2-acetamido-2-[2-(1H-indol-3-yl)ethyl]propanedioic acid

• ChemBase ID: 158944
• Molecular Formular: C15H16N2O5
• Molecular Mass: 304.29794
• Monoisotopic Mass: 304.10592162
• SMILES: c1ccc2c(c1)c(c[nH]2)CCC(NC(=O)C)(C(=O)O)C(=O)O
• Canonical SMILES: CC(=O)NC(C(=O)O)(C(=O)O)CCc1c[nH]c2c1cccc2
• InChI: InChI=1S/C15H16N2O5/c1-9(18)17-15(13(19)20,14(21)22)7-6-10-8-16-12-5-3-2-4-11(10)12/h2-5,8,16H,6-7H2,1H3,(H,17,18)(H,19,20)(H,21,22)
• InChIKey: HLAXNURKPQFWIA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamido-2-[2-(1H-indol-3-yl)ethyl]propanedioic acid
• IUPAC Traditional name: 2-acetamido-2-[2-(1H-indol-3-yl)ethyl]propanedioic acid
• Synonyms: 2-(Acetylamino)-2-[2-(1H-indol-3-yl)ethyl]propanedioic Acid; α-Carboxy D,L-Homotryptophan; α-Acetamino-α-carboxy-(3-indole)-butyric Acid

Database IDs

• CAS Number: 408537-42-8
• PubChem SID: 162253079
• PubChem CID: 3576810

CALCULATED PROPERTIES

• Acid pKa: 2.4763262
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.7200619
• LogD (pH = 7.4): -3.5986037
• Log P: 1.298112
• Molar Refractivity: 76.4471 cm^3
• Polarizability: 30.68938 Å^3
• Polar Surface Area: 119.49 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Red Solid
• Melting Point: 130-132°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A161210

An intermediate in the preparation of D,L-Homotryptophan.

REFERENCES

• J. Am. Chem. Soc., 70, 1962 (1948)