(3R)-3-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]butanenitrile

• ChemBase ID: 167852
• Molecular Formular: C23H37NO2
• Molecular Mass: 359.54538
• Monoisotopic Mass: 359.28242943
• SMILES: C1C[C@H](C[C@@H]2[C@]1([C@@H]1[C@@H]([C@H](C2)O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CC#N)C)C)C)O
• Canonical SMILES: N#CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@@H](O)C[C@H]2[C@]1(C)CC[C@H](C2)O)C
• InChI: InChI=1S/C23H37NO2/c1-14(8-11-24)17-4-5-18-21-19(7-10-23(17,18)3)22(2)9-6-16(25)12-15(22)13-20(21)26/h14-21,25-26H,4-10,12-13H2,1-3H3/t14-,15+,16-,17-,18+,19+,20+,21+,22+,23-/m1/s1
• InChIKey: IYRKNDIHBKVMOV-KHLWDBHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]butanenitrile
• IUPAC Traditional name: (3R)-3-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]butanenitrile
• Synonyms: (3α,5β,7β)-3,7-Dihydroxy-24norcholane-23-nitrile

Database IDs

• CAS Number: 118316-12-4
• PubChem SID: 162261985
• PubChem CID: 10970417

CALCULATED PROPERTIES

• Acid pKa: 18.296339
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.3266854
• LogD (pH = 7.4): 3.3266857
• Log P: 3.3266857
• Molar Refractivity: 103.6521 cm^3
• Polarizability: 41.255276 Å^3
• Polar Surface Area: 64.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere

DETAILS

Toronto Research Chemicals - D453770

Used in the preparation of ursodeoxycholic acid amides as glucocorticoid receptor modulators.

REFERENCES

• Sharma, R. et al.; J. Med. Chem. 54, 122 (2011).