(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-[2-hydroxy(2H2)acetyl]-2,4,6,15-tetramethyl(16,16-2H2)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,17-dione

• ChemBase ID: 176884
• Molecular Formular: C23H30O5
• Molecular Mass: 386.4813
• Monoisotopic Mass: 386.20932406
• SMILES: C1(=C[C@]2(C(=C(C1=O)C)CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1CC[C@@]2(C(=O)CO)O)C)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=C(C(=O)C(=C[C@]12C)C)C
• InChI: InChI=1S/C23H30O5/c1-12-9-21(3)15(13(2)20(12)27)6-5-14-16-7-8-23(28,18(26)11-24)22(16,4)10-17(25)19(14)21/h9,14,16,19,24,28H,5-8,10-11H2,1-4H3/t14-,16-,19+,21-,22-,23-/m0/s1
• InChIKey: SGWZUDFFZPYOSZ-HMPVFERBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,4,6,15-tetramethyl(16,16-^2H₂)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• IUPAC Traditional name: (1S,2R,10S,11S,14R,15S)-14-hydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,4,6,15-tetramethyl(16,16-^2H₂)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• Synonyms: 17,21-Dihydroxypregna-1,4-diene-3,11,20-trione-d4; 1,2-Dehydrocortisone-d4; 1,4-Pregnadiene-17α,21-diol-3,11,20-trione-d4; Adasone-d4; Ancortone-d4; Apo-Prednisone-d4; Bicortone-d4; Prednicorm-d4; Prednicort-d4; Retrocortine-d4; Sone-d4; Ultracorten-d4; Δ1-Dehydrocortisone-d4; Prednisone-d4 (Major)

Database IDs

• PubChem SID: 164232794
• PubChem CID: 71751751

CALCULATED PROPERTIES

• Acid pKa: 12.5762
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.4496052
• LogD (pH = 7.4): 2.4496024
• Log P: 2.4496052
• Molar Refractivity: 106.2823 cm^3
• Polarizability: 41.167843 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 218-221°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P703782

Labelled Prednisone (P703780). Adrenocortical steroid. Glucocorticoid, antiinflammatory.

REFERENCES

• Lennon, V., et al.: Lancet, 364, 2106 (2004)
• Wingerchuk, D., et al.: Neurology, 66, 1485 (2004)
• Fliri, A.F., et al.: J. Med. Chem., 52, 8038 ((2004)