2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,6,6-2H4)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

• ChemBase ID: 178086
• Molecular Formular: C26H45NO6S
• Molecular Mass: 499.7036
• Monoisotopic Mass: 499.29675917
• 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)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]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)NCCS(=O)(=O)O)C)C)O)C
• InChI: InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1
• InChIKey: BHTRKEVKTKCXOH-BJLOMENOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,6,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
• IUPAC Traditional name: 2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,6,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]ethanesulfonic acid
• Synonyms: 2-[[(3α,5β,7α)-3,7-dihydroxy-24-oxocholan-24-yl]amino]-ethanesulfonic Acid-d4; TCD-d4; Chenodeoxycholyltaurine-d4; Chenyltaurine-d4; Taurochenodesoxycholic-d4 Acid; Taurochenodeoxycholic-[2,2,4,4-d4] AcidDiscontinued See T008132

Database IDs

• PubChem SID: 164233996
• PubChem CID: 57369414

CALCULATED PROPERTIES

• Acid pKa: -0.99043494
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.22602968
• LogD (pH = 7.4): -0.22606862
• Log P: 0.80769014
• Molar Refractivity: 130.679 cm^3
• Polarizability: 52.81067 Å^3
• Polar Surface Area: 123.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Methanol
• Apperance: Pale Yellow Foam
• Melting Point: 52-53°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T008125

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 Research, 43, 3 (1998)