2-[(4R)-4-[(1S,2R,5R,7R,8S,10S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

• ChemBase ID: 178085
• 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[C@@H]2O)C2[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@@H](O)C[C@@H]1[C@@H]2CC[C@]2(C1CC[C@@H]2[C@@H](CCC(=O)NCCS(=O)(=O)O)C)C)C
• InChI: InChI=1S/C26H45NO6S/c1-16(4-7-24(30)27-12-13-34(31,32)33)19-5-6-20-18-15-23(29)22-14-17(28)8-10-26(22,3)21(18)9-11-25(19,20)2/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: HMXPOCDLAFAFNT-ICWMSSAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4R)-4-[(1S,2R,5R,7R,8S,10S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[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,2R,5R,7R,8S,10S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]ethanesulfonic acid
• Synonyms: 2-[[(3α,5β,6α)-3,6-Dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic Acid; N-(3α,6α-Dihydroxy-5β-cholan-24-oyl)taurine; Taurine Hyodeoxycholate; Taurohyodeoxycholic Acid

Database IDs

• CAS Number: 2958-04-5
• PubChem SID: 164233995
• PubChem CID: 71752329

CALCULATED PROPERTIES

• Acid pKa: -0.97942597
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.22602938
• LogD (pH = 7.4): -0.22606863
• Log P: 0.8985423
• 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: true

DETAILS

Toronto Research Chemicals - T007900

A bile acid which stimulates the flow of bile salts, for potential treatment of Irritable Bile Syndrome.

REFERENCES

• Gnewuch, C., et al.: World J. Gastroenterol., 15, 3134 (2009)
• Yu, B., et al.: J. Nat. Prod., 72, 24 (2009)
• Lim, S., et al.: Int. J. Cancer, 126, 1582 (2009)