2-(furan-2-ylmethanesulfinyl)-N-[(2E)-4-{[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxy}but-2-en-1-yl]acetamide

• ChemBase ID: 172169
• Molecular Formular: C22H29N3O4S
• Molecular Mass: 431.54836
• Monoisotopic Mass: 431.18787742
• SMILES: S(=O)(CC(=O)NC/C=C/COc1nccc(c1)CN1CCCCC1)Cc1ccco1
• Canonical SMILES: O=C(CS(=O)Cc1ccco1)NC/C=C/COc1nccc(c1)CN1CCCCC1
• InChI: InChI=1S/C22H29N3O4S/c26-21(18-30(27)17-20-7-6-14-28-20)23-9-2-5-13-29-22-15-19(8-10-24-22)16-25-11-3-1-4-12-25/h2,5-8,10,14-15H,1,3-4,9,11-13,16-18H2,(H,23,26)/b5-2+
• InChIKey: KMZQAVXSMUKBPD-GORDUTHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(furan-2-ylmethanesulfinyl)-N-[(2E)-4-{[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxy}but-2-en-1-yl]acetamide
• IUPAC Traditional name: 2-(furan-2-ylmethanesulfinyl)-N-[(2E)-4-{[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxy}but-2-en-1-yl]acetamide
• Synonyms: 2-[(2-Furanylmethyl)sulfinyl]-N-[(2E)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-yl]acetamide; rac trans-Lafutidine

Database IDs

• CAS Number: 206449-94-7
• PubChem SID: 164228079
• PubChem CID: 5353705

CALCULATED PROPERTIES

• Acid pKa: 8.920191
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.4891095
• LogD (pH = 7.4): 0.26669228
• Log P: 0.73591876
• Molar Refractivity: 120.2437 cm^3
• Polarizability: 45.896614 Å^3
• Polar Surface Area: 84.67 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L168505

A trans isomeric impurity of rac Lafutidine (L168500).

REFERENCES

• Onodera, S., et al.: Jpn. J. Pharmacol., 68, 161 (1995)
• Umeda, M., et al.: J. Gastroenterol. Heoatol., 14, 859 (1995)
• Ajioka, H., et al.: Pharmacology, 61, 83 (1995)