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CHEBI:157651 - Glu-Gly-Arg-chloromethylketone

ChEBI IDCHEBI:157651
ChEBI NameGlu-Gly-Arg-chloromethylketone
Stars
DefinitionA 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.
Last Modified11 April 2024
SubmitterMargaret Duesbury
DownloadsMolfile
FormulaC14H25ClN6O5
Net Charge0
Average Mass392.844
Monoisotopic Mass392.15750
SMILESN=C(N)NCCC[C@H](NC(=O)CNC(=O)[C@@H](N)CCC(=O)O)C(=O)CCl
InChIInChI=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
InChIKeyLLKJHSDOKTVQNQ-IUCAKERBSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
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).
ChEBI Ontology
Outgoing Relation(s)
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  Source
H-Glu-Gly-Arg-chloromethylketoneChEBI
Glu-Gly-Arg-chloromethylketoneChEBI
EGRCKChEBI
L-Glu-Gly-L-Arg-chloromethylketoneChEBI
glutamyl-glycyl-arginine chloromethyl ketoneChemIDplus
EGR-CMKChEBI
Registry NumbersSources
CAS:65113-67-9ChemIDplus
Citations