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

• ChemBase ID: 172238
• 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+/m0/s1
• InChIKey: HNPFPERDNWXAGS-NFVOFSAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: latanoprost acid
• Synonyms: (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic Acid; 13,14-Dihydro-17-phenyl-18,19,20-trinor-PGF2α; PhXA 85; Latanoprost Acid

Database IDs

• CAS Number: 41639-83-2
• PubChem SID: 164228148
• PubChem CID: 6441636

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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Oil

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L177310

A metabolite of Latanoprost. Potent, selective FP prostanoid receptor agonist. F-series Prostaglandin analog. 200 times as potent as isopropyl ester form.

REFERENCES

• Sjoquist, B., et al.: Drug Metab. Dispos., 26, 745 (1998)
• Watson, P., et al.: Drugs Today, 35, 449 (1998)
• Kashiwagi, K., et al.: Exp. Eye Res., 74, 41 (1998)