(1S,2R,5S,10R,11S,14R,15S)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-yl acetate

• ChemBase ID: 159050
• Molecular Formular: C23H34O4
• Molecular Mass: 374.51366
• Monoisotopic Mass: 374.24570957
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@]1(OC(=O)C)C(=O)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@]2(OC(=O)C)C(=O)C)C)C1)C
• InChI: InChI=1S/C23H34O4/c1-14(24)23(27-15(2)25)12-9-20-18-6-5-16-13-17(26)7-10-21(16,3)19(18)8-11-22(20,23)4/h5,17-20,26H,6-13H2,1-4H3/t17-,18+,19-,20-,21-,22-,23-/m0/s1
• InChIKey: KRBMZSYRIJAAMS-KIYFCUGLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10R,11S,14R,15S)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl acetate
• IUPAC Traditional name: (1S,2R,5S,10R,11S,14R,15S)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl acetate
• Synonyms: (3β)-17-(Acetyloxy)-3-hydroxypregn-5-en-20-one; 3β,17-Dihydroxypregn-5-en-20-one 17-Acetate; 17-Acetoxy-3β-hydroxypregn-5-en-20-one; NSC 77893; 17α-Acetoxy Pregnenolone

Database IDs

• CAS Number: 2381-45-5
• PubChem SID: 162253185
• PubChem CID: 102250

CALCULATED PROPERTIES

• Acid pKa: 17.829819
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.2750587
• LogD (pH = 7.4): 3.2750587
• Log P: 3.2750587
• Molar Refractivity: 104.3082 cm^3
• Polarizability: 41.39284 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A167680

A 17α-substituted Pregnenolone, an active derivative of Pregnenolone (P712200).

REFERENCES

• Holick, M., et al.: J. Biol. Chem., 250, 226 (1975)
• Yamamoto, J., et al.: Biochemistry, 24, 3338 (1975)
• Tian, X., et al.: J. Biol. Chem., 274 (1975)
• Guo, L., et al.: Steroids, 68, 314174 (1975)