sodium 4-[(2S,3R,4R,6S)-4-hydroxy-3-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-7-oxatricyclo[6.4.0.02,6]dodeca-1(12),8,10-trien-9-yl]butanoate

• ChemBase ID: 161921
• Molecular Formular: C24H29NaO5
• Molecular Mass: 420.47383
• Monoisotopic Mass: 420.19126831
• SMILES: c1(c2c(ccc1)[C@H]1[C@@H](O2)C[C@H]([C@@H]1/C=C/[C@H](C(CC#CC)C)O)O)CCCC(=O)[O-].[Na+]
• Canonical SMILES: CC#CCC([C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1c1cccc(c1O2)CCCC(=O)[O-])O)C.[Na+]
• InChI: InChI=1S/C24H30O5.Na/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28;/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28);/q;+1/p-1/b13-12+;/t15?,17-,19+,20+,21-,23-;/m0./s1
• InChIKey: YTCZZXIRLARSET-VJRSQJMHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 4-[(2S,3R,4R,6S)-4-hydroxy-3-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-7-oxatricyclo[6.4.0.0^2,^6]dodeca-1(12),8,10-trien-9-yl]butanoate
• IUPAC Traditional name: sodium 4-[(2S,3R,4R,6S)-4-hydroxy-3-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-7-oxatricyclo[6.4.0.0^2,^6]dodeca-1(12),8,10-trien-9-yl]butanoate
• Synonyms: dl-4-[(1R,2R,3aS,8bS)-2,3,3a,8b-Tetrahydro-2-hydroxy-[(3S,4RS)-3-hydroxy-4-methyl-oct-6-yne-(E)-1-enyl]-5-cyclopenta[b]benzofuranyl]butanoic Acid Sodium; MDL 201229; ML 1229; Dorner; Procylin; Beraprost Sodium Salt

Database IDs

• CAS Number: 88475-69-8
• PubChem SID: 162256056
• PubChem CID: 23663404

CALCULATED PROPERTIES

• Acid pKa: 4.2007127
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.2790687
• LogD (pH = 7.4): 0.56410855
• Log P: 3.5970807
• Molar Refractivity: 123.5593 cm^3
• Polarizability: 42.919804 Å^3
• Polar Surface Area: 89.82 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 204-206°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B318000

Platelet aggregation inhibitor; stable analog of Prostacyclin. Antithrombotic; vasodilator (peripheral).

REFERENCES

• Kajikawa, N., et al.: Arzneim.-Forsch., 39, 495 (1989)
• Demolis, J.-L., et al.: J. Cardiovasc. Pharmacol., 22, 711 (1989)
• Okuda, Y., et al.: Prostaglandins, 52, 375 (1989)