5-chloro-N-{[(5S)-4-hydroxy-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide

• ChemBase ID: 177577
• Molecular Formular: C19H18ClN3O6S
• Molecular Mass: 451.88072
• Monoisotopic Mass: 451.06048399
• SMILES: c1c(ccc(c1)N1C(=O)COCC1)N1C(=O)O[C@H](C1O)CNC(=O)c1ccc(s1)Cl
• Canonical SMILES: O=C1O[C@H](C(N1c1ccc(cc1)N1CCOCC1=O)O)CNC(=O)c1ccc(s1)Cl
• InChI: InChI=1S/C19H18ClN3O6S/c20-15-6-5-14(30-15)17(25)21-9-13-18(26)23(19(27)29-13)12-3-1-11(2-4-12)22-7-8-28-10-16(22)24/h1-6,13,18,26H,7-10H2,(H,21,25)/t13-,18?/m0/s1
• InChIKey: YGGWNELFPGFWHH-FVRDMJKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-N-{[(5S)-4-hydroxy-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide
• IUPAC Traditional name: 5-chloro-N-{[(5S)-4-hydroxy-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide
• Synonyms: 5-Chloro-N-[[(5S)-4-hydroxy-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-2-thiophenecarboxamide; Rivaroxaban Hydroxyoxazalone Metabolite(Mixture of Diastereomers)

Database IDs

• CAS Number: 1161719-51-2
• PubChem SID: 164233487
• PubChem CID: 71752092

CALCULATED PROPERTIES

• Acid pKa: 12.258605
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.5334207
• LogD (pH = 7.4): 1.5334148
• Log P: 1.5334208
• Molar Refractivity: 105.7736 cm^3
• Polarizability: 41.290604 Å^3
• Polar Surface Area: 108.41 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R538020

A metabolite of Rivaroxaban (R538000).

REFERENCES

• Kubitza, D., et al.: Clin. Pharmacol. Ther., 78, 412 (2005)
• Roehrig, S., et al.: J. Med. Chem., 48, 5900 (2005)
• Biemond, B., et al.: Thromb. Haemost., 97, 471 (2005)
• Lang, D., et al.: Drug Metab. Dispos., 37, 1046 (2005)