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

• ChemBase ID: 3004
• Molecular Formular: C11H11FN2O2
• Molecular Mass: 222.2156432
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: tryptophan, 5-fluoro-, DL-; fluorotryptophane
• Synonyms: 5-Fluoro-L-tryptophan; Fluorotryptophane; 5-Fluoro-L-tryptophan

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.1247466
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.94331914
• LogD (pH = 7.4): -0.94716156
• Log P: -0.9433259
• Molar Refractivity: 56.4192 cm^3
• Polarizability: 22.75195 Å^3
• Polar Surface Area: 79.11 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.02
• LOG S: -2.26
• Solubility (Water): 1.21e+00 g/l

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥98.0% (HPLC)
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C11H11FN2O2

DETAILS

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