(2R)-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate

• ChemBase ID: 168160
• Molecular Formular: C9H15N3O2S
• Molecular Mass: 229.2993
• Monoisotopic Mass: 229.08849774
• SMILES: [nH]1cc([nH]c1=S)C[C@@H]([N+](C)(C)C)C(=O)[O-]
• Canonical SMILES: [O-]C(=O)[C@H]([N+](C)(C)C)Cc1c[nH]c(=S)[nH]1
• InChI: InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m1/s1
• InChIKey: SSISHJJTAXXQAX-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
• IUPAC Traditional name: (2R)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylammonio)propanoate
• Synonyms: (αS)-α-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium Inner Salt; 2-Mercaptohistidine Betaine; NSC 7175; 2-Mercapto-N,N-dimethylhistidine Methyl Ester Betaine; 2-Mercapto-histidine; Sympectothion; Thiasine; Thioneine; Thiotane; L-(+)-Ergothioneine

Database IDs

• CAS Number: 497-30-3
• PubChem SID: 162262292
• PubChem CID: 5351468

CALCULATED PROPERTIES

• Acid pKa: 2.4892666
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -3.2563658
• LogD (pH = 7.4): -3.2570417
• Log P: -4.0265336
• Molar Refractivity: 84.8711 cm^3
• Polarizability: 23.927666 Å^3
• Polar Surface Area: 64.19 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Hot Ethanol; Sil. Sol. Methanol; Water (1g/5ml at 25°C)
• Apperance: White to Off-White Solid
• Melting Point: 214-219°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - E600000

L-Ergothionine is a natural molecule isolated from the rye ergot fungus and later identified in rat erythrocytes and liver and in numerous other animal tissues. Its antioxidizing properties may afford the compound therapeutic potential or it may be used

REFERENCES

• Nakamura, T., et al.: Biol. Pharm. Bull., 31, 1580 (2008)
• Yang, J., et al.: Food Chem., 114, 898 (2008)
• Grigat, S., et al.: Drug Metab. Disposition, 37, 330 (2008)