1.0 2016-09-30 22:20:03 UTC 2020-05-11 20:46:36 UTC BMDB0000138 BMDB00138 Glycocholic acid Glycocholic acid, also known as glycocholate or N-choloyl-glycine, 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. Glycocholic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glycocholic acid has been found to be associated with several diseases known as crohn's disease, hepatobiliary diseases, cystic fibrosis, and portal vein obstruction; also glycocholic acid has been linked to the inborn metabolic disorders including celiac disease. Glycocholate 3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine 3a,7a,12a-Trihydroxy-5b-cholanic acid-24-glycine 3a,7a,12a-Trihydroxy-N-(carboxymethyl)-5b-cholan-24-amide Cholylglycine Glycine cholate Glycoreductodehydrocholic acid Glycylcholate Glycylcholic acid N-(Carboxymethyl)-3a,7a,12a-trihydroxy-5b-cholan-24-amide N-Choloyl-glycine N-Choloylglycine Glycocholic acid, sodium salt Glycocholate sodium C26H43NO6 465.6227 465.309038113 2-[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid [(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid [H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15?,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1 RFDAIACWWDREDC-MZMBZMQMSA-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. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Glycinated bile acids and derivatives 12-hydroxysteroids 3-alpha-hydroxysteroids 7-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives N-acyl amines N-acyl-alpha amino acids Organic oxides Organonitrogen compounds Organopnictogen compounds Polyols Secondary alcohols Secondary carboxylic acid amides Trihydroxy bile acids, alcohols and derivatives 12-hydroxysteroid 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 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 Polyol Secondary alcohol Secondary carboxylic acid amide Trihydroxy bile acid, alcohol, or derivatives Aliphatic homopolycyclic compounds Solid melting_point 170 °C water_solubility 0.0033 mg/mL logp 1.65 RODA,A ET AL. (1990) logp 1.70 ALOGPS logs -4.27 ALOGPS logp 1.38 ChemAxon pka_strongest_acidic 3.77 ChemAxon pka_strongest_basic -0.04 ChemAxon iupac 2-[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid ChemAxon average_mass 465.6227 ChemAxon mono_mass 465.309038113 ChemAxon smiles [H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C ChemAxon formula C26H43NO6 ChemAxon inchi InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15?,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1 ChemAxon inchikey RFDAIACWWDREDC-MZMBZMQMSA-N ChemAxon polar_surface_area 127.09 ChemAxon refractivity 123.59 ChemAxon polarizability 53.03 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Bile Acid Biosynthesis SMP0087236 Specdb::NmrTwoD 1163 Specdb::MsMs 209 Specdb::MsMs 210 Specdb::MsMs 211 Specdb::MsMs 304189 Specdb::MsMs 304190 Specdb::MsMs 304191 Specdb::MsMs 347317 Specdb::MsMs 347318 Specdb::MsMs 347319 Specdb::CMs 17275 Specdb::CMs 37315 Specdb::NmrOneD 1105 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Milk By GC-TOFMS and UPLC-QTOFMS Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 24747221 23617285 Glycocholic acid Cortese, Frank; Bauman, Louis. A synthesis of conjugated bile acids. I. Glycocholic acid. Journal of the American Chemical Society (1935), 57 1393-5. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311