sulfuric acid ethyl N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl]-1-methyl-3-oxo-dodecahydronaphtho[2,3-c]furan-6-yl]carbamate

• ChemBase ID: 179557
• Molecular Formular: C29H35FN2O8S
• Molecular Mass: 590.6602032
• Monoisotopic Mass: 590.20981531
• SMILES: [C@@H]12[C@@H](C[C@H]3[C@H]([C@@H]1/C=C/c1ccc(cn1)c1cc(ccc1)F)CC[C@H](C3)NC(=O)OCC)C(=O)O[C@@H]2C.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.CCOC(=O)N[C@@H]1CC[C@@H]2[C@@H](C1)C[C@@H]1[C@H]([C@H]2/C=C/c2ccc(cn2)c2cccc(c2)F)[C@H](OC1=O)C
• InChI: InChI=1S/C29H33FN2O4.H2O4S/c1-3-35-29(34)32-23-10-11-24-20(14-23)15-26-27(17(2)36-28(26)33)25(24)12-9-22-8-7-19(16-31-22)18-5-4-6-21(30)13-18;1-5(2,3)4/h4-9,12-13,16-17,20,23-27H,3,10-11,14-15H2,1-2H3,(H,32,34);(H2,1,2,3,4)/b12-9+;/t17-,20+,23-,24-,25+,26-,27+;/m1./s1
• InChIKey: NQRYCIGCIAWEIC-CKLVGUEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid ethyl N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl]-1-methyl-3-oxo-dodecahydronaphtho[2,3-c]furan-6-yl]carbamate
• IUPAC Traditional name: sulfuric acid ethyl N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl]-1-methyl-3-oxo-decahydro-1H-naphtho[2,3-c]furan-6-yl]carbamate
• Synonyms: N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(1E)-2-[5-(3-Fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-methyl-3-oxonaphtho[2,3-c]furan-6-yl]carbamic Acid Ethyl Ester Sulfate; Sch 530348; Vorapaxar Sulfate

Database IDs

• CAS Number: 705260-08-8
• PubChem SID: 164235467
• PubChem CID: 10077129

CALCULATED PROPERTIES

• Acid pKa: 14.778974
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.0103884
• LogD (pH = 7.4): 5.036601
• Log P: 5.036947
• Molar Refractivity: 134.5236 cm^3
• Polarizability: 53.488194 Å^3
• Polar Surface Area: 77.52 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V758200

SCH-530348 is a novel antiplatelet agent undergoing development by Schering-Plough Corp for the treatment and prevention of atherothrombosis. It is currently undergoing Phase-III clinical trials for acute coronary syndrome (unstable angina/non-ST segment

REFERENCES

• Boyle, J., et al.: Curr. Vasc. Pharmacol., 3, 63 (2005)
• Jennings, L., et al.: Expert. Opin. Drug Metab. Toxicol., 1, 727 (2005)
• Chackalamannil, S., et al.: J. Med. Chem., 49, 5389 (2005)