(1S,2R,7S,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-3-ene-5,17-dione

• ChemBase ID: 167839
• Molecular Formular: C21H28O5
• Molecular Mass: 360.44402
• Monoisotopic Mass: 360.193674
• SMILES: C1=C[C@]2([C@H](CC1=O)CC[C@@H]1[C@@H]2C(=O)C[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(=O)[C@H]1[C@H]2CC[C@@H]2[C@]1(C)C=CC(=O)C2
• InChI: InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,12,14-15,18,22,26H,3-4,6,8-11H2,1-2H3/t12-,14-,15-,18+,19-,20-,21-/m0/s1
• InChIKey: XGRPDOONUXQWRT-FZPGBCFJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,7S,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-5,17-dione
• IUPAC Traditional name: (1S,2R,7S,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-5,17-dione
• Synonyms: (5α)-17,21-Dihydroxypregn-1-ene-3,11,20-trione; 17,21-Dihydroxy-5α-Pregn-1-ene-3,11,20-trione; 4,5-Dihydro Prednisone

Database IDs

• CAS Number: 103881-93-2
• PubChem SID: 162261972
• PubChem CID: 71316255

CALCULATED PROPERTIES

• Acid pKa: 12.576201
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.7043384
• LogD (pH = 7.4): 1.7043356
• Log P: 1.7043386
• Molar Refractivity: 96.7414 cm^3
• Polarizability: 37.741665 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D453350

A metabolite of Prednisone (P703780) formed via microbial transformation by Cunninghamella elegans.

REFERENCES

• Choudhary, M.I. et al.: Nat. Prod. Res., 19, 311 (2005)