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

• ChemBase ID: 166115
• Molecular Formular: C23H29NO5
• Molecular Mass: 399.48006
• Monoisotopic Mass: 399.20457303
• 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)CO)C)C
• Canonical SMILES: OCC(=O)[C@@]12N=C(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)C
• InChI: InChI=1S/C23H29NO5/c1-12-24-23(18(28)11-25)19(29-12)9-16-15-5-4-13-8-14(26)6-7-21(13,2)20(15)17(27)10-22(16,23)3/h6-8,15-17,19-20,25,27H,4-5,9-11H2,1-3H3/t15-,16-,17-,19+,20+,21-,22-,23+/m0/s1
• InChIKey: KENSGCYKTRNIST-RVUAFKSESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-6,9,13-trimethyl-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)-11-hydroxy-8-(2-hydroxyacetyl)-6,9,13-trimethyl-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)-11,21-Dihydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione; Deacetyldeflazacort; Deflazacortalcohol; L 6485; 21-Desacetyl Deflazacort

Database IDs

• CAS Number: 13649-57-5
• PubChem SID: 162260248
• PubChem CID: 3081431

CALCULATED PROPERTIES

• Acid pKa: 13.753508
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.3610549
• LogD (pH = 7.4): 1.3610594
• Log P: 1.3610597
• Molar Refractivity: 107.9677 cm^3
• Polarizability: 41.800823 Å^3
• Polar Surface Area: 96.19 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 207-210°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D288695

A metabolite of Deflazacort, a systemic corticosteroid, a derivative of prednisolone and used for rheumatoid arthritis and lupus.

REFERENCES

• Hahn, T.J., et al.: Calcif. Tissue Int., 31, 109 (1980)
• Cavall-Perin, P., et al.: Eur. J. Clin. Pharmacol., 26, 357 (1984)