<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">5021</id>
  <title>T3D4963</title>
  <common-name>Lithocholic acid</common-name>
  <description>Lithocholic acid is a bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic. 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. (A3407, A3408, A3409, A3410).</description>
  <cas>434-13-9</cas>
  <pubchem-id>11740284</pubchem-id>
  <chemical-formula>C24H40O3</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>186 °C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>0.000377 mg/mL</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure></route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity></mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>Not listed by IARC.</carcinogenicity>
  <use-source></use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Chronically high levels of lithocholic acid are associated with several forms of cancer including colon cancer.</health-effects>
  <symptoms></symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2014-10-02T18:59:38Z</created-at>
  <updated-at type="dateTime">2026-04-04T01:33:44Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia></wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C03990</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>16325</chebi-id>
  <biocyc-id>TAUROLITHOCHOLATE-SULFATE</biocyc-id>
  <ctd-id>D008095</ctd-id>
  <stitch-id></stitch-id>
  <drugbank-id></drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>C[C@H](CCC(O)=O)[C@H]1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C</moldb-smiles>
  <moldb-formula>C24H40O3</moldb-formula>
  <moldb-inchi>InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16?,17-,18?,19-,20?,21?,23+,24-/m1/s1</moldb-inchi>
  <moldb-inchikey>SMEROWZSTRWXGI-HRFHTWGISA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">376.5726</moldb-average-mass>
  <moldb-mono-mass type="decimal">376.297745146</moldb-mono-mass>
  <origin></origin>
  <state>Solid</state>
  <logp></logp>
  <hmdb-id>HMDB00761</hmdb-id>
  <chembl-id></chembl-id>
  <chemspider-id>9914991</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003919</chemdb-id>
  <dsstox-id>DTXSID6020779</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00031340</susdat-id>
  <iupac>(4R)-4-[(2S,5R,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac>
</compound>
