(2S,3S,4S,5R,6R)-6-{[(2S,5R,7S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 159665
• 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)O)C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)C1[C@H]2CC[C@@H]2[C@]1(C)CC[C@H](C2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H42O11/c1-25-7-5-13(37-24-21(33)19(31)20(32)22(38-24)23(34)35)9-12(25)3-4-14-15-6-8-27(36,17(30)11-28)26(15,2)10-16(29)18(14)25/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: OZINUFSVVJAFHD-GITWFIBDSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 30954-21-3
• PubChem SID: 162253800
• PubChem CID: 71313083

CALCULATED PROPERTIES

• Acid pKa: 3.4672441
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -2.360204
• LogD (pH = 7.4): -3.721982
• 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 - A548510

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

REFERENCES

• Ikegawa, S. et al.: Anal. Chem., 81, 10124 (2009)
• Kornel, L. et al.: J. Steroid. Biochem., 13, 751 (2009)
• Kornel, L. et al.: J. Steroid Biochem., 6, 1267 (2009)