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

• ChemBase ID: 168069
• Molecular Formular: C26H32O8
• Molecular Mass: 472.52748
• Monoisotopic Mass: 472.20971798
• SMILES: O(c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@]2(O)C#C)C)[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)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(32)11-9-18-17-6-4-13-12-14(5-7-15(13)16(17)8-10-25(18,26)2)33-24-21(29)19(27)20(28)22(34-24)23(30)31/h1,5,7,12,16-22,24,27-29,32H,4,6,8-11H2,2H3,(H,30,31)/t16-,17-,18+,19+,20+,21-,22+,24-,25+,26+/m1/s1
• InChIKey: DYBBEZHAELJFKW-IWTIIAAJSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 60134-76-1
• PubChem SID: 162262201
• PubChem CID: 9982244

CALCULATED PROPERTIES

• Acid pKa: 3.3003292
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.23298773
• LogD (pH = 7.4): -1.4764792
• Log P: 1.9495596
• Molar Refractivity: 119.3863 cm^3
• Polarizability: 47.45284 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: White Solid
• Melting Point: 161-163°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E685105

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