(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6,8-trien-5-one

• ChemBase ID: 165680
• Molecular Formular: C21H26O5
• Molecular Mass: 358.42814
• Monoisotopic Mass: 358.17802393
• 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)CO)O)C)O)C
• Canonical SMILES: 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/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h3-5,7,9,14-16,18,22,24,26H,6,8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
• InChIKey: WFFSJFFZKKRVOE-VWUMJDOOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,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]heptadeca-3,6,8-trien-5-one
• IUPAC Traditional name: (1S,2R,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]heptadeca-3,6,8-trien-5-one
• Synonyms: (11β)-11,17,21-Trihydroxypregna-1,4,6-triene-3,20-dione; 11β,17,21-Trihydroxypregna-1,4,6-triene-3,20-dione; NSC 12882; 6(7)-Dehydro Prednisolone; 6-Dehydro Prednisolone

Database IDs

• CAS Number: 2427-64-7
• PubChem SID: 162259813
• PubChem CID: 224451

CALCULATED PROPERTIES

• Acid pKa: 12.584113
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.91106826
• LogD (pH = 7.4): 0.9110654
• Log P: 0.91106826
• Molar Refractivity: 99.6099 cm^3
• Polarizability: 37.7933 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 218-222°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D230000

A metabolite of Prednisone (P703780).

REFERENCES

• Watkins, P., et al.: Clin. Pharmacol. Ther., 52, 265 (1992)
• Hakkola, J., et al.: Biochem. Pharmacol., 52, 379 (1992)
• Nakamura, H., et al.: Eur. J. Clin. Pharmacol., 53, 343 (1992)