methyl (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoate

• ChemBase ID: 164029
• Molecular Formular: C25H42O4
• Molecular Mass: 406.59858
• Monoisotopic Mass: 406.30830982
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)[C@H]2[C@](CC1)([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)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/C25H42O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-21,23,26-27H,5-14H2,1-4H3/t15-,16+,17-,18-,19+,20+,21-,23+,24+,25-/m1/s1
• InChIKey: GRQROVWZGGDYSW-IFJDUOSNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• IUPAC Traditional name: methyl (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• Synonyms: (3α,5β,7α)-3,7-Dihydroxy-cholan-24-oic Acid Methyl Ester; Chenodeoxycholic Acid Methyl Ester; Methyl 3α,7α-Dihydroxy-5β-cholan-24-oate; Methyl 3α,7α-Dihydroxy-5β-cholanoate; Methyl Chenodeoxycholate; Chenodeoxycholic Acid Methyl Ester

Database IDs

• CAS Number: 3057-04-3
• PubChem SID: 162258164
• PubChem CID: 11069533

CALCULATED PROPERTIES

• Acid pKa: 18.296339
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.8591993
• LogD (pH = 7.4): 3.8591995
• Log P: 3.8591995
• Molar Refractivity: 114.0429 cm^3
• Polarizability: 45.86178 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C291905

A bile acid with hemolytic properties. Inhibits the initiation of Clostridium difficile spore germination. Anti-inflamatiory activity.

REFERENCES

• Segal, R. et al.; Life Sci. 10, 685 (1971)
• Sorg, J. et al.; J. Bacteriol. 192, 4983 (2010). Yasukawa, K. et al.; J. Pharm. Pharmacol. 61, 1051 (2009)