sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxo(4,6,13,13-2H4)tetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 168275
• Molecular Formular: C24H29NaO8
• Molecular Mass: 468.47203
• Monoisotopic Mass: 468.17601217
• SMILES: [C@H]1(O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-])Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C.[Na+]
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](Oc2ccc3c(c2)CC[C@@H]2[C@@H]3CC[C@]3([C@H]2CCC3=O)C)O[C@H]([C@H]1O)C(=O)[O-].[Na+]
• InChI: InChI=1S/C24H30O8.Na/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;/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30);/q;+1/p-1/t14-,15-,16+,18+,19+,20-,21+,23-,24+;/m1./s1
• InChIKey: PBULYLQKWDXDFZ-QHIGSJCSSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxo(4,6,13,13-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxo(4,6,13,13-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylate
• Synonyms: 17-Oxoestra-1,3,5(10)-trien-3-yl-d4 β-D-Glucopyranosiduronic Acid Sodium; Estrone-d5 β-Glucuronide Sodium; Estrone-d5 3-Glucuronide Sodium; Estrone-d5 Glucosiduronate Sodium; Estrone-d5 Glucuronide Sodium; Estrone-d5 Monoglucuronide Sodium; Sodium Estrone-d5 Glucuronide; Estrone-d5 β-D-Glucuronide Sodium Salt

Database IDs

• PubChem SID: 162262407
• PubChem CID: 71316491

CALCULATED PROPERTIES

• Acid pKa: 3.3003154
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 0.17867953
• LogD (pH = 7.4): -1.0648052
• Log P: 2.3612354
• Molar Refractivity: 121.9313 cm^3
• Polarizability: 44.23592 Å^3
• Polar Surface Area: 136.35 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E889057

A labelled metabolite of 17β -Estradiol (E888000).

REFERENCES

• Cekan, S., et al.: J. Steroid Biochem., 27, 95 (1989)
• Martin, R., et al.: Clin. Chem., 46, 100 (1989)
• Blackwell, L., et al.: Steroids, 68, 465 (2003)