(2S)-2-amino-3-[1-(2H3)methyl(5-2H)-1H-imidazol-4-yl](2-2H)propanoic acid

• ChemBase ID: 173775
• Molecular Formular: C7H11N3O2
• Molecular Mass: 169.18114
• Monoisotopic Mass: 169.08512661
• SMILES: n1(cc(nc1)C[C@H](N)C(=O)O)C
• Canonical SMILES: Cn1cc(nc1)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
• InChIKey: BRMWTNUJHUMWMS-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[1-(^2H₃)methyl(5-^2H)-1H-imidazol-4-yl](2-^2H)propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-[1-(^2H₃)methyl(5-^2H)imidazol-4-yl](2-^2H)propanoic acid
• Synonyms: L-1-Methylhistidine-d5; (S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic Acid-d5; 1-Methylhistidine-d5; 1-N-Methyl-L-histidine-d5; N1-Methyl-L-histidine-d5; NSC 524367-d5; 1-Methyl-L-histidine-d5

Database IDs

• PubChem SID: 164229685
• PubChem CID: 71750374

CALCULATED PROPERTIES

• Acid pKa: 1.9645875
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.5517554
• LogD (pH = 7.4): -3.0649374
• Log P: -3.0704188
• Molar Refractivity: 42.39 cm^3
• Polarizability: 16.603828 Å^3
• Polar Surface Area: 81.14 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M312052

Labelled 1-Methyl-L-histidine (M312050). The urinary 1- and 3-methylhistidine (1- and 3-MH) metabolites as potential biomarkers of skeletal muscle toxicity. These metabolites were highly correlated to sex-, dose-, and time-dependent development of cerivas

REFERENCES

• Berna, M., et al.: Anal. Chem., 79, 4199 (2007)
• Pritt, M., et al.: Toxicol. Sci., 103, 382 (2007)
• Tonomura, Y., et al.: Toxicology, 266, 48 (2007)