(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyl(13,13,14-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 168231
• Molecular Formular: C24H32O8
• Molecular Mass: 448.50608
• Monoisotopic Mass: 448.20971798
• SMILES: O(c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](Oc2ccc3c(c2)CC[C@@H]2[C@@H]3CC[C@]3([C@H]2CC[C@@H]3O)C)O[C@H]([C@H]1O)C(=O)O
• InChI: InChI=1S/C24H32O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)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: MUOHJTRCBBDUOW-QXYWQCSFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyl(13,13,14-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyl(13,13,14-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (17β)-17-Hydroxyestra-1,3,5(10)-trien-3-yl-d3 β-D-Glucopyranosiduronic Acid; 3-(β-D-Glucopyranuronosyloxy) Estra-1,3,5(10)-trien-17β-ol-d3; Estradiol-16,16,17-d3 3-Glucuronide; 17β-Estradiol-d3 3-β-D-Glucuronide

Database IDs

• CAS Number: 1260231-06-8
• PubChem SID: 162262363
• PubChem CID: 71316461

CALCULATED PROPERTIES

• Acid pKa: 3.3003535
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.384839
• LogD (pH = 7.4): -1.6283308
• Log P: 1.7977078
• Molar Refractivity: 111.9165 cm^3
• Polarizability: 44.877213 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 to Off-White Solid
• Melting Point: 184-189°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E888012

A labelled 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)