(1S,2R,10S,11S,13R,14S,15S,17S)-13,14,17-trihydroxy-14-[2-hydroxy(2H2)acetyl]-2,15-dimethyl(16,16,17-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 178428
• Molecular Formular: C21H28O6
• Molecular Mass: 376.44342
• Monoisotopic Mass: 376.18858862
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]([C@@H](C2)O)(C(=O)CO)O)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](O)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
• InChI: InChI=1S/C21H28O6/c1-19-6-5-12(23)7-11(19)3-4-13-14-8-16(25)21(27,17(26)10-22)20(14,2)9-15(24)18(13)19/h5-7,13-16,18,22,24-25,27H,3-4,8-10H2,1-2H3/t13-,14-,15-,16+,18+,19-,20-,21-/m0/s1
• InChIKey: SEKYBDYVXDAYPY-ILNISADRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,13R,14S,15S,17S)-13,14,17-trihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(16,16,17-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1S,2R,10S,11S,13R,14S,15S,17S)-13,14,17-trihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(16,16,17-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (11β,16α)-11,16,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione-d5; 16α-Hydroxyprednisolone-d5; 11β,16α,17α,21-Tetrahydroxypregna-1,4-diene-3,20-dione-d5See T296078.

Database IDs

• PubChem SID: 164234338
• PubChem CID: 71752478

CALCULATED PROPERTIES

• Acid pKa: 11.756947
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.19808608
• LogD (pH = 7.4): 0.19806725
• Log P: 0.19808632
• Molar Refractivity: 99.8548 cm^3
• Polarizability: 38.68944 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 208-211°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T296077

A labelled metabolite of Budesonide (B689490), an antiinflammatory agent.

REFERENCES

• Cserhati, T., et al.: J. Pharm. Biomed. Anal., 22, 25 (2000)
• Dilger, K., et al.: J. Clin. Pharmacol., 47, 1532 (2000)
• Buchwald, P., et al.: Steroids, 73, 193 (2000)