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

• ChemBase ID: 176904
• Molecular Formular: C23H34O3
• Molecular Mass: 358.51426
• Monoisotopic Mass: 358.25079495
• SMILES: C1[C@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1C(=O)C)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)C)C)C1)C
• InChI: InChI=1S/C23H34O3/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/h5,17-21H,6-13H2,1-4H3/t17-,18+,19-,20+,21+,22+,23-/m1/s1
• InChIKey: CRRKVZVYZQXICQ-QKSXVSAESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl acetate
• IUPAC Traditional name: (1S,2R,5R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl acetate
• Synonyms: (3β)-3-(Acetyloxy)-pregn-5-en-20-one; 3β-Acetoxy-5-pregnen-20-one; 3β-Acetoxy-Δ5-pregnen-20-one; 3β-Hydroxypregn-5-en-20-one Acetate; 3β-Pregn-5-enol-20-one Acetate; 5-Pregnen-3β-ol-20-one Acetate; 5-Pregnene-3β-acetoxy-20-one; Antofin; Artivis; Enescorb; NSC 64827; Pregenolone Acetate; Pregnenolone Acetate; Pregnenolone-3-acetate; Previsone; Sharmone; Pregnenolone Acetate

Database IDs

• CAS Number: 1778-02-5
• PubChem SID: 164232814
• PubChem CID: 11013784

CALCULATED PROPERTIES

• Acid pKa: 19.403038
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.022484
• LogD (pH = 7.4): 4.022484
• Log P: 4.022484
• Molar Refractivity: 102.9082 cm^3
• Polarizability: 40.77005 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Colorless Solid

DETAILS

Toronto Research Chemicals - P712210

Pregnenolone (P712200) derivative, a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens

REFERENCES

• Bjondahl, K., et al.: Med. Biol., 54, 454 (1976)
• Geick, A., et al.: J. Biol. Chem., 276, 14581 (1976)
• Johnson, D., et al.: Toxicol. Sci., 66, 16 (1976)
• Abe, C., et al.: Lipids, 42, 637 (1976)