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

• ChemBase ID: 173505
• Molecular Formular: C22H28O4
• Molecular Mass: 356.45532
• Monoisotopic Mass: 356.19875938
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1C2=CC[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=C1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C22H28O4/c1-13-10-18-16-5-4-14-11-15(24)6-8-20(14,2)17(16)7-9-21(18,3)22(13,26)19(25)12-23/h6-8,11,13,16,18,23,26H,4-5,9-10,12H2,1-3H3/t13-,16-,18+,20+,21+,22+/m1/s1
• InChIKey: ZYTXTXAMMDTYDQ-DGEXFFLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,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-1(17),3,6-trien-5-one
• IUPAC Traditional name: (2S,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-1(17),3,6-trien-5-one
• Synonyms: (16α)-17,21-Dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione; 17α,21-Dihydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione; 16α-Methyl-9,11-dehydro Prednisolone

Database IDs

• CAS Number: 13209-41-1
• PubChem SID: 164229415
• PubChem CID: 3035000

CALCULATED PROPERTIES

• Acid pKa: 12.445657
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.541148
• LogD (pH = 7.4): 2.5411441
• Log P: 2.541148
• Molar Refractivity: 102.2224 cm^3
• Polarizability: 38.995285 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M295300

A related intermediate of Prednisolone (P703740).

REFERENCES

• Cimarusti, C., et al.: J. Med. Chem., 19, 721 (1976)
• Popper, T., et al.: J. Steroid Biochem., 27, 837 (1976)