(2R)-2-amino-3-[(2,4,5,6,7-2H5)-1H-indol-3-yl]propanoic acid

• ChemBase ID: 179371
• Molecular Formular: C11H12N2O2
• Molecular Mass: 204.22518
• Monoisotopic Mass: 204.08987763
• SMILES: c1ccc2c(c1)[nH]cc2C[C@@H](N)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](Cc1c[nH]c2c1cccc2)N
• InChI: InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m1/s1
• InChIKey: QIVBCDIJIAJPQS-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-[(2,4,5,6,7-^2H₅)-1H-indol-3-yl]propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-[(2,4,5,6,7-^2H₅)-1H-indol-3-yl]propanoic acid
• Synonyms: (+)-Tryptophan-d5; (R)-Tryptophan-d5; (R)-α-Amino-3-indolepropionic Acid-d5; (R)-α-Aminoindole-3-propanoic Acid-d5; D-Tryptophane-d5; NSC 97942-d5; D-Tryptophan-d5

Database IDs

• PubChem SID: 164235281
• PubChem CID: 58478580

CALCULATED PROPERTIES

• Acid pKa: 2.5439286
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.0856168
• LogD (pH = 7.4): -1.0892947
• Log P: -1.085457
• Molar Refractivity: 56.2028 cm^3
• Polarizability: 23.11526 Å^3
• Polar Surface Area: 79.11 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T947207

Labelled analogue of an essential amino acid found in naturally produced peptides. Unlike its stereoisomer, L-tryptophan, it is not used in structural or enzyme proteins.

REFERENCES

• Karunakaran, S.et al.: Bochem. J., 414, 343 (2008)
• Pallaghy, P.K. et al.: Biochem., 38, 11553 (2008)