7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl](3,3,4,4-2H4)heptanoic acid

• ChemBase ID: 177071
• Molecular Formular: C20H34O5
• Molecular Mass: 354.48096
• Monoisotopic Mass: 354.24062419
• SMILES: [C@@H]1(CCCCCCC(=O)O)[C@@H](/C=C/[C@H](CCCCC)O)[C@@H](CC1=O)O
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
• InChIKey: GMVPRGQOIOIIMI-DWKJAMRDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl](3,3,4,4-^2H₄)heptanoic acid
• IUPAC Traditional name: 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl](3,3,4,4-^2H₄)heptanoic acid
• Synonyms: Palux-d4; Prostandin-d4; Minprog-d4; NSC 165559-d4; Topiglan-d4; U 10136-d4; Vasaprostan-d4; l-PGE1-d4; l-Prostaglandin E1-d4; Prostaglandin E1-d4; (11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-oic Acid-d4; 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic Acid-d4; Alprostadil-d4; Alprox TD-d4; Caveject-d4; Liprostin-d4; ONO 1608-d4; PGE1-d4

Database IDs

• PubChem SID: 164232981
• PubChem CID: 71751857

CALCULATED PROPERTIES

• Acid pKa: 4.353232
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.4122984
• LogD (pH = 7.4): 0.6635846
• Log P: 3.5871918
• Molar Refractivity: 98.3185 cm^3
• Polarizability: 38.432873 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P838602

Labelled analogue of Prostaglandin E1. A primary Prostaglandin; easily crystallized from purified biological extracts. Vasodilator (peripheral).

REFERENCES

• Anggard, S. et al.: J. Biol. Chem., 239, 4097 (1964)
• Wooster, D.L. et al.: J. Am. Med. Assoc., 245, 1846 (1964)
• Linet, O.I. et al.: N. Engl. J. Med., 334, 873 (1964)