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

• ChemBase ID: 166720
• Molecular Formular: C28H37FO7
• Molecular Mass: 504.5875832
• Monoisotopic Mass: 504.25233174
• 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)OC(=O)CC)C)F)C
• Canonical SMILES: CCC(=O)O[C@@]1([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)C(=O)COC(=O)CC
• InChI: InChI=1S/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19+,20+,21+,25+,26+,27+,28+/m1/s1
• InChIKey: CIWBQSYVNNPZIQ-PKWREOPISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-[(^2H₅)propanoyloxy]tetracyclo[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-17-hydroxy-2,13,15-trimethyl-5-oxo-14-[(^2H₅)propanoyloxy]tetracyclo[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-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-pregna-1,4-diene-3,20-dione-d10; Dexamethasone 17,21-Dipropionate-d10; Methaderm-d10; Dexamethasone Dipropionate-d10

Database IDs

• PubChem SID: 162260853
• PubChem CID: 71315852

CALCULATED PROPERTIES

• Acid pKa: 13.635488
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.9648921
• LogD (pH = 7.4): 3.964892
• Log P: 3.9648921
• Molar Refractivity: 130.0497 cm^3
• Polarizability: 50.98258 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D298817

A labelled analogue of a corticosteroid used in dermatology as a topical vasoconstrictor.

REFERENCES

• Ikeda S., et al.: J. Dermatol. Sci., 5, 205 (1993)
• Tanigawa, K., et al.: Int. Immunopharmacol., 2, 941 (1993)
• Chen, B., et al.: Steroids, 74, 30 (1993)