2-[(4R)-4-[(1S,2S,5S,7R,9R,10R,11S,14S,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

• ChemBase ID: 2416
• Molecular Formular: C26H43NO6
• Molecular Mass: 465.62272
• Monoisotopic Mass: 465.3090381
• SMILES: C[C@H](CCC(=O)NCC(=O)O)[C@@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3C[C@@H](O)[C@]12C
• Canonical SMILES: O[C@H]1CC[C@]2([C@H](C1)C[C@H]([C@@H]1[C@@H]2C[C@@H](O)[C@]2([C@H]1CC[C@H]2[C@@H](CCC(=O)NCC(=O)O)C)C)O)C
• InChI: InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15-,16+,17+,18+,19+,20-,21-,24+,25+,26-/m1/s1
• InChIKey: RFDAIACWWDREDC-YUHACDEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R)-4-[(1S,2S,5S,7R,9R,10R,11S,14S,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
• IUPAC Traditional name: @N-cholylglycine
• Synonyms: N-Cholylglycine

Database IDs

• CAS Number: 475-31-0
• PubChem SID: 160965867; 46507924
• PubChem CID: 46936456

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.773337
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.35080916
• LogD (pH = 7.4): -1.8972445
• Log P: 1.3772112
• Molar Refractivity: 123.5928 cm^3
• Polarizability: 49.32588 Å^3
• Polar Surface Area: 127.09 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.7
• LOG S: -4.27
• Solubility (Water): 2.48e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.0033 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Hydrophobicity(logP): 1.65 [RODA,A ET AL. (1990)]

DETAILS

DrugBank - DB02691

• Drug Groups: experimental
• Description: The glycine conjugate of cholic acid. It acts as a detergent to solubilize fats for absorption and is itself absorbed. [PubChem]