2-[(4R)-4-[(1S,2R,5R,7R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]acetic acid

• ChemBase ID: 169692
• Molecular Formular: C26H43NO5
• Molecular Mass: 449.62332
• Monoisotopic Mass: 449.31412348
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](C[C@@H]2O)[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)[C@@H](O)C[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/C26H43NO5/c1-15(4-7-23(30)27-14-24(31)32)18-5-6-19-17-13-22(29)21-12-16(28)8-10-26(21,3)20(17)9-11-25(18,19)2/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17+,18-,19+,20+,21+,22+,25-,26-/m1/s1
• InChIKey: SPOIYSFQOFYOFZ-BRDORRHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R)-4-[(1S,2R,5R,7R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]acetic acid
• IUPAC Traditional name: [(4R)-4-[(1S,2R,5R,7R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]acetic acid
• Synonyms: N-[(3α,5β,6α)-3,6-Dihydroxy-24-oxocholan-24-yl]glycine; N-(3α,6α-Dihydroxy-5β-cholan-24-oyl)glycine; Glycine Hyodeoxycholate; Glycylhyodeoxycholic Acid; Glycohyodeoxycholic Acid

Database IDs

• CAS Number: 13042-33-6
• PubChem SID: 162263824
• PubChem CID: 114611

CALCULATED PROPERTIES

• Acid pKa: 3.773286
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.88000244
• LogD (pH = 7.4): -0.6664335
• Log P: 2.6080222
• Molar Refractivity: 122.0773 cm^3
• Polarizability: 48.680336 Å^3
• Polar Surface Area: 106.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G641390

Glycine conjugated Hyodeoxycholate, facilitates the biological transport of Hyodeoxycholate within the intestine

REFERENCES

• Yang, L., et al.: Chem. Res. Toxicol. 21, 2280 (2008)
• Sato, H., et al.: J. Med. Chem., 51, 4849 (2008)
• Gnewuch, C., et al.: World J. Gastroenterol., 15, 3134 (2008)