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

• ChemBase ID: 178430
• Molecular Formular: C21H28O6
• Molecular Mass: 376.44342
• Monoisotopic Mass: 376.18858862
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]([C@H](C2)O)(C(=O)CO)O)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@@H](O)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C21H28O6/c1-19-6-5-12(23)7-11(19)3-4-13-14-8-16(25)21(27,17(26)10-22)20(14,2)9-15(24)18(13)19/h5-7,13-16,18,22,24-25,27H,3-4,8-10H2,1-2H3/t13-,14-,15-,16-,18+,19-,20-,21-/m0/s1
• InChIKey: SEKYBDYVXDAYPY-HCMGWXKDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,13S,14S,15S,17S)-13,14,17-trihydroxy-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,10S,11S,13S,14S,15S,17S)-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (11β,16β)-11,16,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione; 16β-Hydroxyprednisolone; 11β,16β,17α,21-Tetrahydroxypregna-1,4-diene-3,20-dione

Database IDs

• PubChem SID: 164234340
• PubChem CID: 71752480

CALCULATED PROPERTIES

• Acid pKa: 11.756947
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.19808608
• LogD (pH = 7.4): 0.19806725
• Log P: 0.19808632
• Molar Refractivity: 99.8548 cm^3
• Polarizability: 38.68944 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T296080

A metabolite of Budesonide (B689490), an antiinflammatory agent.

REFERENCES

• Cserhati, T., et al.: J. Pharm. Biomed. Anal., 22, 25 (2000)
• Dilger, K., et al.: J. Clin. Pharmacol., 47, 1532 (2000)
• Buchwald, P., et al.: Steroids, 73, 193 (2000)