2-amino-3-[(2,4,5-13C3,1,3-15N2)-1H-imidazol-5-yl](1,2,3-13C3)propanoic acid

• ChemBase ID: 169998
• Molecular Formular: C6H9N3O2
• Molecular Mass: 164.09071572
• Monoisotopic Mass: 164.08071025
• SMILES: [15n]1[13cH][13c]([15nH][13cH]1)[13CH2][13CH]([13C](=O)O)[15NH2]
• Canonical SMILES: [15NH2][13CH]([13C](=O)O)[13CH2][13c]1[13cH][15n][13cH][15nH]1
• InChI: InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1,9+1
• InChIKey: HNDVDQJCIGZPNO-RIQGLZQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-[(2,4,5-^1^3C₃,1,3-^1^5N₂)-1H-imidazol-5-yl](1,2,3-^1^3C₃)propanoic acid
• IUPAC Traditional name: 2-amino-3-[(2,4,5-^1^3C₃,1,3-^1^5N₂)-3H-imidazol-4-yl](1,2,3-^1^3C₃)propanoic acid
• Synonyms: DL-Histidine-13C6,15N3; Histidine-13C6,15N3; 1H-Imidazole-4-alanine-13C6,15N3; rac Histidine-13C6,15N3

Database IDs

• PubChem SID: 162264130
• PubChem CID: 46781699

CALCULATED PROPERTIES

• Acid pKa: 1.8499727
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -4.1150556
• LogD (pH = 7.4): -3.6406806
• Log P: -3.6160226
• Molar Refractivity: 38.059 cm^3
• Polarizability: 14.774432 Å^3
• Polar Surface Area: 92.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Crystalline Solid
• Melting Point: 287°C (dec.)

DETAILS

Toronto Research Chemicals - H456002

Essential amino acid for human development; precursor to histamine and a component of carnosine.

REFERENCES

• Sachs, D.H., et al.: J. Biol. Chem., 246, 6576 (1971)
• Mercer, L.P., et al.: Nutrition, 6, 273 (1971)
• Morgan, W.T., et al.: J. Biol. Chem., 268, 6256 (1971)