3-[2-sulfanylidene-2,3-dihydro(1,3-15N2)-1H-imidazol-4-yl]-2-(trimethylazaniumyl)(2-13C)propanoate

• ChemBase ID: 168163
• Molecular Formular: C9H15N3O2S
• Molecular Mass: 232.27877263
• Monoisotopic Mass: 232.08592236
• SMILES: [15nH]1cc([15nH]c1=S)C[13CH]([N+](C)(C)C)C(=O)[O-]
• Canonical SMILES: [O-]C(=O)[13CH]([N+](C)(C)C)Cc1c[15nH]c(=S)[15nH]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)/i7+1,10+1,11+1
• InChIKey: SSISHJJTAXXQAX-NBLDSOAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[2-sulfanylidene-2,3-dihydro(1,3-^1^5N₂)-1H-imidazol-4-yl]-2-(trimethylazaniumyl)(2-^1^3C)propanoate
• IUPAC Traditional name: 3-[2-sulfanylidene-1,3-dihydro(1,3-^1^5N₂)imidazol-4-yl]-2-(trimethylammonio)(2-^1^3C)propanoate
• Synonyms: α-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium-13C,15N2 Inner Salt; (+/-)-Ergothioneine-13C,15N2; DL-Ergothioneine-13C,15N2

Database IDs

• PubChem SID: 162262295
• PubChem CID: 71316408

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

DETAILS

Toronto Research Chemicals - E600012

Labelled DL-Ergothionine. It 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 i

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)