CHEBI:149679 - N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide

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ChEBI Name N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide
ChEBI ID CHEBI:149679
ChEBI ASCII Name N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide
Definition A tripeptide that is L-seryl-L-valyl-L-leucine in which the amino group at the N-terminal is substituted by a tert-butoxycarbonyl group and the carboxy group at the C-terminal is substituted by a {(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}amino group. It is a 3C-like protease inhibitor of MERS-CoV and SARS-CoV.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Supplier Information
Download Molfile XML SDF
Formula C30H51N5O9
Net Charge 0
Average Mass 625.764
Monoisotopic Mass 625.36868
InChI InChI=1S/C30H51N5O9/c1-9-43-23(37)11-10-20(15-19-12-13-31-25(19)38)32-26(39)21(14-17(2)3)33-28(41)24(18(4)5)35-27(40)22(16-36)34-29(42)44-30(6,7)8/h10-11,17-22,24,36H,9,12-16H2,1-8H3,(H,31,38)(H,32,39)(H,33,41)(H,34,42)(H,35,40)/b11-10+/t19-,20+,21-,22-,24-/m0/s1
InChIKey JQGRQEJSWFZWOD-IDAOPYDCSA-N
SMILES O(C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](/C=C/C(=O)OCC)C[C@H]1C(NCC1)=O)=O)CC(C)C)=O)C(C)C)=O)CO)=O)C(C)(C)C
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): anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
(via N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide )
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-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:149679) has role anticoronaviral agent (CHEBI:149553)
N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:149679) has role EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor (CHEBI:147285)
N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:149679) is a tert-butyl ester (CHEBI:140402)
N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:149679) is a enoate ester (CHEBI:51702)
N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:149679) is a ethyl ester (CHEBI:23990)
N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:149679) is a pyrrolidin-2-ones (CHEBI:74223)
N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:149679) is a secondary carboxamide (CHEBI:140325)
N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide (CHEBI:149679) is a tripeptide (CHEBI:47923)
IUPAC Name
N-(tert-butoxycarbonyl)-L-seryl-L-valyl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-leucinamide
Synonym Source
ethyl (6S,9S,12S,15S,16E)-6-(hydroxymethyl)-2,2-dimethyl-12-(2-methylpropyl)-4,7,10,13-tetraoxo-15-{[(3S)-2-oxopyrrolidin-3-yl]methyl}-9-(propan-2-yl)-3-oxa-5,8,11,14-tetraazaoctadec-16-en-18-oate IUPAC
Citations Waiting for Citations Types Sources
17855091 PubMed citation Europe PMC
26055715 PubMed citation SUBMITTER
Last Modified
12 May 2020