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

• ChemBase ID: 132730
• 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]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-/m0/s1
• InChIKey: WWSWYXNVCBLWNZ-CHPNCWRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1S,2S,3S,5R)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: (5Z)-7-[(1S,2S,3S,5R)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• Synonyms: (±)-16-(3-Trifluoromethylphenoxy)tetranorprostaglandin F2α; Fluprostenol

Database IDs

• CAS Number: 40666-16-8
• EC Number: 200-578-6
• MDL Number: MFCD03427566
• PubChem SID: 162227007; 24894969
• PubChem CID: 6436637

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

Safety Information

• European Hazard Symbols: Flammable (F)
• UN Number: 1170
• German water hazard class: 1
• 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: 98%
• Concentration: 10 mg/mL in ethanol

DETAILS

Sigma Aldrich - F8549

Application
Potent FP prostanoid receptor agonist that can be a useful tool for identifying FP receptors in mixed receptor populations.