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

• ChemBase ID: 165613
• 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[C@@H]1O)([C@]1([C@@H](C2)OC(O1)CCC)C(=O)C=O)C)C
• Canonical SMILES: CCCC1O[C@H]2[C@](O1)(C(=O)C=O)[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/h8-10,13,16-18,20-22,28H,4-7,11-12H2,1-3H3/t16-,17?,18-,20+,21?,22+,23-,24-,25+/m0/s1
• InChIKey: UHEOYIKQUMWUPY-CTPKKYTLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,4R,8S,9S,11S,12S,13R)-11-hydroxy-9,13-dimethyl-16-oxo-6-propyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoacetaldehyde
• IUPAC Traditional name: 2-[(1S,4R,8S,9S,11S,12S,13R)-11-hydroxy-9,13-dimethyl-16-oxo-6-propyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoacetaldehyde
• Synonyms: (11β,16α)-16,17-[Butylidenebis(oxy)]-11-hydroxy-3,20-dioxopregna-1,4-dien-21-al; 21-Dehydro Budesonide

Database IDs

• CAS Number: 85234-63-5
• PubChem SID: 162259746
• PubChem CID: 71315297

CALCULATED PROPERTIES

• Acid pKa: 14.879638
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.6408088
• LogD (pH = 7.4): 3.6408088
• Log P: 3.6408088
• Molar Refractivity: 115.2639 cm^3
• Polarizability: 44.905437 Å^3
• Polar Surface Area: 89.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229305

Budesonide (B689490) impurity.

REFERENCES

• Backes, S., et al.: Drug Metab. Rev., 34, 157 (2002)
• Vermeer, H., et al.: Clin. Endocrinol., 59, 49 (2002)
• Assi, K., et al.: J. Pharm. Biomed. Anal., 41, 325 (2002)