{[(3Z)-4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-[(Z)-benzoylsulfanyl]pent-3-en-1-yl]oxy}phosphonic acid

• ChemBase ID: 161190
• Molecular Formular: C19H23N4O6PS
• Molecular Mass: 466.447881
• Monoisotopic Mass: 466.10759211
• SMILES: n1c(nc(c(c1)CN(/C(=C(/CCOP(=O)(O)O)\SC(=O)c1ccccc1)/C)C=O)N)C
• Canonical SMILES: O=CN(/C(=C(\SC(=O)c1ccccc1)/CCOP(=O)(O)O)/C)Cc1cnc(nc1N)C
• InChI: InChI=1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)/b17-13-
• InChIKey: BTNNPSLJPBRMLZ-LGMDPLHJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(3Z)-4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-[(Z)-benzoylsulfanyl]pent-3-en-1-yl]oxy}phosphonic acid
• IUPAC Traditional name: benfotiamine
• Synonyms: Benzenecarbothioic Acid S-[2-[[(4-Amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propen-1-yl] Ester; Benzoylthiamine Monophosphate; Berdi; Betivina; Bietamine; Biotamin; Milgamma; Nitanevril; S-Benzoylthiamine O-Monophosphate; Tabiomyl; Vitanevril; BTMP; Benfotiamine

Database IDs

• CAS Number: 22457-89-2
• PubChem SID: 162255325
• PubChem CID: 3032771

CALCULATED PROPERTIES

• Acid pKa: 1.6822021
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.153027
• LogD (pH = 7.4): -2.5593069
• Log P: -2.202912
• Molar Refractivity: 121.5394 cm^3
• Polarizability: 44.88746 Å^3
• Polar Surface Area: 155.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B136000

Vitamin B1 analog. Synthetic S-acyl derivative of Thiamine (T344185).

REFERENCES

• Stracke, H., et al.: Exper. Clin. Endocrinol., Diabetes, 116, 600 (2008)
• Gohil, V., et al.: Nat., Biotechnol., 28, 249 (2008)