1.0 2010-04-08 22:10:21 UTC 2015-10-09 22:27:46 UTC FDB012780 Deoxycholic acid Emulsifying agent used in foods Deoxycholic acid is a bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent. 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); Deoxycholic acid, also known as deoxycholate, cholanoic acid, and 3?,12?-dihydroxy-5?-cholanate, is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are cholic acid and chenodeoxycholic acid. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid lithocholic acid, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as ursodeoxycholic acid. Deoxycholic acid is soluble in alcohol and acetic acid. When pure, it comes in a white to off-white crystalline powder form.; In China, the traditional medicine "Niuhuang", which in Chinese means "Oxen Yellow" and is actually bilestone of oxen, has been in use for two millennia for the treatment of inflammation as well as to enhance the immune system. One of its main components is DCA. (3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oate (3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oic acid (3a,5b,12a)-3,12-Dihydroxycholan-24-Oate (3a,5b,12a)-3,12-Dihydroxycholan-24-Oic acid (3alpha,5alpha,12alpha)-3,12-DIHYDROXYCHOLAN-24-Oate (3ALPHA,5ALPHA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACID (3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oate (3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acid (3α,5α,12α)-3,12-dihydroxycholan-24-Oate (3α,5α,12α)-3,12-dihydroxycholan-24-Oic acid (3α,5β,12α)-3,12-dihydroxycholan-24-Oate (3α,5β,12α)-3,12-dihydroxycholan-24-Oic acid 17&alpha;, 12&alpha;-diol 3,12-Dihydroxycholanic acid 3a,12a-Dihydroxy-5b-cholanate 3a,12a-Dihydroxy-5b-cholanic acid 3alpha,12alpha-Dihydroxy-5beta-cholanate 3alpha,12alpha-Dihydroxy-5beta-cholanic acid 3α,12α-dihydroxy-5β-cholanate 3α,12α-dihydroxy-5β-cholanic acid 5&alpha;,12&alpha;-dihydroxy- 5b-Cholanic acid-3a,12a-diol 5b-Deoxycholate 5b-Deoxycholic acid 7-Deoxycholate 7-Deoxycholic acid 7&alpha;-Deoxycholic acid 7a-Deoxycholate 7a-Deoxycholic acid 7alpha-Deoxycholate 7alpha-Deoxycholic acid 7α-deoxycholate 7α-deoxycholic acid Cholan-24-oic acid, 3,12-dihydroxy-, (3&alpha;,5&alpha;)- Choleic acid Cholerebic Cholic acid, deoxy- Cholorebic Cholorebic acid Degalol Deoxy-cholate Deoxy-cholic acid Deoxycholatate Deoxycholate Deoxycholatic acid Deoxycholic acid Desoxycholate Desoxycholic acid Desoxycholsaeure Droxolan Pyrochol Septochol C24H40O4 392.572 392.292659768 4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoic acid 4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoic acid 83-44-3 CC(CCC(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28) KXGVEGMKQFWNSR-UHFFFAOYSA-N belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Dihydroxy 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-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols 12-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Dihydroxy bile acid, alcohol, or derivatives Hydrocarbon derivative Hydroxysteroid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Solid logp 3.30 ALOGPS logs -4.35 ALOGPS solubility 1.73e-02 g/l ALOGPS melting_point Mp 187-189° logp 3.79 ChemAxon pka_strongest_acidic 4.65 ChemAxon pka_strongest_basic -0.35 ChemAxon iupac 4-{5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanoic acid ChemAxon average_mass 392.572 ChemAxon mono_mass 392.292659768 ChemAxon smiles CC(CCC(O)=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CC(O)C12C ChemAxon formula C24H40O4 ChemAxon inchi InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28) ChemAxon inchikey KXGVEGMKQFWNSR-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 109.2 ChemAxon polarizability 46.55 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::MsMs 3405025 Specdb::MsMs 3405026 Specdb::MsMs 3405027 Specdb::MsMs 3405028 Specdb::MsMs 3405029 Specdb::MsMs 3405030 Specdb::CMs 111121 Specdb::CMs 124267 Specdb::CMs 820996 Specdb::CMs 820997 Specdb::CMs 820998 Specdb::CMs 820999 Specdb::CMs 821000 Specdb::CMs 821001 Specdb::CMs 821002 Specdb::CMs 821003 Specdb::CMs 821004 Specdb::CMs 821005 Specdb::CMs 821006 Specdb::CMs 821007 Specdb::CMs 821008 Specdb::CMs 821009 HMDB00626 28834 DXC #<Reference:0x000055ce30b5c468> #<Reference:0x000055ce30b5c260> #<Reference:0x000055ce30b5c008> #<Reference:0x000055ce30b4fe20> #<Reference:0x000055ce30b4fc18> #<Reference:0x000055ce30b4fa10> #<Reference:0x000055ce30b4f790> #<Reference:0x000055ce30b4f5d8> #<Reference:0x000055ce30b4f420> #<Reference:0x000055ce30b4f218> #<Reference:0x000055ce30b4efe8> #<Reference:0x000055ce30b4ee30> #<Reference:0x000055ce30b4ec50> #<Reference:0x000055ce30b4ea98> #<Reference:0x000055ce30b4e868> #<Reference:0x000055ce30b4e638> #<Reference:0x000055ce30b4e480> #<Reference:0x000055ce30b4e200> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Bile acid receptor Q96RI1 NR1H4