Cholic acid

Cholic acid

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
CAS Number	81-25-4
ChEBI	CHEBI:16359
ChEMBL	ChEMBL205596
ChemSpider	192176
DrugBank	DB02659
IUPHAR/BPS	609
Jmol interactive 3D	Image
PubChem	221493
UNII	G1JO7801AE
InChI 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 Key: BHQCQFFYRZLCQQ-OELDTZBJSA-N InChI=1/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 Key: BHQCQFFYRZLCQQ-OELDTZBJBZ
SMILES C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
Properties
Chemical formula	C24H40O5
Molar mass	408.57 g/mol
Melting point	200 to 201 °C (392 to 394 °F; 473 to 474 K)
Pharmacology
ATC code	A05AA03
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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

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|{{{bSize}}}px|alt=Statin Pathway edit]]

Statin Pathway edit

1. The interactive pathway map can be edited at WikiPathways: "Statin_Pathway_WP430".

References

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