Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:36:21 UTC
Update Date2024-10-10 23:40:33 UTC
Metabolite IDMMDBc0000113
Metabolite Identification
Common NameChenodeoxycholic acid
DescriptionChenodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the 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.
Structure
Synonyms
ValueSource
3alpha,7alpha-Dihydroxy-5beta-cholanic acidChEBI
7alpha-Hydroxylithocholic acidChEBI
Anthropodeoxycholic acidChEBI
Anthropodesoxycholic acidChEBI
CDCAChEBI
Chenic acidChEBI
ChenixChEBI
ChenodiolChEBI
Gallodesoxycholic acidChEBI
3a,7a-Dihydroxy-5b-cholanateGenerator
3a,7a-Dihydroxy-5b-cholanic acidGenerator
3alpha,7alpha-Dihydroxy-5beta-cholanateGenerator
3Α,7α-dihydroxy-5β-cholanateGenerator
3Α,7α-dihydroxy-5β-cholanic acidGenerator
7a-HydroxylithocholateGenerator
7a-Hydroxylithocholic acidGenerator
7alpha-HydroxylithocholateGenerator
7Α-hydroxylithocholateGenerator
7Α-hydroxylithocholic acidGenerator
AnthropodeoxycholateGenerator
AnthropodesoxycholateGenerator
ChenateGenerator
GallodesoxycholateGenerator
ChenodeoxycholateGenerator
(+)-ChenodeoxycholateHMDB
(+)-Chenodeoxycholic acidHMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-OateHMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oic acidHMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanateHMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanic acidHMDB
3a,7a-Dihydroxy-5b-cholan-24-OateHMDB
3a,7a-Dihydroxy-5b-cholan-24-Oic acidHMDB
7a-Hydroxy-desoxycholsaeureHMDB
ChenodesoxycholsaeureHMDB
Acid, cheniqueHMDB
ChenofalkHMDB
ChenophalkHMDB
Acid, chenodeoxycholicHMDB
Chenodeoxycholate, sodiumHMDB
QuenocolHMDB
Solvay brand OF chenodeoxycholic acidHMDB
Antigen brand OF chenodeoxycholic acidHMDB
Falk brand OF chenodeoxycholic acidHMDB
QuenobilanHMDB
Sodium chenodeoxycholateHMDB
Tramedico brand OF chenodeoxycholic acidHMDB
Zambon brand OF chenodeoxycholic acidHMDB
Acid, chenicHMDB
Acid, gallodesoxycholicHMDB
Chenique acidHMDB
Estedi brand OF chenodeoxycholic acidHMDB
HenoholHMDB
Molecular FormulaC24H40O4
Average Mass392.572
Monoisotopic Mass392.292659768
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
Traditional 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
CAS Registry Number474-25-9
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
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 KeyRUDATBOHQWOJDD-BSWAIDMHSA-N