1.0 2011-09-21 00:23:25 UTC 2015-07-21 06:57:29 UTC FDB023024 Isodeoxycholic acid Isodeoxycholic acid is a human fecal 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: 3667743, 11316487, 16037564, 12576301, 11907135) [HMDB] 3-Deoxycholic acid 7a,12a-dihydroxy-5b-Cholan-24-oate 7a,12a-dihydroxy-5b-Cholan-24-oic acid 7a,12a-Dihydroxy-5b-cholanate 7a,12a-Dihydroxy-5b-cholanic acid 7a,12a-Dihydroxy-5b-cholanoate 7a,12a-Dihydroxy-5b-cholanoic acid 7a,12a-Dihydroxycholanoate 7a,12a-Dihydroxycholanoic acid 7alpha,12alpha-Dihydroxy-5beta-cholan-24-oate 7alpha,12alpha-Dihydroxy-5beta-cholan-24-oic acid 7alpha,12alpha-Dihydroxy-5beta-cholanate 7alpha,12alpha-Dihydroxy-5beta-cholanic acid 7alpha,12alpha-Dihydroxycholanoate 7alpha,12alpha-Dihydroxycholanoic acid 7α,12α-dihydroxy-5β-cholanate 7α,12α-dihydroxy-5β-cholanic acid 7α,12α-dihydroxycholanoate 7α,12α-dihydroxycholanoic acid Isodeoxycholate isodeoxycholic acid C24H40O4 392.572 392.292659768 (4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid (4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid 566-17-6 [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CCCC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O InChI=1S/C24H40O4/c1-14(7-10-21(27)28)16-8-9-17-22-18(13-20(26)24(16,17)3)23(2)11-5-4-6-15(23)12-19(22)25/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1 ZHCAAZIHTDCFJX-QLEQUTGBSA-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 7-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols 12-hydroxysteroid 7-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 C24 bile acids, alcohols, and derivatives C24 bile acids, alcohols, and derivatives cholanoid Solid logp 3.16 ALOGPS logs -4.20 ALOGPS solubility 2.49e-02 g/l ALOGPS logp 3.87 ChemAxon pka_strongest_acidic 4.48 ChemAxon pka_strongest_basic -0.19 ChemAxon iupac (4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid ChemAxon average_mass 392.572 ChemAxon mono_mass 392.292659768 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CCCC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O ChemAxon formula C24H40O4 ChemAxon inchi InChI=1S/C24H40O4/c1-14(7-10-21(27)28)16-8-9-17-22-18(13-20(26)24(16,17)3)23(2)11-5-4-6-15(23)12-19(22)25/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1 ChemAxon inchikey ZHCAAZIHTDCFJX-QLEQUTGBSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 109.12 ChemAxon polarizability 46.11 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21941 Specdb::CMs 38438 Specdb::CMs 160404 Specdb::MsMs 103227 Specdb::MsMs 103228 Specdb::MsMs 103229 Specdb::MsMs 169209 Specdb::MsMs 169210 Specdb::MsMs 169211 Specdb::MsMs 2372394 Specdb::MsMs 2372395 Specdb::MsMs 2372396 Specdb::MsMs 2563266 Specdb::MsMs 2563267 Specdb::MsMs 2563268 HMDB02536 #<Reference:0x00005612729bc140> #<Reference:0x00005612729bbfb0> #<Reference:0x00005612729bbdf8> #<Reference:0x00005612729bbc40> #<Reference:0x00005612729bba88> 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