methyl (4R)-4-[(2S,5R,7S,9R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoate

• ChemBase ID: 164736
• Molecular Formular: C25H42O5
• Molecular Mass: 422.59798
• Monoisotopic Mass: 422.30322444
• SMILES: C1[C@H](C[C@@H]2[C@](C1)(C1C([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([C@H](CC2)[C@@H](CCC(=O)OC)C)C)C)O
• Canonical SMILES: COC(=O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)CC1C2[C@H](O)C[C@H]2[C@]1(C)CC[C@H](C2)O)C
• InChI: InChI=1S/C25H42O5/c1-14(5-8-22(29)30-4)17-6-7-18-23-19(13-21(28)25(17,18)3)24(2)10-9-16(26)11-15(24)12-20(23)27/h14-21,23,26-28H,5-13H2,1-4H3/t14-,15+,16-,17-,18+,19?,20-,21+,23?,24+,25-/m1/s1
• InChIKey: DLYVTEULDNMQAR-VLNLAFDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4R)-4-[(2S,5R,7S,9R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• IUPAC Traditional name: methyl (4R)-4-[(2S,5R,7S,9R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• Synonyms: (3α,5β,7α,12α)-3,7,12-Trihydroxy-cholan-24-oic Acid Methyl Ester; Methyl 3α,7α,12α-Trihydroxy-5β-cholanoate; Methyl cholate; NSC 126794; Cholic Acid Methyl EsterSee M294475

Database IDs

• CAS Number: 1448-36-8
• PubChem SID: 162258871
• PubChem CID: 45039786

CALCULATED PROPERTIES

• Acid pKa: 18.296339
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.628388
• LogD (pH = 7.4): 2.6283884
• Log P: 2.6283884
• Molar Refractivity: 115.5584 cm^3
• Polarizability: 46.491676 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 141-143°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C432610

Protected Cholic Acid

REFERENCES

• Suzuki, T., et al.: J. Pharmacol. Sci., 107, 285 (2008)
• Yasukawa, K., et al.: J. Pharm. Pharmacol., 61, 1051 (2008)
• Aher, N., et al.: Bioorg. Med. Chem. Lett., 19, 5411 (2008)
• Huang, L., et al.: Steroids, 74, 701 (2008)