disodium 2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfonatooxy)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]acetate

• ChemBase ID: 169767
• Molecular Formular: C26H41NNa2O8S
• Molecular Mass: 573.65018
• Monoisotopic Mass: 573.23482684
• 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)OS(=O)(=O)[O-].[Na+].[Na+]
• Canonical SMILES: O=C(NCC(=O)[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)OS(=O)(=O)[O-])C.[Na+].[Na+]
• InChI: InChI=1S/C26H43NO8S.2Na/c1-15(4-7-22(29)27-14-23(30)31)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(35-36(32,33)34)12-16(25)13-21(24)28;;/h15-21,24,28H,4-14H2,1-3H3,(H,27,29)(H,30,31)(H,32,33,34);;/q;2*+1/p-2/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-;;/m1../s1
• InChIKey: MJXWPLXHDUSUKI-KZRRTRIISA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfonatooxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]acetate
• IUPAC Traditional name: disodium 2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfonatooxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]acetate
• Synonyms: N-[(3α,5β,7α)-7-Hydroxy-24-oxo-3-(sulfooxy)cholan-24-yl]glycine Disodium Salt; Glycochenodeoxycholic Acid 3α-Sulfate Disodium Salt; Glycochenodeoxycholic Acid 3-Sulfate Disodium Salt

Database IDs

• CAS Number: 66874-09-7
• PubChem SID: 162263899
• PubChem CID: 71317153

CALCULATED PROPERTIES

• Acid pKa: -1.5329806
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.441398
• LogD (pH = 7.4): -2.9878464
• Log P: 1.132225
• Molar Refractivity: 141.7845 cm^3
• Polarizability: 53.253803 Å^3
• Polar Surface Area: 155.89 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G641270

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 choleretic.

REFERENCES

• Parmentier, G. , et al.: Steroids, 30, 583 (1977)
• Tserng, K.Y., et al.: Lipids, 13, 479 (1977)