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.
In the Vinony graph
Within Vinony's link graph, fMet-Leu-Phe is referenced by 26 other articles, and connects out to molar mass, innate immune response and chemotaxis.
It sits within the topics Chembox image size set, Formamides and Tripeptides.
Its subject is documented across 5 Wikipedia language editions.
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.