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

• ChemBase ID: 109748
• Molecular Formular: C9H14N4O3
• Molecular Mass: 226.23246
• Monoisotopic Mass: 226.10659033
• SMILES: NCCC(=O)N[C@@H](Cc1c[nH]cn1)C(=O)O
• Canonical SMILES: NCCC(=O)N[C@H](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)/t7-/m0/s1
• InChIKey: CQOVPNPJLQNMDC-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(3-aminopropanamido)-3-(1H-imidazol-4-yl)propanoic acid
• IUPAC Traditional name: carnosine
• Synonyms: L-α-ALANYL-L-HISTIDINE; L-Carnosine; β-Alanyl-L-histidine; Carnosine

Database IDs

• CAS Number: 305-84-0
• EC Number: 206-169-9
• MDL Number: MFCD00005207
• Beilstein Number: 87671
• PubChem SID: 162095547; 24893178
• PubChem CID: 439224
• CHEBI ID: 57485
• CHEMBL: 242948
• Chemspider ID: 388363
• KEGG ID: C00386
• Unique Ingredient Identifier: 8HO6PVN24W
• Wikipedia Title: Carnosine

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

Physical Property

• Apperance: crystalline; Crystalline solid
• Melting Point: 253 °C (dec.)(lit.); 253 °C (decomposition)

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CA1(759), CA2(760)

Product Information

• Purity: ~99%

DETAILS

MP Biomedicals - 05212418

MP Biomedicals Rare Chemical collection

Sigma Aldrich - C9625

Amino Acid Sequence
Ala-His
包装
10 mg in poly bottle
5, 25, 100 g in poly bottle
Biochem/physiol Actions
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.
Dipeptide with potent antioxidant and antiglycation activity; blocks nonenzymatic glycosylation and protein cross-linking induced by reactive aldehydes.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C9625.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.