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fMet-Leu-Phe   Click here for help

GtoPdb Ligand ID: 1022

Abbreviated name: fMLP
Synonyms: fMetLeuPhe | fMLF | formyl-Met-Leu-Phe
Compound class: Peptide
Comment: From the bacterium E.coli
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

fMet-Leu-Phe is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CSCCC(C(=O)NC(C(=O)NC(C(=O)O)Cc1ccccc1)CC(C)C)NC=O
Isomeric SMILES CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1ccccc1)CC(C)C)NC=O
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
InChI Key PRQROPMIIGLWRP-BZSNNMDCSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Buyse M, Charrier L, Sitaraman S, Gewirtz A, Merlin D. (2003)
Interferon-gamma increases hPepT1-mediated uptake of di-tripeptides including the bacterial tripeptide fMLP in polarized intestinal epithelia.
Am J Pathol, 163 (5): 1969-77. [PMID:14578196]
2. Charrier L, Driss A, Yan Y, Nduati V, Klapproth JM, Sitaraman SV, Merlin D. (2006)
hPepT1 mediates bacterial tripeptide fMLP uptake in human monocytes.
Lab Invest, 86 (5): 490-503. [PMID:16568107]
3. Freer RJ, Day AR, Radding JA, Schiffmann E, Aswanikumar S, Showell HJ, Becker EL. (1980)
Further studies on the structural requirements for synthetic peptide chemoattractants.
Biochemistry, 19 (11): 2404-10. [PMID:7387981]
4. Hartt JK, Barish G, Murphy PM, Gao JL. (1999)
N-formylpeptides induce two distinct concentration optima for mouse neutrophil chemotaxis by differential interaction with two N-formylpeptide receptor (FPR) subtypes. Molecular characterization of FPR2, a second mouse neutrophil FPR.
J Exp Med, 190 (5): 741-7. [PMID:10477558]
5. He HQ, Ye RD. (2017)
The Formyl Peptide Receptors: Diversity of Ligands and Mechanism for Recognition.
Molecules, 22 (3). [PMID:28335409]
6. Merlin D, Si-Tahar M, Sitaraman SV, Eastburn K, Williams I, Liu X, Hediger MA, Madara JL. (2001)
Colonic epithelial hPepT1 expression occurs in inflammatory bowel disease: transport of bacterial peptides influences expression of MHC class 1 molecules.
Gastroenterology, 120 (7): 1666-79. [PMID:11375948]
7. Merlin D, Steel A, Gewirtz AT, Si-Tahar M, Hediger MA, Madara JL. (1998)
hPepT1-mediated epithelial transport of bacteria-derived chemotactic peptides enhances neutrophil-epithelial interactions.
J Clin Invest, 102 (11): 2011-8. [PMID:9835627]
8. Quehenberger O, Prossnitz ER, Cavanagh SL, Cochrane CG, Ye RD. (1993)
Multiple domains of the N-formyl peptide receptor are required for high-affinity ligand binding. Construction and analysis of chimeric N-formyl peptide receptors.
J Biol Chem, 268 (24): 18167-75. [PMID:8349692]
9. Rabiet MJ, Huet E, Boulay F. (2005)
Human mitochondria-derived N-formylated peptides are novel agonists equally active on FPR and FPRL1, while Listeria monocytogenes-derived peptides preferentially activate FPR.
Eur J Immunol, 35 (8): 2486-95. [PMID:16025565]
10. Showell HJ, Freer RJ, Zigmond SH, Schiffmann E, Aswanikumar S, Corcoran B, Becker EL. (1976)
The structure-activity relations of synthetic peptides as chemotactic factors and inducers of lysosomal secretion for neutrophils.
J Exp Med, 143 (5): 1154-69. [PMID:1262785]
11. Sogawa Y, Ohyama T, Maeda H, Hirahara K. (2011)
Formyl peptide receptor 1 and 2 dual agonist inhibits human neutrophil chemotaxis by the induction of chemoattractant receptor cross-desensitization.
J Pharmacol Sci, 115 (1): 63-8. [PMID:21173551]
12. Southgate EL, He RL, Gao JL, Murphy PM, Nanamori M, Ye RD. (2008)
Identification of formyl peptides from Listeria monocytogenes and Staphylococcus aureus as potent chemoattractants for mouse neutrophils.
J Immunol, 181 (2): 1429-37. [PMID:18606697]
13. Wu SP, Smith DE. (2013)
Impact of intestinal PepT1 on the kinetics and dynamics of N-formyl-methionyl-leucyl-phenylalanine, a bacterially-produced chemotactic peptide.
Mol Pharm, 10 (2): 677-84. [PMID:23259992]
14. Ye RD, Boulay F, Wang JM, Dahlgren C, Gerard C, Parmentier M, Serhan CN, Murphy PM. (2009)
International Union of Basic and Clinical Pharmacology. LXXIII. Nomenclature for the formyl peptide receptor (FPR) family.
Pharmacol Rev, 61 (2): 119-61. [PMID:19498085]
15. Yi X, Tran E, Odiba JO, Qin CX, Ritchie RH, Baell JB. (2024)
The formyl peptide receptors FPR1 and FPR2 as targets for inflammatory disorders: recent advances in the development of small-molecule agonists.
Eur J Med Chem, 265: 115989. [PMID:38199163]