(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid

• ChemBase ID: 108789
• Molecular Formular: C7H11N3O2
• Molecular Mass: 169.18114
• Monoisotopic Mass: 169.08512661
• SMILES: Cn1cncc1C[C@H](N)C(=O)O
• Canonical SMILES: Cn1cncc1C[C@@H](C(=O)O)N
• InChI: InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
• InChIKey: JDHILDINMRGULE-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
• IUPAC Traditional name: 3-methylhistidine; 3,methylhistidine
• Synonyms: 3-METHYL-L-HISTIDINE; π-Methyl-L-histidine; 1-Methyl-L-histidine (archaic); 3-(1-Methylimidazol-5-yl)-L-alanine; 3-Methyl-L-histidine

Database IDs

• CAS Number: 368-16-1
• EC Number: 206-704-6
• MDL Number: MFCD00083658
• PubChem SID: 162088917; 24897303
• PubChem CID: 64969

CALCULATED PROPERTIES

• Acid pKa: 1.9601641
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.8650215
• LogD (pH = 7.4): -3.4100597
• Log P: -3.3952408
• Molar Refractivity: 42.9557 cm^3
• Polarizability: 16.522043 Å^3
• Polar Surface Area: 81.14 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

DETAILS

MP Biomedicals - 05208718

MP Biomedicals Rare Chemical collection

Sigma Aldrich - M9005

Biochem/physiol Actions
3-Methyl-L-histidine is a non-proteinogenic amino acid and an index of muscle breakdown.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M9005.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.