(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoic acid

• ChemBase ID: 178831
• Molecular Formular: C23H29F3O6
• Molecular Mass: 458.4679696
• Monoisotopic Mass: 458.19162331
• SMILES: [C@H]1([C@H]([C@@H](C[C@@H]1O)O)/C=C/[C@H](COc1cccc(c1)C(F)(F)F)O)C/C=C\CCCC(=O)O
• Canonical SMILES: OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/[C@H](COc1cccc(c1)C(F)(F)F)O)O
• InChI: InChI=1S/C23H29F3O6/c24-23(25,26)15-6-5-7-17(12-15)32-14-16(27)10-11-19-18(20(28)13-21(19)29)8-3-1-2-4-9-22(30)31/h1,3,5-7,10-12,16,18-21,27-29H,2,4,8-9,13-14H2,(H,30,31)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1
• InChIKey: WWSWYXNVCBLWNZ-QIZQQNKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: (+)-fluprostenol
• Synonyms: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic Acid; (+)-Fluprostenol; [1R-[1α(Z),2β(1E,3R*),3α,5α]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic Acid; AL 5848; 16-(m-Trifluoromethylphenoxy)-17,18,19,20-tetranorprostaglandin F2α; Travoprost Acid

Database IDs

• CAS Number: 54276-17-4
• PubChem SID: 164234741
• PubChem CID: 5311100

CALCULATED PROPERTIES

• Acid pKa: 4.3552938
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.7469386
• LogD (pH = 7.4): -0.0021406882
• Log P: 2.9199162
• Molar Refractivity: 113.921 cm^3
• Polarizability: 42.78994 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T715620

A metabolically stable analog of Prostaglandin F2α (P838625) with potent FP receptor agonist activity. An impurity of Travoprost (T715600).

REFERENCES

• Abramovitz, M. et al.: J Biol. Chem., 269, 2632 (1994)
• Lake, S. et al.: FEBS Lett., 355, 317 (1994).