propan-2-yl (5Z)-7-[(2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate

• ChemBase ID: 179386
• Molecular Formular: C25H44O5
• Molecular Mass: 424.61386
• Monoisotopic Mass: 424.31887451
• SMILES: C(=C\CCCC(=O)OC(C)C)\CC1[C@@H](CCC(=O)CCCCCCC)[C@@H](C[C@@H]1O)O
• Canonical SMILES: CCCCCCCC(=O)CC[C@H]1[C@H](O)C[C@@H](C1C/C=C\CCCC(=O)OC(C)C)O
• InChI: InChI=1S/C25H44O5/c1-4-5-6-7-10-13-20(26)16-17-22-21(23(27)18-24(22)28)14-11-8-9-12-15-25(29)30-19(2)3/h8,11,19,21-24,27-28H,4-7,9-10,12-18H2,1-3H3/b11-8-/t21?,22-,23+,24-/m1/s1
• InChIKey: XXUPXHKCPIKWLR-VSMUQCRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl (5Z)-7-[(2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate
• IUPAC Traditional name: isopropyl (5Z)-7-[(2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate
• Synonyms: (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-oxodecyl)cyclopenthyl]-5-heptenoic Acid Isopropyl Ester; UF-021; Rescula; Unoprostone Isopropyl Ester

Database IDs

• CAS Number: 120373-24-2
• PubChem SID: 164235296
• PubChem CID: 58649675

CALCULATED PROPERTIES

• Acid pKa: 14.546683
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.832984
• LogD (pH = 7.4): 4.832984
• Log P: 4.832984
• Molar Refractivity: 121.6185 cm^3
• Polarizability: 47.879482 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Clear Colourless Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - U800050

Antiglaucoma; used in treatment of ocular hypertension.

REFERENCES

• Goh, Y., et al.: Jpn. J. Ophthalmol., 38, 236 (1994)
• Nordmann, J.-P., et al.: Am. J. Ophthalmol., 133, 1 (1994)