1.0 2011-09-21 00:05:45 UTC 2015-07-21 06:56:54 UTC FDB021953 12-Ketodeoxycholic acid 12-Ketodeoxycholic acid is a bile acid. 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) [HMDB] (3a,5b)-3-hydroxy-12-oxo-cholan-24-oate (3a,5b)-3-hydroxy-12-oxo-cholan-24-oic acid (3alpha,5beta)-3-hydroxy-12-oxo-cholan-24-oate (3alpha,5beta)-3-hydroxy-12-oxo-cholan-24-oic acid 12-Dehydrodeoxycholate 12-Dehydrodeoxycholic acid 12-Ketodeoxycholate 12-Ketodeoxycholic acid 12-Ketolithocholate 12-Ketolithocholic acid 12-Oxo-3a-hydroxy-5b-cholanate 12-Oxo-3a-hydroxy-5b-cholanic acid 12-Oxolithocholate 12-Oxolithocholic acid 3a-Hydroxy-12-oxo-5b-cholan-24-oate 3a-Hydroxy-12-oxo-5b-cholan-24-oic acid 3a-Hydroxy-12-oxo-5b-cholanate 3a-Hydroxy-12-oxo-5b-cholanic acid 3a-Hydroxy-12-oxo-5b-cholanoate 3a-Hydroxy-12-oxo-5b-cholanoic acid C24H38O4 390.5561 390.277009704 (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid 12-ketolithocholic acid 5130-29-0 [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O InChI=1S/C24H38O4/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/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1 CVNYHSDFZXHMMJ-VPUMZWJWSA-N belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. Monohydroxy bile acids, alcohols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 3-alpha-hydroxysteroids Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Ketones Monocarboxylic acids and derivatives Organic oxides Oxosteroids Secondary alcohols 12-oxosteroid 3-alpha-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Ketone Monocarboxylic acid or derivatives Monohydroxy bile acid, alcohol, or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol C24 bile acids, alcohols, and derivatives Solid logp 3.78 ALOGPS logs -4.49 ALOGPS solubility 1.26e-02 g/l ALOGPS logp 4.35 ChemAxon pka_strongest_acidic 4.56 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid ChemAxon average_mass 390.5561 ChemAxon mono_mass 390.277009704 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O ChemAxon formula C24H38O4 ChemAxon inchi InChI=1S/C24H38O4/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/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1 ChemAxon inchikey CVNYHSDFZXHMMJ-VPUMZWJWSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 108.37 ChemAxon polarizability 45.52 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21191 Specdb::CMs 37434 Specdb::CMs 161239 Specdb::CMs 1058548 Specdb::CMs 1058550 Specdb::CMs 1058552 Specdb::CMs 1058554 Specdb::CMs 1058555 Specdb::CMs 1058558 Specdb::CMs 1058560 Specdb::CMs 1058562 Specdb::CMs 1058564 Specdb::CMs 1058566 Specdb::CMs 1058568 Specdb::MsMs 28589 Specdb::MsMs 28590 Specdb::MsMs 28591 Specdb::MsMs 35147 Specdb::MsMs 35148 Specdb::MsMs 35149 Specdb::MsMs 2245308 Specdb::MsMs 2246924 Specdb::MsMs 2247383 Specdb::MsMs 2249337 Specdb::MsMs 2700346 Specdb::MsMs 2700347 Specdb::MsMs 2700348 Specdb::MsMs 3004917 Specdb::MsMs 3004918 Specdb::MsMs 3004919 HMDB00328 #<Reference:0x00007f41bc31ec50> #<Reference:0x00007f41bc31e9f8> #<Reference:0x00007f41bc31e778> #<Reference:0x00007f41bc31e408> #<Reference:0x00007f41bc31e188> #<Reference:0x00007f41bc31dee0> #<Reference:0x00007f41bc31dbe8> 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