2-(3-aminopropanamido)-3-(1H-imidazol-4-yl)propanoic acid

• ChemBase ID: 102276
• Molecular Formular: C9H14N4O3
• Molecular Mass: 226.23246
• Monoisotopic Mass: 226.10659033
• SMILES: NCCC(=O)NC(Cc1c[nH]cn1)C(=O)O
• Canonical SMILES: NCCC(=O)NC(C(=O)O)Cc1nc[nH]c1
• InChI: InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)
• InChIKey: CQOVPNPJLQNMDC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-aminopropanamido)-3-(1H-imidazol-4-yl)propanoic acid
• IUPAC Traditional name: L-histidine, N-β-alanyl-; carnosine
• Synonyms: L-Carnosine; β-Alanyl-L-histidine; β-ALA-HIS

Database IDs

• CAS Number: 305-84-0
• EC Number: 206-169-9
• PubChem SID: 162088421
• PubChem CID: 9369

CALCULATED PROPERTIES

• Acid pKa: 3.3612406
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -4.928625
• LogD (pH = 7.4): -4.1909065
• Log P: -4.174497
• Molar Refractivity: 54.9962 cm^3
• Polarizability: 21.548273 Å^3
• Polar Surface Area: 121.1 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 0°C
• RTECS: MS3080000

Product Information

• Purity: ~99%
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02100936

Dipeptide with potent antioxidant and antiglycation activity; blocks nonenzymatic glycosylation and protein cross-linking induced by reactive aldehydes.
L-Carosine is a dipeptide found at millimolar concentration in brain, muscle and the lens of the eye. In model systems it is a potent antioxidant that scavenges oxygen free radicals and transition metal ions. It blocks protein-protein and protein-DNA cross-links induced by hypochlorite anions and toxic aldehydes such as acetaldehyde, formaldehyde, and malondialdehyde, the primary product of lipid peroxidation. It also inhibits nonenzymatic protein glycation induced by aldose and ketose reducing sugars and inhibits the formation of toxic advanced glycation end products (AGE). These activities make it of interest in studies of aging, atherosclerosis, Alzheimer's disease, and the secondary effects of diabetes.
Crystalline
Purity: Approx. 99%