2-[(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,8,15-trimethyl-5-oxo(1,16,16,17-2H4)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]-2-oxoethyl acetate

• ChemBase ID: 173786
• Molecular Formular: C24H34O6
• Molecular Mass: 418.52316
• Monoisotopic Mass: 418.23553881
• SMILES: C1CC(=O)C=C2[C@]1([C@@H]1[C@@H](C[C@@H]2C)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)COC(=O)C)O)C)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)CC[C@]12C)C
• InChI: InChI=1S/C24H34O6/c1-13-9-16-17-6-8-24(29,20(28)12-30-14(2)25)23(17,4)11-19(27)21(16)22(3)7-5-15(26)10-18(13)22/h10,13,16-17,19,21,27,29H,5-9,11-12H2,1-4H3/t13-,16-,17-,19-,21?,22-,23-,24-/m0/s1
• InChIKey: ZWEFPCOQVDIOJD-OPDLNKLESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,8,15-trimethyl-5-oxo(1,16,16,17-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,8,15-trimethyl-5-oxo(1,16,16,17-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethyl acetate
• Synonyms: (6α,11β)-21-(Acetyloxy)-11,17-dihydroxy-6-methylpregn-4-ene-3,20-dione-d4; 17-Hydroxy-6α-methylcorticosterone-d4 21-Acetate; 21-Acetoxy-11β,17-dihydroxy-6α-methylpregn-4-ene-3,20-dione-d4; NSC 19988-d4; U 7642-d4; 6α-Methyl Hydrocortisone-d4 21-Acetate

Database IDs

• PubChem SID: 164229696
• PubChem CID: 71750376

CALCULATED PROPERTIES

• Acid pKa: 12.61023
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.003311
• LogD (pH = 7.4): 2.0033083
• Log P: 2.003311
• Molar Refractivity: 111.1001 cm^3
• Polarizability: 43.965054 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M312522

A labelled Methylprednisolone acetate (M326035) USP impurity.

REFERENCES

• Justice, J. B., Jr., et al.: J. Med. Chem., (1978)
• 21, 465 (1978)