(1S,2R,11S,14R,15S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl(1,16,16,17-2H4)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 176878
• Molecular Formular: C21H28O5
• Molecular Mass: 360.44402
• Monoisotopic Mass: 360.193674
• SMILES: C1=C[C@]2(C(=CC1=O)CCC1[C@@H]2C(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)CC(O)[C@H]1C2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C21H28O5/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/h5,7,9,14-16,18,22,24,26H,3-4,6,8,10-11H2,1-2H3/t14?,15-,16?,18?,19-,20-,21-/m0/s1
• InChIKey: OIGNJSKKLXVSLS-JFARSQFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,11S,14R,15S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl(1,16,16,17-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1S,2R,11S,14R,15S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl(1,16,16,17-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (11β)-11,17,21-Trihydroxy-pregna-1,4-diene-3,20-dione; Metacortandralone; Delta F; Delta1-Hydrocortisone; Hydroretrocortine; Codelcortone; Decaprednil; Predonine; Prednisolone

Database IDs

• CAS Number: 50-24-8
• PubChem SID: 164232788
• PubChem CID: 71751744

CALCULATED PROPERTIES

• Acid pKa: 12.584675
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2729899
• LogD (pH = 7.4): 1.2729871
• Log P: 1.2729899
• Molar Refractivity: 98.4933 cm^3
• Polarizability: 38.038647 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dioxane; DMSO; Methanol,
• Apperance: White Solid
• Melting Point: 240-241°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P703740

Synthetic corticosteroid; metabolically interconvertible with prednisone.

REFERENCES

• Jusko, W.J., et al.: Ther. Drug Monit., 2, 169 (1980)
• Ali, S.L., et al.: Anal. Profiles Drug Subs. Excip., 21, 415 (1980)