7-[(1R,2R,3R)-3-hydroxy-2-(4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl]heptanoic acid

• ChemBase ID: 155178
• Molecular Formular: C21H36O5
• Molecular Mass: 368.50754
• Monoisotopic Mass: 368.25627425
• SMILES: CCCCC(C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)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)/t16-,17-,19-,21?/m1/s1
• InChIKey: CNWGPXZGIIOYDL-AOJMRFDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R)-3-hydroxy-2-(4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl]heptanoic acid; 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
• IUPAC Traditional name: 7-[(1R,2R,3R)-3-hydroxy-2-(4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl]heptanoic acid; 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
• Synonyms: (±)-15-Deoxy-(16RS)-16-hydroxy-16-methylprostaglandin E1; Misoprostol free acid; (11α,13E)-(+/-)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic Acid Methyl Ester; Cytotec; Misogon; Misoprostil; SC 29333; Misoprostol Acid, Technical Grade 65%DISCONTINUED. See M368760; (11α,13E)-11,16-Dihydroxy-16-methyl-9-oxo-prost-13-en-1-oic Acid; Misoprostol Free Acid; (+/-)-15-Deoxy-(16RS)-16-hydroxy-16-methylprogestaglandin E1; Misoprostol Acid (10 mg in 1 mL Methyl Acetate)

Database IDs

• CAS Number: 112137-89-0
• MDL Number: MFCD00869984
• PubChem SID: 24897131; 162249316
• PubChem CID: 6436406

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: Chloroform; Methanol; Methyl Acetate
• Apperance: Clear Colorless solution; Pale Yellow Gel

Safety Information

• Storage Condition: -20°C Freezer; -86?C Freezer
• European Hazard Symbols: Toxic (T)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 60-61-25-36/37/38
• Safety Statements: 53-26-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335-H361
• GHS Precautionary statements: P261-P281-P301 + P310-P305 + P351 + P338
• RID/ADR: UN 2810 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%
• Empirical Formula (Hill Notation): C21H36O5

DETAILS

Sigma Aldrich - M6932

Biochem/physiol Actions
Misoprostol is a synthetic prostaglandin E1 (PGE1) analogue use to prevent non steroidal anti inflammatory drug-induced (NSAID) gastric ulcers; as a labor inducing and postpartum hemorrhage treatment agent.

Toronto Research Chemicals - M368760

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

Toronto Research Chemicals - M368761

A cytoprotective prostaglandin PGE1 analogue.

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)
• 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)