(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-6,6-bis(13C)methyl-9,13-dimethyl(6-13C)-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

• ChemBase ID: 166642
• Molecular Formular: C24H32O6
• Molecular Mass: 419.48524451
• Monoisotopic Mass: 419.22995326
• 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)O[13C](O1)([13CH3])[13CH3])C(=O)CO)C)C
• Canonical SMILES: OCC(=O)[C@@]12O[13C](O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1CCC1=CC(=O)C=C[C@]21C)([13CH3])[13CH3]
• InChI: InChI=1S/C24H32O6/c1-21(2)29-19-10-16-15-6-5-13-9-14(26)7-8-22(13,3)20(15)17(27)11-23(16,4)24(19,30-21)18(28)12-25/h7-9,15-17,19-20,25,27H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,20+,22-,23-,24+/m0/s1/i1+1,2+1,21+1
• InChIKey: WBGKWQHBNHJJPZ-ZVJGJQJYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-6,6-bis(^1^3C)methyl-9,13-dimethyl(6-^1^3C)-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• IUPAC Traditional name: (1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-6,6-bis(^1^3C)methyl-9,13-dimethyl(6-^1^3C)-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• Synonyms: (11β,16α)-11,21-Dihydroxy-16,17-[(1-methylethylidene-13C3)bis(oxy)]pregna-1,4-diene-3,20-dione; 16α-Hydroxyprednisolone Acetonide-13C3; Locapred-13C3; Topifug-13C3; Tridesilon-13C3; Desonide-13C3

Database IDs

• PubChem SID: 162260775
• PubChem CID: 71315810

CALCULATED PROPERTIES

• Acid pKa: 13.7431
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.9005109
• LogD (pH = 7.4): 1.9005108
• Log P: 1.9005109
• Molar Refractivity: 112.0618 cm^3
• Polarizability: 43.61315 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D296942

Anti-inflammatory.

REFERENCES

• Phillips, et al.: Toxicol. Appl. Pharmacol., 20, 522 (1971)
• Sanen, F.J., et al.: Int. J. Clin. Pharmacol. Biopharm., 12, 174 (1971)
• Tarayre, J.P., et al.: Pharmacol., 19, 323 (1979).