1.0 2011-09-21 00:09:48 UTC 2015-07-21 06:57:02 UTC FDB022187 Lithocholic acid glycine conjugate Lithocholic acid glycine conjugate is an acyl glycine and a bile acid-glycine conjugate. 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-Hydroxy-5b-cholanic acid glycine ester 3a-Hydroxy-5b-cholanoylglycine 3a-Hydroxy-N-(carboxymethyl)-5b-cholan-24-amide 3alpha-hydroxy-5beta-cholan-24-oate 3alpha-hydroxy-5beta-cholan-24-oic acid 3alpha-hydroxy-5beta-cholan-24-oic acid N-(carboxymethyl)amide glycolithocholate Glycolithocholic acid Lithocholate glycine conjugate Lithocholic acid glycine conjugate Lithocholic acid glycine conjugic acid lithocholoyglycine Lithocholylglycine N-((3-a,5-b)-3-Hydroxy-24-oxocholan-24-yl)glycine N-((3-alpha,5-beta)-3-Hydroxy-24-oxocholan-24-yl)glycine N-((3-α,5-β)-3-hydroxy-24-oxocholan-24-yl)glycine N-(3a-hydroxy-5b-cholan-24-oyl)-Glycine N-(3a-Hydroxy-5b-cholanoyl)glycine N-(carboxymethyl)-3a-hydroxy-5b-Cholan-24-amide C26H43NO4 433.6239 433.319208869 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid [(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid 474-74-8 [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[C@]12C)[C@H](C)CCC(=O)NCC(O)=O InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1 XBSQTYHEGZTYJE-OETIFKLTSA-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 Carbonyl compounds Carboximidic acids Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Monohydroxy bile acids, alcohols and derivatives N-acyl-alpha amino acids Organic oxides Organonitrogen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Secondary alcohols 3-alpha-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alpha-amino acid or derivatives Carbonyl group Carboximidic acid Carboximidic acid derivative Carboxylic acid Carboxylic acid derivative Cyclic alcohol Glycinated bile acid Hydrocarbon derivative Hydroxy bile acid, alcohol, or derivatives Hydroxysteroid Monocarboxylic acid or derivatives Monohydroxy bile acid, alcohol, or derivatives N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Secondary alcohol Glycine conjugates N-acylglycine bile acid glycine conjugate Solid logp 3.71 ALOGPS logs -5.45 ALOGPS solubility 1.53e-03 g/l ALOGPS logp 3.92 ChemAxon pka_strongest_acidic 3.77 ChemAxon pka_strongest_basic -1.1 ChemAxon iupac 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid ChemAxon average_mass 433.6239 ChemAxon mono_mass 433.319208869 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[C@]12C)[C@H](C)CCC(=O)NCC(O)=O ChemAxon formula C26H43NO4 ChemAxon inchi InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1 ChemAxon inchikey XBSQTYHEGZTYJE-OETIFKLTSA-N ChemAxon polar_surface_area 86.63 ChemAxon refractivity 120.48 ChemAxon polarizability 51.32 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::NmrOneD 336038 Specdb::NmrOneD 336039 Specdb::NmrOneD 336040 Specdb::NmrOneD 336041 Specdb::NmrOneD 336042 Specdb::NmrOneD 336043 Specdb::NmrOneD 336044 Specdb::NmrOneD 336045 Specdb::NmrOneD 336046 Specdb::NmrOneD 336047 Specdb::NmrOneD 336048 Specdb::NmrOneD 336049 Specdb::NmrOneD 336050 Specdb::NmrOneD 336051 Specdb::NmrOneD 336052 Specdb::NmrOneD 336053 Specdb::NmrOneD 336054 Specdb::NmrOneD 336055 Specdb::NmrOneD 336056 Specdb::NmrOneD 336057 Specdb::CMs 25041 Specdb::CMs 37702 Specdb::CMs 130358 Specdb::CMs 138092 Specdb::CMs 1072501 Specdb::CMs 1072503 Specdb::CMs 1072505 Specdb::CMs 1072507 Specdb::CMs 1072509 Specdb::CMs 1072511 Specdb::CMs 1072513 Specdb::CMs 1072515 Specdb::CMs 1072516 Specdb::CMs 1072519 Specdb::CMs 1072520 Specdb::MsMs 56001 Specdb::MsMs 56002 Specdb::MsMs 56003 Specdb::MsMs 111306 Specdb::MsMs 111307 Specdb::MsMs 111308 Specdb::MsMs 2755741 Specdb::MsMs 2755742 Specdb::MsMs 2755743 Specdb::MsMs 2952750 Specdb::MsMs 2952751 Specdb::MsMs 2952752 HMDB00698 #<Reference:0x000055ce33293ce8> #<Reference:0x000055ce33293b30> #<Reference:0x000055ce33293978> #<Reference:0x000055ce332937c0> #<Reference:0x000055ce33293608> #<Reference:0x000055ce33293450> #<Reference:0x000055ce33293298> #<Reference:0x000055ce332930e0> #<Reference:0x000055ce33292f28> #<Reference:0x000055ce33292d70> 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 Bile salt sulfotransferase Q06520 SULT2A1 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