(2S)-2-[(2S)-2-[(2S)-2-formamido-4-(methylsulfanyl)butanamido]-4-methylpentanamido]-3-phenylpropanoic acid

• ChemBase ID: 126492
• Molecular Formular: C21H31N3O5S
• Molecular Mass: 437.55294
• Monoisotopic Mass: 437.19844211
• SMILES: OC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCSC)NC=O
• Canonical 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
• InChIKey: PRQROPMIIGLWRP-BZSNNMDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-formamido-4-(methylsulfanyl)butanamido]-4-methylpentanamido]-3-phenylpropanoic acid
• IUPAC Traditional name: chemotactic peptide
• Synonyms: Chemotactic peptide; N-Formyl-L-methionyl-L-leucyl-L-phenylalanine; fMLP (misnomer but widely used); N-Formyl-Met-Leu-Phe; fMLF; N-Formyl-Met-Leu-Phe; N-Formyl-L-methionyl-L-leucyl-L-phenylalanine; Chemotactic peptide; F-Met-Leu-Phe; L-Phenylalanine, N-(N-(N-formyl-L-methionyl)-L-leucyl)-; N-Formylmethionine leucyl-phenylalanine

Database IDs

• CAS Number: 59880-97-6
• MDL Number: MFCD00036780
• Beilstein Number: 2315783
• PubChem SID: 24871354; 24894846; 162220825
• PubChem CID: 443295
• Chemspider ID: 391541; 16125628
• MeSH Name: N-Formylmethionine+Leucyl-Phenylalanine
• Wikipedia Title: N-Formylmethionine_leucyl-phenylalanine; Chemotactic_peptide

CALCULATED PROPERTIES

• Acid pKa: 3.99377
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.16479339
• LogD (pH = 7.4): -1.4823759
• Log P: 1.6802635
• Molar Refractivity: 115.4267 cm^3
• Polarizability: 45.200108 Å^3
• Polar Surface Area: 124.6 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetic acid: soluble20 mg/mL, clear, colorless; DMF: soluble50 mg/mL, clear, colorless

Safety Information

• German water hazard class: 3
• Safety Statements: S22
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... FPR1(2357)

Product Information

• Purity: ≥97% (HPLC); ≥97.0% (HPLC); ≥99.0% (TLC)
• Impurities: ≤1% water
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C21H31N3O5S

DETAILS

Sigma Aldrich - F3506

Amino Acid Sequence
NFor-Met-Leu-Phe
Biochem/physiol Actions
Potent chemotactic peptide.1 Induces a metabolic burst in macrophages accompanied by an increase in respiratory rate, secretion of lysosomal enzymes, and production of superoxide anion.2
Potent inducer of leucocyte chemotaxis and macrophage activator. Receptors that bind formylpeptides are found on phagocytic neutrophils and have recently been identified on cells of the intestinal mucosa.

Sigma Aldrich - 47729

Amino Acid Sequence
NFor-Met-Leu-Phe
Biochem/physiol Actions
N-Formyl-Met-Leu-Phe is a potent chemotactic peptide and formyl peptide receptor (FPR) agonist that induces a metabolic burst in macrophages accompanied by an increase in respiratory rate, secretion of lysosomal enzymes, and production of superoxide anion.
Potent chemotactic peptide. Induces a metabolic burst in macrophages accompanied by an increase in respiratory rate, secretion of lysosomal enzymes, and production of superoxide anion.

Sigma Aldrich - 47732

Amino Acid Sequence
NFor-Met-Leu-Phe
Biochem/physiol Actions
Potent chemotactic peptide.1 Induces a metabolic burst in macrophages accompanied by an increase in respiratory rate, secretion of lysosomal enzymes, and production of superoxide anion.2