(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({5-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-13-yl}oxy)oxane-2-carboxylic acid

• ChemBase ID: 170524
• Molecular Formular: C24H30O9
• Molecular Mass: 462.4896
• Monoisotopic Mass: 462.18898254
• SMILES: c1cc(cc2c1C1C(CC2)C2C(CC1)(C(=O)C(C2)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)C)O
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](OC2CC3C(C2=O)(C)CCC2C3CCc3c2ccc(c3)O)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C24H30O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(21(24)29)32-23-19(28)17(26)18(27)20(33-23)22(30)31/h3,5,8,13-20,23,25-28H,2,4,6-7,9H2,1H3,(H,30,31)/t13?,14?,15?,16?,17-,18-,19+,20-,23+,24?/m0/s1
• InChIKey: JLYJQBHANCHTOW-PSVFNYCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({5-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-13-yl}oxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({5-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-13-yl}oxy)oxane-2-carboxylic acid
• Synonyms: (16α)-3-Hydroxy-17-oxoestra-1,3,5(10)-trien-16-yl β-D-Glucopyranosiduronic Acid; 16α-Hydroxyestrone 16-Glucuronoside; 16α-Hydroxyestrone 16-β-D-Glucuronide

Database IDs

• CAS Number: 15270-34-5
• PubChem SID: 164226434
• PubChem CID: 71749013

CALCULATED PROPERTIES

• Acid pKa: 3.3805783
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.11873881
• LogD (pH = 7.4): -1.4208585
• Log P: 1.987402
• Molar Refractivity: 112.8553 cm^3
• Polarizability: 45.012047 Å^3
• Polar Surface Area: 153.75 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941905

A major metabolite of Estradiol.

REFERENCES

• Fishman, H.G, et al.: Biochemistry, 8, 4304 (1969)
• Ryan, Sugar, J., et al.: J. Clin. Endocrinol. Metab., 50, 137 (1969)
• Numazawa, M., et al.: Steroids, 38, 149 (1969)