(1S,2R,10S,11S,14R,15S,17S)-8-chloro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6,8-trien-5-one

• ChemBase ID: 164920
• Molecular Formular: C21H25ClO5
• Molecular Mass: 392.8732
• Monoisotopic Mass: 392.13905158
• SMILES: C1=C[C@]2(C(=CC1=O)C(=C[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1CC[C@@]2(C(=O)CO)O)C)O)Cl)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C=C(C2=CC(=O)C=C[C@]12C)Cl
• InChI: InChI=1S/C21H25ClO5/c1-19-5-3-11(24)7-14(19)15(22)8-12-13-4-6-21(27,17(26)10-23)20(13,2)9-16(25)18(12)19/h3,5,7-8,12-13,16,18,23,25,27H,4,6,9-10H2,1-2H3/t12-,13-,16-,18+,19-,20-,21-/m0/s1
• InChIKey: YTJIBEDMAQUYSZ-FDNPDPBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S,17S)-8-chloro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-5-one
• IUPAC Traditional name: novacort
• Synonyms: (11β)-6-Chloro-11,17,21-trihydroxypregna-1,4,6-triene-3,20-dione; 6-Chloro-11β,17,21-trihydroxypregna-1,4,6-triene-3,20-dione; Cloprednole; Cloradryn; Novacort; RS 4691; Synestan; Cloprednol

Database IDs

• CAS Number: 5251-34-3
• PubChem SID: 162259054
• PubChem CID: 5284535

CALCULATED PROPERTIES

• Acid pKa: 12.584111
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.1478313
• LogD (pH = 7.4): 1.1478286
• Log P: 1.1478313
• Molar Refractivity: 104.3261 cm^3
• Polarizability: 39.664253 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C587295

A systematic corticosteroid. Anti-inflammatory.

REFERENCES

• Mroszczak, E.J. et al.: J. Pharmac. Sci., 67, 920 (1978)
• Moellmann, H. et al.: Int. J. Clin. Pharmacol. Therap., 34, 1 (1978)