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

• ChemBase ID: 156452
• 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/t15-,16-,17+,18-,20+;/m0./s1
• InChIKey: OURCVRVJQMLUNA-LKBJAGTKSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-3-ylidene]pentanoate
• IUPAC Traditional name: sodium 5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(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; Epoprostenol 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: 162250590
• PubChem CID: 71312320

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, clear, colorless to faintly yellow

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: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C20H31NaO5

DETAILS

Sigma Aldrich - 82478

Biochem/physiol Actions
Prostacyclin therapy improves hemodynamics in pulmonary arterial hypertension.1