benzyl (5Z)-7-[(1R,2S,3R,5S)-5-(acetyloxy)-2-(hydroxymethyl)-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate

• ChemBase ID: 159416
• Molecular Formular: C27H38O7
• Molecular Mass: 474.58642
• Monoisotopic Mass: 474.26175356
• SMILES: C([C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)OCc1ccccc1)OC(=O)C)OC1CCCCO1)O
• Canonical SMILES: OC[C@H]1[C@H](OC2CCCCO2)C[C@@H]([C@@H]1C/C=C\CCCC(=O)OCc1ccccc1)OC(=O)C
• InChI: InChI=1S/C27H38O7/c1-20(29)33-24-17-25(34-27-15-9-10-16-31-27)23(18-28)22(24)13-7-2-3-8-14-26(30)32-19-21-11-5-4-6-12-21/h2,4-7,11-12,22-25,27-28H,3,8-10,13-19H2,1H3/b7-2-/t22-,23-,24+,25-,27?/m1/s1
• InChIKey: NNIVEUYZDZVNLJ-ZYEGOXRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (5Z)-7-[(1R,2S,3R,5S)-5-(acetyloxy)-2-(hydroxymethyl)-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate
• IUPAC Traditional name: benzyl (5Z)-7-[(1R,2S,3R,5S)-5-(acetyloxy)-2-(hydroxymethyl)-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate
• Synonyms: (5Z)-7-[(5-Acetyloxy-2-formyl-3-tetrahydropyranyloxy)cyclopentyl]-5-heptenoic Acid Benzyl Ester

Database IDs

• PubChem SID: 162253551
• PubChem CID: 71312971

CALCULATED PROPERTIES

• Acid pKa: 15.375589
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.5518708
• LogD (pH = 7.4): 3.5518708
• Log P: 3.5518708
• Molar Refractivity: 128.7794 cm^3
• Polarizability: 50.851635 Å^3
• Polar Surface Area: 91.29 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Ethyl Acetate; Methanol; Tetrahydrofuran

DETAILS

Toronto Research Chemicals - A187445

Intermediate in the preparation of Hydroxy Lubiprostone (H943892).