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

• ChemBase ID: 104138
• Molecular Formular: C19H23N4O6PS
• Molecular Mass: 466.447881
• Monoisotopic Mass: 466.10759211
• SMILES: Cc1ncc(CN(C=O)/C(=C(\CCOP(=O)(O)O)/SC(=O)c2ccccc2)/C)c(N)n1
• 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)
• InChIKey: BTNNPSLJPBRMLZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(3E)-4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-[(E)-benzoylsulfanyl]pent-3-en-1-yl]oxy}phosphonic acid; [(4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-(benzoylsulfanyl)pent-3-en-1-yl)oxy]phosphonic acid
• IUPAC Traditional name: benfotiamine; (4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-(benzoylsulfanyl)pent-3-en-1-yl)oxyphosphonic acid
• Synonyms: S-Benzoylthiamine O-monophosphate; Benfotiamine; S-BENZOYLTHIAMINE O-MONOPHOSPHATE; ''S''-benzoylthiamine O-monophosphate; Benfotiamine; S-Benzoylthiamine O-monophosphate

Database IDs

• CAS Number: 22457-89-2
• EC Number: 245-013-4
• MDL Number: MFCD00057343
• PubChem SID: 162092733; 24892147
• PubChem CID: 3032771; 5282168
• ATC CODE: A11DA03
• Chemspider ID: 2297665
• Unique Ingredient Identifier: Y92OUS2H9B
• Wikipedia Title: Benfotiamine

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

PROPERTIES

Safety Information

• Storage Condition: 2-8°C
• RTECS: DH6910000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base
• Empirical Formula (Hill Notation): C19H23N4O6PS

DETAILS

MP Biomedicals - 02154835

(Benfotiamine)

Sigma Aldrich - B9636

Biochem/physiol Actions
Benfotiamine is an amphiphilic S-acyl thiamine derivative used as a lipid soluble alternative source of bioavailable thiamine. Benfotiamine is being investigated in a variety of therapeutic applications.