2-[(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-15-[(1Z)-(hydroxyimino)methyl]-2-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]-2-oxoethyl acetate

• ChemBase ID: 159638
• Molecular Formular: C23H31NO6
• Molecular Mass: 417.49534
• Monoisotopic Mass: 417.21513772
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@H](CC2)C(=O)COC(=O)C)/C=N\O)C
• Canonical SMILES: O/N=C\[C@@]12C[C@H](O)[C@H]3[C@H]([C@@H]2CC[C@@H]1C(=O)COC(=O)C)CCC1=CC(=O)CC[C@]31C
• InChI: InChI=1S/C23H31NO6/c1-13(25)30-11-20(28)18-6-5-17-16-4-3-14-9-15(26)7-8-22(14,2)21(16)19(27)10-23(17,18)12-24-29/h9,12,16-19,21,27,29H,3-8,10-11H2,1-2H3/b24-12-/t16-,17-,18+,19-,21+,22-,23+/m0/s1
• InChIKey: FSQKNRCHTXKHBA-OEHKYLJHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-15-[(1Z)-(hydroxyimino)methyl]-2-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-15-[(1Z)-(hydroxyimino)methyl]-2-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethyl acetate
• Synonyms: Aldosterone Oxime 21-Acetate; (11β)-21-(Acetyloxy)-11-hydroxy-3,20-dioxo-pregn-4-en-18-al 18-Oxime; Aldosterone 18-Oxime 21-Acetate

Database IDs

• CAS Number: 74220-49-8
• PubChem SID: 162253773
• PubChem CID: 71313077

CALCULATED PROPERTIES

• Acid pKa: 9.811092
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.505806
• LogD (pH = 7.4): 1.5045832
• Log P: 1.5062732
• Molar Refractivity: 109.765 cm^3
• Polarizability: 42.94503 Å^3
• Polar Surface Area: 113.26 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - A514720

Used in the preparation of Aldosterone (A514700), an adrenocortical steroid which exerts regulatory influence on metabolism of electrolytes and water

REFERENCES

• Morel, A., et al.: Nature, 356, 523 (1953)
• Arima, S., et al.: Clin. Exp. Nephrol., 7, 172 (2003)
• Simpson, et al.: Experienta, 9, 333 (1953)