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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:20:55 UTC
HMDB IDHMDB0000917
Secondary Accession Numbers
  • HMDB00917
Metabolite Identification
Common NameUrsocholic acid
DescriptionUrsocholic 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 ). Ursocholic acid is the 7 beta-hydroxyepimer of cholic acid. It induces a reduction of bile cholesterol saturation.
Structure
Thumb
Synonyms
ValueSource
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-Oic acidKegg
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanic acidKegg
7beta-Hydroxyisocholic acidKegg
7-Epicholic acidKegg
3a,7b,12a-Trihydroxy-5b-cholan-24-OateGenerator
3a,7b,12a-Trihydroxy-5b-cholan-24-Oic acidGenerator
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-OateGenerator
3α,7β,12α-trihydroxy-5β-cholan-24-OateGenerator
3α,7β,12α-trihydroxy-5β-cholan-24-Oic acidGenerator
UrsocholateGenerator
3a,7b,12a-Trihydroxy-5b-cholanateGenerator
3a,7b,12a-Trihydroxy-5b-cholanic acidGenerator
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanateGenerator
3α,7β,12α-trihydroxy-5β-cholanateGenerator
3α,7β,12α-trihydroxy-5β-cholanic acidGenerator
7b-HydroxyisocholateGenerator
7b-Hydroxyisocholic acidGenerator
7beta-HydroxyisocholateGenerator
7β-hydroxyisocholateGenerator
7β-hydroxyisocholic acidGenerator
7-EpicholateGenerator
3a,7b,12a-Trihydroxy-5b-cholanoateHMDB
3a,7b,12a-Trihydroxy-5b-cholanoic acidHMDB
3a,7b,12a-TrihydroxycholanateHMDB
3a,7b,12a-Trihydroxycholanic acidHMDB
3 alpha,7 beta,12 alpha-Trihydroxy-5 beta-cholan-24-Oic acidMeSH
Chemical FormulaC24H40O5
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Nameursocholic acid
CAS Registry Number2955-27-3
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=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 KeyBHQCQFFYRZLCQQ-UTLSPDKDSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 7-alpha-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
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.074 g/LALOGPS
logP2.26ALOGPS
logP2.48ChemAxon
logS-3.7ALOGPS
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
Polarizability47.04 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-0439000000-abd2a5c162e23ea0d78fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-1100049000-ae391322cbbc458fdb46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0009100000-915584a506714c470270View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0009000000-f970a088fc3d9cdb8fe6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-017j-3109000000-bb054743c390ef266044View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0008900000-ed202aebd950e99a7852View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1009300000-db2a4b9107b891a8ef3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9006000000-87df039839010127a1a0View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Gall Bladder
  • Intestine
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified2.2 (0.2-11.7) uMAdult (>18 years old)Both
    Biliary cirrhosis
    details
    UrineDetected and Quantified1.0 (0.13-2.7) umol/mmol creatinineAdult (>18 years old)Both
    Biliary cirrhosis
    details
    Associated Disorders and Diseases
    Disease References
    Primary biliary cirrhosis
    1. Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. [PubMed:2621422 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022316
    KNApSAcK IDNot Available
    Chemspider ID109088
    KEGG Compound IDC17644
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5871
    PubChem Compound122340
    PDB IDNot Available
    ChEBI ID803879
    References
    Synthesis ReferenceTerada, Masaki; Sato, Manabu; Horie, Yoshiaki; Takatsu, Mitsumune; Minami, Junichi. Production of ursocholic acid. Jpn. Kokai Tokkyo Koho (1986), 9 pp.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Nakashima T, Sakamoto Y, Inaba K, Mitsuyoshi H, Ishikawa H, Nakajima Y, Sakai M, Shima T, Kashima K: A paucity of unusual trihydroxy bile acids in the urine of patients with severe liver diseases. Hepatology. 1999 May;29(5):1518-22. [PubMed:10216137 ]
    2. Batta AK, Salen G, Abroon J: Ursocholic acid, a hydrophilic bile acid, fails to improve liver function parameters in primary biliary cirrhosis: comparison with ursodeoxycholic acid. Am J Gastroenterol. 1997 Jun;92(6):1035-7. [PubMed:9177526 ]
    3. Lanzini A, Pigozzi G, Facchinetti D, Bettini L, Castellano M, Beschi M, Rossi A, Muiesan G: Effect of chronic ursocholic acid administration on bile lipid composition and bile acid pool size in gallstone patients. Scand J Gastroenterol. 1990 Jul;25(7):711-9. [PubMed:2396085 ]
    4. Tint GS, Batta AK, Dayal B, Kovell N, Shefer S, Salen G: Metabolism of ursocholic acid in humans: conversion of ursocholic acid to deoxycholic acid. Hepatology. 1992 Apr;15(4):645-50. [PubMed:1551642 ]
    5. Li H, Chen F, Shang Q, Pan L, Shneider BL, Chiang JY, Forman BM, Ananthanarayanan M, Tint GS, Salen G, Xu G: FXR-activating ligands inhibit rabbit ASBT expression via FXR-SHP-FTF cascade. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G60-6. [PubMed:15591588 ]
    6. Loria P, Carulli N, Medici G, Menozzi D, Salvioli G, Bertolotti M, Montanari M: Effect of ursocholic acid on bile lipid secretion and composition. Gastroenterology. 1986 Apr;90(4):865-74. [PubMed:3949116 ]
    7. 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. [PubMed:11316487 ]
    8. 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. [PubMed:16037564 ]
    9. 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. [PubMed:12576301 ]
    10. 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 ]

    Enzymes

    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
    Gene Name:
    FABP6
    Uniprot ID:
    P51161
    Molecular weight:
    14371.2
    References
    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. [PubMed:12486725 ]

    Transporters

    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)
    Gene Name:
    SLCO1B3
    Uniprot ID:
    Q9NPD5
    Molecular weight:
    77402.2
    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
    Gene Name:
    SLCO1B1
    Uniprot ID:
    Q9Y6L6
    Molecular weight:
    76448.0
    References
    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. [PubMed: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:
    ABCC3
    Uniprot ID:
    O15438
    Molecular weight:
    169341.1
    General function:
    Involved in ATP binding
    Specific function:
    Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
    Gene Name:
    ABCB11
    Uniprot ID:
    O95342
    Molecular weight:
    146405.8
    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
    Gene Name:
    SLC10A2
    Uniprot ID:
    Q12908
    Molecular weight:
    37697.4
    References
    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. [PubMed: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:
    SLC10A1
    Uniprot ID:
    Q14973
    Molecular weight:
    38118.64
    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:
    SLCO1A2
    Uniprot ID:
    P46721
    Molecular weight:
    74144.1
    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
    Gene Name:
    SLCO4A1
    Uniprot ID:
    Q96BD0
    Molecular weight:
    77192.5