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

• ChemBase ID: 153578
• Molecular Formular: C23H29F3O6
• Molecular Mass: 458.4679696
• Monoisotopic Mass: 458.19162331
• SMILES: c1cc(cc(c1)OC[C@@H](C=C[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C/CCCC(=O)O)O)O)O)C(F)(F)F
• Canonical SMILES: OC(=O)CCC/C=C/C[C@H]1[C@@H](O)C[C@H]([C@@H]1C=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)/t16-,18-,19-,20+,21-/m1/s1
• InChIKey: WWSWYXNVCBLWNZ-LELZANKISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• Synonyms: (+)-9α,11α,15R-Trihydroxy-16-[3-(trifluoromethyl)phenoxy]-17,18,19,20-tetranorprosta-5Z,13E-dien-1-oic acid; (+)-16-(m-Trifluoromethylphenoxy)tetranorprostaglandin F2α; (+)-Fluprostenol

Database IDs

• EC Number: 200-578-6
• MDL Number: MFCD00210955
• PubChem SID: 162247717
• PubChem CID: 71311680

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

PROPERTIES

Physical Property

• Apperance: ethanol solution
• Flash Point: 14 °C; 57.2 °F

Safety Information

• European Hazard Symbols: Flammable (F)
• UN Number: 1170
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11
• Safety Statements: 7-16
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• GHS Precautionary statements: P210
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%
• Shipped in: wet ice
• abs.: ε/222 nm 9,700
• Empirical Formula (Hill Notation): C23H29F3O6

DETAILS

Sigma Aldrich - F4176

Biochem/physiol Actions
Metabolically stable analog of PGF2α ; potent FP prostanoid receptor agonist. The optically active enantiomer of fluprostenol. This product is expected to have twice the potency of (+/-)-fluprostenol. It inhibits PGF2α binding to human and rat FP receptors (IC50 values of 3.5 and 7.5 nM respectively). It is a more potent luteolytic agent than PGF2α in rat and also an inhibitor of rat adipose precursor differentiation in primary cultures (IC50 = 3 to 10 ×10-11 M).