(1S,2R,10R,11R,14R,15S,17S)-11,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 171161
• Molecular Formular: C21H28O6
• Molecular Mass: 376.44342
• Monoisotopic Mass: 376.18858862
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@]1(CC[C@@]2(C(=O)CO)O)O)C)O)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@]2([C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C)O
• InChI: InChI=1S/C21H28O6/c1-18-6-5-13(23)9-12(18)3-4-14-17(18)15(24)10-19(2)20(14,26)7-8-21(19,27)16(25)11-22/h5-6,9,14-15,17,22,24,26-27H,3-4,7-8,10-11H2,1-2H3/t14-,15+,17-,18+,19+,20-,21+/m1/s1
• InChIKey: USJJKJYVBSEDNP-CNPAUTQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11R,14R,15S,17S)-11,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1S,2R,10R,11R,14R,15S,17S)-11,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: 11β,14,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione; 14α-Hydroxy PrednisoloneDISCONTINUED

Database IDs

• CAS Number: 95815-58-0
• PubChem SID: 164227071
• PubChem CID: 71749284

CALCULATED PROPERTIES

• Acid pKa: 12.491471
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.19164385
• LogD (pH = 7.4): 0.19164038
• Log P: 0.1916439
• Molar Refractivity: 99.9444 cm^3
• Polarizability: 38.68944 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952355

Prednisolone (P703740) derivative as corticosteroid.

REFERENCES

• Kobayashi, Y., et al.: Biol. Pharm. Bull., 16, 1175 (1993)
• Ogata, M., et al.: J. Pharm. Sci., 87, 91 (1993)
• Hou, S., et al.: J. Pharm. Biomed. Anal., 24, 371 (1993)