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

• ChemBase ID: 171163
• Molecular Formular: C21H30O5
• Molecular Mass: 362.4599
• Monoisotopic Mass: 362.20932406
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1CC[C@@]2([C@@H](CO)O)O)C)O)C
• Canonical SMILES: OC[C@H]([C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C)O
• InChI: InChI=1S/C21H30O5/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/h5,7,9,14-18,22,24-26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,17+,18+,19-,20-,21-/m0/s1
• InChIKey: LCOVYWIXMAJCDS-LCGKLAOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S,17S)-14-[(1R)-1,2-dihydroxyethyl]-14,17-dihydroxy-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,14R,15S,17S)-14-[(1R)-1,2-dihydroxyethyl]-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: 20α-Dihydroprednisolone; 11β,17,20β,21-Tetrahydroxy-1,4-pregnadien-3-one; Pregna-1,4-dien-11β,17α,20β,21-tetrol-3-one; 20β-Hydroxy Prednisolone

Database IDs

• CAS Number: 15847-24-2
• PubChem SID: 164227073
• PubChem CID: 13962390

CALCULATED PROPERTIES

• Acid pKa: 12.9895
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.6578137
• LogD (pH = 7.4): 0.65781265
• Log P: 0.6578137
• Molar Refractivity: 99.26 cm^3
• Polarizability: 38.581844 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952361

Prednisolone (P703740) metabolite.

REFERENCES

• Garg, V., et al.: Biopharm. Drug Disposition, 15, 163 (1994)
• Adham, N., et al.: Proc. Biochem., 38, 897 (1994)