenEye OEToolkits 1.7.6: CC(C)CC(C(=O)NC(CC1CCNC1=O)C(C)O)NC(=O)C(C(C)OCc2ccccc2)NC(=O)C(C(C)C)NC(=O)C

SMILES CANONICAL

• CACTVS 3.370: CC(C)C[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(C)=O)C(C)C)[C@@H](C)OCc1ccccc1)C(=O)N[C@@H](C[C@@H]2CCNC2=O)[C@@H](C)O
• OpenEye OEToolkits 1.7.6: C[C@H]([C@@H](C[C@H]1CCNC1=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)OCc2ccccc2)NC(=O)[C@H](C(C)C)NC(=O)C)O

InChI

• InChI 1.03: InChI=1S/C32H51N5O7/c1-18(2)15-26(30(41)35-25(20(5)38)16-24-13-14-33-29(24)40)36-32(43)28(21(6)44-17-23-11-9-8-10-12-23)37-31(42)27(19(3)4)34-22(7)39/h8-12,18-21,24-28,38H,13-17H2,1-7H3,(H,33,40)(H,34,39)(H,35,41)(H,36,43)(H,37,42)/t20-,21-,24-,25-,26+,27+,28-/m1/s1

InChIKey

• InChI 1.03: MLRKKMKXHXLXOU-WWNXGADFSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N-acetyl-L-valyl-O-benzyl-L-threonyl-N-{(2R,3R)-3-hydroxy-1-[(3R)-2-oxopyrrolidin-3-yl]butan-2-yl}-L-leucinamide
• OpenEye OEToolkits 1.7.6: (2S)-2-[[(2S,3R)-2-[[(2S)-2-acetamido-3-methyl-butanoyl]amino]-3-phenylmethoxy-butanoyl]amino]-4-methyl-N-[(2R,3R)-3-oxidanyl-1-[(3R)-2-oxidanylidenepyrrolidin-3-yl]butan-2-yl]pentanamide

PDB entries

Showing all 2 items

PDB-2z3c:
A Mechanistic view of Enzyme Inhibition and Peptide Hydrolysis in the Active Site of the SARS-CoV 3C-Like peptidase

PDB-2z3e:
A Mechanistic view of Enzyme Inhibition and Peptide Hydrolysis in the Active Site of the SARS-CoV 3C-Like peptidase