2-[(1R,2S,10S,11S,13S,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 propanoate

• ChemBase ID: 162004
• Molecular Formular: C25H33FO6
• Molecular Mass: 448.5243232
• Monoisotopic Mass: 448.226117
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]([C@@]2(C(=O)COC(=O)CC)O)C)C)O)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-/m0/s1
• InChIKey: ALINSFFSOAHJII-XGQKBEPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13S,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 propanoate
• IUPAC Traditional name: 2-[(1R,2S,10S,11S,13S,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 propanoate
• Synonyms: (11β,16β)-9-Fluoro-11,17-dihydroxy-16-methyl-21-(1-oxopropoxy)pregna-1,4-diene-3,20-dione; Betamethasone 21-Propionate

Database IDs

• CAS Number: 75883-07-7
• PubChem SID: 162256139
• PubChem CID: 9981101

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

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 212-214°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B327020

A degradation product of Betamethasone. Glucocorticoid.

REFERENCES

• Andersson, P., et al.: J. Pharm. Pharmacol., 36, 763 (1984)
• Wurthwein, G., et al.: Biopharm. Drug Dispos., 11, 381 (1984)
• Samtani, M., et al.: J. Pharm. Sci., 93, 726 (1984)
• Samtani, M., et al.: Drug Metab. Dispos., 33, 1124 (1984)