Tauroursodeoxycholic acid (CED0004100)

Record Information

Version

1.0

Creation Date

2016-05-25 18:51:22 UTC

Update Date

2026-08-22 07:03:14 UTC

Accession Number

CHEM022766

Identification

Common Name

Tauroursodeoxycholic acid

Class

Small Molecule

Description

Tauroursodeoxycholic acid is an organic compound with the formula C26H45NO6S and an average molecular weight of 499.70 g/mol. Tauroursodeoxycholic acid belongs to the bile acids, alcohols and derivatives, a subclass of steroids and steroid derivatives within the organic compounds. This compound is found in or released from three recorded sources: antennas within electrical and electronic equipment, and bile therapy and unclassified nervous system drugs within healthcare, pharmaceuticals and veterinary products. The recorded exposure route for this substance is oral. Regarding its biological activity, tauroursodeoxycholic acid acts as an activator of the protein target Integrin alpha-5 (ITGA5).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Tauroursodeoxycholate	Generator
2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl) amino)ethanesulfonate	HMDB
2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl) amino)ethanesulfonic acid	HMDB
2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl)amino)-ethanesulfonate	HMDB
2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl)amino)-ethanesulfonic acid	HMDB
3a,7b-Dihydroxy-5b-cholanoyltaurine	HMDB
N-(3-alpha,7-beta-Dihydroxy-5-beta-cholan-24-oyl)-taurine	HMDB
TUDCA	HMDB
UR 906	HMDB
Ursodeoxycholyltaurine	HMDB
Tauroursodeoxycholic acid, monosodium salt, (3alpha,5beta,7alpha)-isomer	MeSH, HMDB
Tauroursodeoxycholic acid, (3alpha,5alpha,7alpha)-isomer	MeSH, HMDB
Tauroursodeoxycholic acid, monosodium salt, (3alpha,7alpha)-isomer	MeSH, HMDB
(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-N-(2-sulfoethyl)pentanimidate	Generator, HMDB
(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-N-(2-sulphoethyl)pentanimidate	Generator, HMDB
(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-N-(2-sulphoethyl)pentanimidic acid	Generator, HMDB

Chemical Formula

C₂₆H₄₅NO₆S

Average Molecular Mass

499.704 g/mol

Monoisotopic Mass

499.297 g/mol

CAS Registry Number

14605-22-2

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

Traditional Name

2-[(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethanesulfonic acid

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCCS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)CC2C[C@H](O)CC[C@]12C

InChI Identifier

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

InChI Key

BHTRKEVKTKCXOH-VSHSPWMTSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Taurinated bile acids and derivatives

Alternative Parents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0075 g/L	ALOGPS
logP	1.38	ALOGPS
logP	0.81	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	-0.99	ChemAxon
pKa (Strongest Basic)	0.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	123.93 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.68 m³·mol⁻¹	ChemAxon
Polarizability	56.31 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-053r-0212900000-14bc097af3f7499753d7	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-004i-4214259000-4a72734ef61b01c2f556	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00e9-0801920000-ecfc97935416325b3ca5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-2901100000-9a3cf7f2963c041be363	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-8904100000-98cfa2606dbba4ef47a0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000t-2001900000-4adf0e40de3812e8d0ba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-6404900000-4d05b6f0352aebf4228d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001l-9102000000-63892e6e06f1123f8bfc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0000900000-31f17d1d48b7afdf3bae	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0000900000-f4f03ef481870394f9e2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9100300000-654e1207ef97c7662b6e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gx0-0000940000-9827b7f4a5b2f54a7bd4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0nmi-4639730000-a8491d87ed7e9a353ee5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f7x-3893000000-cc5d0b26da084a4d3a35	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
5125.0	Log mg/kg	[2900:9100]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
250	Bile therapy	Healthcare, pharmaceuticals & veterinary products	Not Available
384	Unclassified nervous system drugs	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
584	Buoys	Marine, shipping & aquaculture	Not Available
634	Buckles	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	0.155698
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Hepatic sodium/bile acid cotransporter	P26435	Rattus norvegicus	Predicted (SEA)	0.155698
Click to view 3D structure	Hepatic sodium/bile acid cotransporter	Q14973	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Autotaxin	Q13822	Humans	Predicted (SEA)	5.3716
Click to view 3D structure	Ileal sodium/bile acid cotransporter	Q12908	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	3.97031
Click to view 3D structure	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 2	Q11205	Rattus norvegicus	Predicted (SEA)	1.40129
Click to view 3D structure	NPC1-like intracellular cholesterol transporter 1	Q9UHC9	Humans	Predicted (SEA)	4.20386
Click to view 3D structure	Ephrin type-A receptor 2	P29317	Humans	Predicted (SEA)	258.382
Click to view 3D structure	Ephrin type-A receptor 2	Q03145	Mus musculus	Predicted (SEA)	2.33548
Click to view 3D structure	Vitamin D3 receptor	P11473	Humans	Predicted (SEA)	13.2344
Click to view 3D structure	Nuclear receptor ROR-gamma	P51449	Humans	Predicted (SEA)	48.9672
Click to view 3D structure	Ephrin type-A receptor 8	O09127	Mus musculus	Predicted (SEA)	2.25763
Click to view 3D structure	G-protein coupled receptor 183	D4A7K7	Rattus norvegicus	Predicted (SEA)	5.3716
Click to view 3D structure	Oxysterol-binding protein 1	P22059	Humans	Predicted (SEA)	5.99439
Click to view 3D structure	Ephrin type-A receptor 7	Q61772	Mus musculus	Predicted (SEA)	3.42537
Click to view 3D structure	Ephrin type-B receptor 3	P54754	Mus musculus	Predicted (SEA)	3.42537
Click to view 3D structure	Ephrin type-B receptor 1	P09759	Rattus norvegicus	Predicted (SEA)	3.42537
Click to view 3D structure	Ephrin type-A receptor 5	P54757	Rattus norvegicus	Predicted (SEA)	2.41333
Click to view 3D structure	Oxysterols receptor LXR-alpha	Q13133	Humans	Predicted (SEA)	38.3797
Click to view 3D structure	Phospholipase A2	P04054	Humans	Predicted (SEA)	5.68299
Click to view 3D structure	Ephrin type-A receptor 6	Q62413	Mus musculus	Predicted (SEA)	3.11397
Click to view 3D structure	Oxysterol-binding protein 2	Q969R2	Humans	Predicted (SEA)	6.22794
Click to view 3D structure	ATP-binding cassette sub-family C member 4	O15439	Humans	Predicted (SEA)	0.544945