(2S)-2-amino-6-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoic acid

• ChemBase ID: 177224
• Molecular Formular: C12H18N2O4
• Molecular Mass: 254.28232
• Monoisotopic Mass: 254.12665707
• SMILES: n1(CCCC[C@H](N)C(=O)O)c(ccc1CO)C=O
• Canonical SMILES: OCc1ccc(n1CCCC[C@@H](C(=O)O)N)C=O
• InChI: InChI=1S/C12H18N2O4/c13-11(12(17)18)3-1-2-6-14-9(7-15)4-5-10(14)8-16/h4-5,7,11,16H,1-3,6,8,13H2,(H,17,18)/t11-/m0/s1
• InChIKey: VTYFITADLSVOAS-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-6-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoic acid
• IUPAC Traditional name: 2-fhmpn
• Synonyms: (αS)-α-Amino-2-formyl-5-(hydroxymethyl)-1H-pyrrole-1-hexanoic Acid; ε-Pyrrolyllysine; Pyrraline

Database IDs

• CAS Number: 74509-14-1
• PubChem SID: 164233134
• PubChem CID: 122228

CALCULATED PROPERTIES

• Acid pKa: 2.025977
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.2855885
• LogD (pH = 7.4): -2.2902431
• Log P: -2.285638
• Molar Refractivity: 66.7591 cm^3
• Polarizability: 25.459578 Å^3
• Polar Surface Area: 105.55 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P997780

Pyrraline, an advanced Maillard product, was used to evaluate heat damage from the manufacturing and storage of enteral formulas and model systems. A significant increase in Pyrraline content was observed after the heat treatment of common whey proteins.

REFERENCES

• Nakayama, T., et al.: Agr. Biol. Chem., 44, 1201 (1980)
• Morales, F., et al.: J. Food Sci., 64, 855 (1980)