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

• ChemBase ID: 178334
• Molecular Formular: C27H42O10
• Molecular Mass: 526.61638
• Monoisotopic Mass: 526.27779754
• SMILES: C1[C@H](C[C@@H]2[C@](C1)(C1[C@@H](CC2)[C@H]2[C@](CC1)([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)CCC1[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/C27H42O10/c1-25-8-5-14(36-24-21(32)19(30)20(31)22(37-24)23(33)34)11-13(25)3-4-15-16(25)6-9-26(2)17(15)7-10-27(26,35)18(29)12-28/h13-17,19-22,24,28,30-32,35H,3-12H2,1-2H3,(H,33,34)/t13-,14-,15-,16?,17+,19+,20+,21-,22+,24-,25+,26+,27+/m1/s1
• InChIKey: GAIOPZSMDANHBK-JVMSDKPCSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 56162-40-4
• PubChem SID: 164234244
• PubChem CID: 71752449

CALCULATED PROPERTIES

• Acid pKa: 3.4672441
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -1.051439
• LogD (pH = 7.4): -2.4132173
• Log P: 0.97170365
• Molar Refractivity: 128.2896 cm^3
• Polarizability: 52.07563 Å^3
• Polar Surface Area: 173.98 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T293395

The 3-monoglucuronide conjugate of Tetrahydro-11-deoxycortisol (T293390).

REFERENCES

• Hosoda, H. et al.: Chem. Pharmac. Bull., 31, 4001 (1983)
• Ikegawa, S. et al.: Anal. Chem., 81, 10124 (1983)