2-{[(7-carbamimidoylnaphthalen-2-yl)methyl]({4-[(1-ethanimidoylpiperidin-4-yl)oxy]phenyl})sulfamoyl}acetic acid

• ChemBase ID: 179611
• Molecular Formular: C27H31N5O5S
• Molecular Mass: 537.63054
• Monoisotopic Mass: 537.20459012
• SMILES: c1(ccc2c(c1)cc(cc2)CN(c1ccc(cc1)OC1CCN(CC1)C(=N)C)S(=O)(=O)CC(=O)O)C(=N)N
• Canonical SMILES: OC(=O)CS(=O)(=O)N(c1ccc(cc1)OC1CCN(CC1)C(=N)C)Cc1ccc2c(c1)cc(cc2)C(=N)N
• InChI: InChI=1S/C27H31N5O5S/c1-18(28)31-12-10-25(11-13-31)37-24-8-6-23(7-9-24)32(38(35,36)17-26(33)34)16-19-2-3-20-4-5-21(27(29)30)15-22(20)14-19/h2-9,14-15,25,28H,10-13,16-17H2,1H3,(H3,29,30)(H,33,34)
• InChIKey: NPBKHEMDWREFJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(7-carbamimidoylnaphthalen-2-yl)methyl]({4-[(1-ethanimidoylpiperidin-4-yl)oxy]phenyl})sulfamoyl}acetic acid
• IUPAC Traditional name: {[(7-carbamimidoylnaphthalen-2-yl)methyl]({4-[(1-ethanimidoylpiperidin-4-yl)oxy]phenyl})sulfamoyl}acetic acid
• Synonyms: 2-[[[[7-(Aminoiminomethyl)-2-naphthalenyl]methyl][4-[[1-(1-iminoethyl)-4-piperidinyl]oxy]phenyl]amino]sulfonyl]acetic Acid Dihydrochloride; [[[[7-(Aminoiminomethyl)-2-naphthalenyl]methyl][4-[[1-(1-iminoethyl)-4-piperidinyl]oxy]phenyl]amino]sulfonyl]acetic Acid Dihydrochloride; YM 60828

Database IDs

• CAS Number: 179755-65-8
• PubChem SID: 164235521
• PubChem CID: 9807238

CALCULATED PROPERTIES

• Acid pKa: 3.465063
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -2.666385
• LogD (pH = 7.4): -2.6485574
• Log P: -0.4337977
• Molar Refractivity: 165.8847 cm^3
• Polarizability: 57.15739 Å^3
• Polar Surface Area: 160.87 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - Y100575

A potent, selective and orally-bioavailable Factor Xa (FXa) inhibitor; an anticogulant used in treatment of venous thromboembolic disease.

REFERENCES

• Hirayama, F. et al.: Bioorg. Med. Chem., 10, 1509 (2002)
• Chang, P.: IDrugs, 7, 57 (2002)
• Kawasaki, T. et al.: Thromb. Haemost., 79, 543 (2002)