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

• ChemBase ID: 167024
• Molecular Formular: C21H26Cl2O4
• Molecular Mass: 413.33474
• Monoisotopic Mass: 412.12081467
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1CC[C@]2(O)C(=O)CO)C)Cl)Cl)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](Cl)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)Cl
• InChI: InChI=1S/C21H26Cl2O4/c1-18-7-5-13(25)9-12(18)3-4-15-14-6-8-20(27,17(26)11-24)19(14,2)10-16(22)21(15,18)23/h5,7,9,14-16,24,27H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18-,19-,20-,21-/m0/s1
• InChIKey: CZJXBZPJABCCRQ-BULBTXNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,14R,15S,17S)-1,17-dichloro-14-hydroxy-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: dichlorisone
• Synonyms: (11β)-9,11-Dichloro-17,21-dihydroxypregna-1,4-diene-3,20-dione; 9,11β-Dichloro-17,21-dihydroxypregna-1,4-diene-3,20-dione; 9α,11β-Dichloro-17α,21-dihydroxypregna-1,4-diene-3,20-dione; Dichlorisone

Database IDs

• CAS Number: 7008-26-6
• PubChem SID: 162261157
• PubChem CID: 20054892

CALCULATED PROPERTIES

• Acid pKa: 12.588567
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.1346889
• LogD (pH = 7.4): 3.134686
• Log P: 3.1346889
• Molar Refractivity: 105.8154 cm^3
• Polarizability: 41.116688 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D431755

Dichlorisone is a 9α,11β-dichloro corticoid. Dichlorisone has anti-antiinflammatory potency. Dichlorisone could be modifed to be used as glucocorticoid receptor agonists as well as a P-glycoprotein inhibitor.

REFERENCES

• Collins, E.J. et al.: Proc. Int. Congr. Horm. Steroids, 2, 530 (1967)
• Gruol, D.J. et al.: Cancer Res., 57, 720 (1967)