1.0 2011-09-21 00:09:54 UTC 2018-05-02 12:30:47 UTC FDB022194 Glycoursodeoxycholic acid Glycoursodeoxycholic acid is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID:16949895). 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,7b-Dihydroxy-5b-cholanoylglycine Glycoursodeoxycholate Glycoursodeoxycholic acid Glycylursodeoxycholate Glycylursodeoxycholic acid N-(3a,7b-Dihydroxy-5b-cholan-24-oyl)glycine N-[(3a,5b,7b)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine Ursodeoxycholylglycine C26H43NO5 449.6233 449.314123491 2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid [(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid 64480-66-6 [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1 GHCZAUBVMUEKKP-XROMFQGDSA-N belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton. Glycinated bile acids and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 3-alpha-hydroxysteroids 7-alpha-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Dihydroxy bile acids, alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives N-acyl amines N-acyl-alpha amino acids Organic oxides Organonitrogen compounds Organopnictogen compounds Secondary alcohols Secondary carboxylic acid amides 3-alpha-hydroxysteroid 3-hydroxysteroid 7-alpha-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alpha-amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Dihydroxy bile acid, alcohol, or derivatives Fatty acyl Fatty amide Glycinated bile acid Hydrocarbon derivative Hydroxy bile acid, alcohol, or derivatives Hydroxysteroid Monocarboxylic acid or derivatives N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary alcohol Secondary carboxylic acid amide C24 bile acids, alcohols, and derivatives Solid logp 2.40 ALOGPS logs -4.75 ALOGPS solubility 7.93e-03 g/l ALOGPS logp 2.61 ChemAxon pka_strongest_acidic 3.77 ChemAxon pka_strongest_basic -0.49 ChemAxon iupac 2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid ChemAxon average_mass 449.6233 ChemAxon mono_mass 449.314123491 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O ChemAxon formula C26H43NO5 ChemAxon inchi InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1 ChemAxon inchikey GHCZAUBVMUEKKP-XROMFQGDSA-N ChemAxon polar_surface_area 106.86 ChemAxon refractivity 122.08 ChemAxon polarizability 52.19 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 300245 Specdb::NmrOneD 300246 Specdb::NmrOneD 300247 Specdb::NmrOneD 300248 Specdb::NmrOneD 300249 Specdb::NmrOneD 300250 Specdb::NmrOneD 300251 Specdb::NmrOneD 300252 Specdb::NmrOneD 300253 Specdb::NmrOneD 300254 Specdb::NmrOneD 300255 Specdb::NmrOneD 300256 Specdb::NmrOneD 300257 Specdb::NmrOneD 300258 Specdb::NmrOneD 300259 Specdb::NmrOneD 300260 Specdb::NmrOneD 300261 Specdb::NmrOneD 300262 Specdb::NmrOneD 300263 Specdb::NmrOneD 300264 Specdb::CMs 12707 Specdb::CMs 37708 Specdb::CMs 151377 Specdb::CMs 1072565 Specdb::CMs 1072567 Specdb::CMs 1072569 Specdb::CMs 1072571 Specdb::CMs 1072573 Specdb::CMs 1072575 Specdb::CMs 1072576 Specdb::CMs 1072578 Specdb::CMs 1072580 Specdb::CMs 1072582 Specdb::CMs 1072585 Specdb::CMs 1072587 Specdb::CMs 1072589 Specdb::CMs 1072591 Specdb::CMs 1072593 Specdb::CMs 1072595 Specdb::CMs 1072597 Specdb::CMs 1072599 Specdb::CMs 1072601 Specdb::CMs 1072603 Specdb::CMs 1072605 Specdb::CMs 1072607 Specdb::MsMs 61359 Specdb::MsMs 61360 Specdb::MsMs 61361 Specdb::MsMs 117882 Specdb::MsMs 117883 Specdb::MsMs 117884 Specdb::MsMs 2727140 Specdb::MsMs 2727141 Specdb::MsMs 2727142 Specdb::MsMs 2977835 Specdb::MsMs 2977836 Specdb::MsMs 2977837 HMDB00708 #<Reference:0x0000561272ff1010> #<Reference:0x0000561272ff0e58> #<Reference:0x0000561272ff0ca0> #<Reference:0x0000561272ff0ae8> #<Reference:0x0000561272ff0930> #<Reference:0x0000561272ff0778> #<Reference:0x0000561272ff05c0> 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 Glycine N-acyltransferase Q6IB77 GLYAT Glycine N-acyltransferase-like protein 1 Q969I3 GLYATL1 Glycine N-acyltransferase-like protein 2 Q8WU03 GLYATL2 Glycine N-acyltransferase-like protein 3 Q5SZD4 GLYATL3