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

• ChemBase ID: 172236
• Molecular Formular: C26H40O5
• Molecular Mass: 432.5928
• Monoisotopic Mass: 432.28757438
• SMILES: [C@H]1([C@H]([C@@H](C[C@@H]1O)O)CC[C@@H](CCc1ccccc1)O)C/C=C\CCCC(=O)OC(C)C
• Canonical SMILES: O[C@H](CCc1ccccc1)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)OC(C)C)O
• InChI: InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22-,23-,24+,25-/m1/s1
• InChIKey: GGXICVAJURFBLW-SCTZCWPJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
• IUPAC Traditional name: isopropyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
• Synonyms: (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester; (15S)-Latanoprost

Database IDs

• CAS Number: 145773-22-4
• PubChem SID: 164228146
• PubChem CID: 10477939

CALCULATED PROPERTIES

• Acid pKa: 14.468507
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.9810123
• LogD (pH = 7.4): 3.9810123
• Log P: 3.9810123
• Molar Refractivity: 124.3376 cm^3
• Polarizability: 48.735634 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L177285

An impurity of commercially prepared Latanoprost (L177280).

REFERENCES

• Resul, B., et al.: J. Med. Chem., 36, 2242 (1993)