(1S,2R,8S,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,17-dione

• ChemBase ID: 174193
• Molecular Formular: C22H28O5
• Molecular Mass: 372.45472
• Monoisotopic Mass: 372.193674
• SMILES: [C@@H]12[C@H]([C@H]3[C@](CC1=O)([C@](CC3)(C(=O)CO)O)C)C[C@@H](C1=CC(=O)C=C[C@]21C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)C
• InChI: InChI=1S/C22H28O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,19,23,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,19+,20-,21-,22-/m0/s1
• InChIKey: SVYCRJXQZUCUND-PQXSVQADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• IUPAC Traditional name: (1S,2R,8S,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• Synonyms: 17,21-Dihydroxy-6α-methylpregna-1,4-diene-3,11,20-trione; (6α)-17,21-Dihydroxy-6-methylpregna-1,4-diene-3,11,20-trione; 1,4-Pregnadien-6-α-methyl-17,21-diol-3,11,20-trione; NSC 63546; 6α-Methyl Prednisone

Database IDs

• CAS Number: 91523-05-6
• PubChem SID: 164230103
• PubChem CID: 124653

CALCULATED PROPERTIES

• Acid pKa: 12.576199
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.9455233
• LogD (pH = 7.4): 1.9455204
• Log P: 1.9455233
• Molar Refractivity: 102.1167 cm^3
• Polarizability: 39.331356 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White to Off-White Solid
• Melting Point: 227 - 231 °C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M325933

A metabolite of Meprednisone (Methylprednisolone).

REFERENCES

• Hansen, J., et al.: Int. J. Pharm., 6, 307 (1980)
• Edsbacker, S., et al.: Drug Metab. Dispos., 11, 590 (1980)
• Ogata, M., et al.: J. Pharm. Sci., 87, 91 (1980)
• Hou, S., et al.: J. Pharm. Biomed. Anal., 24, 371 (1980)