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CHEBI:53490 - N-formyl-L-methionyl-L-leucyl-L-phenylalanine

ChEBI IDCHEBI:53490
ChEBI NameN-formyl-L-methionyl-L-leucyl-L-phenylalanine
Stars
ASCII NameN-formyl-L-methionyl-L-leucyl-L-phenylalanine
DefinitionA tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.
Last Modified6 February 2023
Submittersjupe
DownloadsMolfile
FormulaC21H31N3O5S
Net Charge0
Average Mass437.562
Monoisotopic Mass437.19844
SMILES[H]C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)O
InChIInChI=1S/C21H31N3O5S/c1-14(2)11-17(23-19(26)16(22-13-25)9-10-30-3)20(27)24-18(21(28)29)12-15-7-5-4-6-8-15/h4-8,13-14,16-18H,9-12H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)(H,28,29)/t16-,17-,18-/m0/s1
InChIKeyPRQROPMIIGLWRP-BZSNNMDCSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
ChEBI Ontology
Outgoing Relation(s)
N-formyl-L-methionyl-L-leucyl-L-phenylalanine (CHEBI:53490) has functional parent N-formyl-L-methionine (CHEBI:16552)
N-formyl-L-methionyl-L-leucyl-L-phenylalanine (CHEBI:53490) has functional parent L-leucine (CHEBI:15603)
N-formyl-L-methionyl-L-leucyl-L-phenylalanine (CHEBI:53490) has functional parent L-phenylalanine (CHEBI:17295)
N-formyl-L-methionyl-L-leucyl-L-phenylalanine (CHEBI:53490) is a tripeptide (CHEBI:47923)
N-formyl-L-methionyl-L-leucyl-L-phenylalanine (CHEBI:53490) is conjugate acid of N-formyl-L-methionyl-L-leucyl-L-phenylalaninate (CHEBI:194314)
Incoming Relation(s)
N-formyl-L-methionyl-L-leucyl-L-phenylalaninate (CHEBI:194314) is conjugate base of N-formyl-L-methionyl-L-leucyl-L-phenylalanine (CHEBI:53490)
IUPAC Name 
N-formyl-L-methionyl-L-leucyl-L-phenylalanine
Synonyms  Source
fMetLeuPheSUBMITTER
fMLPSUBMITTER
fMLFSUBMITTER
N-formyl-Met-Leu-PheSUBMITTER
N-formylmethionine leucyl-phenylalanineChemIDplus
F-Met-Leu-PheChemIDplus
Manual XrefsDatabases
C11596KEGG COMPOUND
N-Formylmethionine-leucyl-phenylalanineWikipedia
Registry NumbersSources
Beilstein:2315783Beilstein
Beilstein:8023425Beilstein
CAS:59880-97-6KEGG COMPOUND
CAS:59880-97-6ChemIDplus
Citations