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

• ChemBase ID: 169999
• Molecular Formular: C7H11N3O2
• Molecular Mass: 169.18114
• Monoisotopic Mass: 169.08512661
• SMILES: n1cc([nH]c1)C[C@H](N)C(=O)OC
• Canonical SMILES: COC(=O)[C@H](Cc1cnc[nH]1)N
• InChI: InChI=1S/C7H11N3O2/c1-12-7(11)6(8)2-5-3-9-4-10-5/h3-4,6H,2,8H2,1H3,(H,9,10)/t6-/m0/s1
• InChIKey: BXRMEWOQUXOLDH-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-amino-3-(1H-imidazol-5-yl)propanoate
• IUPAC Traditional name: methyl (2S)-2-amino-3-(3H-imidazol-4-yl)propanoate
• Synonyms: Histidine Methyl Ester Dihydrochloride; (S)-Histidine Methyl Ester Dihydrochloride; Methyl L-Histidinate Dihydrochloride; NSC 522221; L-Histidine Methyl Ester Dihydrochloride

Database IDs

• CAS Number: 7389-87-9
• PubChem SID: 162264131
• PubChem CID: 92893

CALCULATED PROPERTIES

• Acid pKa: 12.920543
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.0728703
• LogD (pH = 7.4): -1.3936663
• Log P: -1.2036612
• Molar Refractivity: 42.8281 cm^3
• Polarizability: 16.839956 Å^3
• Polar Surface Area: 81.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >190°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - H456020

Used in the preparation of optically pure L-(+)-Ergothioneine.

REFERENCES

• Lehn, J., et al.: Science, 291, 2331 (2001)
• Nicoll, A., et al.: Org. Biomol. Chem., 2, 2175 (2001)