2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl (2H5)propanoate

• ChemBase ID: 166724
• Molecular Formular: C25H33FO6
• Molecular Mass: 448.5243232
• Monoisotopic Mass: 448.226117
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]([C@@H](C2)C)(C(=O)COC(=O)CC)O)C)F)C
• Canonical SMILES: CCC(=O)OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C25H33FO6/c1-5-21(30)32-13-20(29)25(31)14(2)10-18-17-7-6-15-11-16(27)8-9-22(15,3)24(17,26)19(28)12-23(18,25)4/h8-9,11,14,17-19,28,31H,5-7,10,12-13H2,1-4H3/t14-,17+,18+,19+,22+,23+,24+,25+/m1/s1
• InChIKey: ALINSFFSOAHJII-OCUNRLNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl (^2H₅)propanoate
• IUPAC Traditional name: 2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl (^2H₅)propanoate
• Synonyms: (11β,16α)-9-Fluoro-11,17-dihydroxy-16-methyl-21-(1-oxopropoxy)-pregna-1,4-diene-3,20-dione-d5; 9-Fluoro-11β,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione 21-Propionate-d5; Dexamethasone 21-Propionate-d5

Database IDs

• PubChem SID: 162260857
• PubChem CID: 71315854

CALCULATED PROPERTIES

• Acid pKa: 12.440789
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.823231
• LogD (pH = 7.4): 2.823227
• Log P: 2.823231
• Molar Refractivity: 116.2713 cm^3
• Polarizability: 45.300625 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D298827

A labelled Dexamethasone Dipropionate metabolite.

REFERENCES

• Civiale, C., et al.: J. Ocul. Pharmacol. Thera., 20, 75 (2004)