Structure via PubChem · Public domain (PubChem)
fMet-Leu-Phe
Sign in to saveAlso known as fMetLeuPhe, fMLP, formyl-Met-Leu-Phe, N-Formyl-methionyl-leucyl-phenylalanine, F-Met-leu-phe, N-Formylmethionine leucyl-phenylalanine, N-Formyl-Met-Leu-Phe, fMLF
'''N-Formylmethionyl-leucyl-phenylalanine (fMLF, fMLP or N-formyl-met-leu-phe') is an N''-formylated tripeptide and sometimes simply referred to as chemotactic peptide is a potent polymorphonuclear leukocyte (PMN) chemotactic factor and is also a macrophage activator.
Chemical data
- Formula
- C21H31N3O5S
- Molecular weight
- 437.6 g/mol
- IUPAC name
- (2S)-2-[[(2S)-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoic acid
- SMILES
- CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)NC(=O)[C@H](CCSC)NC=O
- InChIKey
- PRQROPMIIGLWRP-BZSNNMDCSA-N
- XLogP
- 1.5
- Polar surface area
- 150 Ų
- H-bond donors
- 4
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
6,969 papers- Dynamics of human neutrophil receptors for the chemoattractant fmet-leu-phe.Agents and actions. Supplements · 1983
- Characterization of fMet-Leu-Phe-stimulated phospholipase C in streptolysin-O-permeabilised cells.European journal of biochemistry · 1991
- Characterization of fMet-Leu-Phe receptor-mediated Ca2+ influx across the plasma membrane of human neutrophils.Molecular pharmacology · 1986
- Pertussis toxin inhibits fMet-Leu-Phe- but not phorbol ester-stimulated changes in rabbit neutrophils: role of G proteins in excitation response coupling.Proceedings of the National Academy of Sciences of the United States of America · 1985
- Cell surface expression of fMet-Leu-Phe receptors on human neutrophils. Correlation to changes in the cytosolic free Ca2+ level and action of phorbol myristate acetate.The Journal of clinical investigation · 1987
via PubMed
Wikidata facts
- Mass
- 437.198442
Show 4 more facts
- chemical formula
- C₂₁H₃₁N₃O₅S
- Commons category
- N-Formylmethionyl-leucyl-phenylalanine
- canonical SMILES
- CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)O)NC(=O)C(CCSC)NC=O
- isomeric SMILES
- CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)NC(=O)[C@H](CCSC)NC=O
via Wikidata · CC0
~6 min read
Encyclopedic overview
4 sectionsContents
- Discovery
- Receptors
- References
- External links
{{chembox | verifiedrevid = 428867069 | Name = N-Formylmethionine leucyl-phenylalanine | ImageFile = Chemotactic peptide.png | ImageSize = 200px | SystematicName = (2S)-2-{(2S)-2-[(2S)-2-Formamido-4-(methylsulfanyl)butanamido]-4-methylpentanamido}-3-phenylpropanoic acid | OtherNames = Chemotactic peptideF-Met-Leu-PheL-Phenylalanine, N-(N-(N-formyl-L-methionyl)-L-leucyl)- fMLP | Section1 = | Section2 = | Section3 = | Section4 = | Section5 = | Section6 = }}
'''N-Formylmethionyl-leucyl-phenylalanine (fMLF, fMLP or N-formyl-met-leu-phe') is an N-formylated tripeptide and sometimes simply referred to as chemotactic peptide is a potent polymorphonuclear leukocyte (PMN) chemotactic factor and is also a macrophage activator.
Excerpted from Wikipedia’s “fMet-Leu-Phe” article, available under the CC BY-SA 4.0 licence.