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

• ChemBase ID: 177072
• Molecular Formular: C20H32O5
• Molecular Mass: 352.46508
• Monoisotopic Mass: 352.22497412
• SMILES: [C@@H]1(C/C=C\CCCC(=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]1C/C=C\CCCC(=O)O)O
• InChI: InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
• InChIKey: XEYBRNLFEZDVAW-ARSRFYASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl](3,3,4,4-^2H₄)hept-5-enoic acid
• IUPAC Traditional name: prostaglandin E2-d4
• Synonyms: (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic Acid-d4; 7-[3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic Acid-d4; (-)-Prostaglandin E2-d4; (15S)-Prostaglandin E2-d4; Cervidil-d4; Cerviprime-d4; Cerviprost-d4; Dinoprostone-d4; Minprostin E2-d4; PGE2-d4; Prepidil-d4; Primiprost-d4; Prostin E2-d4; l-PGE2-d4; Prostaglandin E2-d4

Database IDs

• PubChem SID: 164232982
• PubChem CID: 5283031

CALCULATED PROPERTIES

• Acid pKa: 4.3033595
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.0038702
• LogD (pH = 7.4): 0.2647247
• Log P: 3.22527
• Molar Refractivity: 99.4351 cm^3
• Polarizability: 38.188305 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P838612

Labelled analogue of Prostaglandin E2. The most common and most biologically potent of mammalian prostaglandins. Isolated from sheep prostate. Oxytocic; abortifacient.

REFERENCES

• Van Dorp, D.A. et al.: Biochem. Biopphys. Acta, 90, 204 (1964)
• Hamberg, M. et al.: J. Biol. Chem., 246, 6713 (1964)