methyl 4-{5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl}pentanoate

• ChemBase ID: 173453
• Molecular Formular: C25H42O5
• Molecular Mass: 422.59798
• Monoisotopic Mass: 422.30322444
• SMILES: C12(C(C3C(C4(C(CC3O)CC(CC4)O)C)CC1O)CCC2C(CCC(=O)OC)C)C
• Canonical SMILES: COC(=O)CCC(C1CCC2C1(C)C(O)CC1C2C(O)CC2C1(C)CCC(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
• InChIKey: DLYVTEULDNMQAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 4-{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 4-{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-Trihydroxycholan-24-oic Acid Methyl Ester; Cholic Αcid Μethyl Εster; Methyl 3α,7α,12α-Trihydroxy-5β-cholan-24-oate; Methyl 3α,7α,12α-Trihydroxy-5β-cholanoate; NSC 126794; Methyl CholateSee C432610

Database IDs

• CAS Number: 1448-36-8
• PubChem SID: 164229363
• PubChem CID: 277782

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; Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 152-154°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M294475

A bile acid derivative as anti-inflammatory and antitumor agent.

REFERENCES

• Yasukawa, K., et al.: Chem. Pharm. Bull, 19, 573 (1996)
• Yasukawa, K., et al.: J. Pharm. Pharmacol., 52, 119 (1996)
• Iida, T., et al.: Lipids, 38, 281 (1996)