FComEx: Deoxycholic acid glycine conjugate (PC000416)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:36 UTC

Update date

2017-01-19 02:36:22 UTC

FoodComEx ID

PC000416

FoodDB Record

FDB022152

Chemical Information

Name

Deoxycholic acid glycine conjugate

Description

Deoxycholic acid glycine conjugate, or Deoxygcholylglycine, is an acyl glycine and a bile acid-glycine conjugate. 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). As a bile salt it acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic. [HMDB]

CAS Number

360-65-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Deoxycholic acid glycine conjugate	hmdb
Deoxycholylglycine	hmdb
Deoxyglycocholate	hmdb
Deoxyglycocholic acid	hmdb
Glycodeoxycholate	hmdb
Glycodeoxycholic acid	hmdb
Glycodesoxycholate	hmdb
Glycodesoxycholic acid	hmdb
Glycyldeoxycholate	hmdb
Glycyldeoxycholic acid	hmdb
N-(3a,12a-dihydroxy-5b-cholan-24-oyl)-Glycine	hmdb
N-(carboxymethyl)-3a,12a-dihydroxy-5b-Cholan-24-amide	hmdb

Chemical Formula

C26H43NO5

IUPAC name

2-[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

InChI Identifier

InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18?,19-,20?,21?,22+,25+,26-/m1/s1

InChI Key

WVULKSPCQVQLCU-ZMBDPXIHSA-N

Isomeric SMILES

[H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2

Average Molecular Weight

449.6233

Monoisotopic Molecular Weight

449.314123491

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents