(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 174956
• Molecular Formular: C24H34O8
• Molecular Mass: 450.52196
• Monoisotopic Mass: 450.22536805
• SMILES: C1C(=O)C=C2[C@H](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
• Canonical SMILES: O=C1CC[C@H]2C(=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
• InChI: InChI=1S/C24H34O8/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/h10,13-21,23,26-28H,2-9H2,1H3,(H,29,30)/t13-,14+,15+,16-,17-,18-,19-,20+,21-,23+,24-/m0/s1
• InChIKey: ISBYSZZUCBXGIH-BWMLPLRISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (17β)-3-Oxoestr-4-en-17-yl β-D-Glucopyranosiduronic Acid; Nandrolone β-D-Glucuronide

Database IDs

• CAS Number: 131749-24-1
• PubChem SID: 164230866
• PubChem CID: 20598907

CALCULATED PROPERTIES

• Acid pKa: 3.6274605
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.2540454
• LogD (pH = 7.4): -1.7184501
• Log P: 1.6148151
• Molar Refractivity: 112.2354 cm^3
• Polarizability: 45.004173 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N315030

Metabolite of Nandrolone (N315000)

REFERENCES

• Hoogenboom, L., et al.: Drug Metab. Disposition, 18, 999 (1990)
• Hintikka, L., et al.: Steroids, 73, 257 (1990)