1-{1-[(2S)-3-[(6-chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl]piperidin-4-yl}-1,3-diazinan-2-one

• ChemBase ID: 172266
• Molecular Formular: C22H26ClN3O5S
• Molecular Mass: 479.97694
• Monoisotopic Mass: 479.12816963
• SMILES: c1(ccc2c(c1)ccc(c2)S(=O)(=O)C[C@H](C(=O)N1CCC(CC1)N1CCCNC1=O)O)Cl
• Canonical SMILES: Clc1ccc2c(c1)ccc(c2)S(=O)(=O)C[C@H](C(=O)N1CCC(CC1)N1CCCNC1=O)O
• InChI: InChI=1S/C22H26ClN3O5S/c23-17-4-2-16-13-19(5-3-15(16)12-17)32(30,31)14-20(27)21(28)25-10-6-18(7-11-25)26-9-1-8-24-22(26)29/h2-5,12-13,18,20,27H,1,6-11,14H2,(H,24,29)/t20-/m1/s1
• InChIKey: GEHAEMCVKDPMKO-HXUWFJFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{1-[(2S)-3-[(6-chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl]piperidin-4-yl}-1,3-diazinan-2-one
• IUPAC Traditional name: 1-{1-[(2S)-3-(6-chloronaphthalen-2-ylsulfonyl)-2-hydroxypropanoyl]piperidin-4-yl}-1,3-diazinan-2-one
• Synonyms: 1-[1-[(2S)-3-[(6-chloro-2-naphthalenyl)sulfonyl]-2-hydroxy-1-oxopropyl]-4-piperidinyl]tetrahydro-2(1H)-pyrimidinone; TAK 442; 1-[(2S)-3-[(6-Chloro-2-naphthalenyl)sulfonyl]-2-hydroxy-1-oxopropyl]-4-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)piperidine; 1-[1-[(2S)-3-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl]piperidin-4-yl]tetrahydropyrimidin-2(1H)-one; Letaxaban

Database IDs

• CAS Number: 870262-90-1
• PubChem SID: 164228176
• PubChem CID: 11641515

CALCULATED PROPERTIES

• Acid pKa: 12.314776
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.23177765
• LogD (pH = 7.4): 0.23177265
• Log P: 0.2317779
• Molar Refractivity: 120.7499 cm^3
• Polarizability: 48.701424 Å^3
• Polar Surface Area: 107.02 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L329850

A potent and selective orally active factor Xa (FXa) inhibitor; anticoagulant. Effective in preventing venous thromboembolism in patient undergoing orthopedic surgery.

REFERENCES

• Zufferey, P.J. et al.: Thromb. Haemost., 104, 1083 (2010)
• Kawamura, M. et al.: J. Cardio. Pharmacol., 56, 156 (2010)
• Fujimoto, T. et al.: J. Med. Chem., 53, 3517 (2010)