sodium 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanamido]ethane-1-sulfonate

• ChemBase ID: 103541
• Molecular Formular: C26H44NNaO6S
• Molecular Mass: 521.68543
• Monoisotopic Mass: 521.27870341
• SMILES: [Na+].[O-]S(=O)(=O)CCNC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@@H]([C@@]4([C@H](CC3)C[C@H](O)CC4)C)C[C@H](O)[C@]12C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[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)C.[Na+]
• InChI: InChI=1S/C26H45NO6S.Na/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3;/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33);/q;+1/p-1/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-;/m1./s1
• InChIKey: YXHRQQJFKOHLAP-FVCKGWAHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanamido]ethane-1-sulfonate; sodium 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]ethane-1-sulfonate
• IUPAC Traditional name: sodium taurodeoxycholate
• Synonyms: Sodium taurodeoxycholate; 2-([3α,12α-Dihydroxy-24-oxo-5β-cholan-24-yl]amino)ethanesulfonic acid; TAURODEOXYCHOLIC ACID; Taurodeoxycholic Acid Sodium Salt; Sodium 3α,12α-Dihydroxy-5β-cholanoyltaurate; Sodium Deoxytaurocholate; Sodium Taurodesoxycholate; Taurodeoxycholate Sodium; Taurodeoxychloic Acid Sodium Salt; N-(3α,12α-Dihydroxy-5β-cholan-24-oyl)-taurine Monosodium Salt

Database IDs

• CAS Number: 1180-95-6
• EC Number: 214-652-0
• PubChem SID: 162090453
• PubChem CID: 23664773

CALCULATED PROPERTIES

• Polarizability: 52.698177 Å^3
• Polar Surface Area: 126.76 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false
• Acid pKa: -0.94335264
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.14807612
• LogD (pH = 7.4): -0.14811489
• Log P: 0.84671533
• Molar Refractivity: 129.4803 cm^3

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 200-203°C

Safety Information

• Storage Condition: 2-8°C; Refrigerator

DETAILS

MP Biomedicals - 02152097

Sodium Salt

Toronto Research Chemicals - T009005

Deoxycholyltaurine rescues human colon cancer cells from apoptosis by activating EGFR-dependent PI3K/Akt signaling.

REFERENCES

• Cheng, K., et al.: Biochem. J., 330, 353 (1998)
• Cheng, K., et al.: Cancer Res., 63, 6744 (1998)
• Bellacosa, A., et al.: Adv. Cancer Res., 94, 29 (1998)
• Cheng, K., et al.: Biochem. Pharmacol., 70, 1035 (1998)
• Fang, D., et al.: J. Biol. Chem., 282, 11221