(5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

• ChemBase ID: 177073
• Molecular Formular: C20H34O5
• Molecular Mass: 354.48096
• Monoisotopic Mass: 354.24062419
• SMILES: [C@H]1(C/C=C\CCCC(=O)O)[C@@H](/C=C/[C@H](CCCCC)O)[C@@H](C[C@@H]1O)O
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]([C@H]1C/C=C\CCCC(=O)O)O)O
• InChI: InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1
• InChIKey: PXGPLTODNUVGFL-NAPLMKITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: 8-isoprostane
• Synonyms: (5Z,8β,9α,11α,13E,15S)-9,11,15-trihydroxyprosta-5,13-dien-1-oic Acid; 7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-Heptenoic Acid; 15(S)-8-Iso-PGF2α; 15-F2t-IsoP; 15-F2t-Isoprostane; 8-Isoprostaglandin F2α; 8-epi-PGF2α; 8-iso-Prostaglandin F2α; Isoprostaglandin F2α type-III; 8-Iso-PGF2α; 8-epi-Prostaglandin F2α

Database IDs

• CAS Number: 27415-26-5
• PubChem SID: 164232983
• PubChem CID: 5282263

CALCULATED PROPERTIES

• Acid pKa: 4.355294
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.4380769
• LogD (pH = 7.4): -0.31100234
• Log P: 2.6110544
• Molar Refractivity: 100.4707 cm^3
• Polarizability: 38.732555 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P838620

A major metabolite of PGF2α. A prostaglandin derivative used as a biomarker in the diagnosis and treatment of cardiovascular-related diseases as well as biomarkers of total body oxidative stress.

REFERENCES

• Zou, R. et al.: Yix. Linch. Yan., 26, 1751 (2009)
• Siegel, G. et a.: BIosens. Bioelec., 24, 1512 (2009)
• Nourooz-Zadeh, H. et al.: Biochem. Biophys. Res. Comm., 330, 731 (2009)