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Chemistry

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Also known as: 14605-22-2, Tudca, Ursodeoxycholyltaurine, Tauroursodeoxycholate, Taurursodiol, Taurolite
Molecular Formula
C26H45NO6S
Molecular Weight
499.7  g/mol
InChI Key
BHTRKEVKTKCXOH-LBSADWJPSA-N
FDA UNII
60EUX8MN5X

Tauroursodeoxycholic Acid
tauroursodeoxycholic acid is a natural product found in Homo sapiens with data available.
1 2D Structure

Tauroursodeoxycholic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
2.1.2 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
2.1.3 InChI Key
BHTRKEVKTKCXOH-LBSADWJPSA-N
2.1.4 Canonical SMILES
CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
2.1.5 Isomeric SMILES
C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
2.2 Other Identifiers
2.2.1 UNII
60EUX8MN5X
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Chenyl Taurine Sodium

2. Tauroursodeoxycholate

3. Tauroursodeoxycholate Sodium Salt

4. Tauroursodeoxycholic Acid, (3alpha,5alpha,7alpha)-isomer

5. Tauroursodeoxycholic Acid, Monosodium Salt, (3alpha,5beta,7alpha)-isomer

6. Taurursodiol

7. Tudca

8. Ursodoxicoltaurine

2.3.2 Depositor-Supplied Synonyms

1. 14605-22-2

2. Tudca

3. Ursodeoxycholyltaurine

4. Tauroursodeoxycholate

5. Taurursodiol

6. Taurolite

7. Ursodoxicoltaurine

8. Ur 906

9. Sodium Tauroursodeoxycholate

10. Tauroursodesoxycholic Acid

11. Ursodeoxy Cholic Acid

12. Taurursodiol [usan]

13. 60eux8mn5x

14. Chembl272427

15. Chebi:80774

16. Ur-906

17. Taurursodiol (usan)

18. Ursodoxicoltaurine (inn)

19. Ursodoxicoltaurine [inn]

20. N-(3alpha,7beta-dihydroxy-5beta-cholan-24-oyl)-taurine

21. Tauroursodeoxycholate Sodium

22. 2-[(4r)-4-[(1s,2s,5r,7s,9s,10r,11s,14r,15r)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic Acid

23. 2-{[(3alpha,5beta,7alpha,8alpha,14beta,17alpha)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic Acid

24. Unii-60eux8mn5x

25. N-(3alpha,7beta-dihydroxy-5beta-cholan-24-oyl)taurine

26. Mfcd00065451

27. Tuda

28. N-ursodeoxycholoyltaurine

29. Tauroursodeoxycholic Acid, Sodium Salt

30. Schembl40764

31. Gtpl4746

32. Tauroursodeoxycholic Acid;tudca

33. Dtxsid80932754

34. Ex-a730

35. 2-(((3-alpha,5-beta,7-beta)-3,7-dihydroxy-24-oxocholan-24-yl) Amino)ethanesulfonic Acid

36. Hms3885c19

37. Ursodoxicoltaurine [who-dd]

38. Taurine, N-(3-alpha,7-beta-dihydroxy-5-beta-cholan-24-oyl)-,

39. Zinc3914813

40. 3alpha,7beta-dihydroxy-5beta-cholan-24-oic Acid N-(2-sulfoethyl)amide

41. Bdbm50236230

42. Lmst05040015

43. S3654

44. Sodium Tauroursodeoxycholate, >=95%

45. Who 11388

46. Ccg-269687

47. Db08834

48. 2-(((3-alpha,5-beta,7-beta)-3,7-dihydroxy-24-oxocholan-24-yl)amino)ethanesulfonic Acid

49. Ac-34539

50. Hy-19696

51. Cs-0016289

52. T1567

53. 3alpha,7beta-dihydroxy-5beta-cholanoyltaurine

54. D11836

55. 605t222

56. A808445

57. Q7688907

58. 3,7-dihydroxy-n-(2-sulfoethyl)cholan-24-imidic Acid

59. 3.alpha.,7.beta.-dihydroxy-5.beta.-cholanoyltaurine

60. 2-[(3alpha,7beta-dihydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic Acid

61. 2-{[(3alpha,5beta,7beta)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethane-1-sulfonic Acid

62. Ethanesulfonic Acid,2-[[(3a,5b,7b)-3,7-dihydroxy-24-oxocholan-24-yl]amino]-

63. 2-((r)-4-((3r,5s,7s,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethyl-hexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanamido)ethanesulfonic Acid

64. 2-[[(4r)-4-[(3r,5s,7s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7-bis(oxidanyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic Acid

65. 2-[[(4r)-4-[(3r,5s,7s,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-1-oxopentyl]amino]ethanesulfonic Acid

66. Ethanesulfonic Acid, 2-(((3-alpha,5-beta,7-beta)-3,7-dihydroxy-24-oxocholan-24-yl)amino)-

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 499.7 g/mol
Molecular Formula C26H45NO6S
XLogP33.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Exact Mass499.29675933 g/mol
Monoisotopic Mass499.29675933 g/mol
Topological Polar Surface Area132 Ų
Heavy Atom Count34
Formal Charge0
Complexity858
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Used in the treatment of cholesterol gallstones. Tauroursodeoxycholic acid is also being investigated for use in several conditions such as Primary Biliary Cirrhosis (PBC), insulin resistance, amyloidosis, Cystic Fibrosis, Cholestasis, and Amyotrophic Lateral Sclerosis.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


Cholagogues and Choleretics

Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic). (See all compounds classified as Cholagogues and Choleretics.)


5.2 Mechanism of Action

Tauroursodeoxycholic acid is the more hydrophilic form of ursodeoxycholic acid, which is naturally produced in the body. In patients with properly functioning gallbladders, both of these bile acids inhibit liver cholesterol secretion and synthesis as well as intestinal cholesterol absorption allowing for the promotion of cholesterol gallstone dissolution. The mechanism of action of tauroursodeoxycholic acid in the other conditions is still being investigated.


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