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

• ChemBase ID: 3770
• Molecular Formular: C7H11N3O2
• Molecular Mass: 169.18114
• Monoisotopic Mass: 169.08512661
• SMILES: Cn1cnc(C[C@H](N)C(=O)O)c1
• 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-methyl-1H-imidazol-4-yl)propanoic acid
• IUPAC Traditional name: 4-methyl-histidine; 1 methylhistidine
• Synonyms: 4-Methyl-Histidine; [S]-1-Methylimidazole-5-alanine; π-Methyl-L-histidine; 1-METHYL-L-HISTIDINE; 3-(1-Methylimidazol-4-yl)-L-alanine; 3-Methyl-L-histidine (archaic); Nτ-Methyl-L-histidine; 1-Methyl-L-histidine; 3-(1-methylimidazol-4-yl)-l-alanine; L-1-Methylhistidine; (S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic Acid; 1-Methylhistidine; 1-N-Methyl-L-histidine; N1-Methyl-L-histidine; NSC 524367; 3-(1-甲基咪唑-4-基)-L-丙氨酸; 3-甲基-L-组氨酸（已废用）; Nτ-甲基-L-组氨酸; 1-甲基-L-组氨酸

Database IDs

• CAS Number: 368-16-1; 332-80-9
• EC Number: 206-704-6; 206-368-0
• MDL Number: MFCD00005295
• Beilstein Number: 9727
• PubChem SID: 160967207; 24885268; 46506613
• PubChem CID: 92105

CALCULATED PROPERTIES

JChem

• 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: 16.522066 Å^3
• Polar Surface Area: 81.14 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.95
• LOG S: -1.39
• Solubility (Water): 6.93e+00 g/l

PROPERTIES

Physical Property

• Melting Point: ~240 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -24±1°, c = 2% in H2O

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC); 98%
• Impurities: ≤5% water
• Empirical Formula (Hill Notation): C7H11N3O2

DETAILS

MP Biomedicals - 02155569

([S]-1-Methylimidazole-5-alanine; p-Methyl-L-histidine) IUPAC name is 3-Methyl-L-histidine Crystalline

DrugBank - DB04151

Drug information: experimental

Sigma Aldrich - 67520

Other Notes
Natural but non-proteinogenic amino acid; employed as index of muscle protein breakdown1,2,3
Packaging
50, 250 mg in glass bottle

Toronto Research Chemicals - 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 cerivastatin-induced myotoxicity. Natural but no

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)