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

• ChemBase ID: 165612
• Molecular Formular: C25H32O6
• Molecular Mass: 428.51798
• Monoisotopic Mass: 428.21988874
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)C2=C[C@@H]3[C@@]([C@]2(C[C@@H]1O)C)(C(=O)CO)OC(O3)CCC)C
• Canonical SMILES: CCCC1O[C@H]2[C@](O1)(C(=O)CO)[C@@]1(C(=C2)[C@@H]2CCC3=CC(=O)C=C[C@@]3([C@H]2[C@H](C1)O)C)C
• InChI: InChI=1S/C25H32O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-11,16,18,20-22,26,28H,4-7,12-13H2,1-3H3/t16-,18-,20+,21?,22+,23-,24-,25+/m0/s1
• InChIKey: PMZXYZGZQZYDLA-BQKXZEBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-2,14,17-trien-16-one
• IUPAC Traditional name: (1R,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-2,14,17-trien-16-one
• Synonyms: (11β,16α)-16,17-[Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4,14-triene-3,20-dione; 14,15-Dehydro Budesonide

Database IDs

• CAS Number: 131918-64-4
• PubChem SID: 162259745
• PubChem CID: 12989325

CALCULATED PROPERTIES

• Acid pKa: 13.739649
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.484218
• LogD (pH = 7.4): 2.484218
• Log P: 2.484218
• Molar Refractivity: 116.8058 cm^3
• Polarizability: 45.202858 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229300

Budesonide (B689490) impurity.

REFERENCES

• Aherne, G., et al.: J. Steroid Biochem., 17, 559 (1982)
• Assi, K., et al.: J. Pharm. Biomed. Anal., 41, 325 (1982)