3-(2H-1,3-benzodioxol-5-yl)-5-hydroxy-5-(4-methoxyphenyl)-4-{[3,4,5-tris(2H3)methoxyphenyl]methyl}-2,5-dihydrofuran-2-one

• ChemBase ID: 164739
• Molecular Formular: C28H26O9
• Molecular Mass: 506.50064
• Monoisotopic Mass: 506.15768241
• SMILES: O1C(=O)C(=C(C1(c1ccc(cc1)OC)O)Cc1cc(c(c(c1)OC)OC)OC)c1ccc2c(c1)OCO2
• Canonical SMILES: COc1ccc(cc1)C1(O)OC(=O)C(=C1Cc1cc(OC)c(c(c1)OC)OC)c1ccc2c(c1)OCO2
• InChI: InChI=1S/C28H26O9/c1-31-19-8-6-18(7-9-19)28(30)20(11-16-12-23(32-2)26(34-4)24(13-16)33-3)25(27(29)37-28)17-5-10-21-22(14-17)36-15-35-21/h5-10,12-14,30H,11,15H2,1-4H3
• InChIKey: PWIPORDFWDZCJG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2H-1,3-benzodioxol-5-yl)-5-hydroxy-5-(4-methoxyphenyl)-4-{[3,4,5-tris(^2H₃)methoxyphenyl]methyl}-2,5-dihydrofuran-2-one
• IUPAC Traditional name: 3-(2H-1,3-benzodioxol-5-yl)-5-hydroxy-5-(4-methoxyphenyl)-4-{[3,4,5-tris(^2H₃)methoxyphenyl]methyl}furan-2-one
• Synonyms: 3-(1,3-Benzodioxol-5-yl)-5-hydroxy-5-(4-methoxyphenyl)-4-[(3,4,5-(trimethoxy-d9)phenyl)methyl]-2(5H)-furanone; PD 156707-d9; CI 1020-d9

Database IDs

• PubChem SID: 162258874
• PubChem CID: 71314858

CALCULATED PROPERTIES

• Acid pKa: 10.556184
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 4.6135383
• LogD (pH = 7.4): 4.6132393
• Log P: 4.613542
• Molar Refractivity: 132.0473 cm^3
• Polarizability: 51.77628 Å^3
• Polar Surface Area: 101.91 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C432682

Labelled CI 1020 (C432680). A novel endothelin-A receptor antagonist, in hypoxic pulmonary hypertension.

REFERENCES

• Yanagisawa, M., et al.: Nature, 332, 411 (1988)
• Reynolds, E., et al.: J. Pharmacol. Exp. Ther., 273, 1410 (1988)
• Chen, S., et al.: J. Cardiovasc. Pharmacol., 29, 713 (1988)
• Haleen, S., et al.: Exp. Opin. Invest. Drugs, 6, 475 (1988)