Compound: Glycocholic acid
SMILES: O=C(O)CNC(=O)CC[C@H]([C@@H]1[C@]2([C@@H](O)C[C@@H]3[C@@]4([C@@H](C[C@H](O)CC4)C[C@H]([C@H]3[C@@H]2CC1)O)C)C)C
InChIKey: RFDAIACWWDREDC-FRVQLJSFSA-N
Synonyms: Glycocholic acid, 475-31-0, Cholylglycine, N-Choloylglycine, G59NX3I3RT, DTXSID2047436, 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid, DTXCID0027436, CHEBI:17687, Glycine, N-((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)-, N-(3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholan-24-oyl)-glycine, N-((3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl)glycine, N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine, 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid, Glycine, N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]-, 2-(((4R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)pentanoyl)amino)acetic acid, 2-((4R)-4-((1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-14-yl)pentanamido)acetic acid, RefChem:389020, 207-494-9, glycocholate, Glycine, N-choloyl-, MFCD00065902, N-CHOLYLGLYCINE, CHEMBL411070, ((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyl)glycine, C26H43NO6, 3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oylglycine, 2-((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)acetic acid, N-(3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oyl)glycine, GCH, UNII-G59NX3I3RT, Glycylcholate, N-choloyl-Glycine, 2-[(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanamido]acetic Acid, CAS-475-31-0, Prestwick_768, EINECS 207-494-9, Prestwick0_000521, Prestwick1_000521, Prestwick2_000521, Prestwick3_000521, Spectrum5_002011, bmse000651, Glycocholic acid (Standard), BIDD:PXR0160, Glycoreductodehydrocholic acid, SCHEMBL29022, BSPBio_000501, MLS002153857, GLYCOCHOLIC ACID [MI], SPBio_002422, BPBio1_000553, GTPL4544, orb1304965, HY-N1423R, 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic acid N-(carboxymethyl)amide, GLYCOCHOLIC ACID [WHO-DD], HMS1569J03, HMS2096J03, HMS2231A05, N-(3-alpha,7-alpha,12-alpha-Trihydroxycholan-24-oyl)glycine, HY-N1423, MSK10389, N-(Carboxymethyl)-3alpha,7alpha,12alpha-trihydroxyglycine cholate, Tox21_302549, BDBM50375589, LMST05030001, s4958, STL565148, AKOS015965042, N-(3alpha,7alpha,12alpha-Trihydroxy-24-oxo-5beta-cholan-24-yl)glycine, CCG-269413, CS-W020037, DS-0968, EBC-616015, FG16282, NCGC00163115-02, NCGC00256646-01, 2-[(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-trihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido]acetic acid, AC-30905, SMR001233215, SY111643, NS00014841, ST51037266, 3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine, C01921, 3a,7a,12a-Trihydroxy-5b-cholanic acid-24-glycine, Q2701638, BRD-K54771420-001-03-2, [(3,7,12-Trihydroxy-24-oxocholan-24-yl)amino]acetic acid #, 3a,7a,12a-Trihydroxy-N-(carboxymethyl)-5b-cholan-24-amide, N-(carboxymethyl)-3a,7a,12a-trihydroxy-5b-Cholan-24-amide, 3?,7?,12?-Trihydroxy-5?-cholan-24-oic acid n-[carboxymethyl]amide, 5beta-Cholanic acid-3alpha,7alpha,12alpha-triol N-(carboxymethyl)-amide, N-[(3alpha,5beta,7alpha,8xi,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine, N-[(3beta,5beta,7beta,9beta,12beta)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine, 2-[(4R)-4-((1S,2S,7S,11S,16S,5R,9R,10R,14R,15R)-5,9,16-trihydroxy-2,15-dimethy ltetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-14-yl)pentanoylamino]acetic acid, 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanamido]acetic acid
Theoretical properties:
molecular_formula: C26H43NO6
molecular_weight: 465.6 g/mol
exact_mass: 465.30903809 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 6
heavy_atom_count: 33
topological_polar_surface_area: 127 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Glycocholic acid is a bile acid glycine conjugate having cholic acid as the bile acid component. It has a role as a human metabolite. It is functionally related to a cholic acid and a glycochenodeoxycholic acid. It is a conjugate acid of a glycocholate.
chebi: A bile acid glycine conjugate having cholic acid as the bile acid component.
chembl: GLYCOCHOLIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Glycocholic acid, or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with glycine. Its anion is called glycocholate.
In a prospective study, positive associations were observed between prediagnostic plasma levels of seven conjugated bile acid metabolites, including glycocholic acid, and colon cancer risk. These findings support experimental data suggesting that high circulating bile acids promote colon cancer risk.