2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]acetic acid

• ChemBase ID: 172357
• Molecular Formular: C26H43NO4
• Molecular Mass: 433.62392
• Monoisotopic Mass: 433.31920886
• SMILES: C1C[C@H](C[C@@H]2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CCC(=O)NCC(=O)O)C)C)C)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCC(=O)O)C)C)C
• InChI: InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1
• InChIKey: XBSQTYHEGZTYJE-OETIFKLTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]acetic acid
• IUPAC Traditional name: [(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]acetic acid
• Synonyms: N-[(3α,5β)-3-Ηydroxy-24-oxocholan-24-yl]glycine-d5; 3α-Hydroxy-5β-cholanic Αcid-d5 Glycine Ester; 3α-Hydroxy-5β-cholanoylglycine-d5; N-(3α-Hydroxy-5β-cholanoyl)glycine-d5; Lithocholylglycine-d5

Database IDs

• PubChem SID: 164228267
• PubChem CID: 71749826

CALCULATED PROPERTIES

• Acid pKa: 3.7732894
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.1887672
• LogD (pH = 7.4): 0.6423313
• Log P: 3.9167871
• Molar Refractivity: 120.4848 cm^3
• Polarizability: 48.04392 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L469202

A labelled metabolite in human hepatic bile. A lithocholic acid analog that inhibit sialyltransferase.

REFERENCES

• Ishikawa, H., et al.: J. Lipid. Res., 40, 1920 (1999)
• Gustafsson, U., et al.: Eur. J. Clin. Invest., 30, 1099 (1999)
• Gowda, G., et al.: Lipids, 41, 591 (1999)
• Lindon, J., et al.: Pharm. Res., 23, 1075 (1999)