1.0 2011-09-21 00:23:17 UTC 2015-07-21 06:57:28 UTC FDB023014 N-[(3a,5b,7a)-3-Hydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-glycine N-[(3a,5b,7a)-3-hydroxy-24-oxo-7-(sulfooxy)cholan-24-yl]-Glycine (Glycochenodeoxycholate 7-sulfate) is an acyl glycine and a bile acid-glycine conjugate. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. Glycochenodeoxycholate 7-sulfate is also a sulphated bile acid. Sulphated bile acids are found mainly in the urine. The sulphate group not only prevents its tubular reabsorption but also its absorption from the intestine. [HMDB] Glycochenodeoxycholate 7-sulfate Glycochenodeoxycholate 7-sulphate Glycochenodeoxycholic acid 7-sulfate Glycochenodeoxycholic acid 7-sulphate Glycochenodeoxycholyl 7-sulfate Glycochenodeoxycholyl 7-sulphate N-(3a-Hydroxy-7a-sulfooxy-5b-cholan-24-oyl)glycine N-(3a-Hydroxy-7a-sulphooxy-5b-cholan-24-oyl)glycine N-(3alpha-Hydroxy-7alpha-sulfooxy-5beta-cholan-24-oyl)glycine N-(3alpha-Hydroxy-7alpha-sulphooxy-5beta-cholan-24-oyl)glycine N-(3α-hydroxy-7α-sulfooxy-5β-cholan-24-oyl)glycine N-(3α-hydroxy-7α-sulphooxy-5β-cholan-24-oyl)glycine C26H43NO8S 529.687 529.270938047 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid [(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid 67030-55-1 [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O InChI=1S/C26H43NO8S/c1-15(4-7-22(29)27-14-23(30)31)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)35-36(32,33)34/h15-21,24,28H,4-14H2,1-3H3,(H,27,29)(H,30,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-/m1/s1 GLYPHOJMMLQNJQ-GYPHWSFCSA-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 Alkyl sulfates Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Monohydroxy bile acids, alcohols and derivatives N-acyl amines N-acyl-alpha amino acids Organic oxides Organonitrogen compounds Organopnictogen compounds Secondary alcohols Secondary carboxylic acid amides Sulfated steroids Sulfuric acid monoesters 3-alpha-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alkyl sulfate Alpha-amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Fatty acyl Fatty amide 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 N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organic sulfuric acid or derivatives Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary alcohol Secondary carboxylic acid amide Sulfate-ester Sulfated steroid skeleton Sulfuric acid ester Sulfuric acid monoester Glycine conjugates sulfooxy steroid Solid logp 0.01 ALOGPS logs -4.63 ALOGPS solubility 1.24e-02 g/l ALOGPS logp 1.44 ChemAxon pka_strongest_acidic -1.1 ChemAxon pka_strongest_basic -0.47 ChemAxon iupac 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid ChemAxon average_mass 529.687 ChemAxon mono_mass 529.270938047 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O ChemAxon formula C26H43NO8S ChemAxon inchi InChI=1S/C26H43NO8S/c1-15(4-7-22(29)27-14-23(30)31)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)35-36(32,33)34/h15-21,24,28H,4-14H2,1-3H3,(H,27,29)(H,30,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-/m1/s1 ChemAxon inchikey GLYPHOJMMLQNJQ-GYPHWSFCSA-N ChemAxon polar_surface_area 150.23 ChemAxon refractivity 132.07 ChemAxon polarizability 57.21 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 294475 Specdb::MsMs 294476 Specdb::MsMs 294477 Specdb::MsMs 335206 Specdb::MsMs 335207 Specdb::MsMs 335208 Specdb::MsMs 2364460 Specdb::MsMs 2364461 Specdb::MsMs 2364462 Specdb::MsMs 2597305 Specdb::MsMs 2597306 Specdb::MsMs 2597307 Specdb::CMs 12960 Specdb::CMs 38430 Specdb::CMs 193381 Specdb::CMs 193383 Specdb::CMs 193385 Specdb::CMs 193388 Specdb::CMs 193390 Specdb::CMs 193392 Specdb::CMs 193394 Specdb::CMs 193396 Specdb::CMs 193398 Specdb::CMs 193400 Specdb::CMs 193402 Specdb::CMs 193404 Specdb::CMs 193407 Specdb::CMs 193409 Specdb::CMs 193410 Specdb::CMs 193412 Specdb::CMs 193415 Specdb::CMs 193417 Specdb::CMs 193419 Specdb::CMs 281018 HMDB02496 #<Reference:0x000055ce32fc1538> 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