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

• ChemBase ID: 174649
• Molecular Formular: C22H38O5
• Molecular Mass: 382.53412
• Monoisotopic Mass: 382.27192432
• SMILES: [C@H]1([C@H]([C@@H](CC1=O)O)/C=C/CC(CCCC)(O)C)CCCCCCC(=O)OC
• Canonical SMILES: CCCCC(C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC)(O)C
• InChI: InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1
• InChIKey: OJLOPKGSLYJEMD-URPKTTJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-(^2H₃)methyl(5,5-^2H₂)oct-1-en-1-yl]-5-oxocyclopentyl]heptanoate
• IUPAC Traditional name: methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-(^2H₃)methyl(5,5-^2H₂)oct-1-en-1-yl]-5-oxocyclopentyl]heptanoate
• Synonyms: (11α,13E)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic Acid-d5 Methyl Ester; Cytotec-d5; Misogon-d5; Misoprostil-d5; SC 29333-d5; (8R,11R,12R,16RS)-Misoprostol-d5

Database IDs

• PubChem SID: 164230559
• PubChem CID: 46782383

CALCULATED PROPERTIES

• Acid pKa: 14.680623
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.857755
• LogD (pH = 7.4): 3.857755
• Log P: 3.857755
• Molar Refractivity: 107.8798 cm^3
• Polarizability: 42.359562 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M368752

Labelled Misoprostol, a cytoprotective prostaglandin PGE1 analogue.This compound is a mixture of only 2 diastereomers as opposed to the double racemate (4 diasteromers) of misoprostol.

REFERENCES

• Graham, Y., et al.: Lancet, 2, 1277 (1988)
• Graham, D.Y., et al.: Ann. Int. Med., 119, 257 (1988)
• Fletcher, H., et al.: Obstet. Gynecol., 83, 244 (1994)