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]ethane-1-sulfonic acid

• ChemBase ID: 3947
• Molecular Formular: C26H45NO7S
• Molecular Mass: 515.703
• Monoisotopic Mass: 515.29167379
• SMILES: C[C@H](CCC(=O)NCCS(=O)(=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)NCCS(=O)(=O)O)C)C)O)C
• InChI: InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16-,17+,18+,19+,20+,21-,22-,24+,25+,26-/m1/s1
• InChIKey: WBWWGRHZICKQGZ-GIHLXUJPSA-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]ethane-1-sulfonic acid
• IUPAC Traditional name: @taurocholic acid
• Synonyms: Taurocholic Acid

Database IDs

• CAS Number: 81-24-3
• PubChem SID: 46508273; 160967382
• PubChem CID: 46936954

CALCULATED PROPERTIES

JChem

• Acid pKa: -1.0602118
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.4568411
• LogD (pH = 7.4): -1.4568797
• Log P: -0.533411
• Molar Refractivity: 132.1945 cm^3
• Polarizability: 53.46433 Å^3
• Polar Surface Area: 144.16 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.79
• LOG S: -3.83
• Solubility (Water): 7.71e-02 g/l

DETAILS

DrugBank - DB04348

• Drug Groups: experimental
• Description: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic. [PubChem]