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

• ChemBase ID: 125608
• Molecular Formular: C11H16N4O4
• Molecular Mass: 268.26914
• Monoisotopic Mass: 268.11715501
• SMILES: O=C(NCCC(=O)N[C@H](C(=O)O)Cc1c[nH]cn1)C
• Canonical SMILES: O=C(N[C@H](C(=O)O)Cc1c[nH]cn1)CCNC(=O)C
• InChI: InChI=1S/C11H16N4O4/c1-7(16)13-3-2-10(17)15-9(11(18)19)4-8-5-12-6-14-8/h5-6,9H,2-4H2,1H3,(H,12,14)(H,13,16)(H,15,17)(H,18,19)/t9-/m0/s1
• InChIKey: BKAYIFDRRZZKNF-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(3-acetamidopropanamido)-3-(1H-imidazol-4-yl)propanoic acid; (2S)-2-(3-acetamidopropanamido)-3-(1H-imidazol-5-yl)propanoic acid
• IUPAC Traditional name: (2S)-2-(3-acetamidopropanamido)-3-(1H-imidazol-4-yl)propanoic acid; (2S)-2-(3-acetamidopropanamido)-3-(3H-imidazol-4-yl)propanoic acid
• Synonyms: N-(N-Acetyl-β-alanyl)histidine; N-Acetyl-L-carnosine; N-Acetylcarnosine; Acetylcarnosine; NAC, N-α-Acetyl-N-β-alanyl-L-histidine; N-Acetylcarnosine; N-Acetyl-L-carnosine

Database IDs

• CAS Number: 56353-15-2
• PubChem SID: 162219958
• PubChem CID: 9903482
• Chemspider ID: 8079136
• Wikipedia Title: Acetylcarnosine

CALCULATED PROPERTIES

• Acid pKa: 3.6061845
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.2365506
• LogD (pH = 7.4): -3.9500256
• Log P: -3.2128026
• Molar Refractivity: 65.0057 cm^3
• Polarizability: 24.975485 Å^3
• Polar Surface Area: 124.18 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 123-125°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A172015

Used in the treatment of cataracts and in the treatment of UV-induced immunosuppression.

REFERENCES

• Babizhayev, M., et al.: J. Pharmacol. Toxicol., 1, 201 (2006)
• Min, J., et al.: J. Neurosci. Res., 86, 2984 (2006)
• Babizhayev, M., et al.: J. Drug Target., 17, 36 (2006)