2-[(1R,2S,10S,11S,13S,14Z,15S,17S)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo(6,8,8-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-ylidene]-2-hydroxyacetaldehyde

• ChemBase ID: 161167
• Molecular Formular: C22H27ClO4
• Molecular Mass: 390.90038
• Monoisotopic Mass: 390.15978702
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H](/C/2=C(/O)\C=O)C)C)O)Cl)C
• Canonical SMILES: O=C/C(=C/1\[C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)Cl)/O
• InChI: InChI=1S/C22H27ClO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,11-12,15-16,18,26-27H,4-5,8,10H2,1-3H3/b19-17-/t12-,15-,16-,18-,20-,21-,22-/m0/s1
• InChIKey: YBCQMVHDVBRVFB-NIQJDLCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13S,14Z,15S,17S)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-ylidene]-2-hydroxyacetaldehyde
• IUPAC Traditional name: 2-[(1R,2S,10S,11S,13S,14Z,15S,17S)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-ylidene]-2-hydroxyacetaldehyde
• Synonyms: (11β,16β,17Z)-9-Chloro-11,20-dihydroxy-16-methyl-3-oxo-pregna-1,4,17(20)-trien-21-al-d3; Beclomethasone-Δ17,20-d3 21-Aldehyde

Database IDs

• PubChem SID: 162255302
• PubChem CID: 71313646

CALCULATED PROPERTIES

• Acid pKa: 8.81708
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.7674477
• LogD (pH = 7.4): 2.7513492
• Log P: 2.7676568
• Molar Refractivity: 107.1035 cm^3
• Polarizability: 40.838284 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B131007

Labelled Beclomethasone-Δ17,20 21-Aldehyde (B131005). A degradation and metabolic intermediate of Beclomethasone (B131000).

REFERENCES

• Weiss, G., et al.: J. Clin. Endocrinol. Metab., 43, 696 (1976)
• Singer, C., et al.: Endocrinol., 119, 1356 (1976)
• Herzog, H., et al.: Steroids, 57, 617 (1976)