(3Z)-4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-{[(2Z)-2-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-5-[(2-methylpropanoyl)oxy]pent-2-en-3-yl]disulfanyl}pent-3-en-1-yl 2-methylpropanoate

• ChemBase ID: 177923
• Molecular Formular: C32H46N8O6S2
• Molecular Mass: 702.88764
• Monoisotopic Mass: 702.29817323
• SMILES: S(S/C(=C(\N(Cc1cnc(nc1N)C)C=O)/C)/CCOC(=O)C(C)C)/C(=C(\N(Cc1c(nc(nc1)C)N)C=O)/C)/CCOC(=O)C(C)C
• Canonical SMILES: O=CN(/C(=C(\SS/C(=C(\N(Cc1cnc(nc1N)C)C=O)/C)/CCOC(=O)C(C)C)/CCOC(=O)C(C)C)/C)Cc1cnc(nc1N)C
• InChI: InChI=1S/C32H46N8O6S2/c1-19(2)31(43)45-11-9-27(21(5)39(17-41)15-25-13-35-23(7)37-29(25)33)47-48-28(10-12-46-32(44)20(3)4)22(6)40(18-42)16-26-14-36-24(8)38-30(26)34/h13-14,17-20H,9-12,15-16H2,1-8H3,(H2,33,35,37)(H2,34,36,38)/b27-21-,28-22-
• InChIKey: CKHJPWQVLKHBIH-ZDSKVHJSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3Z)-4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-{[(2Z)-2-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-5-[(2-methylpropanoyl)oxy]pent-2-en-3-yl]disulfanyl}pent-3-en-1-yl 2-methylpropanoate
• IUPAC Traditional name: sulbutiamine
• Synonyms: 2-Methylpropanoic Acid 1,1'-[Dithiobis[3-[1-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]ethylidene]-3,1-propanediyl]] Ester; Bisibutiamine; O-Isobutyroylthiamine Disulfide; O-Isobutyrylthiamine Disulfide; Vitaberin; Sulbutiamine

Database IDs

• CAS Number: 3286-46-2
• PubChem SID: 164233833
• PubChem CID: 20055424

CALCULATED PROPERTIES

• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): -0.757345
• LogD (pH = 7.4): 0.75661784
• Log P: 0.81629956
• Molar Refractivity: 195.966 cm^3
• Polarizability: 72.3812 Å^3
• Polar Surface Area: 196.82 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S689250

Sulbutiamine (isobutyryl thiamine disulfide) is a lipophilic derivative of thiamine used for the treatment of asthenia and other related pathological conditions. Sulbutiamine is available over-the-counter in several countries as a component of nutritional

REFERENCES

• Micheau, J., et al.: Pharmacol. Biochem. Behav., 23, 195 (1985)
• Bettendorff, L., et al.: Biochem. Pharmacol., 40, 2557 (1985)
• van Reeth, O., et al.: Drugs Today, 35, 187 (1985)