(2S)-2-amino-6-(3-hydroxy-2-methyl-4-oxo-1,4-dihydropyridin-1-yl)hexanoic acid

• ChemBase ID: 172521
• Molecular Formular: C12H18N2O4
• Molecular Mass: 254.28232
• Monoisotopic Mass: 254.12665707
• SMILES: c1(c(c(=O)ccn1CCCC[C@H](N)C(=O)O)O)C
• Canonical SMILES: OC(=O)[C@H](CCCCn1ccc(=O)c(c1C)O)N
• InChI: InChI=1S/C12H18N2O4/c1-8-11(16)10(15)5-7-14(8)6-3-2-4-9(13)12(17)18/h5,7,9,16H,2-4,6,13H2,1H3,(H,17,18)/t9-/m0/s1
• InChIKey: XREGTYIADDPJMA-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-6-(3-hydroxy-2-methyl-4-oxo-1,4-dihydropyridin-1-yl)hexanoic acid
• IUPAC Traditional name: (2S)-2-amino-6-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)hexanoic acid
• Synonyms: (αS)-α-Amino-3-hydroxy-2-methyl-4-oxo-1(4H)-pyridinehexanoic Acid; (S)-α-amino-3-hydroxy-2-methyl-4-oxo-1(4H)-pyridinehexanoic Acid; Maltosine

Database IDs

• CAS Number: 121502-04-3
• PubChem SID: 164228431
• PubChem CID: 71749894

CALCULATED PROPERTIES

• Acid pKa: 2.400021
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.7352178
• LogD (pH = 7.4): -1.7397418
• Log P: -1.735153
• Molar Refractivity: 68.5883 cm^3
• Polarizability: 25.54529 Å^3
• Polar Surface Area: 103.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M161500

Maltosine is a product of the Maillard reaction with a pyridone structure. In glycation reactions, the side chains of protein-bound nucleophilic amino acids such as lysine and arginine are post-translationally modified to a variety of derivatives also kno

REFERENCES

• Ahmed, M., et al.: J. Biol. Chem., 261, 4889 (1986)
• Ahmed, N., et al.: Diabetes Obes. Metab., 9, 233 (1986)
• Hellwig, M., et al.: ChemBioChem, 12, 1270 (1986)