(1S,2S,10S,11S,13R,14R,15S,17S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyl-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-5-one

• ChemBase ID: 166715
• Molecular Formular: C22H28O5
• Molecular Mass: 372.45472
• Monoisotopic Mass: 372.193674
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@]32[C@H](C[C@]2([C@H]1C[C@H]([C@@]2(C(=O)CO)O)C)C)O3)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@@H]1O[C@@]31[C@H]2CCC1=CC(=O)C=C[C@]31C
• InChI: InChI=1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-19(13,2)22(15)18(27-22)10-20(16,3)21(12,26)17(25)11-23/h6-7,9,12,15-16,18,23,26H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19+,20+,21+,22-/m1/s1
• InChIKey: GBDXNHBVYAMODG-QDBZYVRYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,10S,11S,13R,14R,15S,17S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyl-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-5-one
• IUPAC Traditional name: (1S,2S,10S,11S,13R,14R,15S,17S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyl-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-5-one
• Synonyms: (9β,11β,16α)-9,11-Epoxy-17,21-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione; 9,11β-Epoxy-17,21-dihydroxy-16α-methyl-9β-pregna-1,4-diene-3,20-dione; Dexamethasone 9,11-Epoxide

Database IDs

• CAS Number: 24916-90-3
• PubChem SID: 162260848
• PubChem CID: 11143226

CALCULATED PROPERTIES

• Acid pKa: 12.450934
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.9521815
• LogD (pH = 7.4): 1.9521776
• Log P: 1.9521815
• Molar Refractivity: 100.6749 cm^3
• Polarizability: 39.224995 Å^3
• Polar Surface Area: 87.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 230-235°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D298795

Dexamethasone intermediate.

REFERENCES

• Isogai, M., et al.: J. Steroid Biochem. Mol. Biol., 44, 141 (1993)