Cholic acid

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Cholic acid
Cholic acid
Cholic acid ball-and-stick.png
Identifiers
CAS number 81-25-4 YesY
PubChem 221493
ChemSpider 192176 YesY
UNII G1JO7801AE YesY
DrugBank DB02659
ChEBI CHEBI:16359 N
ChEMBL CHEMBL205596 N
ATC code A05AA03
Jmol-3D images Image 1
Properties
Molecular formula C24H40O5
Molar mass 408.57 g/mol
Melting point 200-201 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Cholic acid is a bile acid[1] that is insoluble in water (soluble in alcohol and acetic acid), it is a white crystalline substance. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid, is one of two major bile acids produced by the liver where it is synthesized from cholesterol. Of the two major bile acids, cholate derivatives represent approximately eighty percent of all bile acids. These derivatives are made from cholyl-CoA, which exchanges its CoA with either glycine, or taurine, yielding glycocholic and taurocholic acid respectively.[2]

Cholic acid downregulates cholesterol-7-α-hydroxylase (rate-limiting step in bile acid synthesis), and cholesterol does the opposite. This is why chenodeoxycholic acid, and not cholic acid, can be used to treat gallstones (because decreasing bile acid synthesis would supersaturate the stones even more).[3][4]

Cholic acid and chenodeoxycholic acid are the most important human bile acids. Some other mammals synthesize predominantly deoxycholic acid.[5]

Structure of cholic acid showing relationship to other bile acids

Interactive pathway map[edit]

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

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Statin_Pathway_WP430 go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article
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Statin Pathway edit
  1. ^ The interactive pathway map can be edited at WikiPathways: "Statin_Pathway_WP430". 

References[edit]

  1. ^ Colleen Smith; Lieberman, Michael; Marks, Dawn B.; Allan D. Marks (2007). Marks' essential medical biochemistry. Hagerstwon, MD: Lippincott Williams & Wilkins. ISBN 0-7817-9340-8. 
  2. ^ Chiang JY (October 2009). "Bile acids: regulation of synthesis". Journal of Lipid Research 50 (10): 1955–66. doi:10.1194/jlr.R900010-JLR200. PMC 2739756. PMID 19346330. 
  3. ^ Iser JH, Dowling H, Mok HY, Bell GD (August 1975). "Chenodeoxycholic acid treatment of gallstones. A follow-up report and analysis of factors influencing response to therapy". The New England Journal of Medicine 293 (8): 378–83. doi:10.1056/NEJM197508212930804. PMID 1152936. 
  4. ^ Alan F. Hofmann, Johnson L. Thistle, Peter D. Klein, Patricia A. Szczepanik, Paulina Y. S. Yu (1978). "Chenotherapy for Gallstone Dissolution, II. Induced Changes in Bile Composition and Gallstone Response". JAMA 239 (12): 1138–1144. doi:10.1001/jama.1978.03280390034017. 
  5. ^ Urich, Klaus (1994). Comparative animal biochemistry. Berlin: Springer-Verlag. ISBN 3-540-57420-4.