2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-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: 178090
• 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](CC2)[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)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
• InChI: InChI=1S/C26H45NO6S/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)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1
• InChIKey: AWDRATDZQPNJFN-VAYUFCLWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-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,10R,11S,14R,15R,16S)-5,16-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,12β)-3,12-Dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic Acid-d5; N-(3α,12α-Dihydroxy-5β-cholan-24-oyl)taurine-d5; Deoxycholyltaurine-d5; Deoxytaurocholic-d5 Acid; Taurodesoxycholic-d5 Acid; Tudcabil-d5; Taurodeoxycholic-2,2,3,4,4-d5 Acid (d5 major)

Database IDs

• PubChem SID: 164234000
• PubChem CID: 46782973

CALCULATED PROPERTIES

• Acid pKa: -0.94335264
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.14807612
• LogD (pH = 7.4): -0.14811489
• Log P: 0.84671533
• Molar Refractivity: 130.602 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: Methanol
• Apperance: White Solid
• Melting Point: >170°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T009002

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