(2S)-2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid

• ChemBase编号: 3004
• 分子式: C11H11FN2O2
• 平均质量: 222.2156432
• 单一同位素质量: 222.08045582
• SMILES: N[C@@H](Cc1c[nH]c2c1cc(F)cc2)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)Cc1c[nH]c2c1cc(F)cc2
• InChI: InChI=1S/C11H11FN2O2/c12-7-1-2-10-8(4-7)6(5-14-10)3-9(13)11(15)16/h1-2,4-5,9,14H,3,13H2,(H,15,16)/t9-/m0/s1
• InChIKey: INPQIVHQSQUEAJ-VIFPVBQESA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid
• IUPAC传统名: tryptophan, 5-fluoro-, DL-; fluorotryptophane
• 别名: 5-Fluoro-L-tryptophan; Fluorotryptophane; 5-Fluoro-L-tryptophan

登记号

• CAS号: 16626-02-1
• MDL号: MFCD00066470
• Beilstein号: 5052680
• PubChem SID: 24871158; 160966451; 46508536
• PubChem CID: 688357

理论计算性质

JChem

• Acid pKa: 2.1247466
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -0.94331914
• LogD (pH = 7.4): -0.94716156
• Log P: -0.9433259
• 摩尔折射率: 56.4192 cm^3
• 极化性: 22.75195 Å^3
• 极化表面积: 79.11 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.02
• LOG S: -2.26
• 溶解度: 1.21e+00 g/l

分子性质

安全信息

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

产品相关信息

• 纯度: ≥98.0% (HPLC)
• 光学纯度: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C11H11FN2O2

详细说明

DrugBank - DB03314

• Drug Groups: experimental
• Description: Fluorotryptophane can be used as substrate analogue to study enzyme mechanisms by NMR spectroscopy.

Sigma Aldrich - 47568

Application
Exogenous 5-fluoro-Trp is incorporated into proteins in normal protein synthesis3. Since 19F is a useful reporter group, this provides a method for studying enzyme mechanisms by NMR4.
Biochem/physiol Actions
5-Fluoro-Trp is nonspecifically cytotoxic. It is believed this is due to malfunctioning enzymes that have had replacements of Trp residues by 5-fluoro-Trp.1 However, at least one case is known where 5-fluoro-Trp substitution leads to significantly greater catalytic activity.2