2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-9,13-dimethyl-16-oxo-6-(2H7)propyl(6-2H)-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl acetate

• ChemBase ID: 158990
• Molecular Formular: C27H36O7
• Molecular Mass: 472.57054
• Monoisotopic Mass: 472.24610349
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]1([C@@H](C2)OC(O1)CCC)C(=O)COC(=O)C)C)C
• Canonical SMILES: CCCC1O[C@H]2[C@](O1)(C(=O)COC(=O)C)[C@@]1([C@@H](C2)[C@@H]2CCC3=CC(=O)C=C[C@@]3([C@H]2[C@H](C1)O)C)C
• InChI: InChI=1S/C27H36O7/c1-5-6-23-33-22-12-19-18-8-7-16-11-17(29)9-10-25(16,3)24(18)20(30)13-26(19,4)27(22,34-23)21(31)14-32-15(2)28/h9-11,18-20,22-24,30H,5-8,12-14H2,1-4H3/t18-,19-,20-,22+,23?,24+,25-,26-,27+/m0/s1
• InChIKey: QZIYSFVNRMBENV-PONRWWDOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-9,13-dimethyl-16-oxo-6-(^2H₇)propyl(6-^2H)-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 acetate
• IUPAC Traditional name: 2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-9,13-dimethyl-16-oxo-6-(^2H₇)propyl(6-^2H)-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 acetate
• Synonyms: 21-(Acetoxy)-16α,17α-(butylidenedioxy)-11β-hydroxypregna-1,4diene-3,20-dione-d8; (11β,16α)-21-(Acetyloxy)-16,17-[butylidenebis(oxy)]-11-hydroxy-pregna-1,4-diene-3,20-dione; 21-Acetyloxy Budesonide-d8

Database IDs

• PubChem SID: 162253125
• PubChem CID: 71312766

CALCULATED PROPERTIES

• Acid pKa: 14.778119
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.1750154
• LogD (pH = 7.4): 3.1750154
• Log P: 3.1750154
• Molar Refractivity: 125.2613 cm^3
• Polarizability: 49.29415 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A164487

Protected Budesonide-d8 (B689492), a non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.

REFERENCES

• Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979)
• Roth, G., et al.: J. Pharm. Sci., 69, 766 (1979)
• Clissold, S.P., et al.: Drugs, 28, 485 (1984)