(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxo-5-phenylpentyl)cyclopentyl]hept-5-enoic acid

• ChemBase ID: 172083
• Molecular Formular: C23H32O5
• Molecular Mass: 388.49718
• Monoisotopic Mass: 388.22497412
• SMILES: [C@H]1([C@H]([C@@H](C[C@@H]1O)O)CCC(=O)CCc1ccccc1)C/C=C\CCCC(=O)O
• Canonical SMILES: O=C(CCc1ccccc1)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O
• InChI: InChI=1S/C23H32O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,19-22,25-26H,2,7,10-16H2,(H,27,28)/b6-1-/t19-,20-,21+,22-/m1/s1
• InChIKey: OFISZERSIOETNK-LYTHEMCMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxo-5-phenylpentyl)cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxo-5-phenylpentyl)cyclopentyl]hept-5-enoic acid
• Synonyms: (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-oxo-5-phenylpentyl)cyclopentyl]-5-heptenoic Acid; 15-Keto Latanoprost Acid

Database IDs

• CAS Number: 369585-22-8
• PubChem SID: 164227993
• PubChem CID: 71749686

CALCULATED PROPERTIES

• Acid pKa: 4.3063054
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.0505922
• LogD (pH = 7.4): 0.31084228
• Log P: 3.269236
• Molar Refractivity: 109.373 cm^3
• Polarizability: 42.489822 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K195360

15-Keto Latanoprost Acid is a Prostaglandin keto analog for glaucoma treatment.