N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-{1-[(4E)-2-oxo-1,3-oxathian-4-ylidene]ethyl}formamide

• ChemBase ID: 165309
• Molecular Formular: C13H16N4O3S
• Molecular Mass: 308.35614
• Monoisotopic Mass: 308.09431139
• SMILES: O1C(=O)S/C(=C(/N(Cc2c(nc(nc2)C)N)C=O)\C)/CC1
• Canonical SMILES: O=CN(/C(=C/1\CCOC(=O)S1)/C)Cc1cnc(nc1N)C
• InChI: InChI=1S/C13H16N4O3S/c1-8(11-3-4-20-13(19)21-11)17(7-18)6-10-5-15-9(2)16-12(10)14/h5,7H,3-4,6H2,1-2H3,(H2,14,15,16)/b11-8+
• InChIKey: LLJDJQYGZBQFIF-DHZHZOJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-{1-[(4E)-2-oxo-1,3-oxathian-4-ylidene]ethyl}formamide
• IUPAC Traditional name: N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-{1-[(4E)-2-oxo-1,3-oxathian-4-ylidene]ethyl}formamide
• Synonyms: N-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-N-[1-(2-oxo-1,3-oxathian-4-ylidene)ethyl]formamide; CCT; Carbothiamine; Cometamine; Commetamin; Cyclocarbothiamine; Cyclothiamine; Cyclotiamine; Cycothiamine; Thiocarbonic Acid Cyclic O,S-ester with N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide; Cycotiamine

Database IDs

• CAS Number: 6092-18-8
• PubChem SID: 162259442
• PubChem CID: 3034024

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.0850048
• LogD (pH = 7.4): -0.35291174
• Log P: -0.32349858
• Molar Refractivity: 83.3583 cm^3
• Polarizability: 30.359444 Å^3
• Polar Surface Area: 98.41 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C988970

Thiamine (T344185) derivative used in the treatment of neurogenic bladder dysfunction. It is absorbed from the intestine and rapidly metabolized into thiamine in the blood. Studies suggest that it has stimulant action on intestinal motility.

REFERENCES

• Nihira, H. et al.: Hinyok. Kiyo, 12, 823 (1966)
• Shiobara, Y. et al.: Bitamin, 37, 306 (1966)
• Kuriaki, K. et al.: Bitamin, 41, 30 (1966)