sodium 2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]acetate

• ChemBase ID: 169766
• Molecular Formular: C26H42NNaO5
• Molecular Mass: 471.60515
• Monoisotopic Mass: 471.29606773
• 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)NCC(=O)[O-])C)C)C)O.[Na+]
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCC(=O)[O-])C)C)O)C.[Na+]
• InChI: InChI=1S/C26H43NO5.Na/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29;/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32);/q;+1/p-1/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-;/m1./s1
• InChIKey: AAYACJGHNRIFCT-YRJJIGPTSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-dihydroxy-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]acetate
• IUPAC Traditional name: sodium 2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-dihydroxy-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]acetate
• Synonyms: N-[(3α,5β,7α)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine-d5 Sodium Salt; N-[(3α,5β,7α)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine-d5 Monosodium Salt; NSC 681056-d5 Sodium Chenodeoxycholylglycine-d5; Sodium Glycochenodeoxycholate-d5; Sodium Glycochenodesoxycholate-d5; Glycochenodeoxycholic Acid-d5 Sodium Salt

Database IDs

• PubChem SID: 162263898
• PubChem CID: 71317151

CALCULATED PROPERTIES

• Acid pKa: 3.7733076
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.8800022
• LogD (pH = 7.4): -0.66643345
• Log P: 2.6080222
• Molar Refractivity: 132.9144 cm^3
• Polarizability: 48.56865 Å^3
• Polar Surface Area: 109.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G641257

Labelled Glycochenodeoxycholic Acid (G641255). A bile salt formed in the liver from chenodeoxycholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleret

REFERENCES

• Ollila, F., et al.: Langmuir, 17, 7107 (2001)
• Uekama, K., et al.: Chem. Pharm. Bull., 52, 900 (2001)
• Tongiani, S., et al.: J. Pharm. Sci., 94, 2380 (2001)