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tauroursodeoxycholic acid , CAS No.14605-22-2
Basic Description
Synonyms
.alpha.-Methyl-3,4-(methylenedioxy)phenethylamine hydrochloride | 2-{[(3alpha,5beta,7beta)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethane-1-sulfonic acid | Tauroursodeoxycholic Acid, Sodium Salt | Ursodeoxy cholic acid | DB08834 | HY-19696 | NCGC00163569-0
Specifications & Purity
Moligand™, ≥98%
Storage Temp
Store at -20°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Grade
Moligand™
Product Description
Tauroursodeoxycholate (Tauroursodeoxycholic acid) is an endoplasmic reticulum (ER) stress inhibitor. Tauroursodeoxycholate significantly reduces expression of apoptosis molecules, such as caspase-3 and caspase-12. Tauroursodeoxycholate also inhibits ERK.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Subclass
Bile acids, alcohols and derivatives
Intermediate Tree Nodes
Not available
Direct Parent
Taurinated bile acids and derivatives
Alternative Parents
Dihydroxy bile acids, alcohols and derivatives 7-alpha-hydroxysteroids 3-alpha-hydroxysteroids N-acyl amines Sulfonyls Organosulfonic acids Alkanesulfonic acids Secondary carboxylic acid amides Secondary alcohols Cyclic alcohols and derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Molecular Framework
Aliphatic homopolycyclic compounds
Substituents
Taurinated bile acid - Dihydroxy bile acid, alcohol, or derivatives - Hydroxy bile acid, alcohol, or derivatives - 3-hydroxysteroid - Hydroxysteroid - 3-alpha-hydroxysteroid - 7-alpha-hydroxysteroid - 7-hydroxysteroid - Fatty amide - N-acyl-amine - Fatty acyl - Sulfonyl - Organosulfonic acid - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Alkanesulfonic acid - Cyclic alcohol - Secondary carboxylic acid amide - Secondary alcohol - Carboxamide group - Carboxylic acid derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Organic oxygen compound - Organonitrogen compound - Organosulfur compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Alcohol - Aliphatic homopolycyclic compound
Description
This compound belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.
External Descriptors
Taurine conjugates
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
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
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
InChIKey
BHTRKEVKTKCXOH-LBSADWJPSA-N
Smiles
CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
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
WGK Germany
2
Alternate CAS
117609-50-4
PubChem CID
9848818
Molecular Weight
499.71
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Specific Rotation[α]
46 ° (C=1, EtOH)
Molecular Weight
499.700 g/mol
XLogP3
3.600
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
7
Exact Mass
499.297 Da
Monoisotopic Mass
499.297 Da
Topological Polar Surface Area
132.000 Ų
Heavy Atom Count
34
Formal Charge
0
Complexity
858.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
10
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Citations of This Product
1.
Jiating Zheng, Xiaoru Peng, Taifeng Zhu, Shuyao Huang, Chao Chen, Guosheng Chen, Shuqin Liu, Gangfeng Ouyang.
(2022)
Detection of bile acids in small volume human bile samples via an amino metal-organic framework composite based solid-phase microextraction probe. JOURNAL OF CHROMATOGRAPHY A,
1685
(463634).
2.
Ma Wen, Yang Bingxin, Li Jun, Liu Mingxia, Li Xianjiang, Liu Huwei.
(2022)
Maltose-functional metal–organic framework assisted laser desorption/ionization mass spectrometry for small biomolecule determination. MICROCHIMICA ACTA,
189
(7):
(1-8).
3.
Xiaoxu Cheng, Zifeng Pi, Zhong Zheng, Shu Liu, Fengrui Song, Zhiqiang Liu.
(2022)
Combined 16S rRNA gene sequencing and metabolomics to investigate the protective effects of Wu-tou decoction on rheumatoid arthritis in rats. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,
1199
(123249).
4.
Wentao Sun, Yang Zhou, Hongmei Xue, Haitao Hou, Guowei He, Qin Yang.
(2022)
Endoplasmic reticulum stress mediates homocysteine-induced hypertrophy of cardiac cells through activation of cyclic nucleotide phosphodiesterase 1C. ACTA BIOCHIMICA ET BIOPHYSICA SINICA,
54
(3):
(388-399).
5.
Yufei Sun, Zhiqiang Liu, Zifeng Pi, Fengrui Song, Jianlin Wu, Shu Liu.
(2021)
Poria cocos could ameliorate cognitive dysfunction in APP/PS1 mice by restoring imbalance of Aβ production and clearance and gut microbiota dysbiosis. PHYTOTHERAPY RESEARCH,
35
(5):
(2678-2690).
6.
Chen Guang, Gao Cheng, Yan Ya’nan, Wang Tao, Luo Chengliang, Zhang Mingyang, Chen Xiping, Tao Luyang.
(2020)
Inhibiting ER Stress Weakens Neuronal Pyroptosis in a Mouse Acute Hemorrhagic Stroke Model. MOLECULAR NEUROBIOLOGY,
57
(12):
(5324-5335).
7.
Di Wu, Yuanming Zhai, Jin Yan, Kailin Xu, Qing Wang, Yuanzhi Li, Hui Li.
(2015)
Binding mechanism of tauroursodeoxycholic acid to human serum albumin: insights from NMR relaxation and docking simulations. RSC Advances,
5
(15):
(11036-11042).
8.
Shun Zhang, Ting Cai, Jing Lin, Jia-Juan Liu, Yong-Gang Zhao, Min-Yi Cao.
(2024)
Analysis of 15 bile acids in human plasma based on C18 functionalized magnetic organic polymer nanocomposite coupled with liquid chromatography-tandem mass spectrometry. JOURNAL OF CHROMATOGRAPHY A,
1725
(464962).
9.
Xinye Shi, Yuandi Xue, Yuxin Tu, Canrong Chen, Yajing Zhang, Zian Lin, Zongwei Cai.
(2025)
Covalent organic framework-based solid phase microextraction coupled with electrospray ionization mass spectrometry for the quantitative assessment of abnormal bile acids by triclosan exposure in mice. TALANTA,
285
(127398).
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9 Citations