CHEBI:39900 - N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide

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ChEBI Name N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide
ChEBI ID CHEBI:39900
ChEBI ASCII Name N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide
Definition A tripeptide resulting from the formal condensation of the carboxy group of N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valine with the amino group of benzyl (2E,4S)-4-(L-leucylamino)-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate. It is an inhibitor of the main protease of SARS-CoV-2.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kalpana P
Secondary ChEBI IDs CHEBI:147376
Supplier Information
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Formula C35H48N6O8
Net Charge 0
Average Mass 680.803
Monoisotopic Mass 680.35336
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
InChIKey IDBWWEGDLCFCTD-VNEMRZQUSA-N
SMILES C([C@H](CC(C)C)NC([C@@H](NC(=O)[C@@H](NC(=O)C1=NOC(=C1)C)C)C(C)C)=O)(=O)N[C@H](/C=C/C(OCC2=CC=CC=C2)=O)C[C@H]3C(NCC3)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of SARS coronavirus main proteinase (EC 3.4.22.69).
(via N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide )
anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
(via N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide )
antiviral agent
A substance that destroys or inhibits replication of viruses.
(via N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:39900) has role anticoronaviral agent (CHEBI:149553)
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:39900) has role antiviral agent (CHEBI:22587)
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:39900) has role EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor (CHEBI:147285)
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:39900) is a benzyl ester (CHEBI:90628)
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:39900) is a isoxazoles (CHEBI:55373)
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:39900) is a pyrrolidin-2-ones (CHEBI:74223)
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:39900) is a tripeptide (CHEBI:47923)
IUPAC Name
N-[(5-methyl-1,2-oxazol-3-yl)carbonyl]-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide
Synonyms Sources
Inhibitor N3 ChEBI
N-(5-methyl-1,2-oxazole-3-carbonyl)-L-alanyl-L-valyl-N-{(2S,3E)-5-(benzyloxy)-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide IUPAC
Manual Xrefs Databases
3IH PDBeChem
4883311 ChemSpider
DB04595 DrugBank
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Citations Waiting for Citations Types Sources
16128623 PubMed citation Europe PMC
18094151 PubMed citation Europe PMC
Last Modified
06 April 2021