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Taurodeoxycholic Acid

PubChem CID
2733768
Structure
Taurodeoxycholic Acid_small.png
Taurodeoxycholic Acid_3D_Structure.png
Molecular Formula
Synonyms
  • TAURODEOXYCHOLIC ACID
  • 516-50-7
  • Deoxycholyltaurine
  • Taurodeoxycholate
  • Tudcabil
Molecular Weight
499.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-18
Description
Taurodeoxycholic acid is a bile acid taurine conjugate of deoxycholic acid. It has a role as a human metabolite. It is functionally related to a deoxycholic acid. It is a conjugate acid of a taurodeoxycholate.
Taurodeoxycholic acid has been reported in Streptomyces nigra, Homo sapiens, and other organisms with data available.
TAURODEOXYCHOLIC ACID is a small molecule drug with a maximum clinical trial phase of II (across all indications) and has 3 investigational indications.
See also: Sodium Taurodeoxycholate (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Taurodeoxycholic Acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-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
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

AWDRATDZQPNJFN-VAYUFCLWSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C26H45NO6S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

1180-95-6

2.3.2 Deprecated CAS

882214-17-7

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 Lipid Maps ID (LM_ID)

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Acid, Taurodeoxycholic
  • Deoxycholate, Taurine
  • Deoxycholyltaurine
  • Sodium Taurodeoxycholate
  • Taurine Deoxycholate
  • Taurodeoxycholate
  • Taurodeoxycholate, Sodium
  • Taurodeoxycholic Acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
499.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
499.29675933 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
499.29675933 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
132 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
34
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
858
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
10
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Melting Point

204 - 208 °C

3.2.3 Solubility

41 mg/mL

3.2.4 Collision Cross Section

204.37 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

204.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

221.79 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
221 Ų [M-H]-
S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.3 Chemical Classes

3.3.1 Lipids

Lipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Taurine conjugates [ST0504]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Spectra ID
Instrument Type
Varian
Frequency
600 MHz
Solvent
Water
pH
7.02
Shifts [ppm]:Intensity
1.70:14.18, 1.40:53.05, 0.98:61.26, 1.21:14.61, 2.14:8.34, 1.60:7.19, 1.51:18.38, 1.80:21.32, 2.12:5.08, 4.02:21.35, 3.61:10.41, 1.78:21.28, 1.74:16.18, 1.58:11.59, 7.93:12.27, 3.54:39.78, 3.56:37.18, 2.31:12.54, 1.29:11.37, 2.15:9.07, 1.55:12.18, 1.75:19.62, 1.90:9.49, 2.30:8.17, 1.22:11.98, 7.95:11.94, 1.27:17.46, 1.57:12.31, 7.94:23.57, 2.33:6.20, 3.07:44.05, 3.05:40.45, 1.26:8.46, 3.57:14.81, 3.06:78.25, 1.64:19.92, 0.68:99.02, 1.72:16.85, 1.49:19.37, 2.14:10.62, 1.53:14.55, 3.53:18.79, 0.91:100.00, 1.28:13.11, 0.99:61.14
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
1.40:44.78:0.17, 0.70:15.12:0.26, 1.40:38.36:0.20, 3.60:74.13:0.18, 1.41:28.70:0.12, 1.29:29.73:0.13, 4.02:75.68:0.43, 2.32:35.19:0.20, 0.91:25.60:0.74, 3.06:52.41:1.00, 1.66:31.79:0.12, 1.91:30.10:0.10, 2.90:56.85:0.05, 1.41:34.15:0.11, 1.82:29.73:0.09, 1.54:31.06:0.10, 3.55:37.59:0.30, 1.50:38.06:0.12, 1.58:50.31:0.12, 1.37:31.94:0.07, 1.70:34.15:0.13, 1.74:48.91:0.13, 1.22:30.24:0.11, 1.65:26.33:0.08, 0.97:37.77:0.08, 1.78:37.84:0.16, 1.20:28.77:0.07, 1.05:26.33:0.07, 0.98:19.25:0.18, 2.14:35.26:0.18, 1.81:36.00:0.09
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4.3 Mass Spectrometry

4.3.1 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

500.3041 100

482.2939 31.76

464.2828 31.73

483.297 8.92

502.3076 7.47

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2 of 6
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

464.283 100

465.2869 34.63

482.294 10.04

466.2863 6.85

483.297 3.03

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4.3.2 LC-MS

1 of 12
View All
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
4.401 min
Precursor m/z
500.304
Precursor Adduct
[M+H]+
Top 5 Peaks

500.3041 999

482.2939 317

464.2828 316

483.297 89

502.3076 74

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License
CC BY
2 of 12
View All
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
4.401 min
Precursor m/z
500.304
Precursor Adduct
[M+H]+
Top 5 Peaks

464.283 999

465.2869 345

482.294 100

466.2863 68

483.297 30

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License
CC BY

4.3.3 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
[M-H]-
Precursor m/z
498.2895
Ionization
ESI
Ionization Mode
negative
Collision Energy
30.0,50.0,70.0
Retention Time
1.63916
Top 5 Peaks

498.2899 100

79.9575 5.30

124.0076 3.80

106.9810 3

80.9653 2.10

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2 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
[M+H-H2O]+
Precursor m/z
482.2934
Ionization
ESI
Ionization Mode
positive
Collision Energy
30.0,50.0,70.0
Retention Time
1.90889
Top 5 Peaks

126.0217 100

464.2823 58.70

339.2677 37.40

107.0853 33.60

81.0697 33

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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

7.2.2 EU Clinical Trials Register

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

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.)
Detergents
Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties. (See all compounds classified as Detergents.)

9.2 Human Metabolite Information

9.2.1 Tissue Locations

Intestine

9.2.2 Cellular Locations

Extracellular

9.2.3 Metabolite Pathways

10 Safety and Hazards

10.1 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Taurodeoxycholic acid sodium salt: Does not have an individual approval but may be used under an appropriate group standard

11 Associated Disorders and Diseases

Disease
Hepatocellular carcinoma
References
Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Metastatic melanoma
References
PubMed: 28923537

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Nature Journal References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

14.2 Chemical-Target Interactions

14.3 Pathways

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 LIPID MAPS Classification

17.4 ChEMBL Target Tree

17.5 NORMAN Suspect List Exchange Classification

17.6 CCSBase Classification

17.7 EPA DSSTox Classification

17.8 LOTUS Tree

17.9 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  4. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  5. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  6. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  7. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    (S)-Taurodeoxycholic Acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  8. ChEBI
  9. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  10. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  11. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  12. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  13. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  14. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  15. EU Clinical Trials Register
  16. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  17. Japan Chemical Substance Dictionary (Nikkaji)
  18. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  19. Natural Product Activity and Species Source (NPASS)
  20. MassBank Europe
  21. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  22. Metabolomics Workbench
  23. Nature Chemical Biology
  24. Protein Data Bank in Europe (PDBe)
  25. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  26. Springer Nature
  27. Wikidata
  28. Wikipedia
  29. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  30. PubChem
  31. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  32. PATENTSCOPE (WIPO)
CONTENTS