(2S)-2-amino-6-[(2-amino-2-carboxyethyl)amino]hexanoic acid

• ChemBase ID: 172456
• Molecular Formular: C9H19N3O4
• Molecular Mass: 233.26486
• Monoisotopic Mass: 233.1375561
• SMILES: [C@@H](CCCCNCC(N)C(=O)O)(N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CCCCNCC(C(=O)O)N
• InChI: InChI=1S/C9H19N3O4/c10-6(8(13)14)3-1-2-4-12-5-7(11)9(15)16/h6-7,12H,1-5,10-11H2,(H,13,14)(H,15,16)/t6-,7?/m0/s1
• InChIKey: IMSOBGJSYSFTKG-PKPIPKONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-6-[(2-amino-2-carboxyethyl)amino]hexanoic acid
• IUPAC Traditional name: (2S)-2-amino-6-[(2-amino-2-carboxyethyl)amino]hexanoic acid
• Synonyms: N6-(2-Amino-2-carboxyethyl)-L-lysine DiHydrochloride; Lysinoalanine Dihydrochloride

Database IDs

• CAS Number: 4418-81-9
• PubChem SID: 164228366
• PubChem CID: 29269

CALCULATED PROPERTIES

• Polarizability: 23.00079 Å^3
• Polar Surface Area: 138.67 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true
• Acid pKa: 1.7560825
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -7.276266
• LogD (pH = 7.4): -6.180866
• Log P: -6.140532
• Molar Refractivity: 56.3638 cm^3

DETAILS

Toronto Research Chemicals - L488650

This not naturally occurring amino acid was first observed after alkali treatment of different proteins. Synthetic Lysinoalanine was found to have a strong chelating ability for metals.

REFERENCES

• Schwass, D., et al.: J. Agric. Food Chem., 32, 1377 (1984)
• Ahmed, M., et al.: J. Biol. Chem., 261, 8816 (1984)
• Wells-Knecht, K., et al.: Biochem., 34, 3702 (1984)