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

• ChemBase ID: 159154
• Molecular Formular: C24H30O6
• Molecular Mass: 414.4914
• Monoisotopic Mass: 414.20423868
• 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)COC(=O)C)O)C)C)O3)C
• Canonical SMILES: CC(=O)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/C24H30O6/c1-13-9-18-17-6-5-15-10-16(26)7-8-21(15,3)24(17)20(30-24)11-22(18,4)23(13,28)19(27)12-29-14(2)25/h7-8,10,13,17-18,20,28H,5-6,9,11-12H2,1-4H3/t13-,17+,18+,20+,21+,22+,23+,24-/m1/s1
• InChIKey: MONKXVNQUJNHLQ-WMHQAVGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,10S,11S,13R,14R,15S,17S)-14-hydroxy-2,13,15-trimethyl-5-oxo-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2S,10S,11S,13R,14R,15S,17S)-14-hydroxy-2,13,15-trimethyl-5-oxo-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• Synonyms: (9β,11β,16α)-21-(Acetyloxy)-9,11-epoxy-17-hydroxy-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; 21-O-Acetyl Dexamethasone 9,11-Epoxide

Database IDs

• CAS Number: 2884-51-7
• PubChem SID: 162253289
• PubChem CID: 11026076

CALCULATED PROPERTIES

• Acid pKa: 12.46911
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.3933067
• LogD (pH = 7.4): 2.3933032
• Log P: 2.393307
• Molar Refractivity: 109.8264 cm^3
• Polarizability: 43.07077 Å^3
• Polar Surface Area: 93.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A168495

Dexamethasone intermediate.

REFERENCES

• Shapiro, E., et al.: J. Med. Chem., 30, 1581 (1987)