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

• ChemBase ID: 153767
• Molecular Formular: C23H34O5
• Molecular Mass: 390.51306
• Monoisotopic Mass: 390.24062419
• SMILES: c1ccc(cc1)CC[C@@H](CC[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C/CCCC(=O)O)O)O)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)/t18-,19+,20+,21-,22+/m0/s1
• InChIKey: HNPFPERDNWXAGS-AHJNKEMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid; 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid; 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid
• Synonyms: (5E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic Acid; trans-Latanoprost Acid; (5Z,9α,11α,15R)-9,11,15-Trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oic acid; PhXA 85; Latanoprost acid

Database IDs

• CAS Number: 903549-49-5; 41639-83-2
• MDL Number: MFCD08056084
• PubChem SID: 24724524; 162247906
• PubChem CID: 6506408

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: freely soluble; methanol: soluble
• Apperance: pale yellow, oil

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: mouse ... Ptgfr(19220)

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C23H34O5

DETAILS

Sigma Aldrich - L1292

Biochem/physiol Actions
Potent, selective FP prostanoid receptor agonist, F-series prostaglandin analog. 200 times as potent as isopropyl ester form.
Packaging
Store tightly sealed, under desiccant.

Toronto Research Chemicals - L177315

The trans metabolite of Latanoprost (L177280), Prostaglandin analog.

REFERENCES

• Botchkareva, N., et al.: FASEB J., 115, 645 (2001)