(1S,2R,10S,11S,14R,15S)-14-(1-hydroxypropan-2-yl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 170924
• Molecular Formular: C22H34O2
• Molecular Mass: 330.50416
• Monoisotopic Mass: 330.25588033
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)C(CO)C)C)C
• Canonical SMILES: OCC([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C
• InChI: InChI=1S/C22H34O2/c1-14(13-23)18-6-7-19-17-5-4-15-12-16(24)8-10-21(15,2)20(17)9-11-22(18,19)3/h12,14,17-20,23H,4-11,13H2,1-3H3/t14?,17-,18+,19-,20-,21-,22+/m0/s1
• InChIKey: ZNWOYQVXPIEQRC-ZRFCQXGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-14-(1-hydroxypropan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10S,11S,14R,15S)-14-(1-hydroxypropan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 23,24-Bisnorchol-4-en-3-on-22-ol; 3-keto-23,24-Bisnorchol-4-en-22-ol; (20S)-21-Hydroxy-20-methylpregn-4-en-3-one

Database IDs

• CAS Number: 40736-33-2
• PubChem SID: 164226834
• PubChem CID: 6454094

CALCULATED PROPERTIES

• Acid pKa: 17.706207
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.2561164
• LogD (pH = 7.4): 4.2561164
• Log P: 4.2561164
• Molar Refractivity: 98.4642 cm^3
• Polarizability: 38.79139 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948415

(20S)-21-Hydroxy-20-methylpregn-4-en-3-one is a side chain degradation product of natural sterols. It is also an intermediate in the preparation of follicular fluid-meiosis activating sterol.

REFERENCES

• Andor, A. et al.: Appl. Environ. Microbiol., 72, 6554 (2006)
• Blume, T. et al.: Org, Lett., 5, 1837 (2006)