(2S)-2-amino-6-[(1-carboxyethyl)amino]hexanoic acid

• ChemBase ID: 163739
• Molecular Formular: C9H18N2O4
• Molecular Mass: 218.25022
• Monoisotopic Mass: 218.12665707
• SMILES: C(NCCCC[C@H](N)C(=O)O)(C)C(=O)O
• Canonical SMILES: OC(=O)[C@H](CCCCNC(C(=O)O)C)N
• InChI: InChI=1S/C9H18N2O4/c1-6(8(12)13)11-5-3-2-4-7(10)9(14)15/h6-7,11H,2-5,10H2,1H3,(H,12,13)(H,14,15)/t6?,7-/m0/s1
• InChIKey: XCYPSOHOIAZISD-MLWJPKLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-6-[(1-carboxyethyl)amino]hexanoic acid
• IUPAC Traditional name: CEL
• Synonyms: Nε-(1-Carboxyethyl)lysine; N6-(1-Carboxyethyl)-L-lysine; N6-(1'-Carboxyethyl)lysine; CEL; Nε-(1-Carboxyethyl)-L-lysine(Mixture of Diastereomers)

Database IDs

• PubChem SID: 162257874
• PubChem CID: 23400779

CALCULATED PROPERTIES

• Acid pKa: 1.660836
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.9651513
• LogD (pH = 7.4): -4.96798
• Log P: -4.9649553
• Molar Refractivity: 53.1626 cm^3
• Polarizability: 21.472143 Å^3
• Polar Surface Area: 112.65 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >180°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C178070

CEL and CML are two stable, nonenzymatic chemical modifications of protein lysine residues resulting from glycation and oxidation reactions.

REFERENCES

• Fu, M.X., et al.: J. Biol. Chem., 271, 9982 (1996)
• Ahmed M.U., et al.: Biochem.J., 324, 565 (1996)
• Schleicher, E.D., et al.: J. Clin. Invest., 99, 457 (1996)
• Shibayama, R., et al.: Diabetes, 48, 1842 (1996)