propan-2-yl (5E)-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-enoate

• ChemBase ID: 155588
• Molecular Formular: C26H35F3O6
• Molecular Mass: 500.5477096
• Monoisotopic Mass: 500.2385735
• SMILES: CC(C)OC(=O)CCC/C=C/C[C@H]1[C@H](C[C@H]([C@@H]1C=C[C@H](COc1cccc(c1)C(F)(F)F)O)O)O
• Canonical SMILES: CC(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)C
• InChI: InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/t19-,21-,22-,23+,24-/m1/s1
• InChIKey: MKPLKVHSHYCHOC-XJUGCWAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl (5E)-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-enoate; propan-2-yl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoate
• IUPAC Traditional name: isopropyl (5E)-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-enoate; isopropyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoate
• Synonyms: (5E)-7-[(1R,3R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester; 5,6-trans Travoprost; (±)-16-(m-Trifluoromethylphenoxy)tetranorprostaglandin F2; Travoprost; Fluprostenol isopropyl ester

Database IDs

• MDL Number: MFCD03411995
• PubChem SID: 162249726
• PubChem CID: 71312160

CALCULATED PROPERTIES

• Acid pKa: 13.948069
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.839193
• LogD (pH = 7.4): 3.839193
• Log P: 3.839193
• Molar Refractivity: 127.8575 cm^3
• Polarizability: 48.49126 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: ethanol solution
• Flash Point: 17 °C; 62 °F

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1170
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C26H35F3O6

DETAILS

Sigma Aldrich - F2427

Biochem/physiol Actions
Potent FP prostanoid receptor agonist used in animal models for glaucoma.

Toronto Research Chemicals - T715610

An 5,6-trans isomeric impurity of the selective FP prostaglandin receptor agonist Travoprost (T715600).