methyl 7-[(1R,2S)-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoate

• ChemBase ID: 165711
• Molecular Formular: C22H36O4
• Molecular Mass: 364.51884
• Monoisotopic Mass: 364.26135963
• SMILES: [C@H]1([C@H](C=CC1=O)/C=C/CC(CCCC)(O)C)CCCCCCC(=O)OC
• Canonical SMILES: CCCCC(C/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)OC)(O)C
• InChI: InChI=1S/C22H36O4/c1-4-5-16-22(2,25)17-10-11-18-14-15-20(23)19(18)12-8-6-7-9-13-21(24)26-3/h10-11,14-15,18-19,25H,4-9,12-13,16-17H2,1-3H3/b11-10+/t18-,19+,22?/m0/s1
• InChIKey: OCWJVIUDOHXKHI-PWNUKQCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 7-[(1R,2S)-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoate
• IUPAC Traditional name: methyl 7-[(1R,2S)-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoate
• Synonyms: (13E)-(+/-)-16-Hydroxy-16-methyl-9-oxoprosta-10,13-dien-1-oic Acid Methyl Ester; 10,11-Dehydro Misoprostol(Mixture of Diastereomers)

Database IDs

• CAS Number: 58682-86-3
• PubChem SID: 162259844
• PubChem CID: 6443814

CALCULATED PROPERTIES

• Acid pKa: 18.789791
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.0084357
• LogD (pH = 7.4): 5.0084357
• Log P: 5.0084357
• Molar Refractivity: 107.5346 cm^3
• Polarizability: 41.492405 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D230590

Misoprostol (M368750) impurity.

REFERENCES

• Lee, H.K., et al.: J. Pharma. Sci., 73, 306 (1984)