(2S,11S,13R,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-1(10),3,6-trien-5-one

• ChemBase ID: 166711
• Molecular Formular: C22H28O5
• Molecular Mass: 372.45472
• Monoisotopic Mass: 372.193674
• SMILES: C1=CC(=O)C=C2[C@]1(C1=C(CC2)[C@H]2[C@](C[C@@H]1O)([C@]([C@@H](C2)C)(C(=O)CO)O)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)C1=C2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-20(13,2)19(15)17(25)10-21(16,3)22(12,27)18(26)11-23/h6-7,9,12,16-17,23,25,27H,4-5,8,10-11H2,1-3H3/t12-,16+,17+,20+,21+,22+/m1/s1
• InChIKey: HBFNXGQYHPXHCK-CCDZBXPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,11S,13R,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(10),3,6-trien-5-one
• IUPAC Traditional name: (2S,11S,13R,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(10),3,6-trien-5-one
• Synonyms: (11β,16α)-11,17,21-Trihydroxy-16-methyl-pregna-1,4,8-triene-3,20-dione; 11β,17,21-Trihydroxy-16α-methylpregna-1,4,8-triene-3,20-dione; Δ8(9)-Dexamethasone

Database IDs

• PubChem SID: 162260844
• PubChem CID: 71315846

CALCULATED PROPERTIES

• Acid pKa: 12.4374695
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2666792
• LogD (pH = 7.4): 1.2666752
• Log P: 1.2666792
• Molar Refractivity: 103.4713 cm^3
• Polarizability: 39.629925 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - D298780

Dexamethasone (D298800) derivative.