methyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-hydroxy-4-phenoxybut-1-en-1-yl]cyclopentyl]hepta-4,5-dienoate

• ChemBase ID: 168928
• Molecular Formular: C23H30O6
• Molecular Mass: 402.4807
• Monoisotopic Mass: 402.20423868
• SMILES: [C@@H]1(CC=C=CCCC(=O)OC)[C@@H](/C=C/C(COc2ccccc2)O)[C@@H](C[C@@H]1O)O
• Canonical SMILES: COC(=O)CCC=C=CC[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/C(COc1ccccc1)O)O
• InChI: InChI=1S/C23H30O6/c1-28-23(27)12-8-3-2-7-11-19-20(22(26)15-21(19)25)14-13-17(24)16-29-18-9-5-4-6-10-18/h3-7,9-10,13-14,17,19-22,24-26H,8,11-12,15-16H2,1H3/b14-13+/t2?,17?,19-,20-,21+,22-/m1/s1
• InChIKey: BYNHBQROLKAEDQ-VBEMFLDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-hydroxy-4-phenoxybut-1-en-1-yl]cyclopentyl]hepta-4,5-dienoate
• IUPAC Traditional name: methyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-hydroxy-4-phenoxybut-1-en-1-yl]cyclopentyl]hepta-4,5-dienoate
• Synonyms: (4S)-rel-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]cyclopentyl]-4,5-heptadienoic Acid Methyl Ester; [1α(S*),2β(1E,3R*),3α,5α]-7-[3,5-Dihydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)cyclopentyl]-4,5-heptadienoic Acid Methyl Ester; Bovilene; Fenprostalene

Database IDs

• CAS Number: 69381-94-8
• PubChem SID: 162263060
• PubChem CID: 71316741

CALCULATED PROPERTIES

• Acid pKa: 13.947922
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.9803151
• LogD (pH = 7.4): 1.980315
• Log P: 1.9803151
• Molar Refractivity: 112.3971 cm^3
• Polarizability: 43.18639 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F249700

Synthetic analog of Prostaglandin F2α, related structurally to Prostalene. Luteolytic.

REFERENCES

• Concannon, P., et al.: Prostaglandins, 13, 533 (1977)
• Hase, M., et al.: J. Vet. Med. Sci., 62, 243 (1977)