Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:22 UTC |
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Update date | 2019-11-26 03:07:39 UTC |
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Primary ID | FDB012810 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Cholic acid |
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Description | Emulsifying agent in foods
A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. ; 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. (PMID: 11316487, 16037564, 12576301, 11907135); Cholic acid is a bile acid, a white crystalline substance insoluble in water (soluble in alcohol and acetic acid), with a melting point of 200-201 °C. 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 forms a conjugate with either glycine, or taurine, yielding glycocholic and taurocholic acid respectively. |
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CAS Number | 81-25-4 |
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Structure | |
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Synonyms | Synonym | 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 | (3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oate | Generator | (3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid | Generator | 3-&alpha,7-&alpha,12-&alpha-trihydroxy-5-&beta-cholanate | biospider | 3,7,12-Trihydroxy-cholan-24-oic acid | biospider | 3,7,12-Trihydroxycholanic acid | biospider | 3a,7a,12a-Trihydroxy-5b-cholan-24-oate | biospider | 3a,7a,12a-Trihydroxy-5b-cholan-24-oic acid | biospider | 3alpha,7alpha-Dihydroxy-5beta-cholanic acid | biospider | 3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oic acid | biospider | 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanic acid | biospider | 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanoic acid | biospider | 3alpha,7alpha,12alpha-Trihydroxy-beta-cholanic acid | biospider | 3alpha,7alpha,12alpha-Trihydroxycholanic acid | biospider | 3α,7α,12α-trihydroxy-5β-cholanate | Generator | 3α,7α,12α-trihydroxy-5β-cholanic acid | Generator | 5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy- | biospider | 5beta-Cholanic acid-3alpha,7alpha-diol | biospider | Chenodiol | biospider | Cholagit | db_source | Cholan-24-oic acid | biospider | Cholanic acid | biospider | Cholic acid, 5beta- | biospider | Hypocholate | db_source | NSC 6135 | db_source |
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Predicted Properties | |
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Chemical Formula | C24H40O5 |
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IUPAC name | (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid |
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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) |
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InChI Key | BHQCQFFYRZLCQQ-UHFFFAOYSA-N |
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Isomeric SMILES | CC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C |
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Average Molecular Weight | 408.5714 |
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Monoisotopic Molecular Weight | 408.28757439 |
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Classification |
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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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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 70.55%; H 9.87%; O 19.58% | DFC |
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Melting Point | Mp 197° (anhyd.) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.175 mg/mL at 20 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 2.02 | RODA,A ET AL. (1990) |
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Experimental pKa | pKa1 4.98 (20°) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]20D +37 (EtOH) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0596-9642000000-e425981b8a0ac72ea6ee | 2014-09-20 | View Spectrum | GC-MS | cholate, non-derivatized, GC-MS Spectrum | splash10-0fk9-5796000000-2876080f3fa17fb96370 | Spectrum | GC-MS | cholate, non-derivatized, GC-MS Spectrum | splash10-0fk9-5796000000-2876080f3fa17fb96370 | Spectrum | Predicted GC-MS | cholate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03dl-0439000000-4e43231560df6c61b96d | Spectrum | Predicted GC-MS | cholate, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001i-1100049000-86faaffe1dc0eadf9e75 | Spectrum | Predicted GC-MS | cholate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | cholate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0000900000-806d3b03c76019afbf7d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0000900000-4edb603ca5534669120e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0000900000-4a76e64b2f0411d0b701 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0001900000-41aa3a7cb25fcf549046 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0057900000-790a3808fa512d5d1687 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0010900000-e6bedfc253363160a37e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0030900000-da4a7bfccbaf1e42171c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0020900000-772055897702843a1d50 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0021900000-0405fe63d70d3a88bf6f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0aou-3844900000-cb3c2aba1b9a29785616 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-0007-0019000000-fb9a5b5952cf65eb7988 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-0001900000-9583bd9c6c0d2b069b68 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-1027900000-31f3cf065ad48561c0a2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-0000900000-b0504ee652d51a711f3a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-0000900000-18dd8b6be45775ec83c2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0007-0019000000-285d3d0d87f5471b419a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0007-0019000000-0fcb0f6819b05ab63c12 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-0000900000-b0504ee652d51a711f3a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-0000900000-18dd8b6be45775ec83c2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0007-0019000000-285d3d0d87f5471b419a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0007-0019000000-0fcb0f6819b05ab63c12 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000900000-6fe7340aea27993f6ecb | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0a4i-0001900000-9e5ac05d22599c16d77a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0000900000-a58dbdca74695c9c40e1 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000900000-1c1c35b35f948ca53943 | 2021-09-20 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum |
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External Links |
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ChemSpider ID | 192176 |
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ChEMBL ID | CHEMBL205596 |
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KEGG Compound ID | C00695 |
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Pubchem Compound ID | 221493 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16359 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB02659 |
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HMDB ID | HMDB00619 |
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CRC / DFC (Dictionary of Food Compounds) ID | HLJ16-X:HLJ07-V |
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EAFUS ID | 628 |
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Dr. Duke ID | Not Available |
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BIGG ID | 35720 |
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KNApSAcK ID | Not Available |
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HET ID | CHD |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Cholic acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Liver carboxylesterase 1 | CES1 | P23141 | Acyl-coenzyme A thioesterase 8 | ACOT8 | O14734 | Ferrochelatase | DKFZp686P18130 | Q7KZA3 | Cytochrome c oxidase subunit 7A1, mitochondrial | COX7A1 | P24310 | Bile acyl-CoA synthetase | SLC27A5 | Q9Y2P5 | Cytochrome c oxidase subunit 6A2, mitochondrial | COX6A2 | Q02221 | Cytochrome c oxidase subunit 7B, mitochondrial | COX7B | P24311 | Cytochrome c oxidase subunit 7C, mitochondrial | COX7C | P15954 | Cytochrome c oxidase subunit 5B, mitochondrial | COX5B | P10606 | Cytochrome c oxidase subunit 6B1 | COX6B1 | P14854 | Cytochrome c oxidase subunit 4 isoform 1, mitochondrial | COX4I1 | P13073 | Cytochrome c oxidase subunit 8A, mitochondrial | COX8A | P10176 | Cytochrome c oxidase subunit 6C | COX6C | P09669 | Cytochrome c oxidase subunit 3 | MT-CO3 | P00414 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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