| Record Information |
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| Version | 1.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2024-04-19 09:50:50 UTC |
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| NP-MRD ID | NP0001393 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Cholic acid |
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| Description | Cholic acid is a major primary bile acid produced in the liver and is usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the 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 (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). When present in sufficiently high levels, cholic acid can act as a hepatotoxin and a metabotoxin. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875 ). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. Chronically high levels of cholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids, including cholic acid, are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood. The bile acid ursodiol (ursodeoxycholic acid) can improve symptoms associated with familial hypercholanemia. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid | ChEBI | | 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate | ChEBI | | 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid | ChEBI | | Cholsaeure | ChEBI | | Cholate | Kegg | | (3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate | Generator | | (3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid | Generator | | (3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate | Generator | | (3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oate | Generator | | (3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid | Generator | | 3a,7a,12a-Trihydroxy-5b-cholanate | Generator | | 3a,7a,12a-Trihydroxy-5b-cholanic acid | Generator | | 3Α,7α,12α-trihydroxy-5β-cholanate | Generator | | 3Α,7α,12α-trihydroxy-5β-cholanic acid | Generator | | Allocholate | HMDB | | 17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triol | HMDB | | 3a,7a,12a-Trihydroxy-5b-cholan-24-Oate | HMDB | | 3a,7a,12a-Trihydroxy-5b-cholan-24-Oic acid | HMDB | | 3a,7a,12a-Trihydroxy-5b-cholanoate | HMDB | | 3a,7a,12a-Trihydroxy-5b-cholanoic acid | HMDB | | 3a,7a,12a-Trihydroxy-b-cholanate | HMDB | | 3a,7a,12a-Trihydroxy-b-cholanic acid | HMDB | | 3a,7a,12a-Trihydroxy-beta-cholanate | HMDB | | 3a,7a,12a-Trihydroxy-beta-cholanic acid | HMDB | | 3a,7a,12a-Trihydroxycholanate | HMDB | | 3a,7a,12a-Trihydroxycholanic acid | HMDB | | 5b-Cholanic acid-3a,7a,12a-triol | HMDB | | 5b-Cholate | HMDB | | 5b-Cholic acid | HMDB | | Cholalate | HMDB | | Cholalic acid | HMDB | | Cholalin | HMDB | | Colalin | HMDB | | Acid, cholic | HMDB | | Cholic acid | Generator |
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| Chemical Formula | C24H40O5 |
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| Average Mass | 408.5714 Da |
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| Monoisotopic Mass | 408.28757 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 81-25-4 |
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| SMILES | Not Available |
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| 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 |
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| InChI Key | BHQCQFFYRZLCQQ-OELDTZBJSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Not Available | Not Available | 2023-08-14 | View Spectrum | | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Not Available | Not Available | 2023-08-14 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Bile acids, alcohols and derivatives |
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| Direct Parent | Trihydroxy bile acids, alcohols and derivatives |
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| Alternative Parents | |
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| Substituents | - Trihydroxy bile acid, alcohol, or derivatives
- 3-hydroxysteroid
- 12-hydroxysteroid
- 7-hydroxysteroid
- 3-alpha-hydroxysteroid
- Hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Polyol
- Monocarboxylic acid or derivatives
- Organic oxide
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 197 - 201 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.18 mg/mL | Not Available | | LogP | 2.02 | Roda, A., Minutello, A., Angellotti, M. A., & Fini, A. (1990). Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. Journal of lipid research, 31(8), 1433-1443. |
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| Predicted Properties | Not Available |
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| General References | - Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [PubMed:16548228 ]
- Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
- Kuramoto T, Furukawa Y, Nishina T, Sugimoto T, Mahara R, Tohma M, Kihira K, Hoshita T: Identification of short side chain bile acids in urine of patients with cerebrotendinous xanthomatosis. J Lipid Res. 1990 Oct;31(10):1895-902. [PubMed:2079611 ]
- Wildgrube HJ, Stang H, Winkler M, Mauritz G: [Value of serum levels of conjugated cholic acid in the diagnosis of liver disease (author's transl)]. Dtsch Med Wochenschr. 1982 Aug 20;107(33):1235-7. [PubMed:7106004 ]
- Rodrigues CM, Marin JJ, Brites D: Bile acid patterns in meconium are influenced by cholestasis of pregnancy and not altered by ursodeoxycholic acid treatment. Gut. 1999 Sep;45(3):446-52. [PubMed:10446117 ]
- Einarsson K, Reihner E, Ewerth S, Bjorkhem I: Serum concentrations of unconjugated and conjugated cholic acid in portal venous and systemic venous blood of fasting man. Scand J Clin Lab Invest. 1989 Feb;49(1):83-91. [PubMed:2727621 ]
- Briz O, Macias RI, Serrano MA, Gonzalez-Gallego J, Bayon JE, Marin JJ: Excretion of foetal bilirubin by the rat placenta-maternal liver tandem. Placenta. 2003 May;24(5):462-72. [PubMed:12744922 ]
- Gustafsson J, Alvelius G, Bjorkhem I, Nemeth A: Bile acid metabolism in extrahepatic biliary atresia: lithocholic acid in stored dried blood collected at neonatal screening. Ups J Med Sci. 2006;111(1):131-6. [PubMed:16553252 ]
- Salen G, Shefer S, Tint GS, Nicolau G, Dayal B, Batta AK: Biosynthesis of bile acids in cerebrotendinous xanthomatosis. Relationship of bile acid pool sizes and synthesis rates to hydroxylations at C-12, C-25, and C-26. J Clin Invest. 1985 Aug;76(2):744-51. [PubMed:4031069 ]
- Brites D, Poeiras J, Rodrigues C: [Intrahepatic cholestasis in pregnancy. Its etiopathogenesis, prognosis and therapy]. Acta Med Port. 1994 Mar;7(3):181-8. [PubMed:8209706 ]
- Van Den Berg JW, Van Blankenstein M, Bosman-Jacobs EP, Frenkel M, Horchner P, Ooost-Harwig OI, Wilson JH: Solid phase radioimmunoassay for determination of conjugated cholic acid in serum. Clin Chim Acta. 1976 Dec 1;73(2):277-83. [PubMed:1000848 ]
- Pomare EW, Low-Beer TS: Proceedings: Effect of administration of a colonic metabolite of cholic acid on cholesterol levels in bile and blood. Gut. 1974 Oct;15(10):830. [PubMed:4434946 ]
- Einarsson K, Bergstrom M, Eklof R, Nord CE, Bjorkhem I: Comparison of the proportion of unconjugated to total serum cholic acid and the [14C]-xylose breath test in patients with suspected small intestinal bacterial overgrowth. Scand J Clin Lab Invest. 1992 Sep;52(5):425-30. [PubMed:1514020 ]
- Ewerth S, Bjorkhem I, Einarsson K, Ost L: Lymphatic transport of bile acids in man. J Lipid Res. 1982 Nov;23(8):1183-6. [PubMed:7175375 ]
- LaRusso NF, Hoffman NE, Hofmann AF, Korman MG: Validity and sensitivity of an intravenous bile acid tolerance test in patients with liver disease. N Engl J Med. 1975 Jun 5;292(23):1209-14. [PubMed:1128572 ]
- Lillienau J, Schteingart CD, Hofmann AF: Physicochemical and physiological properties of cholylsarcosine. A potential replacement detergent for bile acid deficiency states in the small intestine. J Clin Invest. 1992 Feb;89(2):420-31. [PubMed:1371123 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Delzenne NM, Calderon PB, Taper HS, Roberfroid MB: Comparative hepatotoxicity of cholic acid, deoxycholic acid and lithocholic acid in the rat: in vivo and in vitro studies. Toxicol Lett. 1992 Jul;61(2-3):291-304. [PubMed:1641875 ]
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