2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid sodium

• ChemBase ID: 178089
• Molecular Formular: C26H45NNaO7S
• Molecular Mass: 538.69277
• Monoisotopic Mass: 538.28144307
• SMILES: [Na].C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([C@H](CC2)[C@@H](CCC(=O)NCCS(=O)(=O)O)C)C)C)O
• 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.[Na]
• InChI: InChI=1S/C26H45NO7S.Na/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: LHLYEKPSOJJBMK-IZYKLYLVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid sodium
• IUPAC Traditional name: taurocholic acid sodium
• Synonyms: 2-[[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic Acid; Cholaic Acid Sodium Salt Hydrate; Cholic Acid Taurine Conjugate Sodium Salt Hydrate; Cholyltaurine Sodium Salt Hydrate; N-Choloyltaurine Sodium Salt Hydrate; Taurocholic Acid Sodium Salt Hydrate

Database IDs

• CAS Number: 345909-26-4
• PubChem SID: 164233999
• PubChem CID: 45055433

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: White Solid
• Melting Point: 168-170°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T008851

Choleretic; Its sodium salt is a lipase accelerator. Also used as a method for the quantitation of conjugated bile acids in dried blood spots using electrospray ionization-mass spectrometry.

REFERENCES

• Mills, K.A., et al.: Pedatric Res., 43, 3 (1998).