(1S,2S,9S,11S,12S,13R,19S)-11,19-dihydroxy-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: 170433
• Molecular Formular: C23H29NO6
• Molecular Mass: 415.47946
• Monoisotopic Mass: 415.19948765
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](C[C@@H]2O)[C@H]2[C@](C[C@@H]1O)(C1(C(C2)OC(=N1)C)C(=O)CO)C)C
• Canonical SMILES: OCC(=O)C12N=C(OC1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1C[C@@H](C1=CC(=O)C=C[C@]21C)O)C
• InChI: InChI=1S/C23H29NO6/c1-11-24-23(18(29)10-25)19(30-11)8-14-13-7-16(27)15-6-12(26)4-5-21(15,2)20(13)17(28)9-22(14,23)3/h4-6,13-14,16-17,19-20,25,27-28H,7-10H2,1-3H3/t13-,14-,16-,17-,19?,20+,21-,22-,23?/m0/s1
• InChIKey: GUUSJROCWMOQNZ-JKJUMEMCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,9S,11S,12S,13R,19S)-11,19-dihydroxy-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,9S,11S,12S,13R,19S)-11,19-dihydroxy-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: (6α,11β,16β)-Trihydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione; 6α-Hydroxy-21-desacetyl Deflazacort

Database IDs

• CAS Number: 87539-45-5
• PubChem SID: 164226343
• PubChem CID: 71748972

CALCULATED PROPERTIES

• Acid pKa: 13.6869755
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.1302446
• LogD (pH = 7.4): 0.13024837
• Log P: 0.13024864
• Molar Refractivity: 109.4832 cm^3
• Polarizability: 42.45282 Å^3
• Polar Surface Area: 116.42 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H935805

The minor metabolite of Deflazacort.

REFERENCES

• Bernareggi, A., et al.: J. Pharma. Biomed. Anal., 5, 177-81 (1987)
• Assandri, A., et al.: Xenobiotica, 13(1987)
• 185 (1987)
• Martinelli, E., et al.: Drug Metab. Dispos., 7, 335 (1987)