Glycocholic acid

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.^[1] Its anion is called glycocholate.

Glycocholic acid

Glycocholic acid
Names
IUPAC name N-(3α,7α,12α-Trihydroxy-5β-cholan-24-oyl)glycine
Systematic IUPAC name {(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-Trihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanamido}acetic acid
Identifiers
CAS Number	475-31-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17687 Y
ChEMBL	ChEMBL411070 Y
ChemSpider	9734 Y
ECHA InfoCard	100.006.815
IUPHAR/BPS	4544
PubChem CID	10140
UNII	G59NX3I3RT Y
CompTox Dashboard (EPA)	DTXSID2047436
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 Y Key: RFDAIACWWDREDC-FRVQLJSFSA-N Y InChI=1/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 Key: RFDAIACWWDREDC-FRVQLJSFBG
SMILES C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
Properties
Chemical formula	C26H43NO6
Molar mass	465.631 g·mol−1
Melting point	130 °C (266 °F; 403 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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.^[2] These findings support experimental data suggesting that high circulating bile acids promote colon cancer risk.^[2][3]

See also

• Taurocholic acid