MiMeDB: Showing metabocard for Taurocholic acid (MMDBc0000009)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:24:37 UTC

Update Date

2023-08-08 20:12:29 UTC

Metabolite ID

MMDBc0000009

Metabolite Identification

Common Name

Taurocholic acid

Description

Taurocholic acid is a bile acid and is the product of the conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. 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 ). Taurocholic acid, as with all bile acids, acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic (a bile purging agent). Hydrolysis of taurocholic acid yields taurine, a nonessential amino acid. Taurocholic acid is one of the main components of urinary nonsulfated bile acids in biliary atresia. Raised levels of taurocholate in fetal serum in obstetric cholestasis may result in the development of a fetal dysrhythmia and sudden intra-uterine death (PMID: 3944741 , 11256973 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₂₆H₄₅NO₇S

Average Mass

515.703

Monoisotopic Mass

515.291673489

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

81-24-3

SMILES

Not Available

InChI Identifier

InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1

InChI Key

WBWWGRHZICKQGZ-HZAMXZRMSA-N

Chemical Taxonomy

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
Fibroblasts
Intestine
Liver
Neuron
Placenta
Urine

Tissue Locations

Fibroblasts
Intestine
Liver
Neuron
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191911	Bile salt-activated lipase	Unknown	P19835	Homo sapiens
MMDBp0192108	Solute carrier organic anion transporter family member 1B3	Transporter	Q9NPD5	Homo sapiens
MMDBp0192113	Solute carrier organic anion transporter family member 1C1	Transporter	Q9NYB5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0192158	Cholesterol 7-alpha-monooxygenase	Unknown	P22680	Homo sapiens
MMDBp0192196	Bile acid-CoA:amino acid N-acyltransferase	Enzyme	Q14032	Homo sapiens
MMDBp0192716	Monocarboxylate transporter 1	Transporter	P53985	Homo sapiens
MMDBp0193190	Canalicular multispecific organic anion transporter 1	Transporter	Q92887	Homo sapiens
MMDBp0193300	Multidrug resistance-associated protein 1	Transporter	P33527	Homo sapiens
MMDBp0193386	Solute carrier organic anion transporter family member 2B1	Transporter	O94956	Homo sapiens
MMDBp0193395	Canalicular multispecific organic anion transporter 2	Transporter	O15438	Homo sapiens
MMDBp0193400	Bile salt export pump	Transporter	O95342	Homo sapiens
MMDBp0193419	Multidrug resistance protein 1	Transporter	P08183	Homo sapiens
MMDBp0193475	ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	Homo sapiens
MMDBp0193547	Ileal sodium/bile acid cotransporter	Transporter	Q12908	Homo sapiens
MMDBp0193577	Sodium/bile acid cotransporter	Transporter	Q14973	Homo sapiens
MMDBp0193588	Solute carrier family 22 member 1	Transporter	O15245	Homo sapiens
MMDBp0193639	Solute carrier organic anion transporter family member 1A2	Transporter	P46721	Homo sapiens
MMDBp0193865	Solute carrier organic anion transporter family member 4A1	Transporter	Q96BD0	Homo sapiens
MMDBp0193945	Multidrug resistance-associated protein 4	Transporter	O15439	Homo sapiens
MMDBp0194010	Solute carrier organic anion transporter family member 3A1	Transporter	Q9UIG8	Homo sapiens
MMDBp0194757	Solute carrier family 22 member 6	Transporter	Q4U2R8	Homo sapiens
MMDBp0194875	ATP-binding cassette sub-family C member 11	Transporter	Q96J66	Homo sapiens
MMDBp0195864	Gastrotropin	Unknown	P51161	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000367	Choloyl-CoA	Coenzyme A	Bile acid coa:amino acid n-acyltransferase	Bile Acid Coenzyme A: Amino Acid N-Acyltransferase	VMH	30371894
MMDBr0002197	Hydrogen carbonate	Hydrogen carbonate	Solute carrier organic anion transporter family, member 1a2	Taurocholate Transport via Bicarbonate Antiport	VMH	12507753 9007731 9334206
MMDBr0002198	Sodium	Sodium	Solute carrier family 10 (sodium/bile acid cotransporter), member 1	Taurocholate Transport via Sodium Symport	VMH	12851823 7592981 8132774 9109432
MMDBr0002199	Taurocholic acid	Taurocholic acid	Not Available	Bile Acid Intracellular Transport	VMH	30371894
MMDBr0002200	Taurocholic acid	Taurocholic acid	Not Available	Bile Acid Intracellular Transport	VMH	30371894
MMDBr0002632	Choloyl-CoA	Coenzyme A	Bile acid coa:amino acid n-acyltransferase	Choloyl Coenzyme A:Glycine N-Choloyltransferase Bile Acid Biosynthesis	VMH	10884298 12239217 12543708 15026425 3741411 6884990
MMDBr0002817	Sodium	Sodium	Solute carrier family 10 (sodium/bile acid cotransporter), member 1	Na (+)Bile Acid Symporter Active Transport	VMH	6469982
MMDBr0002818	Adenosine triphosphate	ADP	Not Available	Vesicular Transport	VMH	12663868 14716480 15209530 15297262 1599411 17416343 9068608
MMDBr0003554	Glutathione	Glutathione	Solute carrier organic anion transporter family, member 1a2	Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.14	VMH	11076394 11076396 14579113
MMDBr0003570	1-(S-Glutathionyl)-2,4-Dinitrobenzene	1-(S-Glutathionyl)-2,4-Dinitrobenzene	Solute carrier organic anion transporter family, member 1a2	Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.14	VMH	11076394 11076396 14579113
MMDBr0003571	S-Glutathionyl-Ethacrynic-Acid	S-Glutathionyl-Ethacrynic-Acid	Solute carrier organic anion transporter family, member 1a2	Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.14	VMH	11076394 11076396 14579113
MMDBr0005672	Adenosine triphosphate	ADP	Atp-binding cassette, sub-family a (abc1), member 8	Bile Acid Transport by ABCa8	VMH	30371894
MMDBr0005685	Adenosine triphosphate	ADP	Atp-binding cassette, sub-family b (mdr/tap), member 11	ABC Bile Acid Transporter	VMH	30371894
MMDBr0012625	Water	Cholic acid	Not Available	Taurocholate hydrolysis by bile salt hydrolase (EC 3.5.1.24)	VMH	30371894
MMDBr0016276	Cholic acid	Water	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0016277	Water	Cholic acid	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0016708	NAD	7-oxo-taurodeoxycholic acid	7alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016709	NAD	7-oxo-taurodeoxycholic acid	7alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880

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	107	Human feces; Human ; Human urine; Human mucosa; Goat feces; Sheep feces; Human saliva; Human sputum; Pig	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Bacteroidetes	54	Human feces; Human ; Human urine; Human stool; Human appendix biopsy; Human saliva	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	37	Human ; Human feces; Human saliva; Human mucosa; Human stool	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	5	Human feces; Human	Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.15	0.087			umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	HMDB	3944741
Human Blood	Detected and Quantified	0.1		0.1	0.5	uM	Infant (0-1 year old)	Both	Normal	HMDB	27163928
Human Feces	Detected and Quantified	5.78	4.32			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Bile	Detected and Quantified	9910		9600	10220	uM	Adult (>18 years old)	Both	Normal	HMDB	11160372
Human Blood	Detected and Quantified	0.38	0.20			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 Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	19636438
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	25037050
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

Not Available

References

Synthesis Reference

Not Available

General References

Hoekman MF, Rientjes JM, Twisk J, Planta RJ, Princen HM, Mager WH: Transcriptional regulation of the gene encoding cholesterol 7 alpha-hydroxylase in the rat. Gene. 1993 Aug 25;130(2):217-23. doi: 10.1016/0378-1119(93)90422-y. [PubMed:8359688 ]
Sandker GW, Weert B, Olinga P, Wolters H, Slooff MJ, Meijer DK, Groothuis GM: Characterization of transport in isolated human hepatocytes. A study with the bile acid taurocholic acid, the uncharged ouabain and the organic cations vecuronium and rocuronium. Biochem Pharmacol. 1994 Jun 15;47(12):2193-200. doi: 10.1016/0006-2952(94)90255-0. [PubMed:7913319 ]
Kullak-Ublick GA, Glasa J, Boker C, Oswald M, Grutzner U, Hagenbuch B, Stieger B, Meier PJ, Beuers U, Kramer W, Wess G, Paumgartner G: Chlorambucil-taurocholate is transported by bile acid carriers expressed in human hepatocellular carcinomas. Gastroenterology. 1997 Oct;113(4):1295-305. doi: 10.1053/gast.1997.v113.pm9322525. [PubMed:9322525 ]
Claudel T, Inoue Y, Barbier O, Duran-Sandoval D, Kosykh V, Fruchart J, Fruchart JC, Gonzalez FJ, Staels B: Farnesoid X receptor agonists suppress hepatic apolipoprotein CIII expression. Gastroenterology. 2003 Aug;125(2):544-55. doi: 10.1016/s0016-5085(03)00896-5. [PubMed:12891557 ]
Rizzo G, Renga B, Mencarelli A, Pellicciari R, Fiorucci S: Role of FXR in regulating bile acid homeostasis and relevance for human diseases. Curr Drug Targets Immune Endocr Metabol Disord. 2005 Sep;5(3):289-303. doi: 10.2174/1568008054863781. [PubMed:16178789 ]
Duan RD, Cheng Y, Tauschel HD, Nilsson A: Effects of ursodeoxycholate and other bile salts on levels of rat intestinal alkaline sphingomyelinase: a potential implication in tumorigenesis. Dig Dis Sci. 1998 Jan;43(1):26-32. doi: 10.1023/a:1018807600683. [PubMed:9508530 ]
Akao T: Influence of various bile acids on the metabolism of glycyrrhizin and glycyrrhetic acid by Ruminococcus sp. PO1-3 of human intestinal bacteria. Biol Pharm Bull. 1999 Aug;22(8):787-93. doi: 10.1248/bpb.22.787. [PubMed:10480314 ]
Jigorel E, Le Vee M, Boursier-Neyret C, Bertrand M, Fardel O: Functional expression of sinusoidal drug transporters in primary human and rat hepatocytes. Drug Metab Dispos. 2005 Oct;33(10):1418-22. doi: 10.1124/dmd.105.004762. Epub 2005 Jul 13. [PubMed:16014767 ]
Zahner D, Eckhardt U, Petzinger E: Transport of taurocholate by mutants of negatively charged amino acids, cysteines, and threonines of the rat liver sodium-dependent taurocholate cotransporting polypeptide Ntcp. Eur J Biochem. 2003 Mar;270(6):1117-27. doi: 10.1046/j.1432-1033.2003.03463.x. [PubMed:12631271 ]
Wang LF, Luo H, Miyoshi M, Imoto T, Hiji Y, Sasaki T: Inhibitory effect of gymnemic acid on intestinal absorption of oleic acid in rats. Can J Physiol Pharmacol. 1998 Oct-Nov;76(10-11):1017-23. doi: 10.1139/cjpp-76-10-11-1017. [PubMed:10100884 ]
Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D: Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. doi: 10.1053/jhep.2003.50331. [PubMed:12883481 ]
Yamamoto Y, Moore R, Hess HA, Guo GL, Gonzalez FJ, Korach KS, Maronpot RR, Negishi M: Estrogen receptor alpha mediates 17alpha-ethynylestradiol causing hepatotoxicity. J Biol Chem. 2006 Jun 16;281(24):16625-31. doi: 10.1074/jbc.M602723200. Epub 2006 Apr 10. [PubMed:16606610 ]
Kwekkeboom J, Princen HM, van Voorthuizen EM, Meijer P, Kempen HJ: Comparison of taurocholate accumulation in cultured hepatocytes of pig, rat and man. Biochem Biophys Res Commun. 1989 Jul 31;162(2):619-25. doi: 10.1016/0006-291x(89)92355-3. [PubMed:2757635 ]
Claudel T, Sturm E, Duez H, Torra IP, Sirvent A, Kosykh V, Fruchart JC, Dallongeville J, Hum DW, Kuipers F, Staels B: Bile acid-activated nuclear receptor FXR suppresses apolipoprotein A-I transcription via a negative FXR response element. J Clin Invest. 2002 Apr;109(7):961-71. doi: 10.1172/JCI14505. [PubMed:11927623 ]
Perwaiz S, Tuchweber B, Mignault D, Gilat T, Yousef IM: Determination of bile acids in biological fluids by liquid chromatography-electrospray tandem mass spectrometry. J Lipid Res. 2001 Jan;42(1):114-9. [PubMed:11160372 ]
Johnson RC, Shah SN: Cholesterol ester hydrolase(s) in mammalian brain: is there a myelin-specific cholesterol ester hydrolase? Neurochem Res. 1986 Nov;11(11):1571-82. doi: 10.1007/BF00965776. [PubMed:3683732 ]
van Montfoort JE, Muller M, Groothuis GM, Meijer DK, Koepsell H, Meier PJ: Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5. [PubMed:11408531 ]
Balakrishnan A, Sussman DJ, Polli JE: Development of stably transfected monolayer overexpressing the human apical sodium-dependent bile acid transporter (hASBT). Pharm Res. 2005 Aug;22(8):1269-80. doi: 10.1007/s11095-005-5274-8. Epub 2005 Aug 3. [PubMed:16078136 ]
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 ]
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 ]
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 ]
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 ]
Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. doi: 10.1097/00005176-198601000-00005. [PubMed:3944741 ]
Williamson C, Gorelik J, Eaton BM, Lab M, de Swiet M, Korchev Y: The bile acid taurocholate impairs rat cardiomyocyte function: a proposed mechanism for intra-uterine fetal death in obstetric cholestasis. Clin Sci (Lond). 2001 Apr;100(4):363-9. [PubMed:11256973 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Taurocholic acid (MMDBc0000009)

MOL for #<Metabolite:0x00005619a482f0a0>

3D MOL for #<Metabolite:0x00005619a482f0a0>

3D SDF for #<Metabolite:0x00005619a482f0a0>

3D-SDF for #<Metabolite:0x00005619a482f0a0>

PDB for #<Metabolite:0x00005619a482f0a0>

3D PDB for #<Metabolite:0x00005619a482f0a0>

SMILES for #<Metabolite:0x00005619a482f0a0>

INCHI for #<Metabolite:0x00005619a482f0a0>

Structure for #<Metabolite:0x00005619a482f0a0>

3D Structure for #<Metabolite:0x00005619a482f0a0>