(1S,2S,4R,8S,9S,11S,12S,13R)-8-acetyl-11-hydroxy-6,9,13-trimethyl(10,10,11-2H3)-5-oxa-7-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-6,14,17-trien-16-one

• ChemBase ID: 165436
• Molecular Formular: C23H29NO4
• Molecular Mass: 383.48066
• Monoisotopic Mass: 383.20965841
• 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(=N1)C)C(=O)C)C)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2([C@H]1C[C@@H]1[C@]2(N=C(O1)C)C(=O)C)C)C
• InChI: InChI=1S/C23H29NO4/c1-12(25)23-19(28-13(2)24-23)10-17-16-6-5-14-9-15(26)7-8-21(14,3)20(16)18(27)11-22(17,23)4/h7-9,16-20,27H,5-6,10-11H2,1-4H3/t16-,17-,18-,19+,20+,21-,22-,23+/m0/s1
• InChIKey: WQUXBQVUVGNOKK-AAZVSSJSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12S,13R)-8-acetyl-11-hydroxy-6,9,13-trimethyl(10,10,11-^2H₃)-5-oxa-7-azapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-6,14,17-trien-16-one
• IUPAC Traditional name: (1S,2S,4R,8S,9S,11S,12S,13R)-8-acetyl-11-hydroxy-6,9,13-trimethyl(10,10,11-^2H₃)-5-oxa-7-azapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-6,14,17-trien-16-one
• Synonyms: (11β,16β)-11-Hydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione-d3; (11β,16β)-11β-Hydroxy-2'-methyl-5βH-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione-d3; 11β-Hydroxy-2'-methyl-5'βH-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione-d3; Desacetoxy Deflazacort-d3; 21-Deacetoxy Deflazacort-d3

Database IDs

• PubChem SID: 162259569
• PubChem CID: 71315199

CALCULATED PROPERTIES

• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 14.879515
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.1783006
• LogD (pH = 7.4): 2.1783075
• Log P: 2.1783078
• Molar Refractivity: 106.2655 cm^3
• Polarizability: 41.158867 Å^3
• Polar Surface Area: 75.96 Å^2

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - D198002

A labeled intermediate of Deflazacort (D228975), a systematic corticosteroid.

REFERENCES

• Nathansohn, G. et al.: Steroids, 13, 365 (1969)
• Nathansohn, G., et al.: J. Med. Chem., 10,799 (1969)
• Schiatti, P., et al.: Arzneim. Forsch., 30, 1543 (1969)