2-amino-4-(1H-indol-3-yl)butanoic acid

• ChemBase ID: 169946
• Molecular Formular: C12H14N2O2
• Molecular Mass: 218.25176
• Monoisotopic Mass: 218.1055277
• SMILES: c1ccc2c(c1)c(c[nH]2)CCC(N)C(=O)O
• Canonical SMILES: OC(=O)C(CCc1c[nH]c2c1cccc2)N
• InChI: InChI=1S/C12H14N2O2/c13-10(12(15)16)6-5-8-7-14-11-4-2-1-3-9(8)11/h1-4,7,10,14H,5-6,13H2,(H,15,16)
• InChIKey: ADJZXDVMJPTFKT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(1H-indol-3-yl)butanoic acid
• IUPAC Traditional name: 2-amino-4-(1H-indol-3-yl)butanoic acid
• Synonyms: α-Amino-γ-(3-indole)-butyric Acid; α-Amino-1H-indole-3-butanoic Acid; D,L-Homotryptophan

Database IDs

• CAS Number: 26988-87-4
• PubChem SID: 162264078
• PubChem CID: 4153394

CALCULATED PROPERTIES

• Acid pKa: 2.6029308
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.6412323
• LogD (pH = 7.4): -0.64386886
• Log P: -0.6410054
• Molar Refractivity: 60.8038 cm^3
• Polarizability: 24.936804 Å^3
• Polar Surface Area: 79.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid; Slightly in Chloroform and Dichloromethane
• Apperance: Off-White Solid
• Melting Point: >227°C (dec.)

REFERENCES

• J. Am. Chem. Soc., 70, 1962 (1948)