(2S)-2-amino-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)propanoic acid

• ChemBase ID: 172769
• Molecular Formular: C6H9N3O2S
• Molecular Mass: 187.21956
• Monoisotopic Mass: 187.04154754
• SMILES: [nH]1cc([nH]c1=S)C[C@H](N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)Cc1c[nH]c(=S)[nH]1
• InChI: InChI=1S/C6H9N3O2S/c7-4(5(10)11)1-3-2-8-6(12)9-3/h2,4H,1,7H2,(H,10,11)(H2,8,9,12)/t4-/m0/s1
• InChIKey: FVNKWWBXNSNIAR-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)propanoic acid
• Synonyms: (αS)-α-Amino-2,3-dihydro-2-thioxo-1H-Imidazole-4-propanoic Acid; 2-Thiolhistidine 1H-Imidazole-4-propanoic Acid; L-2-Mercaptohistidine; L-2-Thiolhistidine; L-Thiohistidine; 2-Mercapto-L-histidine

Database IDs

• CAS Number: 2002-22-4
• PubChem SID: 164228679
• PubChem CID: 2733604

CALCULATED PROPERTIES

• Acid pKa: 2.419025
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): -2.938494
• LogD (pH = 7.4): -2.962235
• Log P: -2.9389703
• Molar Refractivity: 48.0511 cm^3
• Polarizability: 18.594006 Å^3
• Polar Surface Area: 87.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colourless Crystals
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M253000

An intermediate in the formation of L-egothioneine, a natural amino acid ubiquitously present in cells and tissues of most plants and mammalian species. In humans, L-ergothioneine is found in red blood cells, liver, kidney, brain, seminal fluid, and cata

REFERENCES

• Makinen, K.K., et al.: Eur. J. Biochem., 123, 171 (1982)
• Howard, R.J., et al.: Biochem. Pharmacol., 35, 1589 (1982)