8-[(1R,2R,5R)-2-(carboxymethyl)-5-hydroxy-3-oxocyclopentyl]-6-oxooctanoic acid

• ChemBase ID: 176428
• Molecular Formular: C15H22O7
• Molecular Mass: 314.33098
• Monoisotopic Mass: 314.13655304
• SMILES: [C@@H]1(CC(=O)O)[C@@H](CCC(=O)CCCCC(=O)O)[C@@H](CC1=O)O
• Canonical SMILES: O=C(CC[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)O)CCCCC(=O)O
• InChI: InChI=1S/C15H22O7/c16-9(3-1-2-4-14(19)20)5-6-10-11(7-15(21)22)13(18)8-12(10)17/h10-12,17H,1-8H2,(H,19,20)(H,21,22)/t10-,11-,12-/m1/s1
• InChIKey: JQPGYJSSJIANAB-IJLUTSLNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[(1R,2R,5R)-2-(carboxymethyl)-5-hydroxy-3-oxocyclopentyl]-6-oxooctanoic acid
• IUPAC Traditional name: 8-[(1R,2R,5R)-2-(carboxymethyl)-5-hydroxy-3-oxocyclopentyl]-6-oxooctanoic acid
• Synonyms: (1R,2R,5R)-2-(2-Carboxyethyl)-5-hydroxy-ε,3-dioxocyclopentaneoctanoic Acid; (-)-7α-Hydroxy-5,11-diketotetranorprostan-1,16-dioic Acid; (-)-PGE2UM; 7-Hydroxy-5,11-diketotetranorprosta-1,16-dioic Acid; PGE2UM; PGE-M

Database IDs

• CAS Number: 24769-56-0
• PubChem SID: 164232338
• PubChem CID: 71751558

CALCULATED PROPERTIES

• Acid pKa: 3.9676275
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.0328796
• LogD (pH = 7.4): -5.495626
• Log P: 0.4576217
• Molar Refractivity: 74.9882 cm^3
• Polarizability: 29.615044 Å^3
• Polar Surface Area: 128.97 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P294100

The major urinary metabolite of Prostaglandin E2 (P838610).

REFERENCES

• Boot, J., et al.: Prostaglandins, 8, 439 (1974)
• Huang, M., et al.: Cancer Res., 58, 1208 (1974)
• Dohadwala, M., et al.: J. Biol. Chem., 277, 50828 (1974)