Cholic acid (T3D4343)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (22)XML
Targets (22)
Record Information
Version2.0
Creation Date2014-08-29 06:30:26 UTC
Update Date2018-03-21 17:46:18 UTC
Accession NumberT3D4343
Identification
Common NameCholic acid
ClassSmall Molecule
DescriptionCholic acid is a major primary bile acid produced in the liver and is usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends 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). When present in sufficiently high levels, cholic acid can act as a hepatotoxin and a metabotoxin. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. Chronically high levels of cholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids, including cholic acid, are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood. The bile acid ursodiol (ursodeoxycholic acid) can improve symptoms associated with familial hypercholanemia.
Compound Type
  • Animal Toxin
  • Food Toxin
  • Mammal Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triol
3a,7a,12a-Trihydroxy-5b-cholan-24-oate
3a,7a,12a-Trihydroxy-5b-cholan-24-oic acid
3a,7a,12a-Trihydroxy-5b-cholanate
3a,7a,12a-Trihydroxy-5b-cholanic acid
3a,7a,12a-Trihydroxy-5b-cholanoate
3a,7a,12a-Trihydroxy-5b-cholanoic acid
3a,7a,12a-Trihydroxy-b-cholanate
3a,7a,12a-Trihydroxy-b-cholanic acid
3a,7a,12a-Trihydroxy-beta-cholanate
3a,7a,12a-Trihydroxy-beta-cholanic acid
3a,7a,12a-Trihydroxycholanate
3a,7a,12a-Trihydroxycholanic acid
5b-Cholanic acid-3a,7a,12a-triol
5b-Cholate
5b-Cholic acid
Cholalate
Cholalic acid
Cholalin
Cholate
Colalin
Chemical FormulaC24H40O5
Average Molecular Mass408.571 g/mol
Monoisotopic Mass408.288 g/mol
CAS Registry Number81-25-4
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
SMILES[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C
InChI IdentifierInChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
InChI KeyInChIKey=BHQCQFFYRZLCQQ-OELDTZBJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Intestine
  • Kidney
  • Liver
  • Placenta
  • Platelet
  • Small Intestine
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 Not Available
Familial Hypercholanemia (FHCA)SMP00317 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point197 - 201°C
Boiling PointNot Available
Solubility0.175 mg/mL
LogP2.02
Predicted Properties
PropertyValueSource
logP2.48ChemAxon
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.79 m³·mol⁻¹ChemAxon
Polarizability47.05 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fk9-5796000000-2876080f3fa17fb963702017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fk9-5796000000-2876080f3fa17fb963702018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-0439000000-4e43231560df6c61b96d2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-1100049000-86faaffe1dc0eadf9e752017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0000900000-806d3b03c76019afbf7d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0000900000-4edb603ca5534669120e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0000900000-4a76e64b2f0411d0b7012017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0001900000-41aa3a7cb25fcf5490462017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0057900000-790a3808fa512d5d16872017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0010900000-e6bedfc253363160a37e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0030900000-da4a7bfccbaf1e42171c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0020900000-772055897702843a1d502017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0021900000-0405fe63d70d3a88bf6f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0aou-3844900000-cb3c2aba1b9a297856162017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0007-0019000000-fb9a5b5952cf65eb79882017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0001900000-9583bd9c6c0d2b069b682017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-1027900000-31f3cf065ad48561c0a22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000900000-b0504ee652d51a711f3a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000900000-18dd8b6be45775ec83c22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0007-0019000000-285d3d0d87f5471b419a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0007-0019000000-0fcb0f6819b05ab63c122017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000900000-b0504ee652d51a711f3a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000900000-18dd8b6be45775ec83c22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0007-0019000000-285d3d0d87f5471b419a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0007-0019000000-0fcb0f6819b05ab63c122017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-6fe7340aea27993f6ecb2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0001900000-9e5ac05d22599c16d77a2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-a58dbdca74695c9c40e12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-1c1c35b35f948ca539432021-09-20View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0596-9642000000-e425981b8a0ac72ea6ee2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)Not Available2014-09-23View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsChronically high levels of cholic acid are associated with Familial Hypercholanemia.
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB02659
HMDB IDHMDB00619
PubChem Compound ID221493
ChEMBL IDCHEMBL205596
ChemSpider ID192176
KEGG IDC00695
UniProt IDNot Available
OMIM ID
ChEBI ID16359
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDCHD
ACToR IDNot Available
Wikipedia LinkCholic acid
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. 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. [11316487 ]
  2. 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. Epub 2005 Jul 21. [16037564 ]
  3. 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. [12576301 ]
  4. 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. [11907135 ]
  5. Wildgrube HJ, Stang H, Winkler M, Mauritz G: [Value of serum levels of conjugated cholic acid in the diagnosis of liver disease (author's transl)]. Dtsch Med Wochenschr. 1982 Aug 20;107(33):1235-7. [7106004 ]
  6. Rodrigues CM, Marin JJ, Brites D: Bile acid patterns in meconium are influenced by cholestasis of pregnancy and not altered by ursodeoxycholic acid treatment. Gut. 1999 Sep;45(3):446-52. [10446117 ]
  7. Einarsson K, Reihner E, Ewerth S, Bjorkhem I: Serum concentrations of unconjugated and conjugated cholic acid in portal venous and systemic venous blood of fasting man. Scand J Clin Lab Invest. 1989 Feb;49(1):83-91. [2727621 ]
  8. Briz O, Macias RI, Serrano MA, Gonzalez-Gallego J, Bayon JE, Marin JJ: Excretion of foetal bilirubin by the rat placenta-maternal liver tandem. Placenta. 2003 May;24(5):462-72. [12744922 ]
  9. Gustafsson J, Alvelius G, Bjorkhem I, Nemeth A: Bile acid metabolism in extrahepatic biliary atresia: lithocholic acid in stored dried blood collected at neonatal screening. Ups J Med Sci. 2006;111(1):131-6. [16553252 ]
  10. Kuramoto T, Furukawa Y, Nishina T, Sugimoto T, Mahara R, Tohma M, Kihira K, Hoshita T: Identification of short side chain bile acids in urine of patients with cerebrotendinous xanthomatosis. J Lipid Res. 1990 Oct;31(10):1895-902. [2079611 ]
  11. Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [15185309 ]
  12. Salen G, Shefer S, Tint GS, Nicolau G, Dayal B, Batta AK: Biosynthesis of bile acids in cerebrotendinous xanthomatosis. Relationship of bile acid pool sizes and synthesis rates to hydroxylations at C-12, C-25, and C-26. J Clin Invest. 1985 Aug;76(2):744-51. [4031069 ]
  13. Brites D, Poeiras J, Rodrigues C: [Intrahepatic cholestasis in pregnancy. Its etiopathogenesis, prognosis and therapy]. Acta Med Port. 1994 Mar;7(3):181-8. [8209706 ]
  14. Van Den Berg JW, Van Blankenstein M, Bosman-Jacobs EP, Frenkel M, Horchner P, Ooost-Harwig OI, Wilson JH: Solid phase radioimmunoassay for determination of conjugated cholic acid in serum. Clin Chim Acta. 1976 Dec 1;73(2):277-83. [1000848 ]
  15. Pomare EW, Low-Beer TS: Proceedings: Effect of administration of a colonic metabolite of cholic acid on cholesterol levels in bile and blood. Gut. 1974 Oct;15(10):830. [4434946 ]
  16. Einarsson K, Bergstrom M, Eklof R, Nord CE, Bjorkhem I: Comparison of the proportion of unconjugated to total serum cholic acid and the [14C]-xylose breath test in patients with suspected small intestinal bacterial overgrowth. Scand J Clin Lab Invest. 1992 Sep;52(5):425-30. [1514020 ]
  17. Ewerth S, Bjorkhem I, Einarsson K, Ost L: Lymphatic transport of bile acids in man. J Lipid Res. 1982 Nov;23(8):1183-6. [7175375 ]
  18. Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [16548228 ]
  19. LaRusso NF, Hoffman NE, Hofmann AF, Korman MG: Validity and sensitivity of an intravenous bile acid tolerance test in patients with liver disease. N Engl J Med. 1975 Jun 5;292(23):1209-14. [1128572 ]
  20. Lillienau J, Schteingart CD, Hofmann AF: Physicochemical and physiological properties of cholylsarcosine. A potential replacement detergent for bile acid deficiency states in the small intestine. J Clin Invest. 1992 Feb;89(2):420-31. [1371123 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Ferrochelatase, mitochondrial
General Function:
Iron-responsive element binding
Specific Function:
Catalyzes the ferrous insertion into protoporphyrin IX.
Gene Name:
FECH
Uniprot ID:
P22830
Molecular Weight:
47861.77 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
2. G-protein coupled bile acid receptor 1
General Function:
G-protein coupled bile acid receptor activity
Specific Function:
Receptor for bile acid. Bile acid-binding induces its internalization, activation of extracellular signal-regulated kinase and intracellular cAMP production. May be involved in the suppression of macrophage functions by bile acids.
Gene Name:
GPBAR1
Uniprot ID:
Q8TDU6
Molecular Weight:
35247.795 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC506 uMNot AvailableBindingDB 50236237
References
  1. Herbert MR, Siegel DL, Staszewski L, Cayanan C, Banerjee U, Dhamija S, Anderson J, Fan A, Wang L, Rix P, Shiau AK, Rao TS, Noble SA, Heyman RA, Bischoff E, Guha M, Kabakibi A, Pinkerton AB: Synthesis and SAR of 2-aryl-3-aminomethylquinolines as agonists of the bile acid receptor TGR5. Bioorg Med Chem Lett. 2010 Oct 1;20(19):5718-21. doi: 10.1016/j.bmcl.2010.08.014. Epub 2010 Aug 10. [20801037 ]
  2. Ishizawa M, Matsunawa M, Adachi R, Uno S, Ikeda K, Masuno H, Shimizu M, Iwasaki K, Yamada S, Makishima M: Lithocholic acid derivatives act as selective vitamin D receptor modulators without inducing hypercalcemia. J Lipid Res. 2008 Apr;49(4):763-72. doi: 10.1194/jlr.M700293-JLR200. Epub 2008 Jan 7. [18180267 ]
Target Details
3. Phospholipase A2
General Function:
Receptor binding
Specific Function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides, this releases glycerophospholipids and arachidonic acid that serve as the precursors of signal molecules.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular Weight:
16359.535 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Dissociation>150 uMNot AvailableBindingDB 50236237
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
  2. Yu BZ, Kaimal R, Bai S, El Sayed KA, Tatulian SA, Apitz RJ, Jain MK, Deng R, Berg OG: Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia. J Nat Prod. 2009 Jan;72(1):24-8. doi: 10.1021/np8004453. [19102680 ]
Target Details
4. Alcohol dehydrogenase 1C
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular Weight:
39867.27 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
5. Bile acid receptor
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
Gene Name:
NR1H4
Uniprot ID:
Q96RI1
Molecular Weight:
55913.915 Da
References
  1. Fujino T, Une M, Imanaka T, Inoue K, Nishimaki-Mogami T: Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation. J Lipid Res. 2004 Jan;45(1):132-8. Epub 2003 Sep 16. [13130122 ]
Target Details
6. Cytochrome c oxidase subunit 1
General Function:
Iron ion binding
Specific Function:
Cytochrome c oxidase is the component of the respiratory chain that catalyzes the reduction of oxygen to water. Subunits 1-3 form the functional core of the enzyme complex. CO I is the catalytic subunit of the enzyme. Electrons originating in cytochrome c are transferred via the copper A center of subunit 2 and heme A of subunit 1 to the bimetallic center formed by heme A3 and copper B.
Gene Name:
MT-CO1
Uniprot ID:
P00395
Molecular Weight:
57040.91 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
7. Cytochrome c oxidase subunit 2
General Function:
Cytochrome-c oxidase activity
Specific Function:
Cytochrome c oxidase is the component of the respiratory chain that catalyzes the reduction of oxygen to water. Subunits 1-3 form the functional core of the enzyme complex. Subunit 2 transfers the electrons from cytochrome c via its binuclear copper A center to the bimetallic center of the catalytic subunit 1.
Gene Name:
MT-CO2
Uniprot ID:
P00403
Molecular Weight:
25564.73 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
8. Cytochrome c oxidase subunit 3
General Function:
Cytochrome-c oxidase activity
Specific Function:
Subunits I, II and III form the functional core of the enzyme complex.
Gene Name:
MT-CO3
Uniprot ID:
P00414
Molecular Weight:
29950.6 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
9. Cytochrome c oxidase subunit 4 isoform 1, mitochondrial
General Function:
Cytochrome-c oxidase activity
Specific Function:
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name:
COX4I1
Uniprot ID:
P13073
Molecular Weight:
19576.6 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
10. Cytochrome c oxidase subunit 5A, mitochondrial
General Function:
Metal ion binding
Specific Function:
This is the heme A-containing chain of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name:
COX5A
Uniprot ID:
P20674
Molecular Weight:
16761.985 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
11. Cytochrome c oxidase subunit 5B, mitochondrial
General Function:
Metal ion binding
Specific Function:
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name:
COX5B
Uniprot ID:
P10606
Molecular Weight:
13695.57 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
12. Cytochrome c oxidase subunit 6A2, mitochondrial
General Function:
Cytochrome-c oxidase activity
Specific Function:
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name:
COX6A2
Uniprot ID:
Q02221
Molecular Weight:
10815.32 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
13. Cytochrome c oxidase subunit 6B1
General Function:
Cytochrome-c oxidase activity
Specific Function:
Connects the two COX monomers into the physiological dimeric form.
Gene Name:
COX6B1
Uniprot ID:
P14854
Molecular Weight:
10192.345 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
14. Cytochrome c oxidase subunit 6C
General Function:
Cytochrome-c oxidase activity
Specific Function:
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name:
COX6C
Uniprot ID:
P09669
Molecular Weight:
8781.36 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
15. Cytochrome c oxidase subunit 7A1, mitochondrial
General Function:
Cytochrome-c oxidase activity
Specific Function:
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name:
COX7A1
Uniprot ID:
P24310
Molecular Weight:
9117.44 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
16. Cytochrome c oxidase subunit 7B, mitochondrial
General Function:
Cytochrome-c oxidase activity
Specific Function:
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport. Plays a role in proper central nervous system (CNS) development in vertebrates.
Gene Name:
COX7B
Uniprot ID:
P24311
Molecular Weight:
9160.485 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
17. Cytochrome c oxidase subunit 7C, mitochondrial
General Function:
Cytochrome-c oxidase activity
Specific Function:
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name:
COX7C
Uniprot ID:
P15954
Molecular Weight:
7245.45 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
18. Cytochrome c oxidase subunit 8A, mitochondrial
General Function:
Cytochrome-c oxidase activity
Specific Function:
This protein is one of the nuclear-coded polypeptide chains of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport.
Gene Name:
COX8A
Uniprot ID:
P10176
Molecular Weight:
7579.0 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
19. Estrogen-related receptor gamma
General Function:
Zinc ion binding
Specific Function:
Orphan receptor that acts as transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response elements (By similarity). Induces the expression of PERM1 in the skeletal muscle.
Gene Name:
ESRRG
Uniprot ID:
P62508
Molecular Weight:
51305.485 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
20. Ferrochelatase
General Function:
Ferrochelatase activity
Specific Function:
Catalyzes the ferrous insertion into protoporphyrin IX.
Gene Name:
DKFZp686P18130
Uniprot ID:
Q7KZA3
Molecular Weight:
47131.925 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
21. Gastrotropin
General Function:
Transporter activity
Specific Function:
Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis.
Gene Name:
FABP6
Uniprot ID:
P51161
Molecular Weight:
14371.245 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
22. Liver carboxylesterase 1
General Function:
Triglyceride lipase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular Weight:
62520.62 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]