1.0 2010-04-08 22:10:22 UTC 2025-11-18 23:39:43 UTC FDB012810 Cholic acid 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. (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 acid 17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triol 3-&alpha,7-&alpha,12-&alpha-trihydroxy-5-&beta-cholanate 3,7,12-Trihydroxy-cholan-24-oic acid 3,7,12-Trihydroxycholanic acid 3a,7a,12a-Trihydroxy-5b-cholan-24-oate 3a,7a,12a-Trihydroxy-5b-cholan-24-oic acid 3a,7a,12a-Trihydroxy-5b-cholanate 3a,7a,12a-Trihydroxy-5b-cholanic acid 3a,7a,12a-Trihydroxy-5b-cholanoate 3a,7a,12a-Trihydroxy-5b-cholanoic acid 3a,7a,12a-Trihydroxy-b-cholanate 3a,7a,12a-Trihydroxy-b-cholanic acid 3a,7a,12a-Trihydroxy-beta-cholanate 3a,7a,12a-Trihydroxy-beta-cholanic acid 3a,7a,12a-Trihydroxycholanate 3a,7a,12a-Trihydroxycholanic acid 3alpha,7alpha-Dihydroxy-5beta-cholanic acid 3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oic acid 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanic acid 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanoic acid 3alpha,7alpha,12alpha-Trihydroxy-beta-cholanic acid 3alpha,7alpha,12alpha-Trihydroxycholanic acid 3α,7α,12α-trihydroxy-5β-cholanate 3α,7α,12α-trihydroxy-5β-cholanic acid 5b-Cholanic acid-3a,7a,12a-triol 5b-Cholate 5b-Cholic acid 5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy- 5beta-Cholanic acid-3alpha,7alpha-diol Chenodiol Cholagit Cholalate Cholalic acid Cholalin Cholan-24-oic acid Cholanic acid Cholate Cholic acid Cholic acid, 5beta- Cholsaeure Colalin Hypocholate NSC 6135 C24H40O5 408.5714 408.28757439 (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 acid 81-25-4 CC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C 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) 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 derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 12-hydroxysteroids 3-alpha-hydroxysteroids 7-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Polyols Secondary alcohols 12-hydroxysteroid 3-alpha-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Trihydroxy bile acid, alcohol, or derivatives C24 bile acids, alcohols, and derivatives C24 bile acids, alcohols, and derivatives Cholane and derivatives bile acid trihydroxy-5beta-cholanic acid Solid melting_point Mp 197° (anhyd.) logp 2.48 ChemAxon pka_strongest_acidic 4.48 ChemAxon pka_strongest_basic -0.16 ChemAxon iupac (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 ChemAxon average_mass 408.5714 ChemAxon mono_mass 408.28757439 ChemAxon smiles CC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C ChemAxon formula C24H40O5 ChemAxon 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) ChemAxon inchikey BHQCQFFYRZLCQQ-UHFFFAOYSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 110.79 ChemAxon polarizability 47.05 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::EiMs 32 Specdb::CMs 15789 Specdb::CMs 29924 Specdb::CMs 37652 Specdb::CMs 99586 Specdb::CMs 133327 Specdb::CMs 141061 Specdb::CMs 1070316 Specdb::CMs 1070318 Specdb::CMs 1070320 Specdb::CMs 1070321 Specdb::CMs 1070322 Specdb::CMs 1070323 Specdb::CMs 1070325 Specdb::CMs 1070327 Specdb::CMs 1070329 Specdb::CMs 1070331 Specdb::CMs 1070333 Specdb::CMs 1070334 Specdb::CMs 1070336 Specdb::CMs 1070338 Specdb::CMs 1070340 Specdb::CMs 1070342 Specdb::CMs 1070344 Specdb::CMs 1070346 Specdb::CMs 1070348 Specdb::NmrOneD 3347 Specdb::NmrOneD 261428 Specdb::NmrOneD 261429 Specdb::NmrOneD 261430 Specdb::NmrOneD 261431 Specdb::NmrOneD 261432 Specdb::NmrOneD 261433 Specdb::NmrOneD 261434 Specdb::NmrOneD 261435 Specdb::NmrOneD 261436 Specdb::NmrOneD 261437 Specdb::NmrOneD 261438 Specdb::NmrOneD 261439 Specdb::NmrOneD 261440 Specdb::NmrOneD 261441 Specdb::NmrOneD 261442 Specdb::NmrOneD 261443 Specdb::NmrOneD 261444 Specdb::NmrOneD 261445 Specdb::NmrOneD 261446 Specdb::NmrOneD 261447 Specdb::MsMs 29420 Specdb::MsMs 29421 Specdb::MsMs 29422 Specdb::MsMs 35978 Specdb::MsMs 35979 Specdb::MsMs 35980 Specdb::MsMs 437441 Specdb::MsMs 437442 Specdb::MsMs 437443 Specdb::MsMs 437444 Specdb::MsMs 437445 Specdb::MsMs 437470 Specdb::MsMs 437471 Specdb::MsMs 437472 Specdb::MsMs 437473 Specdb::MsMs 437474 Specdb::MsMs 438637 Specdb::MsMs 439180 Specdb::MsMs 439181 Specdb::MsMs 439333 Specdb::MsMs 439334 Specdb::MsMs 439335 Specdb::MsMs 439336 Specdb::MsMs 440681 Specdb::MsMs 440682 HMDB00619 16359 CHD #<Reference:0x000055ce30e9fc88> #<Reference:0x000055ce30e9fad0> #<Reference:0x000055ce30e9f8f0> #<Reference:0x000055ce30e9f4b8> #<Reference:0x000055ce30e9f120> #<Reference:0x000055ce30e9ed60> #<Reference:0x000055ce30e9eab8> #<Reference:0x000055ce30e9e7e8> #<Reference:0x000055ce30e9e130> #<Reference:0x000055ce30e9dcf8> #<Reference:0x000055ce30e9db18> #<Reference:0x000055ce30e9d708> #<Reference:0x000055ce30e9d438> #<Reference:0x000055ce30e9d0c8> #<Reference:0x000055ce30e9cee8> #<Reference:0x000055ce30e9cc90> #<Reference:0x000055ce30e9c9e8> #<Reference:0x000055ce30e9c7b8> #<Reference:0x000055ce30e9c2e0> #<Reference:0x000055ce30e9c0d8> Milk (Cow) Type 2 specific bitter Acyl-coenzyme A thioesterase 8 O14734 ACOT8 Bile acyl-CoA synthetase Q9Y2P5 SLC27A5 Cytochrome c oxidase subunit 3 P00414 MT-CO3 Cytochrome c oxidase subunit 4 isoform 1, mitochondrial P13073 COX4I1 Cytochrome c oxidase subunit 5B, mitochondrial P10606 COX5B Cytochrome c oxidase subunit 6A2, mitochondrial Q02221 COX6A2 Cytochrome c oxidase subunit 6B1 P14854 COX6B1 Cytochrome c oxidase subunit 6C P09669 COX6C Cytochrome c oxidase subunit 7A1, mitochondrial P24310 COX7A1 Cytochrome c oxidase subunit 7B, mitochondrial P24311 COX7B Cytochrome c oxidase subunit 7C, mitochondrial P15954 COX7C Cytochrome c oxidase subunit 8A, mitochondrial P10176 COX8A Ferrochelatase Q7KZA3 DKFZp686P18130 Liver carboxylesterase 1 P23141 CES1