(2R,3R,4R,5S,6R)-6-{[(1S,10R,11S,14S,15S)-14-ethynyl-5-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168070
• Molecular Formular: C26H32O8
• Molecular Mass: 472.52748
• Monoisotopic Mass: 472.20971798
• SMILES: Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@]2(C#C)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)C
• Canonical SMILES: C#C[C@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C26H32O8/c1-3-26(34-24-21(30)19(28)20(29)22(33-24)23(31)32)11-9-18-17-6-4-13-12-14(27)5-7-15(13)16(17)8-10-25(18,26)2/h1,5,7,12,16-22,24,27-30H,4,6,8-11H2,2H3,(H,31,32)/t16-,17-,18+,19-,20-,21+,22-,24-,25+,26-/m1/s1
• InChIKey: SQQXJBRONRGLRT-APVVUOJSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-{[(1S,10R,11S,14S,15S)-14-ethynyl-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-{[(1S,10R,11S,14S,15S)-14-ethynyl-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (17α)-3-Hydroxy-19-norpregna-1,3,5(10)-trien-20-yn-17-yl β-D-Glucopyranosiduronic Acid; Ethynyl Estradiol 17-β-D-Glucuronide

Database IDs

• CAS Number: 75803-39-3
• PubChem SID: 162262202
• PubChem CID: 57369869

CALCULATED PROPERTIES

• Acid pKa: 3.5531397
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.50625336
• LogD (pH = 7.4): -0.91254926
• Log P: 2.446792
• Molar Refractivity: 119.6552 cm^3
• Polarizability: 47.45543 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 156-158°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E685110

A metabolite of Ethynylestradiol.

REFERENCES

• Hadd, H.H., et al.: J. Steroid Biochem., 13,1107 (1980)
• Meyers, M., et al.: J. Pharmacol. Exp. Ther., 214, 887 (1980)
• Poupon, R., et al.: Pharmacol. Ther., 66, 1 (1980)
• Catania, V., et al.: Biochem. Pharmacol., 50, 509 (1980)
• Schuetz, E., et al.: J. B