(1S,2R,10S,11S,13R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,17-dione

• ChemBase ID: 173506
• Molecular Formular: C22H28O5
• Molecular Mass: 372.45472
• Monoisotopic Mass: 372.193674
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1C[C@H]([C@@]2(C(=O)CO)O)C)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-20(13,2)19(15)17(25)10-21(16,3)22(12,27)18(26)11-23/h6-7,9,12,15-16,19,23,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,19-,20+,21+,22+/m1/s1
• InChIKey: PIDANAQULIKBQS-VUOZLLHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,13R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[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,13R,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• Synonyms: (16α)-17,21-Dihydroxy-16-methylpregna-1,4-diene-3,11,20-trione; 16α-Methyl-11-oxo Prednisolone

Database IDs

• CAS Number: 2036-77-3
• PubChem SID: 164229416
• PubChem CID: 68141632

CALCULATED PROPERTIES

• Acid pKa: 12.440329
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.0234768
• LogD (pH = 7.4): 2.023473
• Log P: 2.023477
• Molar Refractivity: 102.0397 cm^3
• Polarizability: 39.331356 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M295350

A 16α-substituted Prednisolone as potent topical antiinflammatory agent.

REFERENCES

• Lutsky, B.N., et al.: Arzneim.-Forsch., 29, 1662 (1979)