(1R,2S,8R,10S,11S,13R,14R,15S,17S)-1-fluoro-8,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 170451
• Molecular Formular: C22H29FO6
• Molecular Mass: 408.4604632
• Monoisotopic Mass: 408.19481687
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](C[C@H]2O)[C@H]2[C@](C[C@@H]1O)([C@]([C@@H](C2)C)(C(=O)CO)O)C)F)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@H](C2=CC(=O)C=C[C@]12C)O)F
• InChI: InChI=1S/C22H29FO6/c1-11-6-13-14-8-16(26)15-7-12(25)4-5-19(15,2)21(14,23)17(27)9-20(13,3)22(11,29)18(28)10-24/h4-5,7,11,13-14,16-17,24,26-27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16-,17+,19+,20+,21+,22+/m1/s1
• InChIKey: RVBSTEHLLHXILB-QODHSQIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8R,10S,11S,13R,14R,15S,17S)-1-fluoro-8,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1R,2S,8R,10S,11S,13R,14R,15S,17S)-1-fluoro-8,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (6β,11β,16α)-9-Fluoro-6,11,17,21-tetrahydroxy-16-methylpregna-1,4-diene-3,20-dione; 6-Hydroxydexamethasone; 6β-Hydroxy Dexamethasone

Database IDs

• CAS Number: 55879-47-5
• PubChem SID: 164226361
• PubChem CID: 63050

CALCULATED PROPERTIES

• Acid pKa: 12.420291
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.45075855
• LogD (pH = 7.4): 0.45075446
• Log P: 0.4507586
• Molar Refractivity: 104.0084 cm^3
• Polarizability: 40.2855 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 259-262°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H939500

The hydrophilic metabolite of Dexamethasone (D298800).

REFERENCES

• Draper, R., et al.: Drug Res., 32, 317 (1982)
• Watkins, P., et al.: Clin. Pharmacol. Ther., 52, 265 (1982)
• Yamamoto, N., et al.: J. Clin. Oncol., 18, 2301 (1982)
• Slaviero, K., et al.: Br. J. Clin. Pharmacol., 57, 44 (1982)