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

• ChemBase ID: 133752
• Molecular Formular: C20H31NaO5
• Molecular Mass: 374.44691
• Monoisotopic Mass: 374.20691837
• SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1/C(=C\CCCC(=O)[O-])/CO2)O)O.[Na+]
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1/C(=C\CCCC(=O)[O-])/CO2)O.[Na+]
• InChI: InChI=1S/C20H32O5.Na/c1-2-3-4-8-15(21)10-11-16-17(22)12-18-20(16)14(13-25-18)7-5-6-9-19(23)24;/h7,10-11,15-18,20-22H,2-6,8-9,12-13H2,1H3,(H,23,24);/q;+1/p-1/b11-10+,14-7-;/t15-,16-,17+,18-,20+;/m0./s1
• InChIKey: OURCVRVJQMLUNA-QFDVFERUSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 5-[(3E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-3-ylidene]pentanoate
• IUPAC Traditional name: sodium 5-[(3E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydrocyclopenta[b]furan-3-ylidene]pentanoate
• Synonyms: (5Z,9α,11α,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid sodium salt; PGI2-Na; Prostacyclin sodium salt; Prostaglandin I2 sodium salt; Epoprostenol 钠

Database IDs

• CAS Number: 61849-14-7
• EC Number: 263-273-7
• MDL Number: MFCD00135629
• Beilstein Number: 6472195
• PubChem SID: 24898653; 162228029
• PubChem CID: 23702145

CALCULATED PROPERTIES

• Acid pKa: 4.398562
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.1578689
• LogD (pH = 7.4): -0.59833145
• Log P: 2.2907794
• Molar Refractivity: 109.2534 cm^3
• Polarizability: 37.96977 Å^3
• Polar Surface Area: 89.82 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble50 mg/mL; H2O: soluble1 mg/mL (Hydrolyzes to 6-ketoprostaglandin F1α in aqueous solution.)
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥96% (HPLC)
• Biological Source: synthetic

DETAILS

Sigma Aldrich - P6188

Biochem/physiol Actions
Prostacyclin is a short-lived product of the cyclooxygenase pathway in vascular endothelial cells. It is a potent inhibitor of platelet aggregation by antagonizing thromboxane A2 and stimulating platelet adenylyl cyclase.1 Nitric oxide is also produced in vascular endothelium where it inhibits platelet aggregation, regulates inducible cyclooxygenase production, and may work synergistically with prostacyclin to attenuate the thrombotic process. Prostacyclin is vasoprotective, protecting arterial walls from injury-induced lesions and cytoprotective in the liver and gastrointestinal tract.
Prostacyclin therapy improves hemodynamics in pulmonary arterial hypertension.