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-oxoacetaldehyde

• ChemBase ID: 176885
• Molecular Formular: C21H24O5
• Molecular Mass: 356.41226
• Monoisotopic Mass: 356.16237387
• 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)C=O)O)C)C
• Canonical SMILES: O=CC(=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/C21H24O5/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/h5,7,9,11,14-15,18,26H,3-4,6,8,10H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
• InChIKey: ZJGKMJHMOAPNRY-ZPOLXVRWSA-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-oxoacetaldehyde
• 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-oxoacetaldehyde
• Synonyms: 17-Hydroxy-3,11,20-trioxopregna-1,4-dien-21-al; Prednisone 21-Aldehyde

Database IDs

• CAS Number: 70522-55-3
• PubChem SID: 164232795
• PubChem CID: 57369834

CALCULATED PROPERTIES

• Acid pKa: 12.510128
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.5654228
• LogD (pH = 7.4): 2.5654194
• Log P: 2.565423
• Molar Refractivity: 96.7222 cm^3
• Polarizability: 36.953156 Å^3
• Polar Surface Area: 88.51 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Pale Yellow Solid

Safety Information

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

DETAILS

Toronto Research Chemicals - P703800

Prednisone derivative. An antiviral compound. Corticosteroid.

REFERENCES

• Monder, C., et al.: J. Biol. Chem., 238, 767 (1963)
• Cavallini, G., et al.: J. Med. Chem., 7, 673 (1963)