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

• ChemBase ID: 172082
• Molecular Formular: C26H38O5
• Molecular Mass: 430.57692
• Monoisotopic Mass: 430.27192432
• SMILES: [C@H]1([C@H]([C@@H](C[C@@H]1O)O)CCC(=O)CCc1ccccc1)C/C=C\CCCC(=O)OC(C)C
• Canonical SMILES: O=C(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/C26H38O5/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/h3,5-8,10-11,19,22-25,28-29H,4,9,12-18H2,1-2H3/b8-3-/t22-,23-,24+,25-/m1/s1
• InChIKey: DKYCMQSMHPIBBZ-VIZYZFHWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 135646-98-9
• PubChem SID: 164227992
• PubChem CID: 9867370

CALCULATED PROPERTIES

• Acid pKa: 14.5466795
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.1885133
• LogD (pH = 7.4): 4.1885133
• Log P: 4.1885133
• Molar Refractivity: 123.3095 cm^3
• Polarizability: 48.264664 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K195350

15-Keto Latanoprost is a metabolite of Latanoprost (L177280).

REFERENCES

• Sjoquist, B., et al.: Drug Metab. Dispos., 26, 745 (1998)
• Watson, P., et al.: Drugs Today, 35, 449 (1998)