1.0 2011-09-21 00:09:18 UTC 2015-07-21 06:57:01 UTC FDB022157 Chenodeoxycholic acid glycine conjugate Chenodeoxycholic acid glycine conjugate is an acyl glycine and a bile acid-glycine conugate. 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). This compound usually exists as the sodium salt and acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic. [HMDB] (23R)-Hydroxychenodeoxycholylglycine 12-Deoxycholylglycine 12-Desoxycholylglycine 3a,7a-Dihydroxy-N-(carboxymethyl)-5b-cholan-24-amide Chenodeoxycholic acid glycine conjugate Chenodeoxycholylglycine Glycine chenodeoxycholate Glycochenodeoxycholate Glycochenodeoxycholic acid Glycylchenodeoxycholate Glycylchenodeoxycholic acid N-(3a,7a-dihydroxy-5b-cholan-24-oyl)-Glycine N-(carboxymethyl)-3a,7a-dihydroxy-5b-Cholan-24-amide C26H43NO5 449.6233 449.314123491 2-[(4R)-4-[(2S,5R,7S,9R,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-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid 640-79-9 [H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[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-AHBZRTSYSA-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-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-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 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-[(2S,5R,7S,9R,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@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[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-AHBZRTSYSA-N ChemAxon polar_surface_area 106.86 ChemAxon refractivity 122.08 ChemAxon polarizability 52.08 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::CMs 11250 Specdb::CMs 37665 Specdb::MsMs 66087 Specdb::MsMs 66088 Specdb::MsMs 66089 Specdb::MsMs 123558 Specdb::MsMs 123559 Specdb::MsMs 123560 HMDB00637 1FMC #<Reference:0x0000561272875e08> #<Reference:0x0000561272875b88> #<Reference:0x0000561272875958> #<Reference:0x0000561272875778> #<Reference:0x00005612728755c0> #<Reference:0x00005612728753e0> 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 acid-CoA:amino acid N-acyltransferase Q14032 BAAT 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