1.0 2011-09-21 00:40:27 UTC 2017-04-03 05:02:17 UTC FDB024135 5b-Cyprinol sulfate 5b-Cyprinol sulfate is an intermediate in bile acid biosynthesis. 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] 5b-Cyprinosulfate 5b-Cyprinosulphate 5beta-Cyprinol sulfate 5beta-Cyprinol sulphate 5beta-Cyprinolsulfate 5beta-Cyprinolsulphate C27H48O8S 532.73 532.306989202 (3-hydroxy-2-{4-[(2S,5R,9R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentyl}propoxy)sulfonic acid 3-hydroxy-2-{4-[(2S,5R,9R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentyl}propoxysulfonic acid 14808-79-8 CC(CCCC(CO)COS(O)(=O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3C[C@@H](O)[C@]12C InChI=1S/C27H48O8S/c1-16(5-4-6-17(14-28)15-35-36(32,33)34)20-7-8-21-25-22(13-24(31)27(20,21)3)26(2)10-9-19(29)11-18(26)12-23(25)30/h16-25,28-31H,4-15H2,1-3H3,(H,32,33,34)/t16?,17?,18?,19-,20?,21?,22?,23-,24-,25?,26+,27-/m1/s1 KAOLEMQCYWHOJQ-UQACNIHJSA-N belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Tetrahydroxy 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 Alkyl sulfates Cyclic alcohols and derivatives Hydrocarbon derivatives Organic oxides Polyols Primary alcohols Secondary alcohols Sulfated steroids Sulfuric acid monoesters 12-hydroxysteroid 26-hydroxysteroid 3-alpha-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alkyl sulfate Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Organic oxide Organic oxygen compound Organic sulfuric acid or derivatives Organooxygen compound Polyol Primary alcohol Secondary alcohol Sulfate-ester Sulfated steroid skeleton Sulfuric acid ester Sulfuric acid monoester Tetrahydroxy bile acid, alcohol, or derivatives Solid logp 0.77 ALOGPS logs -3.98 ALOGPS solubility 5.57e-02 g/l ALOGPS logp 0.63 ChemAxon pka_strongest_acidic -1.8 ChemAxon pka_strongest_basic -0.14 ChemAxon iupac (3-hydroxy-2-{4-[(2S,5R,9R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentyl}propoxy)sulfonic acid ChemAxon average_mass 532.73 ChemAxon mono_mass 532.306989202 ChemAxon smiles CC(CCCC(CO)COS(O)(=O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3C[C@@H](O)[C@]12C ChemAxon formula C27H48O8S ChemAxon inchi InChI=1S/C27H48O8S/c1-16(5-4-6-17(14-28)15-35-36(32,33)34)20-7-8-21-25-22(13-24(31)27(20,21)3)26(2)10-9-19(29)11-18(26)12-23(25)30/h16-25,28-31H,4-15H2,1-3H3,(H,32,33,34)/t16?,17?,18?,19-,20?,21?,22?,23-,24-,25?,26+,27-/m1/s1 ChemAxon inchikey KAOLEMQCYWHOJQ-UQACNIHJSA-N ChemAxon polar_surface_area 144.52 ChemAxon refractivity 136.55 ChemAxon polarizability 59.39 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::MsMs 315382 Specdb::MsMs 315383 Specdb::MsMs 315384 Specdb::MsMs 361339 Specdb::MsMs 361340 Specdb::MsMs 361341 Specdb::MsMs 2285035 Specdb::MsMs 2285036 Specdb::MsMs 2285037 Specdb::MsMs 3080787 Specdb::MsMs 3080788 Specdb::MsMs 3080789 Specdb::CMs 22240 Specdb::CMs 39132 Specdb::CMs 235083 Specdb::CMs 235085 Specdb::CMs 235088 Specdb::CMs 235090 Specdb::CMs 235092 Specdb::CMs 235094 Specdb::CMs 235096 Specdb::CMs 235098 Specdb::CMs 235100 Specdb::CMs 235102 Specdb::CMs 235104 Specdb::CMs 235106 Specdb::CMs 235108 Specdb::CMs 235110 Specdb::CMs 235112 Specdb::CMs 235115 Specdb::CMs 235117 Specdb::CMs 235119 Specdb::CMs 235121 Specdb::CMs 235123 Specdb::CMs 235125 Specdb::CMs 235127 Specdb::CMs 235129 HMDB06888 2149 #<Reference:0x0000559ad66ffb00> #<Reference:0x0000559ad66ff768> #<Reference:0x0000559ad66ff4c0> #<Reference:0x0000559ad66ff268> 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