CHEBI:157651 - Glu-Gly-Arg-chloromethylketone

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ChEBI Name Glu-Gly-Arg-chloromethylketone
ChEBI ID CHEBI:157651
Definition A tripeptide composed of L-glutamic acid, glycine and L-arginine joined in sequence by peptide linkages and in which the carboxy terminus is substituted by a chloroacetyl group. It is a potent and irreversible inhibitor of urokinase-type plasminogen activator (uPA) and factor Xa.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Supplier Information
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Formula C14H25ClN6O5
Net Charge 0
Average Mass 392.840
Monoisotopic Mass 392.15750
InChI InChI=1S/C14H25ClN6O5/c15-6-10(22)9(2-1-5-19-14(17)18)21-11(23)7-20-13(26)8(16)3-4-12(24)25/h8-9H,1-7,16H2,(H,20,26)(H,21,23)(H,24,25)(H4,17,18,19)/t8-,9-/m0/s1
InChIKey LLKJHSDOKTVQNQ-IUCAKERBSA-N
SMILES N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)CCl
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 3.4.21.6 (coagulation factor Xa) inhibitor
An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of coagulation factor Xa (EC 3.4.21.6).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing Glu-Gly-Arg-chloromethylketone (CHEBI:157651) has functional parent L-arginine (CHEBI:16467)
Glu-Gly-Arg-chloromethylketone (CHEBI:157651) has functional parent L-glutamic acid (CHEBI:16015)
Glu-Gly-Arg-chloromethylketone (CHEBI:157651) has functional parent glycine (CHEBI:15428)
Glu-Gly-Arg-chloromethylketone (CHEBI:157651) has role EC 3.4.21.6 (coagulation factor Xa) inhibitor (CHEBI:68581)
Glu-Gly-Arg-chloromethylketone (CHEBI:157651) is a organochlorine compound (CHEBI:36683)
Glu-Gly-Arg-chloromethylketone (CHEBI:157651) is a tripeptide (CHEBI:47923)
IUPAC Name
L-α-glutamyl-N-[(3S)-6-carbamimidamido-1-chloro-2-oxohexan-3-yl]glycinamide
Synonyms Sources
chloromethylketone-EGR ChEBI
EGR-chloromethylketone ChEBI
EGR-CMK ChEBI
EGRCK ChEBI
Glu-Gly-Arg-chloromethylketone ChEBI
glutamyl-glycyl-arginine chloromethyl ketone ChemIDplus
H-Glu-Gly-Arg-CH2Cl ChEBI
H-Glu-Gly-Arg-chloromethylketone ChEBI
L-Glu-Gly-L-Arg-chloromethylketone ChEBI
Registry Number Type Source
65113-67-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10805774 PubMed citation Europe PMC
1310986 PubMed citation Europe PMC
17563121 PubMed citation Europe PMC
1828371 PubMed citation Europe PMC
18803401 PubMed citation Europe PMC
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21454081 PubMed citation Europe PMC
24900505 PubMed citation Europe PMC
29164060 PubMed citation Europe PMC
36780344 PubMed citation Europe PMC
7918392 PubMed citation Europe PMC
8900128 PubMed citation Europe PMC
Last Modified
11 April 2024