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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-08-17 21:45:04 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameNutriacholic acid
DescriptionNutriacholic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on 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 ).
3a-Hydroxy-7-oxo-5b-cholanoic acidHMDB
5b-Cholanic acid-3a-ol-7-oneHMDB
7-Ketochenodeoxycholic acidHMDB
7-Ketolithocholic acidHMDB
7-oxo-3a-Hydroxycholan-24-Oic acidHMDB
7-Oxolithocholic acidHMDB
Chemical FormulaC24H38O4
Average Molecular Weight390.5561
Monoisotopic Molecular Weight390.277009704
IUPAC Name(4S)-4-[(1S,2S,5R,7S,10R,11S,15R)-5-hydroxy-2,15-dimethyl-9-oxotetracyclo[²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name(4S)-4-[(1S,2S,5R,7S,10R,11S,15R)-5-hydroxy-2,15-dimethyl-9-oxotetracyclo[²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
CAS Registry Number4651-67-6
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentMonohydroxy bile acids, alcohols and derivatives
Alternative Parents
  • Monohydroxy bile acid, alcohol, or derivatives
  • 7-oxosteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclohexanone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
StatusDetected but not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fat solubilization and Waste products
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.013 mg/mLALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.35 m3·mol-1ChemAxon
Polarizability44.77 Å3ChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0291000000-9f5bf5f94dd6944d6d6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052r-2962000000-f18d1686d1ac8b6e93f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05o1-2900000000-681b2fd8ee33b91d7a44View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Feces
Tissue Location
  • Gall Bladder
  • Intestine
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Not AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022059
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00467
Metagene LinkHMDB00467
PubChem Compound53477693
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceKimura, Noriyuki; Mikami, Kazutoshi; Iwase, Mitsuyoshi. 3a,7b-Dihydroxy-5b-cholanic acid. Jpn. Kokai Tokkyo Koho (1985), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  2. Fromm H, Sarva RP, Bazzoli F: Formation of ursodeoxycholic acid from chenodeoxycholic acid in the human colon: studies of the role of 7-ketolithocholic acid as an intermediate. J Lipid Res. 1983 Jul;24(7):841-53. [6631218 ]
  3. Amuro Y, Yamade W, Kudo K, Yamamoto T, Hada T, Higashino K: Reduction of 7-ketolithocholic acid by human liver enzyme preparations in vitro. Am J Physiol. 1989 Jan;256(1 Pt 1):G67-71. [2912152 ]
  4. Salen G, Verga D, Batta AK, Tint GS, Shefer S: Effect of 7-ketolithocholic acid on bile acid metabolism in humans. Gastroenterology. 1982 Aug;83(2):341-7. [7084613 ]
  5. Albini E, Marca G, Mellerio G: Further observations on the in vitro metabolism of chenodeoxycholic acid and ursodeoxycholic acid. Arzneimittelforschung. 1982;32(12):1554-7. [6891595 ]
  6. Higashi S, Setoguchi T, Katsuki T: Conversion of 7-ketolithocholic acid to ursodeoxycholic acid by human intestinal anaerobic microorganisms: interchangeability of chenodeoxycholic acid and ursodeoxycholic acid. Gastroenterol Jpn. 1979 Oct;14(5):417-24. [520764 ]
  7. Fedorowski T, Salen G, Tint GS, Mosbach E: Transformation of chenodeoxycholic acid and ursodeoxycholic acid by human intestinal bacteria. Gastroenterology. 1979 Nov;77(5):1068-73. [488633 ]
  8. Akao T, Akao T, Hattori M, Namba T, Kobashi K: Enzymes involved in the formation of 3 beta, 7 beta-dihydroxy-12-oxo-5 beta-cholanic acid from dehydrocholic acid by Ruminococcus sp. obtained from human intestine. Biochim Biophys Acta. 1987 Sep 25;921(2):275-80. [3477291 ]
  9. Fromm H, Carlson GL, Hofmann AF, Farivar S, Amin P: Metabolism in man of 7-ketolithocholic acid: precursor of cheno- and ursodeoxycholic acids. Am J Physiol. 1980 Sep;239(3):G161-6. [7435569 ]
  10. Miwa H, Yamamoto M, Nishida T, Yao T: Transformation of chenodeoxycholic acid to ursodeoxycholic acid in patients with Crohn's disease. Gastroenterology. 1986 Mar;90(3):718-23. [3943699 ]
  11. Roda A, Cappelleri G, Aldini R, Roda E, Barbara L: Quantitative aspects of the interaction of bile acids with human serum albumin. J Lipid Res. 1982 Mar;23(3):490-5. [7077161 ]
  12. Salen G, Tint GS, Eliav B, Deering N, Mosbach EH: Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest. 1974 Feb;53(2):612-21. [11344576 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]


General function:
Involved in binding
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
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  1. Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [12486725 ]


General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
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General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
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  1. Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [12196548 ]
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
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Molecular weight:
General function:
Involved in bile acid:sodium symporter activity
Specific function:
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
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Molecular weight:
  1. Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [11447228 ]
General function:
Involved in bile acid:sodium symporter activity
Specific function:
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
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