1.02010-04-08 22:10:22 UTC2019-11-26 03:07:39 UTCFDB012810Cholic acidEmulsifying 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.(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oate(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triol3-&alpha,7-&alpha,12-&alpha-trihydroxy-5-&beta-cholanate3,7,12-Trihydroxy-cholan-24-oic acid3,7,12-Trihydroxycholanic acid3a,7a,12a-Trihydroxy-5b-cholan-24-oate3a,7a,12a-Trihydroxy-5b-cholan-24-oic acid3a,7a,12a-Trihydroxy-5b-cholanate3a,7a,12a-Trihydroxy-5b-cholanic acid3a,7a,12a-Trihydroxy-5b-cholanoate3a,7a,12a-Trihydroxy-5b-cholanoic acid3a,7a,12a-Trihydroxy-b-cholanate3a,7a,12a-Trihydroxy-b-cholanic acid3a,7a,12a-Trihydroxy-beta-cholanate3a,7a,12a-Trihydroxy-beta-cholanic acid3a,7a,12a-Trihydroxycholanate3a,7a,12a-Trihydroxycholanic acid3alpha,7alpha-Dihydroxy-5beta-cholanic acid3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oic acid3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate3alpha,7alpha,12alpha-trihydroxy-5beta-cholanic acid3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanoic acid3alpha,7alpha,12alpha-Trihydroxy-beta-cholanic acid3alpha,7alpha,12alpha-Trihydroxycholanic acid3α,7α,12α-trihydroxy-5β-cholanate3α,7α,12α-trihydroxy-5β-cholanic acid5b-Cholanic acid-3a,7a,12a-triol5b-Cholate5b-Cholic acid5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy-5beta-Cholanic acid-3alpha,7alpha-diolChenodiolCholagitCholalateCholalic acidCholalinCholan-24-oic acidCholanic acidCholateCholic acidCholic acid, 5beta-CholsaeureColalinHypocholateNSC 6135C24H40O5408.5714408.28757439(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(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 acid81-25-4CC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12CInChI=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)BHQCQFFYRZLCQQ-UHFFFAOYSA-N 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.Trihydroxy bile acids, alcohols and derivativesOrganic compoundsLipids and lipid-like moleculesSteroids and steroid derivativesBile acids, alcohols and derivativesAliphatic homopolycyclic compounds12-hydroxysteroids3-alpha-hydroxysteroids7-hydroxysteroidsCarbonyl compoundsCarboxylic acidsCyclic alcohols and derivativesHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesPolyolsSecondary alcohols12-hydroxysteroid3-alpha-hydroxysteroid3-hydroxysteroid7-hydroxysteroidAlcoholAliphatic homopolycyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic alcoholHydrocarbon derivativeHydroxysteroidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundPolyolSecondary alcoholTrihydroxy bile acid, alcohol, or derivativesC24 bile acids, alcohols, and derivativesC24 bile acids, alcohols, and derivativesCholane and derivativesbile acidtrihydroxy-5beta-cholanic acidSolidmelting_pointMp 197° (anhyd.)logp2.48pka_strongest_acidic4.48pka_strongest_basic-0.16iupac(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 acidaverage_mass408.5714mono_mass408.28757439smilesCC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12CformulaC24H40O5inchiInChI=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)inchikeyBHQCQFFYRZLCQQ-UHFFFAOYSA-Npolar_surface_area97.99refractivity110.79polarizability47.05rotatable_bond_count4acceptor_count5donor_count4physiological_charge-1formal_charge0Bile Acid BiosynthesisSMP00035map00120Specdb::EiMs32Specdb::CMs15789Specdb::CMs29924Specdb::CMs37652Specdb::CMs99586Specdb::CMs133327Specdb::CMs141061Specdb::CMs1070316Specdb::CMs1070318Specdb::CMs1070320Specdb::CMs1070321Specdb::CMs1070322Specdb::CMs1070323Specdb::CMs1070325Specdb::CMs1070327Specdb::CMs1070329Specdb::CMs1070331Specdb::CMs1070333Specdb::CMs1070334Specdb::CMs1070336Specdb::CMs1070338Specdb::CMs1070340Specdb::CMs1070342Specdb::CMs1070344Specdb::CMs1070346Specdb::CMs1070348Specdb::NmrOneD3347Specdb::NmrOneD261428Specdb::NmrOneD261429Specdb::NmrOneD261430Specdb::NmrOneD261431Specdb::NmrOneD261432Specdb::NmrOneD261433Specdb::NmrOneD261434Specdb::NmrOneD261435Specdb::NmrOneD261436Specdb::NmrOneD261437Specdb::NmrOneD261438Specdb::NmrOneD261439Specdb::NmrOneD261440Specdb::NmrOneD261441Specdb::NmrOneD261442Specdb::NmrOneD261443Specdb::NmrOneD261444Specdb::NmrOneD261445Specdb::NmrOneD261446Specdb::NmrOneD261447Specdb::MsMs437441Specdb::MsMs437442Specdb::MsMs437443Specdb::MsMs437444Specdb::MsMs437445Specdb::MsMs437470Specdb::MsMs437471Specdb::MsMs437472Specdb::MsMs437473Specdb::MsMs437474Specdb::MsMs438637Specdb::MsMs439180Specdb::MsMs439181Specdb::MsMs439333Specdb::MsMs439334Specdb::MsMs439335Specdb::MsMs439336Specdb::MsMs440681Specdb::MsMs440682Specdb::MsMs440683Specdb::MsMs440684Specdb::MsMs2236387Specdb::MsMs2236979Specdb::MsMs2238303Specdb::MsMs2238551HMDB0061916359CHD#<Reference:0x00005556748cf418>#<Reference:0x00005556748cf1e8>#<Reference:0x00005556748cefe0>#<Reference:0x00005556748cedb0>#<Reference:0x00005556748ceb58>#<Reference:0x00005556748ce9a0>#<Reference:0x00005556748ce798>#<Reference:0x00005556748ce540>#<Reference:0x00005556748ce360>#<Reference:0x00005556748ce130>#<Reference:0x00005556748cdf28>#<Reference:0x00005556748cdd48>#<Reference:0x00005556748cdb18>#<Reference:0x00005556748cd898>#<Reference:0x00005556748cd690>#<Reference:0x00005556748cd488>#<Reference:0x00005556748cd208>#<Reference:0x00005556748cd028>#<Reference:0x00005556748cce70>#<Reference:0x00005556748ccc90>Milk (Cow)Type 2specificbitterAcyl-coenzyme A thioesterase 8O14734ACOT8Bile acyl-CoA synthetaseQ9Y2P5SLC27A5Cytochrome c oxidase subunit 3P00414MT-CO3Cytochrome c oxidase subunit 4 isoform 1, mitochondrialP13073COX4I1Cytochrome c oxidase subunit 5B, mitochondrialP10606COX5BCytochrome c oxidase subunit 6A2, mitochondrialQ02221COX6A2Cytochrome c oxidase subunit 6B1P14854COX6B1Cytochrome c oxidase subunit 6CP09669COX6CCytochrome c oxidase subunit 7A1, mitochondrialP24310COX7A1Cytochrome c oxidase subunit 7B, mitochondrialP24311COX7BCytochrome c oxidase subunit 7C, mitochondrialP15954COX7CCytochrome c oxidase subunit 8A, mitochondrialP10176COX8AFerrochelataseQ7KZA3DKFZp686P18130Liver carboxylesterase 1P23141CES1