2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6,8-trien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 165681
• Molecular Formular: C23H28O6
• Molecular Mass: 400.46482
• Monoisotopic Mass: 400.18858862
• SMILES: C1=C[C@]2(C(=CC1=O)C=C[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1CC[C@@]2(C(=O)COC(=O)C)O)C)O)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C=CC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C23H28O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h4-6,8,10,16-18,20,26,28H,7,9,11-12H2,1-3H3/t16-,17-,18-,20+,21-,22-,23-/m0/s1
• InChIKey: HOYYRILTTRZHTJ-JZYPGELDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-14-yl]-2-oxoethyl acetate
• Synonyms: (11β)-11,17,21-Trihydroxypregna-1,4,6-triene-3,20-dione 21-Acetate; 6,7-Dehydro Prednisolone 21-Acetate

Database IDs

• CAS Number: 2427-45-4
• PubChem SID: 162259814
• PubChem CID: 18594066

CALCULATED PROPERTIES

• Acid pKa: 12.609578
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.3521936
• LogD (pH = 7.4): 1.352191
• Log P: 1.3521937
• Molar Refractivity: 108.7614 cm^3
• Polarizability: 41.63834 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - D230010

Protected Prednisone metabolite.

REFERENCES

• Csanadi, A., et al.: Pharm., 59, 349 (2004)