(1R,2S,10S,11S,13S,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: 176074
• Molecular Formular: C20H25FO3
• Molecular Mass: 332.4091032
• Monoisotopic Mass: 332.17877288
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)(C(=O)[C@H](C2)C)C)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-/m0/s1
• InChIKey: IZLVPOBNINIXJM-BUMFJRDRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,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,13S,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: (11β,16β)- 9-Fluoro-11-hydroxy-16-methyl-androsta-1,4-diene-3,17-dione; 9α-Fluoro-11β-hydroxy-16β-methyl-1,4-androstadiene-3,17-dione; NSC 52437; 17-Oxo Betamethasone

Database IDs

• CAS Number: 3109-01-1
• PubChem SID: 164231984
• PubChem CID: 243151

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; Methanol
• Apperance: White Solid
• Melting Point: 272-276°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O869850

A metabolite of Betamethasone.

REFERENCES

• Juenge, E., et al.: J. Pharm. Sci., 68, 551 (1979)