(2S)-2-amino-6-[(carboxymethyl)amino](4,4,5,5-2H4)hexanoic acid

• ChemBase ID: 163704
• Molecular Formular: C8H16N2O4
• Molecular Mass: 204.22364
• Monoisotopic Mass: 204.111007
• SMILES: C(NCCCC[C@H](N)C(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CNCCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C8H16N2O4/c9-6(8(13)14)3-1-2-4-10-5-7(11)12/h6,10H,1-5,9H2,(H,11,12)(H,13,14)/t6-/m0/s1
• InChIKey: NUXSIDPKKIEIMI-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-6-[(carboxymethyl)amino](4,4,5,5-^2H₄)hexanoic acid
• IUPAC Traditional name: (2S)-2-amino-6-[(carboxymethyl)amino](4,4,5,5-^2H₄)hexanoic acid
• Synonyms: 2-Amino-6-(carboxymethylamino)hexanoic Acid-d4; N6-(Carboxymethyl)lysine-d4; N6-(Carboxymethyl)-L-lysine-d4; CML-d4; Nε-(1-Carboxymethyl)-L-lysine-d4

Database IDs

• PubChem SID: 162257839
• PubChem CID: 45158903

CALCULATED PROPERTIES

• Acid pKa: 1.6051481
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.5339365
• LogD (pH = 7.4): -5.5368657
• Log P: -5.5337768
• Molar Refractivity: 48.6687 cm^3
• Polarizability: 19.650055 Å^3
• Polar Surface Area: 112.65 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Beige Solid
• Melting Point: >195°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - C180077

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)