FComEx: Chenodeoxycholic acid (PC000049)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:43 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000049

FoodDB Record

FDB022087

Chemical Information

Name

Chenodeoxycholic acid

Description

A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135) Usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones. [HMDB]

CAS Number

474-25-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(+)-chenodeoxycholate	hmdb
(+)-chenodeoxycholic acid	hmdb
(3a,5b,7a)-3,7-dihydroxy-cholan-24-oate	hmdb
(3a,5b,7a)-3,7-dihydroxy-cholan-24-oic acid	hmdb
3a,7a-dihydroxy-5b-cholan-24-oate	hmdb
3a,7a-dihydroxy-5b-cholan-24-oic acid	hmdb
3a,7a-dihydroxy-5b-cholanate	hmdb
3a,7a-dihydroxy-5b-cholanic acid	hmdb
3a,7a-dihydroxy-5b,14a,17b-cholanate	hmdb
3a,7a-dihydroxy-5b,14a,17b-cholanic acid	hmdb
3alpha,7alpha-Dihydroxy-5beta-cholanate	Generator
3α,7α-dihydroxy-5β-cholanate	Generator
3α,7α-dihydroxy-5β-cholanic acid	Generator
7a-Hydroxy-desoxycholsaeure	hmdb
7a-Hydroxylithocholate	Generator
7a-Hydroxylithocholic acid	Generator
7alpha-Hydroxylithocholate	Generator
7alpha-Hydroxylithocholic acid	ChEBI
7α-hydroxylithocholate	Generator
7α-hydroxylithocholic acid	Generator
Anthropodeoxycholate	Generator
Anthropodeoxycholic acid	ChEBI
Anthropodesoxycholate	Generator
Anthropodesoxycholic acid	ChEBI
CDCA	ChEBI
Chenate	Generator
Chenic acid	ChEBI
Chenix	ChEBI
Chenodeoxycholate	hmdb
Chenodesoxycholsaeure	hmdb
Gallodesoxycholate	Generator
Gallodesoxycholic acid	ChEBI

Chemical Formula

C24H40O4

IUPAC name

(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

InChI Identifier

InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1

InChI Key

RUDATBOHQWOJDD-BSWAIDMHSA-N

Isomeric SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O

Average Molecular Weight

392.572

Monoisotopic Molecular Weight

392.292659768

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents