(2S)-2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid

• ChemBase ID: 164689
• Molecular Formular: C11H11ClN2O2
• Molecular Mass: 238.67024
• Monoisotopic Mass: 238.05090528
• SMILES: c1c(cc2c(c1)c(c[nH]2)C[C@H](N)C(=O)O)Cl
• Canonical SMILES: OC(=O)[C@H](Cc1c[nH]c2c1ccc(c2)Cl)N
• InChI: InChI=1S/C11H11ClN2O2/c12-7-1-2-8-6(3-9(13)11(15)16)5-14-10(8)4-7/h1-2,4-5,9,14H,3,13H2,(H,15,16)/t9-/m0/s1
• InChIKey: FICLVQOYKYBXFN-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid
• Synonyms: 6-Chloro (R)-Tryptophan; 6-Chloro D-Tryptophan; 6-Chloro (S)-Tryptophan; 6-Chlorotryptophan; L-6-Chlorotryptophan; 6-Chloro L-Tryptophan

Database IDs

• CAS Number: 33468-35-8; 56632-86-1
• PubChem SID: 162258824
• PubChem CID: 10062693

CALCULATED PROPERTIES

• Acid pKa: 2.1106248
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.4819777
• LogD (pH = 7.4): -0.48590592
• Log P: -0.48198998
• Molar Refractivity: 61.0076 cm^3
• Polarizability: 24.955748 Å^3
• Polar Surface Area: 79.11 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid; Aqueous Base; DMSO
• Apperance: Off-White Solid
• Melting Point: >226°C (dec.); 244-246°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C423210

The natural enantiomer of Chlorotryptophan.

Toronto Research Chemicals - C423200

The unnatural enantiomer of Chlorotryptophan.

REFERENCES

• Bae, J., et al.: J. Mol. Biol., 309, 925 (2001)
• Budisa, N., et al.: Biol. Chem., 385, 191 (2001)
• Kodama, K., et al.: ChemBioChem., 7, 134 (2001)
• Bae, J., et al.: J. Mol. Biol., 309, 925 (2001)
• Budisa, N., et al.: Biol. Chem., 385, 191 (2001)
• Kodama, K., et al.: ChemBioChem., 7, 134 (2001)