1.0 2011-09-21 00:09:02 UTC 2015-07-21 06:56:59 UTC FDB022137 Coprocholic acid 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,7a,12a)-3,7,12-Trihydroxycholestan-26-Oate (3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-Oic acid (3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-Oate (3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-Oic acid (3α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-Oate (3α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-Oic acid 3,7,12-Trihydroxycholestan-26-Oate 3,7,12-Trihydroxycholestan-26-Oic acid 3a,7a,12a-trihydroxy-(6CI,7CI,8CI)5b-Cholestan-26-oate 3a,7a,12a-trihydroxy-(6CI,7CI,8CI)5b-Cholestan-26-oic acid 3a,7a,12a-Trihydroxy-5b-cholestan-26-oate 3a,7a,12a-Trihydroxy-5b-cholestan-26-oic acid 3a,7a,12a-Trihydroxy-5b-cholestanate 3a,7a,12a-Trihydroxy-5b-cholestanic acid 3a,7a,12a-Trihydroxy-5b-cholestanoate 3a,7a,12a-Trihydroxy-5b-cholestanoic acid 3a,7a,12a-Trihydroxycoprostanate 3a,7a,12a-Trihydroxycoprostanic acid 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-Oate 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-Oic acid 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanate 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanic acid 3α,7α,12α-trihydroxy-5β-cholestan-26-Oate 3α,7α,12α-trihydroxy-5β-cholestan-26-Oic acid 3α,7α,12α-trihydroxy-5β-cholestanate 3α,7α,12α-trihydroxy-5β-cholestanic acid 3α,7α,12α-trihydroxy-5β-cholestanoate 3α,7α,12α-trihydroxy-5β-cholestanoic acid 5b-Cholestane-3a,7a,12a-triol-26-oate 5b-Cholestane-3a,7a,12a-triol-26-oic acid Coprocholate Coprocholic acid C27H46O5 450.6511 450.334524582 (6R)-2-methyl-6-[(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]heptanoic acid (6R)-2-methyl-6-[(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]heptanoic acid 547-98-8 [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1 CNWPIIOQKZNXBB-VCVMUKOKSA-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 Hydroxy fatty acids Medium-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Polyols Secondary alcohols Steroid acids 12-hydroxysteroid 3-alpha-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Fatty acid Fatty acyl Hydrocarbon derivative Hydroxy fatty acid Hydroxysteroid Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Steroid acid Trihydroxy bile acid, alcohol, or derivatives 12alpha-hydroxy steroid 3alpha-hydroxy steroid 7alpha-hydroxy steroid C27 bile acids, alcohols, and derivatives hydroxy monocarboxylic acid steroid acid Solid logp 3.12 ALOGPS logs -4.30 ALOGPS solubility 2.25e-02 g/l ALOGPS logp 3.91 ChemAxon pka_strongest_acidic 4.62 ChemAxon pka_strongest_basic -0.16 ChemAxon iupac (6R)-2-methyl-6-[(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]heptanoic acid ChemAxon average_mass 450.6511 ChemAxon mono_mass 450.334524582 ChemAxon smiles [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C ChemAxon formula C27H46O5 ChemAxon inchi InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1 ChemAxon inchikey CNWPIIOQKZNXBB-VCVMUKOKSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 124.57 ChemAxon polarizability 53.32 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15974 Specdb::CMs 37645 Specdb::CMs 171079 Specdb::CMs 1070021 Specdb::CMs 1070023 Specdb::CMs 1070025 Specdb::CMs 1070027 Specdb::CMs 1070029 Specdb::CMs 1070031 Specdb::CMs 1070033 Specdb::CMs 1070035 Specdb::CMs 1070037 Specdb::CMs 1070039 Specdb::CMs 1070041 Specdb::CMs 1070044 Specdb::CMs 1070046 Specdb::CMs 1070048 Specdb::CMs 1070050 Specdb::CMs 1070052 Specdb::CMs 1070054 Specdb::CMs 1070056 Specdb::CMs 1070058 Specdb::CMs 1070060 Specdb::CMs 1070062 Specdb::CMs 1070064 Specdb::MsMs 301384 Specdb::MsMs 301385 Specdb::MsMs 301386 Specdb::MsMs 343891 Specdb::MsMs 343892 Specdb::MsMs 343893 Specdb::MsMs 2424463 Specdb::MsMs 2424464 Specdb::MsMs 2424465 Specdb::MsMs 2514586 Specdb::MsMs 2514587 Specdb::MsMs 2514588 HMDB00601 #<Reference:0x000055ce3347e8f0> #<Reference:0x000055ce3347e738> #<Reference:0x000055ce3347e580> #<Reference:0x000055ce3347e3c8> 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