(1S,2R,8S,11S,14R,15S,17R)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyl(1,16,16,17-2H4)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 174195
• Molecular Formular: C22H30O5
• Molecular Mass: 374.4706
• Monoisotopic Mass: 374.20932406
• SMILES: [C@@H]12C([C@H]3[C@](CC1O)([C@@](CC3)(O)C(=O)CO)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]1C2C[C@@H](C2=CC(=O)C=C[C@]12C)C
• InChI: InChI=1S/C22H30O5/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/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14?,15-,17-,19?,20-,21-,22-/m0/s1
• InChIKey: VHRSUDSXCMQTMA-JJOGLPADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,11S,14R,15S,17R)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyl(1,16,16,17-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1S,2R,8S,11S,14R,15S,17R)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyl(1,16,16,17-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (6α,11β)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione-d4; Medrone-d3 Medrol-d3; Medrate-d3; 6α-Methyl Prednisolone-d3 (Major)

Database IDs

• PubChem SID: 164230105
• PubChem CID: 46782298

CALCULATED PROPERTIES

• Acid pKa: 12.584675
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.560009
• LogD (pH = 7.4): 1.5600061
• Log P: 1.560009
• Molar Refractivity: 103.0419 cm^3
• Polarizability: 39.87477 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 228-237°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M325937

A labelled glucocorticoid.

REFERENCES

• Hall, E.D., et al.: J. Neurosurg., 76, 13 (1992)
• Hommes, O.R., et al.: Mult. Scler., 1, 327 (1992)
• Bracken, M.B., et al.: J. Neurosurg., 89, 699 (1992)
• Dammers, J.W.H.H., et al.: Brit. Med. J., 319, 884 (1999)