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

• ChemBase ID: 172237
• Molecular Formular: C23H34O5
• Molecular Mass: 390.51306
• Monoisotopic Mass: 390.24062419
• SMILES: [C@@H]1(C/C=C\CCCC(=O)O)[C@H]([C@@H](C[C@@H]1O)O)CC[C@@H](CCc1ccccc1)O
• Canonical SMILES: O[C@H](CCc1ccccc1)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O
• InChI: InChI=1S/C23H34O5/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/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19-,20-,21+,22-/m1/s1
• InChIKey: HNPFPERDNWXAGS-PUJPTKFWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 41639-84-3
• PubChem SID: 164228147
• PubChem CID: 11741139

CALCULATED PROPERTIES

• Acid pKa: 4.3063054
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.8430915
• LogD (pH = 7.4): 0.10334147
• Log P: 3.0617352
• Molar Refractivity: 110.4011 cm^3
• Polarizability: 42.960205 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L177295

The 15-epimer of Latanoprost Acid (L177310).

REFERENCES

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