2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl (2H3)acetate

• ChemBase ID: 176886
• Molecular Formular: C23H28O6
• Molecular Mass: 400.46482
• Monoisotopic Mass: 400.18858862
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1CC[C@@]2(C(=O)COC(=O)C)O)C)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=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/h6,8,10,16-17,20,28H,4-5,7,9,11-12H2,1-3H3/t16-,17-,20+,21-,22-,23-/m0/s1
• InChIKey: MOVRKLZUVNCBIP-RFZYENFJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl (^2H₃)acetate
• IUPAC Traditional name: 2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl (^2H₃)acetate
• Synonyms: Nisone-d3; NSC 10965-d3; Prednisone 21-Acetate-d3; 21-(Acetyloxy-d3)-17-hydroxy-pregna-1,4-diene-3,11,20-trione; 21-(Acetoxy-d3)-17α-hydroxypregna-1,4-diene-3,11,20-trione; Prednisone Acetate-d3; 1-Cortisone 21-Acetate-d3; 1-Dehydrocortisone Acetate-d3; Cortancyl-d3; Delcortin-d3; Δ-Corlin-d3; Deltalone-d3; Ferrosan-d3

Database IDs

• PubChem SID: 164232796
• PubChem CID: 71751752

CALCULATED PROPERTIES

• Acid pKa: 12.601158
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.0996296
• LogD (pH = 7.4): 2.0996268
• Log P: 2.0996296
• Molar Refractivity: 106.7196 cm^3
• Polarizability: 41.342445 Å^3
• Polar Surface Area: 97.74 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P703827

Labelled Prednisone 21-Acetate (P703825). Adrenocortical steroid antiinflammatory.

REFERENCES

• Zhang, L., et al.: App. Biochem. Biotechnol., 159, 642 (2009)
• Ma, Y., J. Steroid Biochem. Mol. Biol., 117, 146 (2009)