4-[(2S,3R,4R,6S)-4-hydroxy-3-[(1E,3S)-3-hydroxy-4-(2H3)methyloct-1-en-6-yn-1-yl]-7-oxatricyclo[6.4.0.02,6]dodeca-1(12),8,10-trien-9-yl]butanoic acid

• ChemBase ID: 161922
• Molecular Formular: C24H30O5
• Molecular Mass: 398.492
• Monoisotopic Mass: 398.20932406
• 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
• 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
• InChI: InChI=1S/C24H30O5/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)/b13-12+/t15?,17-,19+,20+,21-,23-/m0/s1
• InChIKey: CTPOHARTNNSRSR-APJZLKAGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2S,3R,4R,6S)-4-hydroxy-3-[(1E,3S)-3-hydroxy-4-(^2H₃)methyloct-1-en-6-yn-1-yl]-7-oxatricyclo[6.4.0.0^2,^6]dodeca-1(12),8,10-trien-9-yl]butanoic acid
• IUPAC Traditional name: 4-[(2S,3R,4R,6S)-4-hydroxy-3-[(1E,3S)-3-hydroxy-4-(^2H₃)methyloct-1-en-6-yn-1-yl]-7-oxatricyclo[6.4.0.0^2,^6]dodeca-1(12),8,10-trien-9-yl]butanoic acid
• Synonyms: dl-4-[(1R,2R,3aS,8bS)-2,3,3a,8b-Tetrahydro-2-hydroxy-[(3S,4RS)-3-hydroxy-4-(methyl-d3)-oct-6-yne-(E)-1-enyl]-5-cyclopenta[b]benzofuranyl]butanoic Acid; Befaprost-d3; MDL 201229-d3; ML 1229-d3; Beraprost-d3

Database IDs

• PubChem SID: 162256057
• PubChem CID: 46780792

CALCULATED PROPERTIES

• Acid pKa: 4.2007127
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.2790687
• LogD (pH = 7.4): 0.56410855
• Log P: 3.5970807
• Molar Refractivity: 112.7222 cm^3
• Polarizability: 43.030773 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B318002

Labelled Beraprost. 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)