N-[3-(4-carbamimidoylphenyl)-1-oxo-1-(piperidin-1-yl)propan-2-yl]-2-(naphthalene-2-sulfonamido)acetamide

• ChemBase ID: 174964
• Molecular Formular: C27H31N5O4S
• Molecular Mass: 521.63114
• Monoisotopic Mass: 521.2096755
• SMILES: c1ccc2c(c1)cc(cc2)S(=O)(=O)NCC(=O)NC(C(=O)N1CCCCC1)Cc1ccc(cc1)C(=N)N
• Canonical SMILES: O=C(NC(C(=O)N1CCCCC1)Cc1ccc(cc1)C(=N)N)CNS(=O)(=O)c1ccc2c(c1)cccc2
• InChI: InChI=1S/C27H31N5O4S/c28-26(29)21-10-8-19(9-11-21)16-24(27(34)32-14-4-1-5-15-32)31-25(33)18-30-37(35,36)23-13-12-20-6-2-3-7-22(20)17-23/h2-3,6-13,17,24,30H,1,4-5,14-16,18H2,(H3,28,29)(H,31,33)
• InChIKey: XXTWZTPVNIYSJZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[3-(4-carbamimidoylphenyl)-1-oxo-1-(piperidin-1-yl)propan-2-yl]-2-(naphthalene-2-sulfonamido)acetamide
• IUPAC Traditional name: N-[3-(4-carbamimidoylphenyl)-1-oxo-1-(piperidin-1-yl)propan-2-yl]-2-(naphthalene-2-sulfonamido)acetamide
• Synonyms: (+/-)-N-[1-[[4-(Aminoiminomethyl)phenyl]methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[(2-naphthalenylsulfonyl)amino]acetamide; α-NAPAP; Thrombstop; Thromstop; Nα-(2-Naphthalenesulfonylglycyl)-4-amidino-D,L-phenylalaninepiperidide

Database IDs

• CAS Number: 86125-48-6
• PubChem SID: 164230874
• PubChem CID: 4406

CALCULATED PROPERTIES

• Acid pKa: 10.02981
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.6121197
• LogD (pH = 7.4): -0.48596027
• Log P: 1.407331
• Molar Refractivity: 152.9939 cm^3
• Polarizability: 56.49289 Å^3
• Polar Surface Area: 145.45 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N359250

A selective inhibitor of thrombins.

REFERENCES

• Svendsen, L., et al.: Thromb. Res., 34, 457 (1984)