(1S,2R,5R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-7,13-dien-5-yl acetate

• ChemBase ID: 165683
• Molecular Formular: C23H32O3
• Molecular Mass: 356.49838
• Monoisotopic Mass: 356.23514488
• SMILES: C1[C@H](CC2=CCC3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC=C1C(=O)C)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1CC[C@]2(C(=CCC3[C@@H]2CC[C@]2([C@H]3CC=C2C(=O)C)C)C1)C
• InChI: InChI=1S/C23H32O3/c1-14(24)19-7-8-20-18-6-5-16-13-17(26-15(2)25)9-11-22(16,3)21(18)10-12-23(19,20)4/h5,7,17-18,20-21H,6,8-13H2,1-4H3/t17-,18?,20+,21+,22+,23-/m1/s1
• InChIKey: MZWRIOUCMXPLKV-VMNVZBNLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,13-dien-5-yl acetate
• IUPAC Traditional name: (1S,2R,5R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,13-dien-5-yl acetate
• Synonyms: 3β-Hydroxypregna-5,16-dien-20-one Acetate; (-)-16-Dehydropregnenolone Acetate; 16,17-Didehydropregnenolone Acetate; 16-DPA; 16-Dehydropregnenolone-3β-acetate; 20-Oxopregna-5,16-dien-3β-yl Acetate; 3β-Acetoxypregna-5,16-dien-20-one; 3β-Acetyloxy-pregna-5,16-dien-20-one; NSC 37741; Pregnadienolone Acetate; 16-Dehydro Pregnenolone Acetate; (3β)-3-(Acetyloxy)pregna-5,16-dien-20-one

Database IDs

• CAS Number: 979-02-2
• PubChem SID: 162259816
• PubChem CID: 71315333

CALCULATED PROPERTIES

• Acid pKa: 19.657377
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.8728716
• LogD (pH = 7.4): 3.8728716
• Log P: 3.8728716
• Molar Refractivity: 103.7841 cm^3
• Polarizability: 40.529503 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230030

16-Dehydropregnenolone Acetate is the dehydration product of Pregnenolone Acetate (). 16-Dehydropregnenolone Acetate is used in the preparation of pregnane derivatives and its glycosides as potential anticancer agents.

REFERENCES

• Pandey, A.K. et al.: Ind. J. Heterocyc. Chem., 15, 353 (2006)