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

• ChemBase编号: 126492
• 分子式: C21H31N3O5S
• 平均质量: 437.55294
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S)-2-[(2S)-2-[(2S)-2-formamido-4-(methylsulfanyl)butanamido]-4-methylpentanamido]-3-phenylpropanoic acid
• IUPAC传统名: chemotactic peptide
• 别名: 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

登记号

• CAS号: 59880-97-6
• MDL号: MFCD00036780
• Beilstein号: 2315783
• PubChem SID: 24871354; 24894846; 162220825
• PubChem CID: 443295
• Chemspider ID: 391541; 16125628
• 医学主题词(MeSH): N-Formylmethionine+Leucyl-Phenylalanine
• 维基百科标题: Chemotactic_peptide; N-Formylmethionine_leucyl-phenylalanine

理论计算性质

• Acid pKa: 3.99377
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): 0.16479339
• LogD (pH = 7.4): -1.4823759
• Log P: 1.6802635
• 摩尔折射率: 115.4267 cm^3
• 极化性: 45.200108 Å^3
• 极化表面积: 124.6 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: true

分子性质

理化性质

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

安全信息

• 德国WGK号: 3
• 安全公开号: S22
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C; 2-8°C

药理学性质

• 相关基因信息: human ... FPR1(2357)

产品相关信息

• 纯度: ≥97% (HPLC); ≥97.0% (HPLC); ≥99.0% (TLC)
• 杂质: ≤1% water
• 产品线: BioXtra
• Empirical Formula (Hill Notation): C21H31N3O5S

详细说明

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