(2S)-3-(2-sulfanyl-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate

• ChemBase ID: 132831
• Molecular Formular: C9H15N3O2S
• Molecular Mass: 229.2993
• Monoisotopic Mass: 229.08849774
• SMILES: C[N+](C)(C)[C@@H](Cc1c[nH]c(n1)S)C(=O)[O-]
• Canonical SMILES: [O-]C(=O)[C@@H]([N+](C)(C)C)Cc1nc([nH]c1)S
• 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-/m0/s1
• InChIKey: SSISHJJTAXXQAX-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-(2-sulfanyl-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
• IUPAC Traditional name: ergothioneine
• Synonyms: (S)-α-Carboxy-N,N,N-trimethyl-2-mercapto-1H-imidazole-4-ethanaminium inner salt; Thioneine; L-(+)-Ergothioneine

Database IDs

• CAS Number: 497-30-3
• EC Number: 207-843-5
• MDL Number: MFCD00167474
• PubChem SID: 24894650; 162227108
• PubChem CID: 5351619

CALCULATED PROPERTIES

• Acid pKa: 1.8737687
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.9433136
• LogD (pH = 7.4): -2.9378083
• Log P: -4.266047
• Molar Refractivity: 81.7964 cm^3
• Polarizability: 23.158247 Å^3
• Polar Surface Area: 68.81 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - E7521

Biochem/physiol Actions
Antioxidant which protects against γ and UV radiation.
Other Notes
Natural amino acid found in the fungus Claviceps purpurea