propan-2-yl (5Z)-7-[(1R,2R,3S,5S)-3-(formyloxy)-5-hydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

• ChemBase ID: 169387
• Molecular Formular: C27H40O6
• Molecular Mass: 460.6029
• Monoisotopic Mass: 460.282489
• SMILES: [C@H]1([C@H]([C@H](C[C@@H]1O)OC=O)CC[C@H](CCc1ccccc1)O)C/C=C\CCCC(=O)OC(C)C
• Canonical SMILES: O=CO[C@H]1C[C@@H]([C@@H]([C@H]1CC[C@H](CCc1ccccc1)O)C/C=C\CCCC(=O)OC(C)C)O
• InChI: InChI=1S/C27H40O6/c1-20(2)33-27(31)13-9-4-3-8-12-23-24(26(32-19-28)18-25(23)30)17-16-22(29)15-14-21-10-6-5-7-11-21/h3,5-8,10-11,19-20,22-26,29-30H,4,9,12-18H2,1-2H3/b8-3-/t22-,23+,24+,25-,26-/m0/s1
• InChIKey: XMNLNTCBRUDGKU-FMLBJTEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl (5Z)-7-[(1R,2R,3S,5S)-3-(formyloxy)-5-hydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
• IUPAC Traditional name: isopropyl (5Z)-7-[(1R,2R,3S,5S)-3-(formyloxy)-5-hydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
• Synonyms: 11-O-Formyl Latanoprost

Database IDs

• PubChem SID: 162263519
• PubChem CID: 71316941

CALCULATED PROPERTIES

• Acid pKa: 14.6985445
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.373439
• LogD (pH = 7.4): 4.373439
• Log P: 4.373439
• Molar Refractivity: 128.9986 cm^3
• Polarizability: 50.727253 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F700475

A formyl-substituted Latanoprost (L177280).