(1S,2R,9R,10S,11S,13R,14R,15S,17S)-9-chloro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 164452
• Molecular Formular: C22H29ClO5
• Molecular Mass: 408.91566
• Monoisotopic Mass: 408.17035171
• SMILES: [C@@H]12[C@H]([C@H]3[C@](C[C@@H]1O)([C@@]([C@@H](C3)C)(O)C(=O)CO)C)[C@@H](CC1=CC(=O)C=C[C@]21C)Cl
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2[C@H](Cl)CC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C22H29ClO5/c1-11-6-14-18-15(23)8-12-7-13(25)4-5-20(12,2)19(18)16(26)9-21(14,3)22(11,28)17(27)10-24/h4-5,7,11,14-16,18-19,24,26,28H,6,8-10H2,1-3H3/t11-,14+,15-,16+,18-,19+,20+,21+,22+/m1/s1
• InChIKey: FJXOGVLKCZQRDN-PHCHRAKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,9R,10S,11S,13R,14R,15S,17S)-9-chloro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: alclometasone
• Synonyms: (7α,11β,16α)-7-Chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; 7α-Chloro-16α-methylprednisolone; Alclometasone; Alclomethasone; 7α-Chloro-16α-methyl Prednisolone

Database IDs

• CAS Number: 67452-97-5
• PubChem SID: 162258587
• PubChem CID: 5311000

CALCULATED PROPERTIES

• Acid pKa: 12.449506
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6837897
• LogD (pH = 7.4): 1.6837859
• Log P: 1.6837898
• Molar Refractivity: 107.6084 cm^3
• Polarizability: 41.73316 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C369475

A metabolite of Alclometasone dipropionate; a synthetic glucocorticoid steroid for topical use in dermatology as anti-inflammatory, antipruritic, antiallergic, antiproliferative and vasoconstrictive agent.

REFERENCES

• Aoyama, S. et al.: Drug Metab. Disp., 18, 409 (1990)
• Green, M.J. et al.: J. Steroid Biochem., 11, 61 (1990)
• De, K. et al.: J. Ind. Chem. Soc., 79, 513 (1990)