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Structure Database (LMSD)

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Common Name

Tauroursodeoxycholic acid

Systematic Name

N-(3α,7β-dihydroxy-5β-cholan-24-oyl)-taurine

Synonyms

Tauroursodeoxycholate
TUDCA
3alpha,7beta-dihydroxy-5beta-cholanoyl Taurine

LM ID

LMST05040015

Formula

C₂₆H₄₅NO₆S

Exact Mass

Calculate m/z

499.296761

Sum Composition

ST 24:1;O3;Tau

Status

Curated

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Classification

Biological Context

Tauroursodeoxycholic acid (TUDCA) is a taurine-conjugated form of the secondary bile acid ursodeoxycholic acid .^1,2 TUDCA is found in small quantities in human bile but at a higher concentration in the bile of black bears.² It demonstrates anti-apoptotic activity in rodent models of tauopathy, Huntington's disease, ischemic brain injury, and retinal disorders.^3,2

This information has been provided by Cayman Chemical

References

1. Vang, S., Longley, K., Steer, C.J., et al. The unexpected uses of urso- and tauroursodeoxycholic acid in the treatment of non-liver diseases. Glob. Adv. Health Med. 3(3), 58-69 (2014).

2. Boatright, J.H., Nickerson, J.M., Moring, A.G., et al. Bile acids in treatment of ocular disease. J. Ocul. Biol. Dis. Infor. 2(3), 149-159 (2009).

3. Beuers, U. Effects of bile acids on hepatocellular signaling and secretion. Yale J. Biol. Med. 70(4), 341-346 (1997).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Ursus americanus (#9643)

Mammalia (#40674)

Ursodeoxycholic acid in the Ursidae: biliary bile acids of bears, pandas, and related carnivores.,
J Lipid Res, 1993

Pubmed ID: 8263415

String Representations

InChiKey (Click to copy)

BHTRKEVKTKCXOH-LBSADWJPSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@]12([C@@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCC(=O)NCCS(=O)(O)=O)CC[C@@]21[H])[H]