MiMeDB: Showing metabocard for Taurochenodesoxycholic acid (MMDBc0000173)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:33 UTC

Update Date

2024-10-11 04:14:51 UTC

Metabolite ID

MMDBc0000173

Metabolite Identification

Common Name

Taurochenodesoxycholic acid

Description

Taurochenodesoxycholic acid is a bile acid formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). Taurochenodesoxycholic acid has been found to be a microbial metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Chenodeoxycholoyltaurine	ChEBI
Taurine chenodeoxycholate	ChEBI
Taurochenodeoxycholate	ChEBI
Taurochenodeoxycholic acid	Kegg
Taurine chenodeoxycholic acid	Generator
Taurochenodesoxycholate	Generator
12-Deoxycholyltaurine	HMDB
12-Desoxycholyltaurine	HMDB
3a,7a-Dihydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide	HMDB
Chenodeoxycholyltaurine	HMDB
Chenyltaurine	HMDB
N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-taurine	HMDB
Acid, taurochenodeoxycholic	HMDB
Chenodeoxycholate, taurine	HMDB

Molecular Formula

C₂₆H₄₅NO₆S

Average Mass

499.704

Monoisotopic Mass

499.296758867

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

516-35-8

SMILES

Not Available

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-BJLOMENOSA-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-hydroxysteroid
Fatty acyl
Fatty amide
N-acyl-amine
Alkanesulfonic acid
Cyclic alcohol
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid taurine conjugate (CHEBI:16525 )
C26 bile acids, alcohols, and derivatives (C05465 )
Taurine conjugates (C05465 )
Taurine conjugates (LMST05040005 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192196	Bile acid-CoA:amino acid N-acyltransferase	Enzyme	Q14032	Homo sapiens
MMDBp0192630	Cytochrome P450 3A4	Unknown	P08684	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0004104	Chenodeoxycholoyl-CoA	Taurochenodesoxycholic acid	bile acid CoA:amino acid N-acyltransferase	VMH; KEGG	30371894
MMDBr0004105	Chenodeoxycholoyl-CoA	Taurochenodesoxycholic acid	bile acid CoA:amino acid N-acyltransferase	VMH	11980911
MMDBr0012411	Taurochenodesoxycholic acid	Taurohyocholate	cytochrome P450, family 3, subfamily A, polypeptide 4	VMH	30371894
MMDBr0012624	Taurochenodesoxycholic acid	Chenodeoxycholic acid	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Biliary atresia		Association	Human Urine	HMDB	3944741

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	104	Human ; Human mucosa; Human vaginal fluid; Human supragingival plaque; Human feces; Human saliva; Human urine; Human sputum; Pig	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Bacteroidetes	52	Human feces; Human ; Human urine; Human stool; Human appendix biopsy; Human saliva	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	6	Human ; Human feces	Microbial culture; Metabolic reconstruction
Bacteria	Actinobacteria	38	Human ; Human feces; Human saliva; Human mucosa; Human stool	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Bile	Detected and Quantified	>0.01				uM	Adult (>18 years old)	Both	Normal	HMDB	659989
Human Urine	Detected and Quantified	0.013	0.021			umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	HMDB	3944741
Human Urine	Detected and Quantified	0.00065	0.0019			umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	3944741
Human Feces	Detected and Quantified	6.03	5			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Recurrent Clostridium difficile infection	HMDB	24284963
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Recurrent Clostridium difficile infection	HMDB	24284963
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Clostridium difficile infection	HMDB	24284963
Human Blood	Detected and Quantified	0.4		0.3	1.2	uM	Infant (0-1 year old)	Both	Severe acute malnutrition	HMDB	27163928
Human Blood	Detected and Quantified	0.3		0.1	0.3	uM	Infant (0-1 year old)	Both	Normal	HMDB	27163928
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Crohns disease	HMDB	27609529
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Ulcerative colitis	HMDB	27609529
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Unclassified IBD	HMDB	27609529
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected and Quantified	0.3	0.08			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.013	0.021			umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	HMDB	3944741
Human Bile	Detected and Quantified	>0.01				uM	Adult (>18 years old)	Both	Normal	HMDB	659989
Human Urine	Detected and Quantified	0.00065	0.0019			umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	3944741
Human Blood	Detected and Quantified	0.3		0.1	0.3	uM	Infant (0-1 year old)	Both	Normal	HMDB	27163928
Human Feces	Detected and Quantified	6.03	5.00			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Blood	Detected and Quantified	0.30	0.08			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000951

DrugBank ID

DB08833

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022335

KNApSAcK ID

Not Available

Chemspider ID

343282

KEGG Compound ID

C05465

BioCyc ID

CHENODEOXYCHOLOYLTAURINE

BiGG ID

45864

Wikipedia Link

Not Available

METLIN ID

5897

PubChem Compound

387316

PDB ID

Not Available

ChEBI ID

16525

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Schwenk M, Hofmann AF, Carlson GL, Carter JA, Coulston F, Greim H: Bile acid conjugation in the chimpanzee: effective sulfation of lithocholic acid. Arch Toxicol. 1978 Apr 27;40(2):109-18. doi: 10.1007/BF01891965. [PubMed:580732 ]
Bloch CA, Watkins JB: Determination of conjugated bile acids in human bile and duodenal fluid by reverse-phase high-performance liquid chromatography. J Lipid Res. 1978 May;19(4):510-3. [PubMed:659989 ]
Bolhuis PA, Sinaasappel M: Bile acid clearance and biocompatibility of XAD-4 haemoperfusion. Int J Artif Organs. 1978 May;1(3):135-41. [PubMed:689756 ]
Makino I, Shinozaki K, Nakagawa S, Mashimo K: Measurement of sulfated and nonsulfated bile acids in human serum and urine. J Lipid Res. 1974 Mar;15(2):132-8. [PubMed:4832755 ]
Roda A, Pellicciari R, Polimeni C, Cerre C, Forti GC, Sadeghpour B, Sapigni E, Gioacchini AM, Natalini B: Metabolism, pharmacokinetics, and activity of a new 6-fluoro analogue of ursodeoxycholic acid in rats and hamsters. Gastroenterology. 1995 Apr;108(4):1204-14. doi: 10.1016/0016-5085(95)90221-x. [PubMed:7698590 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. doi: 10.1242/jeb.204.10.1673. [PubMed:11316487 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. doi: 10.1152/ajpgi.00417.2002. [PubMed:12576301 ]
Pouwels MJ, Tack CJ, Span PN, Olthaar AJ, Sweep CG, Huvers FC, Lutterman JA, Hermus AR: Role of hexosamines in insulin resistance and nutrient sensing in human adipose and muscle tissue. J Clin Endocrinol Metab. 2004 Oct;89(10):5132-7. doi: 10.1210/jc.2004-0291. [PubMed:15472217 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. doi: 10.1161/01.ATV.0000178994.21828.a7. Epub 2005 Jul 21. [PubMed:16037564 ]
Ijare OB, Somashekar BS, Jadegoud Y, Nagana Gowda GA: 1H and 13C NMR characterization and stereochemical assignments of bile acids in aqueous media. Lipids. 2005 Oct;40(10):1031-41. doi: 10.1007/s11745-005-1466-1. [PubMed:16382575 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Taurochenodesoxycholic acid (MMDBc0000173)

MOL for #<Metabolite:0x00007fdb583777e8>

3D MOL for #<Metabolite:0x00007fdb583777e8>

3D SDF for #<Metabolite:0x00007fdb583777e8>

3D-SDF for #<Metabolite:0x00007fdb583777e8>

PDB for #<Metabolite:0x00007fdb583777e8>

3D PDB for #<Metabolite:0x00007fdb583777e8>

SMILES for #<Metabolite:0x00007fdb583777e8>

INCHI for #<Metabolite:0x00007fdb583777e8>

Structure for #<Metabolite:0x00007fdb583777e8>

3D Structure for #<Metabolite:0x00007fdb583777e8>