7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-(2H3)methyl(5,5-2H2)oct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

• ChemBase ID: 174650
• Molecular Formular: C21H36O5
• Molecular Mass: 368.50754
• Monoisotopic Mass: 368.25627425
• SMILES: [C@H]1([C@H]([C@@H](CC1=O)O)/C=C/CC(CCCC)(O)C)CCCCCCC(=O)O
• Canonical SMILES: CCCCC(C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O)(O)C
• InChI: InChI=1S/C21H36O5/c1-3-4-13-21(2,26)14-9-11-17-16(18(22)15-19(17)23)10-7-5-6-8-12-20(24)25/h9,11,16-17,19,23,26H,3-8,10,12-15H2,1-2H3,(H,24,25)/b11-9+/t16-,17-,19-,21?/m1/s1
• InChIKey: CNWGPXZGIIOYDL-MKYGPDKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-(^2H₃)methyl(5,5-^2H₂)oct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
• IUPAC Traditional name: 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-(^2H₃)methyl(5,5-^2H₂)oct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
• Synonyms: (11α,13E)-11,16-Dihydroxy-16-methyl-9-oxo-prost-13-en-1-oic Acid-d5; Misoprostol-d5 Free Acid; (+/-)-15-Deoxy-(16RS)-16-hydroxy-16-methylprogestaglandin E1-d5; (8R,11R,12R,16RS)-Misoprostol Acid-d5

Database IDs

• PubChem SID: 164230560
• PubChem CID: 46782384

CALCULATED PROPERTIES

• Acid pKa: 4.353234
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.5369675
• LogD (pH = 7.4): 0.7882538
• Log P: 3.711861
• Molar Refractivity: 103.1107 cm^3
• Polarizability: 40.270283 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform
• Apperance: Yellow Oil

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M368762

A labelled metabolite of Misoprostol. Cytoprotective PGE1 analog that prevents NSAID-induced gastric ulceration.

REFERENCES

• Graham, Y., et al.: Lancet, 2, 1277 (1988)
• 11) Garris, R., et al.: Clin. Pharmacol., 8, 627 (1988)
• Karim, A., et al.: J. Clin. Pharmacol., 29, 439 (1988)