1-[(1S,2R,5S,11R,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-7,9-dien-14-yl]ethan-1-one

• ChemBase ID: 165682
• Molecular Formular: C21H30O2
• Molecular Mass: 314.4617
• Monoisotopic Mass: 314.2245802
• SMILES: C1[C@@H](CC2=CC=C3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1C(=O)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC=C3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)C)C)C1)C
• InChI: InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,15,17-19,23H,6-12H2,1-3H3/t15-,17+,18-,19-,20-,21+/m0/s1
• InChIKey: QTVNPWWLYMFLEI-UIALTGQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,5S,11R,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,9-dien-14-yl]ethan-1-one
• IUPAC Traditional name: 1-[(1S,2R,5S,11R,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,9-dien-14-yl]ethanone
• Synonyms: (3β,9β)-3-Hydroxy-pregna-5,7-dien-20-one; 7,8-Dehydro Pregnenolone

Database IDs

• CAS Number: 1158830-87-5
• PubChem SID: 162259815
• PubChem CID: 99475

CALCULATED PROPERTIES

• Acid pKa: 18.270805
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.1757789
• LogD (pH = 7.4): 3.1757789
• Log P: 3.1757789
• Molar Refractivity: 94.6067 cm^3
• Polarizability: 36.70867 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D230020

Vitamin D3 derivative.

REFERENCES

• Zmijewski, M. et al.: Photochemical & Photobiological Sciences 7, 1570 (2008)