Cholic acid

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Cholic acid
Cholic acid
Cholic acid ball-and-stick.png
Names
IUPAC name
(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
Other names
3α,7α,12α-Trihydroxy-5β-cholanoic acid
Identifiers
ATC code A05AA03
81-25-4 YesY
ChEBI CHEBI:16359 N
ChEMBL ChEMBL205596 N
ChemSpider 192176 YesY
DrugBank DB02659 N
Jmol-3D images Image
PubChem 221493
UNII G1JO7801AE YesY
Properties
C24H40O5
Molar mass 408.57 g/mol
Melting point 200 to 201 °C (392 to 394 °F; 473 to 474 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Cholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary 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 the two major bile acids produced by the liver where it is synthesized from cholesterol. These two major bile acids are roughly equal in concentration in humans.[2] Derivatives are made from cholyl-CoA, which exchanges its CoA with either glycine, or taurine, yielding glycocholic and taurocholic acid respectively.[3]

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).[4][5]

Cholic acid and chenodeoxycholic acid are the most important human bile acids. Other species may synthesize different bile acids as their predominant primary bile acids.[6]

Cholic acid, formulated as Cholbam capsules, is approved by the United States Food and Drug Administration as a treatment for children and adults with bile acid synthesis disorders due to single enzyme defects, and for peroxisomal disorders (such as Zellweger syndrome).[7]

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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  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. ^ Bennion LJ, Ginsberg RL, Gernick MB, Bennett PH (January 1976). "Effects of oral contraceptives on the gallbladder bile of normal women". N. Engl. J. Med. 294 (4): 189–92. doi:10.1056/NEJM197601222940403. PMID 1244533. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ Hofmann AF, Hagey LR, Krasowski MD (February 2010). "Bile salts of vertebrates: structural variation and possible evolutionary significance". J. Lipid Res. 51 (2): 226–46. doi:10.1194/jlr.R000042. PMC 2803226. PMID 19638645. 
  7. ^ http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm438572.htm