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

• ChemBase ID: 179143
• Molecular Formular: C21H26O6
• Molecular Mass: 374.42754
• Monoisotopic Mass: 374.17293855
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=O)([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)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C21H26O6/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/h5-7,13-14,16,18,22,25,27H,3-4,8-10H2,1-2H3/t13-,14-,16+,18+,19-,20-,21-/m0/s1
• InChIKey: QUDYJOZZUZDXCV-QLONCABFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,13R,14S,15S)-13,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[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,14S,15S)-13,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• Synonyms: 16α,17,21-Trihydroxy-pregna-1,4-diene-3,11,20-trione

Database IDs

• CAS Number: 3754-05-0
• PubChem SID: 164235053
• PubChem CID: 71752789

CALCULATED PROPERTIES

• Acid pKa: 11.746089
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.58360034
• LogD (pH = 7.4): 0.58358103
• Log P: 0.5836006
• Molar Refractivity: 98.9296 cm^3
• Polarizability: 38.148365 Å^3
• Polar Surface Area: 111.9 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - T795230

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)