(1R,2S,10S,11S,13R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,14-dione

• ChemBase ID: 176006
• Molecular Formular: C20H25FO3
• Molecular Mass: 332.4091032
• Monoisotopic Mass: 332.17877288
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H](C2=O)C)C)O)F)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H](C2=O)C)C)C
• InChI: InChI=1S/C20H25FO3/c1-11-8-15-14-5-4-12-9-13(22)6-7-19(12,3)20(14,21)16(23)10-18(15,2)17(11)24/h6-7,9,11,14-16,23H,4-5,8,10H2,1-3H3/t11-,14+,15+,16+,18+,19+,20+/m1/s1
• InChIKey: IZLVPOBNINIXJM-FETOPEPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,14-dione
• IUPAC Traditional name: (1R,2S,10S,11S,13R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,14-dione
• Synonyms: 9-Fluoro-11-hydroxy-16-methyl-(11β,16α ) Androsta-1,4-diene-3,17-dione; 9-Fluoro-11β-hydroxy-16α-methyl Androsta-1,4-diene-3,17-dione; NSC 50909; 17-Oxo Dexamethasone

Database IDs

• CAS Number: 1880-61-1
• PubChem SID: 164231916
• PubChem CID: 242348

CALCULATED PROPERTIES

• Acid pKa: 13.629727
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.204603
• LogD (pH = 7.4): 3.2046027
• Log P: 3.204603
• Molar Refractivity: 90.3958 cm^3
• Polarizability: 34.641968 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 242-244°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - O855200

A metabolite of Dexamethasone.

REFERENCES

• Minagawa, K., et al.: Steroids, 47, 175 (1986)
• Murray, G., et al.: Br. J. Clin. Pharmacol., 25, 465 (1986)
• Ravichandran, K., et al.: Science, 1993, 261, 731 (1986)