(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 166002
• Molecular Formular: C21H28O4
• Molecular Mass: 344.44462
• Monoisotopic Mass: 344.19875938
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@]2(C(=O)CO)O)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C21H28O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h5,8,11,15-17,22,25H,3-4,6-7,9-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1
• InChIKey: BVAYTJBBDODANA-OBQKJFGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: 17,21-Dihydroxypregna-1,4-diene-3,20-dione; 17α,21-Dihydroxypregna-1,4-diene-3,20-dione; 1,4-Reichstein S; Δ'-Dehydrocortexolone; 11-Deoxy Prednisolone

Database IDs

• CAS Number: 1807-14-3
• PubChem SID: 162260135
• PubChem CID: 21679441

CALCULATED PROPERTIES

• Acid pKa: 12.591037
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.5817547
• LogD (pH = 7.4): 2.5817518
• Log P: 2.5817547
• Molar Refractivity: 96.9008 cm^3
• Polarizability: 37.39907 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D249850

Prednisolone (P703740) derivative as a corticosteroid.

REFERENCES

• Kobayashi, Y., et al.: Biol. Pharm. Bull., 16, 1175 (1993)
• Ogata, M., et al.: J. Pharm. Sci., 87, 91 (1993)
• Hou, S., et al.: J. Pharm. Biomed. Anal., 24, 371 (1993)