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

ChEBI IDCHEBI:152561
ChEBI Name3-fluoro-Nα-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
Stars
ASCII Name3-fluoro-Nalpha-(1H-indol-2-ylcarbonyl)-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
DefinitionA 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).
Last Modified2 June 2020
SubmitterMargaret Duesbury
DownloadsMolfile
FormulaC25H25FN4O4
Net Charge0
Average Mass464.497
Monoisotopic Mass464.18598
SMILES[H]C(=O)[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@H](Cc1cccc(F)c1)NC(=O)c1cc2ccccc2n1
InChIInChI=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
InChIKeyHCRBVFBQANEDDM-CUWPLCDZSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
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).
ChEBI Ontology
Outgoing Relation(s)
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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