7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]heptanoic acid

• ChemBase ID: 171963
• Molecular Formular: C20H32O5
• Molecular Mass: 352.46508
• Monoisotopic Mass: 352.22497412
• SMILES: [C@H]1([C@H]([C@@H](CC1=O)O)/C=C/C(=O)CCCCC)CCCCCCC(=O)O
• Canonical SMILES: CCCCCC(=O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O
• InChI: InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,16-17,19,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t16-,17-,19-/m1/s1
• InChIKey: VXPBDCBTMSKCKZ-XQHNHVHJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]heptanoic acid
• IUPAC Traditional name: 15-keto-PGE1
• Synonyms: (11α,13E)-11-Hydroxy-9,15-dioxo-prost-13-en-1-oic Acid; 3-Hydroxy-5-oxo-2-(3-oxo-1-octenyl)-cyclopentaneheptanoic Acid; 15-Keto-PGE1; 15-Oxo-PGE1; 15-Oxoprostaglandin E1; U 22409; 15-Keto Prostaglandin E1

Database IDs

• CAS Number: 22973-19-9
• PubChem SID: 164227873
• PubChem CID: 5280710

CALCULATED PROPERTIES

• Acid pKa: 4.3532314
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.8236368
• LogD (pH = 7.4): 1.074923
• Log P: 3.9985304
• Molar Refractivity: 97.4211 cm^3
• Polarizability: 37.889194 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Light Yellow Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - K202050

Alprostadil impurity C.

REFERENCES

• Rosen, E., et al.: J. Biol. Chem., 276, 37731 (2001)
• Xu, H., et al.: J. Clin. Investig., 112, 1821 (2001)
• Fain, J., et al.: Endocrinology, 145, 2273 (2001)
• Evans, R., et al.: Nat. Med., 10, 355 (2001)