2-[(4R,8S,9S,11S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate

• ChemBase ID: 179691
• Molecular Formular: C32H44O7
• Molecular Mass: 540.68756
• Monoisotopic Mass: 540.30870375
• SMILES: [C@]12([C@@]3(C(C4C([C@@]5(C(=CC(=O)C=C5)CC4)C)[C@H](C3)O)C[C@H]2OC(O1)C1CCCCC1)C)C(=O)COC(=O)C(C)C
• Canonical SMILES: O=C(C(C)C)OCC(=O)[C@@]12OC(O[C@@H]1CC1[C@]2(C)C[C@H](O)C2C1CCC1=CC(=O)C=C[C@]21C)C1CCCCC1
• InChI: InChI=1S/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22?,23?,24-,26+,27?,29?,30-,31-,32+/m0/s1
• InChIKey: LUKZNWIVRBCLON-DPTRQJQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R,8S,9S,11S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate
• IUPAC Traditional name: 2-[(4R,8S,9S,11S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate
• Synonyms: Ciclesonide

Database IDs

• CAS Number: 126544-47-6
• PubChem SID: 164235601
• PubChem CID: 17571846

CALCULATED PROPERTIES

• Acid pKa: 14.7785225
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 5.3232727
• LogD (pH = 7.4): 5.3232727
• Log P: 5.3232727
• Molar Refractivity: 146.2789 cm^3
• Polarizability: 57.75212 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Glucocorticoid

Product Information

• Application(s): Antiinflammatory agent

REFERENCES

• Ger. Pat., 1992, 4 129 535; CA, 117, 26918q, (synth, pharmacol)