N-Formyl-Met-Leu-Phe - Moligand™, ≥97% , Agonist of FPR1;Agonist of FPR2/ALX, CAS No.59880-97-6, Agonist of FPR1;Agonist of FPR2/ALX

CAS: 59880-97-6 Cat. No.: F113682 Peso molecular: 437.55 Beilstein Registry Number: 2315783

GRADE & PURITY Moligand™, ≥97%

Synonyms

fMLP | NSC-350593 | MLS002207097 | F30153 | fMLP; N-Formyl-MLF | N-Formyl-MLF | HY-P0224 | (S)-2-((S)-2-((S)-2-Formamido-4-(methylthio)butanamido)-4-methylpentanamido)-3-phenylpropanoicacid | (E)-methyl 4-hydroxycinnamate | fMLF | fMLP;N-Formyl-MLF | L-Ph

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

N-Formyl-Met-Leu-Phe has been used for:

· creating gradients in Zigmond chamber chemotaxis assay performed on neutrophils

· use in neutrophil chemotaix assayand

· determination of the involvement of MAPK-activating protein kinase-2 (MAPKAPK-2) and/or p38, in the signaling pathway of human polymorphonuclear leukocytes (PMNs) stimulated by N-Formyl-Met-Leu-Phe.

Specifications

Sinónimos

fMLP | NSC-350593 | MLS002207097 | F30153 | fMLP; N-Formyl-MLF | N-Formyl-MLF | HY-P0224 | (S)-2-((S)-2-((S)-2-Formamido-4-(methylthio)butanamido)-4-methylpentanamido)-3-phenylpropanoicacid | (E)-methyl 4-hydroxycinnamate | fMLF | fMLP;N-Formyl-MLF | L-Ph

Especificaciones y pureza

Moligand™, ≥97%

Mecanismos bioquímicos y fisiológicos

N-Formyl-Met-Leu-Phe induced chemotaxis in phosphoinositide 3-kinase γ (PI3K)γ-/- neutrophils, and promotes adhesion, polymerization of F-actin, Fcγ receptor-mediated phagocytosis and intracellular Ca2+ release. It acts as an inflammatory agent and activa

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

AGONIST

Mecanismo de acción

Agonist of FPR1;Agonist of FPR2/ALX

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one week. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥97%

Nombres e identificadores

• Pubchem Sid: 504758797
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758797
• Sonrisas canónicas: CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)O)NC(=O)C(CCSC)NC=O
• IUPAC Name: (2S)-2-[[(2S)-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoic acid
• InChIKey: PRQROPMIIGLWRP-BZSNNMDCSA-N
• 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
• Isómeros 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
• WGK Alemania: 3
• CAS alternativo: 59880-97-6
• Términos de entrada MeSH: F Met Leu Phe;F-Met-Leu-Phe;fMet Leu Phe;fMet-Leu-Phe;Formylmet Leu Phe;Formylmet-Leu-Phe;Formylmethionyl Leucyl Phenylalanine;Formylmethionyl Peptide;Formylmethionyl-Leucyl-Phenylalanine;Formylmethionylleucylphenylalanine;Leucyl-Phenylalanine, N-Formylme
• Peso molecular: 437.55
• Beilstein: 2315783
• Reaxy-Rn: 8397445
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8397445&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Oligopeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Oligopeptides
• Alternative Parents: Phenylalanine and derivatives Leucine and derivatives Methionine and derivatives N-acyl-L-alpha-amino acids Alpha amino acid amides N-formyl-alpha amino acids Phenylpropanoic acids Amphetamines and derivatives N-acyl amines Secondary carboxylic acid amides Sulfenyl compounds Carboxylic acids Dialkylthioethers Monocarboxylic acids and derivatives Carbonyl compounds Hydrocarbon derivatives Organonitrogen compounds Organic oxides Organopnictogen compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alpha-oligopeptide - Phenylalanine or derivatives - Leucine or derivatives - Methionine or derivatives - N-acyl-alpha-amino acid - N-acyl-l-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - N-formyl-alpha-amino acid - N-formyl-alpha amino acid or derivatives - 3-phenylpropanoic-acid - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - Monocyclic benzene moiety - Fatty amide - N-acyl-amine - Fatty acyl - Benzenoid - Secondary carboxylic acid amide - Carboxamide group - Thioether - Dialkylthioether - Sulfenyl compound - Carboxylic acid - Monocarboxylic acid or derivatives - Organonitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organooxygen compound - Organosulfur compound - Organic oxide - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
• External Descriptors: tripeptide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

FPR1 Tchem fMet-Leu-Phe receptor (5 Activities)

Discover Target: FPR1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FPR2 Tchem N-formyl peptide receptor 2 (0 Activities)

Discover Target: FPR2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)

Discover Target: ABL1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

Discover Target: AGTR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

Discover Target: GSK3B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CSNK1D Tchem Casein kinase I delta (4546 Activities)

Discover Target: CSNK1D

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC15A1 Tchem Oligopeptide transporter small intestine isoform (922 Activities)

Discover Target: SLC15A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

S1PR1 Tclin Sphingosine 1-phosphate receptor Edg-1 (5806 Activities)

Discover Target: S1PR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

Discover Target: CDK2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

Discover Target: GLP1R

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

C5AR1 Tclin C5a anaphylatoxin chemotactic receptor (2677 Activities)

Discover Target: C5AR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FPR1 Tchem Formyl peptide receptor 1 (1372 Activities)

Discover Target: FPR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)

Discover Target: AURKA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

U2OS (164939 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CX3CR1 Tchem C-X3-C chemokine receptor 1 (1686 Activities)

Discover Target: CX3CR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FPR2 Tchem Lipoxin A4 receptor (3472 Activities)

Discover Target: FPR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FFAR4 Tchem G-protein coupled receptor 120 (2999 Activities)

Discover Target: FFAR4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FPRL2 FML2_HUMAN (519 Activities)

Discover Target: FPRL2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)

Discover Target: BRD4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GPR35 Tchem G-protein coupled receptor 35 (2643 Activities)

Discover Target: GPR35

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TRIM24 Tchem Transcription intermediary factor 1-alpha (2087 Activities)

Discover Target: TRIM24

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BRPF1 Tchem Peregrin (2217 Activities)

Discover Target: BRPF1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK-293T (167025 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

ampC Beta-lactamase AmpC (62480 Activities)

Discover Target: ampC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Aplnr Apelin receptor (201 Activities)

Discover Target: Aplnr

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Fgfr3 Fibroblast growth factor receptor 3 (21 Activities)

Discover Target: Fgfr3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasmodium falciparum (966862 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Gpr119 Glucose-dependent insulinotropic receptor (270 Activities)

Discover Target: Gpr119

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TGR Thioredoxin glutathione reductase (28579 Activities)

Discover Target: TGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Fpr-s1 Formyl peptide receptor-related sequence 1 (29 Activities)

Discover Target: Fpr-s1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: heat sensitive；Moisture sensitive
• Rotación específica [α]: -8° (C=1,AcOH)
• Punto de fusión (°C): 213 °C
• Peso molecular: 437.600 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 437.198 Da
• Monoisotopic Mass: 437.198 Da
• Topological Polar Surface Area: 150.000 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 567.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Xueming Dang, Huimin Zhao.  (2019)  Bimetallic Fe/Mn metal-organic-frameworks and Au nanoparticles anchored carbon nanotubes as a peroxidase-like detection platform with increased active sites and enhanced electron transfer.  TALANTA,      [PMID:31987183] [10.1016/j.talanta.2019.120678]

2. Xiaoheng Qi, Huiming Tian, Xueming Dang, Yaofang Fan, Yaobin Zhang, Huimin Zhao.  (2019)  A bimetallic Co/Mn metal–organic-framework with a synergistic catalytic effect as peroxidase for the colorimetric detection of H2O2.  Analytical Methods,  11  (8): (1111-1124).  [PMID:] [10.1039/C8AY02514B]

3. Gen Liu, Cheng Ma, Bao-Kang Jin, Zixuan Chen, Jun-Jie Zhu.  (2018)  Direct Electrochemiluminescence Imaging of a Single Cell on a Chitosan Film Modified Electrode.  ANALYTICAL CHEMISTRY,      [PMID:29506381] [10.1021/acs.analchem.8b00194]

4. Yang Yufang, Shen Dongjun, Long Yijuan, Xie Zhixiong, Zheng Huzhi.  (2017)  Intrinsic Peroxidase-like Activity of Ficin.  Scientific Reports,  7  (1): (1-8).  [PMID:28224979] [10.1038/srep43141]

5. Yan Zhang, Tao Lin, Minghui Han, Min Hu, Yun Xu, Wei Huang, Fei Xiao, Anshun Zhao.  (2024)  A microelectrode electrochemical sensing platform based on heteroatoms doped carbon nanotubes arrays with peroxidase-like activity for in-situ detection in live cell.  ANALYTICA CHIMICA ACTA,      [PMID:38438231] [10.1016/j.aca.2024.342386]

6. Wenbin Wen, Yuan Dang, Jieli Tang, Changluo Su, Sha Yu, Junping Ma, Yuanzhen Zhou.  (2024)  A Novel MXene@MOF@Pt NPs-Based Enzyme-Free Electrochemical Sensor for highly Sensitive Detection of Hydrogen Peroxide Released from Living Cells.  JOURNAL OF THE ELECTROCHEMICAL SOCIETY,      [PMID:] [10.1149/1945-7111/ad4ba3]

7. Shuai-Qun Yu, Pan Li, Hao-Jie Li, Ling-Jun Shang, Rui Guo, Xu-Ming Sun, Qiong-Qiong Ren.  (2024)  Highly Sensitive Detection of Hydrogen Peroxide in Cancer Tissue Based on 3D Reduced Graphene Oxide–MXene–Multi-Walled Carbon Nanotubes Electrode.  Biosensors-Basel,  14  (6): (261).  [PMID:38920565] [10.3390/bios14060261]

8. Yuanyuan Lu, Yueying Dai, Yushi Qin, Xiaoru Jia, Xiaoya Li, Shuang Lu, Xinrong Liu, Yanzhi Song, Yihui Deng.  (2025)  An in vivo combined induction strategy of whole cancer cell vaccines triggers systemic immunity to eradicate triple-negative breast cancer.  JOURNAL OF CONTROLLED RELEASE,      [PMID:40681021] [10.1016/j.jconrel.2025.114045]

9. Xue-Bo Hu, Yi-Peng Zhang, Zi-He Jin, Yi-Xiao Zhang, Yu-Ling Wang, Xiao-Long Fu, Jun-Tao Cao, Yan-Ming Liu.  (2025)  A sandwiched PEDOT@Pt-based antifouling electrochemical sensor for real-time monitoring of cells cultured in three-dimensional hydrogel.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.115202]

10. Yaqing Kang, Xiaoqing Han, Shijie Zhou, Xingbo Wang, Yanjing Wang, Panpan Song, Xiaochen Su, Mengmeng Qin, Dongyang Qian, Huan Meng, Jiao Yan, Fang Pu, Haiyuan Zhang.  (2025)  Engineered Apoptotic Extracellular Vesicles for Programmable Regulation of Neutrophil-Macrophage-ROS Pathogenic Axis to Reconstruct Rheumatoid Arthritis Microenvironment.  ADVANCED MATERIALS,      [PMID:41041946] [10.1002/adma.202508072]

11. Yufang Guo, Longjie Li, Yongjun Wang, Zexu Wang, Wei Qiu, Qian Li, Li Wang, Bing Wan.  (2025)  The role of the MYL12A liquid-liquid phase separation in neutrophil improves the prognosis of acute respiratory distress syndrome: a multi-omics analysis.  Frontiers in Immunology,      [PMID:41235230] [10.3389/fimmu.2025.1662680]