4-{[(1S,2R,8S,10S,11S,14R,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]oxy}-4-oxobutanoic acid

• ChemBase ID: 174274
• Molecular Formular: C26H34O8
• Molecular Mass: 474.54336
• Monoisotopic Mass: 474.22536805
• SMILES: [C@@H]12[C@@H](C[C@@H](C3=CC(=O)C=C[C@]23C)C)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)CO)OC(=O)CCC(=O)O)C
• Canonical SMILES: OCC(=O)[C@]1(CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)C)OC(=O)CCC(=O)O
• InChI: InChI=1S/C26H34O8/c1-14-10-16-17-7-9-26(20(30)13-27,34-22(33)5-4-21(31)32)25(17,3)12-19(29)23(16)24(2)8-6-15(28)11-18(14)24/h6,8,11,14,16-17,19,23,27,29H,4-5,7,9-10,12-13H2,1-3H3,(H,31,32)/t14-,16-,17-,19-,23+,24-,25-,26-/m0/s1
• InChIKey: VDJNUHGXSJAWMH-XYMSELFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1S,2R,8S,10S,11S,14R,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]oxy}-4-oxobutanoic acid
• IUPAC Traditional name: 4-{[(1S,2R,8S,10S,11S,14R,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]oxy}-4-oxobutanoic acid
• Synonyms: (6α,11β)-17-(3-Carboxy-1-oxopropoxy)-11,21-dihydroxy-6-methylpregna-1,4-diene-3,20-dione; 6α-Methyl Prednisolone 17-Hemisuccinate

Database IDs

• CAS Number: 77074-42-1
• PubChem SID: 164230184
• PubChem CID: 63017

CALCULATED PROPERTIES

• Acid pKa: 4.0031934
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.31958115
• LogD (pH = 7.4): -1.3312384
• Log P: 1.8259972
• Molar Refractivity: 123.0867 cm^3
• Polarizability: 47.97793 Å^3
• Polar Surface Area: 138.2 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M326300

An impurity of Methyl Prednisolone (M325934).

REFERENCES

• Anderson, B., et al.: J. Pharm. Sci., 70, 181 (1981)
• Ebling, W., et al.: Drug Metab. Dispos., 13, 296 (1981)