(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{2-oxo-2-[(2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]ethoxy}oxane-2-carboxylic acid

• ChemBase ID: 159667
• Molecular Formular: C27H42O11
• Molecular Mass: 542.61578
• Monoisotopic Mass: 542.27271216
• SMILES: C1[C@H](C[C@H]2[C@](C1)(C1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)CO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)O)C)C)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1C2[C@@H](O)C[C@]2([C@H]1CC[C@]2(O)C(=O)CO[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C)C
• InChI: InChI=1S/C27H42O11/c1-25-7-5-13(28)9-12(25)3-4-14-15-6-8-27(36,26(15,2)10-16(29)18(14)25)17(30)11-37-24-21(33)19(31)20(32)22(38-24)23(34)35/h12-16,18-22,24,28-29,31-33,36H,3-11H2,1-2H3,(H,34,35)/t12-,13+,14-,15-,16-,18?,19-,20-,21+,22-,24+,25-,26-,27-/m0/s1
• InChIKey: MTWBRGYEFAXTHE-GITWFIBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{2-oxo-2-[(2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{2-oxo-2-[(2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethoxy}oxane-2-carboxylic acid
• Synonyms: (3α,5α,11β)-3,11,17-Trihydroxy-20-oxopregnan-21-yl β-D-Glucopyranosiduronic Acid; allo-Tetrahydrocortisol 21-Glucuronide; Allo-3α-tetrahydro Cortisol 21-O-β-D-Glucuronide

Database IDs

• CAS Number: 131061-62-6
• PubChem SID: 162253802
• PubChem CID: 71313085

CALCULATED PROPERTIES

• Acid pKa: 3.126716
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -2.6828933
• LogD (pH = 7.4): -3.794542
• Log P: -0.33706114
• Molar Refractivity: 129.8821 cm^3
• Polarizability: 52.7527 Å^3
• Polar Surface Area: 194.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A548520

The 21-monoglucuronide conjugate of Allo-3α-tetrahydrocortisol (A548500).

REFERENCES

• Ikegawa, S. et al.: Anal. Chem., 81, 10124 (2009)