2-[(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

• ChemBase ID: 178087
• 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]([C@@H](CCC(=O)NCCS(=O)(=O)O)C)CC2)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(4,4,5,6,6-^2H₅)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(4,4,5,6,6-^2H₅)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-d5; N-(3α,7α-dihydroxy-5β-cholan-24-oyl)taurine-d5; 12-Deoxycholyltaurine-d5; 12-Desoxycholyltaurine-d5; 3α,7α-Dihydroxy-N-(2-sulfoethyl)-5β-cholan-24-amide-d5; Chenodeoxycholyltaurine-d5; Chenyltaurine-d5; Taurochenodesoxycholic acid; Taurochenodeoxycholic Acid-d5 (Major)

Database IDs

• PubChem SID: 164233997
• PubChem CID: 71752330

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

DETAILS

Toronto Research Chemicals - T008132

Labelled analogue of Taurochenodeoxycholic Acid, a bile acid conjugate and metabolite Taurolithocholic Acid (T009100) with antiinflammatory activity. Taurochenodeoxycholic Acid has been shown to inhibit hepatocyte apoptosis through suppression of Bid tran

REFERENCES

• Emerman, S. et al.: J. Biol. Chem., 242, 661 (1967)
• Takikawa, Y. et al.: Falk Symp., 120, 249 (1967)
• Li, P. et al.: Zhong. Shour. Xue., 28, 1317 (1967)