5-[(2E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene](2,2,3,3-2H4)pentanoic acid

• ChemBase ID: 171528
• Molecular Formular: C22H32O4
• Molecular Mass: 360.48708
• Monoisotopic Mass: 360.2300595
• SMILES: [C@@H]1([C@@H]([C@@H]2[C@H](C1)C/C(=C\CCCC(=O)O)/C2)/C=C/[C@H](C(CC#CC)C)O)O
• Canonical SMILES: CC#CCC([C@@H](/C=C/[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)C
• InChI: InChI=1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18+,19-,20+,21+/m0/s1
• InChIKey: HIFJCPQKFCZDDL-ACWOEMLNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene](2,2,3,3-^2H₄)pentanoic acid
• IUPAC Traditional name: 5-[(2E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-hexahydro-1H-pentalen-2-ylidene](2,2,3,3-^2H₄)pentanoic acid
• Synonyms: (5E)-5-[(3aS,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-yn-1-yl]-2(1H)-pentalenylidene]pentanoic Acid-d4; (1S,2R,3R,5S)-7-[(E)-4-Carboxybutylidene]-2-[(3S,1E)-3-hydroxy-4-methyl-6-octyn-1-enyl]-bicyclo[3.3.0]octane-d4; Ciloprost-d4; Endoprost-d4; Ilomedin-d4; ZK 36374-d4; Iloprost-d4

Database IDs

• PubChem SID: 164227438
• PubChem CID: 58025202

CALCULATED PROPERTIES

• Acid pKa: 4.664816
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.6708264
• LogD (pH = 7.4): 0.8930734
• Log P: 3.5643785
• Molar Refractivity: 105.1822 cm^3
• Polarizability: 39.96046 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I267302

A labelled synthetic analogue of Prostacyclin (PGI2) used to treat pulmonary arterial hypertension (PAH), scleroderma, Raynaud's phenomenon and ischemia. It acts through elevation of cAMP by binding to the prostacyclin receptor (IP receptor). Iloprost inh

REFERENCES

• Zamudio, T.P.: Arch. Cardiol. Mex., 77, 198 (2007)
• Lai, Y. et al.: Am. J. Resp. Crit. Care Med., 178, 188 (2007)
• Scorza, R. et al.: J. Rheutamol., 24, 1944 (2007)
• Melillo, E. et al.: Int. J. Microcircul. Clin. Exp., 15, 60 (2007)