3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-2,3-dihydro-1,3-thiazole-2-thione

• ChemBase ID: 178585
• Molecular Formular: C12H16N4OS2
• Molecular Mass: 296.41164
• Monoisotopic Mass: 296.07655315
• SMILES: c1(nc(c(cn1)Cn1c(=S)sc(c1C)CCO)N)C
• Canonical SMILES: OCCc1sc(=S)n(c1C)Cc1cnc(nc1N)C
• InChI: InChI=1S/C12H16N4OS2/c1-7-10(3-4-17)19-12(18)16(7)6-9-5-14-8(2)15-11(9)13/h5,17H,3-4,6H2,1-2H3,(H2,13,14,15)
• InChIKey: SQOCQQPFEFRKBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-2,3-dihydro-1,3-thiazole-2-thione
• IUPAC Traditional name: 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazole-2-thione
• Synonyms: 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-2(3H)-thiazolethione; SB; Thiamin Thiothiazolone; Thiothiamin; 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-4-thiazoline-2-thione; Thioxothiamine; Thiamine Impurity A; Thiothiamine

Database IDs

• CAS Number: 299-35-4
• PubChem SID: 164234495
• PubChem CID: 67530

CALCULATED PROPERTIES

• Acid pKa: 15.898934
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.41588122
• LogD (pH = 7.4): 1.192856
• Log P: 1.2229205
• Molar Refractivity: 86.6882 cm^3
• Polarizability: 31.64853 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T375250

Thiothiamine is an impurity of Thiamine (T344185). Thiothiamine inhibits the activity of glutamate decarboxylase and decreases the concentration of GABA in brain tissue. Thiamine Impurity A;

REFERENCES

• Koval'chuk, V.G. et al.: Tezisy Dokl.- Konf. Beloruss. Biokhim. O-va., 2, 135 (1974)
• Ostrovskii, Y. et al.: Biokhimiya, 34, 488 (1974)