CHEBI:152561 - 3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide

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ChEBI Name 3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
ChEBI ID CHEBI:152561
ChEBI ASCII Name 3-fluoro-Nalpha-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
Definition A secondary carboxamide resulting from the formal condensation of the carboxy group of 1H-indole-2-carboxylic acid with the primary amino group of 3-fluoro-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide. It is an inhibitor of SARS coronavirus main proteinase and inhibits SARS-CoV-2 replication in cell culture (EC50 = 0.72 μM).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
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Formula C25H25FN4O4
Net Charge 0
Average Mass 464.497
Monoisotopic Mass 464.18598
InChI InChI=1S/C25H25FN4O4/c26-18-6-3-4-15(10-18)11-21(24(33)28-19(14-31)12-17-8-9-27-23(17)32)30-25(34)22-13-16-5-1-2-7-20(16)29-22/h1-7,10,13-14,17,19,21,29H,8-9,11-12H2,(H,27,32)(H,28,33)(H,30,34)/t17-,19-,21-/m0/s1
InChIKey HCRBVFBQANEDDM-CUWPLCDZSA-N
SMILES C12=CC=CC=C1NC(=C2)C(=O)N[C@@H](CC=3C=CC=C(C3)F)C(N[C@H](C(=O)[H])C[C@H]4C(NCC4)=O)=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 3-fluoro-Nalpha-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide )
anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
(via 3-fluoro-Nalpha-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide (CHEBI:152561) has role anticoronaviral agent (CHEBI:149553)
3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide (CHEBI:152561) has role EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor (CHEBI:147285)
3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide (CHEBI:152561) is a aldehyde (CHEBI:17478)
3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide (CHEBI:152561) is a indolecarboxamide (CHEBI:46921)
3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide (CHEBI:152561) is a monofluorobenzenes (CHEBI:83575)
3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide (CHEBI:152561) is a oligopeptide (CHEBI:25676)
3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide (CHEBI:152561) is a pyrrolidin-2-ones (CHEBI:74223)
3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide (CHEBI:152561) is a secondary carboxamide (CHEBI:140325)
IUPAC Name
3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
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Citation Waiting for Citations Type Source
32321856 PubMed citation SUBMITTER
Last Modified
02 June 2020
General Comment
2020-06-02 Entry is for compound 11b in PMID:32321856