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

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ChEBI Name N-formyl-L-methionyl-L-leucyl-L-phenylalanine ChEBI ID CHEBI:53490 ChEBI ASCII Name N-formyl-L-methionyl-L-leucyl-L-phenylalanine Definition A 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. Stars This entity has been manually annotated by the ChEBI Team. Submitter Steve Jupe Supplier Information Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Read full article at Wikipedia Formula C21H31N3O5S Net Charge 0 Average Mass 437.55300 Monoisotopic Mass 437.19844 InChI InChI=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 InChIKey PRQROPMIIGLWRP-BZSNNMDCSA-N 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 Roles Classification Chemical Role(s): Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) View more via ChEBI Ontology ChEBI Ontology Outgoing 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 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 Sources F-Met-Leu-Phe ChemIDplus fMetLeuPhe SUBMITTER fMLF SUBMITTER fMLP SUBMITTER N-formyl-L-Met-L-Leu-L-Phe ChEBI N-formyl-L-methionyl-L-leucyl-L-phenylalanine KEGG COMPOUND N-formyl-Met-Leu-Phe SUBMITTER N-formyl-Met-Leu-Phe-OH ChEBI N-formyl-methionyl-leucyl-phenylalanine ChemIDplus N-formylmethionine leucyl-phenylalanine ChemIDplus Manual Xrefs Databases C11596 KEGG COMPOUND N-Formylmethionine-leucyl-phenylalanine Wikipedia View more database links Registry Numbers Types Sources 2315783 Beilstein Registry Number Beilstein 59880-97-6 CAS Registry Number KEGG COMPOUND 59880-97-6 CAS Registry Number ChemIDplus 8023425 Beilstein Registry Number Beilstein Citations Types Sources 16236365 PubMed citation Europe PMC 17907740 PubMed citation Europe PMC 18092743 PubMed citation Europe PMC 19067145 PubMed citation Europe PMC 19069235 PubMed citation Europe PMC 21126546 PubMed citation Europe PMC 21372136 PubMed citation Europe PMC 22484311 PubMed citation Europe PMC 23002436 PubMed citation Europe PMC 23109426 PubMed citation Europe PMC 23259992 PubMed citation Europe PMC 28711992 PubMed citation Europe PMC 29176405 PubMed citation Europe PMC 31033193 PubMed citation Europe PMC 34435345 PubMed citation Europe PMC 34572316 PubMed citation Europe PMC 35058789 PubMed citation Europe PMC Last Modified 06 February 2023