sodium (2S,3S,4S,5R,6R)-6-{[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 178185
• Molecular Formular: C25H35NaO8
• Molecular Mass: 486.53037
• Monoisotopic Mass: 486.22296236
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)[O-])O)O)O)C)C.[Na+]
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O)C)C.[Na+]
• InChI: InChI=1S/C25H36O8.Na/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31;/h11,14-21,23,27-29H,3-10H2,1-2H3,(H,30,31);/q;+1/p-1/t14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-;/m0./s1
• InChIKey: JUXKYFINRYJTDA-XHPOIRKISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6R)-6-{[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6R)-6-{[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: (17β)-3-Oxoandrost-4-en-17-yl β-D-Glucopyranosiduronic Acid Monosodium; Testosterone 17-Glucosiduronate Monosodium; Testosterone 17-Glucuronide Monosodium; Testosterone Glucuronoside Monosodium; Testosterone β-D-Glucuronide Monosodium Salt

Database IDs

• CAS Number: 4145-59-9
• PubChem SID: 164234095
• PubChem CID: 71752376

CALCULATED PROPERTIES

• Acid pKa: 3.6274605
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 0.046001736
• LogD (pH = 7.4): -1.4184029
• Log P: 1.9148622
• Molar Refractivity: 127.5476 cm^3
• Polarizability: 46.71854 Å^3
• Polar Surface Area: 136.35 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 287-290°C (dec.)

DETAILS

Toronto Research Chemicals - T155040

Metabolite of Testosterone (T155000).

REFERENCES

• Shibata, N., et al.: Biochem. J., 368, 783 (2002)
• Sonneveld, E., et al.: Toxicol. Sci., 83, 136 (2002)
• Schulze, J., et al.: J. Clin. Endocrinol. Metab., 93, 2500 (2002)
• Sten, T., et al.: Drug Metab. Disposition, 37, 417 (2002)