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

• ChemBase ID: 170450
• Molecular Formular: C22H31FO5
• Molecular Mass: 394.4769432
• Monoisotopic Mass: 394.21555231
• SMILES: C1=CC(C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]([C@@H](C2)C)(C(=O)CO)O)C)F)C)O
• 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]2CCC2=CC(C=C[C@]12C)O)F
• InChI: InChI=1S/C22H31FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,14-17,24-26,28H,4-5,8,10-11H2,1-3H3/t12-,14?,15+,16+,17+,19+,20+,21+,22+/m1/s1
• InChIKey: AHCZVAORYHARLA-PYZGQABGSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 922713-68-6
• PubChem SID: 164226360
• PubChem CID: 71748979

CALCULATED PROPERTIES

• Acid pKa: 12.423716
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.0663935
• LogD (pH = 7.4): 1.0663894
• Log P: 1.0663935
• Molar Refractivity: 103.2596 cm^3
• Polarizability: 40.158863 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H939480

A metabolite of Dexamethasone (D298800).

REFERENCES

• Lowry, O., et al.: J. Biol. Chem., 193, 265 (1951)
• LaemmLi, U., et al.: Nature, 227, 680 (1951)