CHEBI:147346 - SG85

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ChEBI Name SG85
ChEBI ID CHEBI:147346
Definition A secondary carboxamide resulting from the formal condensation of the carboxy group of N-[(benzyloxy)carbonyl]-O-tert-butyl-L-serine with the primary amino group of ethyl (2E,4S)-5-[(3S)-2-oxopyrrolidin-3-yl]-4-(L-phenylalanylamino)pent-2-enoate. It is a potent enterovirus 3C protease inhibitor with EC50 of 180 nM against enterovirus 71 (EV71) and 60 nM against human rhinovirus 14 in a live virus-cell-based assay.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Yingtong Liu
Supplier Information
Download Molfile XML SDF
Formula C35H46N4O8
Net Charge 0
Average Mass 650.773
Monoisotopic Mass 650.33156
InChI InChI=1S/C35H46N4O8/c1-5-45-30(40)17-16-27(21-26-18-19-36-31(26)41)37-32(42)28(20-24-12-8-6-9-13-24)38-33(43)29(23-47-35(2,3)4)39-34(44)46-22-25-14-10-7-11-15-25/h6-17,26-29H,5,18-23H2,1-4H3,(H,36,41)(H,37,42)(H,38,43)(H,39,44)/b17-16+/t26-,27+,28-,29-/m0/s1
InChIKey CTAXDRJNQQBEIB-VCJIVHKYSA-N
SMILES C=1C(=CC=CC1)COC(N[C@H](C(N[C@H](C(N[C@H](/C=C/C(OCC)=O)C[C@H]2C(NCC2)=O)=O)CC=3C=CC=CC3)=O)COC(C)(C)C)=O
Roles Classification
Biological Role(s): antiviral agent
A substance that destroys or inhibits replication of viruses.
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).
anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing SG85 (CHEBI:147346) has role anticoronaviral agent (CHEBI:149553)
SG85 (CHEBI:147346) has role antiviral agent (CHEBI:22587)
SG85 (CHEBI:147346) has role EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor (CHEBI:147285)
SG85 (CHEBI:147346) is a L-phenylalanine derivative (CHEBI:84144)
SG85 (CHEBI:147346) is a L-serine derivative (CHEBI:84135)
SG85 (CHEBI:147346) is a benzyl ester (CHEBI:90628)
SG85 (CHEBI:147346) is a enoate ester (CHEBI:51702)
SG85 (CHEBI:147346) is a ether (CHEBI:25698)
SG85 (CHEBI:147346) is a ethyl ester (CHEBI:23990)
SG85 (CHEBI:147346) is a pyrrolidin-2-ones (CHEBI:74223)
SG85 (CHEBI:147346) is a secondary carboxamide (CHEBI:140325)
IUPAC Name
N-[(benzyloxy)carbonyl]-O-tert-butyl-L-seryl-N-{(2S,3E)-5-ethoxy-5-oxo-1-[(3S)-2-oxopyrrolidin-3-yl]pent-3-en-2-yl}-L-phenylalaninamide
Synonyms Sources
SG 85 ChEBI
SG-85 ChEBI
Registry Number Type Source
1575662-24-6 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
23388726 PubMed citation Europe PMC
25039866 PubMed citation Europe PMC
25199773 PubMed citation Europe PMC
26055377 PubMed citation Europe PMC
27668727 PubMed citation Europe PMC
Last Modified
23 April 2020