sodium 5-[(2Z,3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoate

• ChemBase ID: 177085
• Molecular Formular: C20H31NaO5
• Molecular Mass: 374.44691
• Monoisotopic Mass: 374.20691837
• SMILES: [C@H]12[C@H](C/C(=C/CCCC(=O)[O-])/O1)[C@H]([C@@H](C2)O)/C=C/[C@H](CCCCC)O.[Na+]
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)[O-])/O2)O.[Na+]
• InChI: InChI=1S/C20H32O5.Na/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22;/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24);/q;+1/p-1/b11-10+,15-8-;/t14-,16+,17+,18+,19-;/m0./s1
• InChIKey: LMHIPJMTZHDKEW-XQYLJSSYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 5-[(2Z,3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoate
• IUPAC Traditional name: sodium prostaglandin I2(1-)
• Synonyms: (5Z,9α,11α,13E,15S)-6,9-epoxy-11,15-Dihydroxy-prosta-5,13-dien-1-oic Acid Sodium Salt; Epoprostenol Sodium; Flolan; Prostacyclin Sodium Salt

Database IDs

• CAS Number: 61849-14-7
• PubChem SID: 164232995
• PubChem CID: 6364626

CALCULATED PROPERTIES

• Acid pKa: 4.4292903
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.3110825
• LogD (pH = 7.4): -0.44954696
• Log P: 2.4157045
• Molar Refractivity: 109.844 cm^3
• Polarizability: 37.96977 Å^3
• Polar Surface Area: 89.82 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P839060

An Eicosanoid which prevents the formation of platelet plugs and is an effective vasodilator.

REFERENCES

• Badesch, D., et al.: J. Rheumatol., 36, 2244 (2009)
• Darios, F., et al.: Neuron, 62, 683 (2009)
• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2009)