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

• ChemBase ID: 168232
• Molecular Formular: C24H32O8
• Molecular Mass: 448.50608
• Monoisotopic Mass: 448.20971798
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](O[C@H]2CC[C@@H]3[C@]2(C)CC[C@H]2[C@H]3CCc3c2ccc(c3)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C24H32O8/c1-24-9-8-14-13-5-3-12(25)10-11(13)2-4-15(14)16(24)6-7-17(24)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-21,23,25-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,17+,18+,19+,20-,21+,23-,24+/m1/s1
• InChIKey: MTKNDAQYHASLID-QXYWQCSFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: estradiol-17β-glucuronide
• Synonyms: (17β)-3-Hydroxyestra-1,3,5(10)-trien-17-yl β-D-Glucopyranosiduronic Acid; Estradiol 17-Glucuronide; Estradiol 17β-(β-D-Glucuronide); 17β-Estradiol 17β-D-Glucuronide

Database IDs

• CAS Number: 1806-98-0
• PubChem SID: 162262364
• PubChem CID: 5281887

CALCULATED PROPERTIES

• Acid pKa: 3.6274602
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.42607334
• LogD (pH = 7.4): -1.0388355
• Log P: 2.2949402
• Molar Refractivity: 112.1854 cm^3
• Polarizability: 44.87979 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E888015

A metabolite of Estradiol (E888000).

REFERENCES

• Agasan, A., et al.: J. Immunol. Methods., 177, 251 (1994)
• Stone, R., et al.: Science, 265, 308 (1994)
• Tacey, R., et al.: J. Pharm. Biomed. Anal., 2, 1303 (1994)