(1S,2S,4R,8S,9S,11S,12S,13R,19S)-11,19-dihydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-(2H7)propyl(6-2H)-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

• ChemBase ID: 170297
• Molecular Formular: C25H34O7
• Molecular Mass: 446.53326
• Monoisotopic Mass: 446.23045343
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](C[C@@H]2O)[C@H]2[C@](C[C@@H]1O)([C@]1([C@@H](C2)OC(O1)CCC)C(=O)CO)C)C
• Canonical SMILES: CCCC1O[C@H]2[C@](O1)(C(=O)CO)[C@@]1([C@@H](C2)[C@@H]2C[C@H](O)C3=CC(=O)C=C[C@@]3([C@H]2[C@H](C1)O)C)C
• InChI: InChI=1S/C25H34O7/c1-4-5-21-31-20-10-15-14-9-17(28)16-8-13(27)6-7-23(16,2)22(14)18(29)11-24(15,3)25(20,32-21)19(30)12-26/h6-8,14-15,17-18,20-22,26,28-29H,4-5,9-12H2,1-3H3/t14-,15-,17-,18-,20+,21?,22+,23-,24-,25+/m0/s1
• InChIKey: JBVVDXJXIDYDMF-HLQSUVNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12S,13R,19S)-11,19-dihydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-(^2H₇)propyl(6-^2H)-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• IUPAC Traditional name: (1S,2S,4R,8S,9S,11S,12S,13R,19S)-11,19-dihydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-(^2H₇)propyl(6-^2H)-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• Synonyms: (6α,11β,16α,17α)-16,17-[(Butylidene-d8)bis(oxy)]-6,11,17,21-trihydroxypregna-1,4-diene-3,20-dione; 6α-Hydroxy Budesonide-d8

Database IDs

• PubChem SID: 164226207
• PubChem CID: 71748909

CALCULATED PROPERTIES

• Acid pKa: 13.6779995
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 1.5030789
• LogD (pH = 7.4): 1.5030787
• Log P: 1.5030789
• Molar Refractivity: 117.6253 cm^3
• Polarizability: 46.09864 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H830347

A labelled metabolite of Budesonide (B689490), a non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.

REFERENCES

• Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979)
• Roth, G., et al.: J. Pharm. Sci., 69, 766 (1979)