(2S)-1-[(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-1-oxopropan-2-yl acetate

• ChemBase ID: 169282
• Molecular Formular: C24H31FO6
• Molecular Mass: 434.4977432
• Monoisotopic Mass: 434.21046693
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1CC[C@@]2(C(=O)[C@@H](OC(=O)C)C)O)C)O)F)C
• Canonical SMILES: CC(=O)O[C@H](C(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F)C
• InChI: InChI=1S/C24H31FO6/c1-13(31-14(2)26)20(29)23(30)10-8-17-18-6-5-15-11-16(27)7-9-21(15,3)24(18,25)19(28)12-22(17,23)4/h7,9,11,13,17-19,28,30H,5-6,8,10,12H2,1-4H3/t13-,17-,18-,19-,21-,22-,23-,24-/m0/s1
• InChIKey: HHPZZKDXAFJLOH-QZIXMDIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-1-oxopropan-2-yl acetate
• IUPAC Traditional name: methral
• Synonyms: (11β,17α)-17-[(2S)-2-(Acetyloxy)-1-oxopropyl]-9-fluoro-11,17-dihydroxyandrosta-1,4-dien-3-one; 9-Fluoro-11β,17α-dihydroxy-17-(S)-lactoylandrosta-1,4-dien-3-one 17β-Acetate; 9α-Fluoro-11β,17α,21-trihydroxy-21-methylpregna-1,4-diene-3,20-dione 21-Acetate; Alacortril; Falban-Crema; Flu-Korti; Fluperolone 21-Acetate; Methral; P 1742; Fluperolone Acetate

Database IDs

• CAS Number: 2119-75-7
• PubChem SID: 162263414
• PubChem CID: 66257

CALCULATED PROPERTIES

• Acid pKa: 12.566792
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.3264866
• LogD (pH = 7.4): 2.3264835
• Log P: 2.3264866
• Molar Refractivity: 111.6667 cm^3
• Polarizability: 43.471127 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F598150

A corticosteroid with antiinflammatory activity.

REFERENCES

• Child, K.J. et al.: Arch. Dermatol., 97, 407 (1968)
• Selye, H.: Rev. Can. Biol., 29, 49 (1968)