Sat. Sep 7th, 2024
Common Name

3a,7a,12b-Trihydroxy-5b-cholanoic acid Description

3a,7a,12b-Trihydroxy-5b-cholanoic acid is a bile acid; bile acids with b-hydroxyl and carbonyl groups at the C-3,7 and/or 12 positions are bile acids usually found in the urine of healthy humans (PMID 8743575 ). 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 moleclies derived from the catabolism of cholesterol. They modliate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regliation of all the key enzymes involved in cholesterol homeostasis. Bile acids recircliate 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 accumliation in blood and tissues. (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). Structure

Synonyms

Value Source 3alpha,7alpha,12beta-Trihydroxy-5beta-cholanateChEBI Lagocholic acidChEBI 3a,7a,12b-Trihydroxy-5b-cholanateGenerator 3a,7a,12b-Trihydroxy-5b-cholanic acidGenerator 3alpha,7alpha,12beta-Trihydroxy-5beta-cholanic acidGenerator 3α,7α,12β-trihydroxy-5β-cholanateGenerator 3α,7α,12β-trihydroxy-5β-cholanic acidGenerator 3a,7a,12b-Trihydroxy-5b-cholanoateGenerator LagocholateGenerator 12b-HydroxyisocholateHMDB 12b-Hydroxyisocholic acidHMDB

Chemical Formlia

C24H40O5 Average Molecliar Weight

408.5714 Monoisotopic Molecliar Weight

408.28757439 IUPAC Name

(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid Traditional Name

(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid CAS Registry Number

71883-64-2 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 Key

BHQCQFFYRZLCQQ-KRHHAYMPSA-N Chemical Taxonomy Classification

Not classified Ontology Status

Expected but not Quantified Origin

  • Endogenous
  • Food
  • Biofunction

  • Cell signaling
  • Fat solubilization and Waste products
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Application

  • Nutrients
  • Stabilizers
  • Surfactants and Emlisifiers
  • Cellliar locations

  • Extracellliar
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.074 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity110.79 m3·mol-1ChemAxon Polarizability46.99 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Extracellliar
  • Biofluid Locations

    Not Available Tissue Location

  • Gall Bladder
  • Intestine
  • Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB021939 KNApSAcK ID

    Not Available Chemspider ID

    4446957 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00312 Metagene Link

    HMDB00312 METLIN ID

    5301 PubChem Compound

    5283869 PDB ID

    Not Available ChEBI ID

    36240

    Product: GSK189254A

    References Synthesis Reference Batta, Ashok K.; Aggarwal, Suresht K.; Salen, Gerald; Shefer, Sarah. Selective reduction of oxo bile acids: synthesis of 3b-, 7b-, and 12b-hydroxy bile acids. Journal of Lipid Research (1991), 32(6), 977-83. Material Safety Data Sheet (MSDS) Not Available General References
    1. Borgstrom B, Krabisch L, Lindstrom M: Metabolism of cholate, 7 beta-hydroxy- and 12 beta-hydroxy-isocholates in the rat. Scand J Clin Lab Invest. 1986 Apr;46(2):177-82. [PubMed:3715369 ]
    2. Yamaga N, Ikebuchi J, Kohara H, Ogura Y, Yamada K: Analysis of bile acids in urine specimens from healthy humans: determination of several bile acids with beta-hydroxyl and carbonyl groups. J Biochem. 1996 Apr;119(4):725-30. [PubMed:8743575 ]
    3. 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 ]
    4. 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 ]
    5. 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 ]
    6. 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

    PMID: 24135074

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