sodium (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-14-[2-(sulfonatooxy)acetyl](1,4,6,8,8,16,16,17-2H8)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 176883
• Molecular Formular: C21H27NaO8S
• Molecular Mass: 462.48905
• Monoisotopic Mass: 462.13243311
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1CC[C@@]2(C(=O)COS(=O)(=O)[O-])O)C)O)C.[Na+]
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2([C@H]1CC[C@]2(O)C(=O)COS(=O)(=O)[O-])C)C.[Na+]
• InChI: InChI=1S/C21H28O8S.Na/c1-19-7-5-13(22)9-12(19)3-4-14-15-6-8-21(25,17(24)11-29-30(26,27)28)20(15,2)10-16(23)18(14)19;/h5,7,9,14-16,18,23,25H,3-4,6,8,10-11H2,1-2H3,(H,26,27,28);/q;+1/p-1/t14-,15-,16-,18?,19-,20-,21-;/m0./s1
• InChIKey: LTWZNVWFOGRESW-JJXJRDLHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-14-[2-(sulfonatooxy)acetyl](1,4,6,8,8,16,16,17-^2H₈)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: sodium (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-14-[2-(sulfonatooxy)acetyl](1,4,6,8,8,16,16,17-^2H₈)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (11β)-11,17-Dihydroxy-21-(sulfooxy)-pregna-1,4-diene-3,20-dione-d8 Sodium Salt; 11β,17,21-Trihydroxypregna-1,4-diene-3,20-dione-d8 21-(Hydrogen Sulfate) Monosodium Salt; Prednisolone-d8 21-Sulfate Sodium Salt

Database IDs

• PubChem SID: 164232793
• PubChem CID: 71751749

CALCULATED PROPERTIES

• Acid pKa: -1.626268
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.0484154
• LogD (pH = 7.4): -1.0484257
• Log P: -0.23752208
• Molar Refractivity: 107.3634 cm^3
• Polarizability: 42.746952 Å^3
• Polar Surface Area: 141.03 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P703757

Labelled Prednisolone 21-Sulfate (P703755). Prednisolone 21-Sulfate is a metabolite of Prednisolone (P703740).

REFERENCES

• Hutzler, J., ET AL.: Drug Metab. Dispos., 30, 355 (2002)
• Sugiyama, D., et al.: J. Biol. Chem., 278, 43489 (2002)
• Hagenbuch, B., et al.: Xenobiotica, 38, 778 (2002)