(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

• ChemBase ID: 163676
• Molecular Formular: C21H36O5
• Molecular Mass: 368.50754
• Monoisotopic Mass: 368.25627425
• SMILES: [C@H]1([C@H]([C@@H](C[C@@H]1O)O)/C=C/[C@@](CCCCC)(C)O)C/C=C\CCCC(=O)O
• Canonical SMILES: CCCCC[C@@](/C=C/[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)(O)C
• InChI: InChI=1S/C21H36O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,19-,21+/m1/s1
• InChIKey: DLJKPYFALUEJCK-IIELGFQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: carboprost
• Synonyms: (5Z,9α,11α,13E,15S)-9,11,15-Trihydroxy-15-methylprosta-5,13-dien-1-oic Acid; (15S)-15-Methyl-PGF2α; (15S)-15-Methylprostaglandin F2α; 15-Methyl-PGF2α; 15-Methylprostaglandin F2α; U 32921; Carboprost

Database IDs

• CAS Number: 35700-23-3
• PubChem SID: 162257811
• PubChem CID: 5281075

CALCULATED PROPERTIES

• Acid pKa: 4.3552947
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.7186534
• LogD (pH = 7.4): -0.030425675
• Log P: 2.8916311
• Molar Refractivity: 105.1089 cm^3
• Polarizability: 40.570885 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off- White Solid
• Melting Point: 79-82°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C177580

Analog of prostaglandin F2α. Oxytocic.

REFERENCES

• Weeks, J.R., et al.: J. Pharmacol. Exp. Ther., 67, 186 (1973)
• Csapo, A.I., et al.: Prostaglandins, 18, 479 (1973)
• Schwallie, P.C., et al.: J. Reprod. Med., 23, 289 (1973)
• Mapa, M.P., et al.: Int. J. Gynaecol. Obstet., 20, 125 (1973)