Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 21:49:52 UTC
Update Date2024-04-30 20:35:36 UTC
Metabolite IDMMDBc0048064
Metabolite Identification
Common NameIsochenodeoxycholic acid; 3beta,7alpha,12alpha-Trihydroxy-5beta-cholanic acid
Description3beta,7alpha,12alpha-Trihydroxy-5beta-cholanic acid, also known as 3b,7a-Dihydroxy-5b-cholanoic acid or Isochenodeoxycholic 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 ).
Structure
Synonyms
ValueSource
(3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-Oic acidChEBI
3-Epi-chenodeoxycholic acidChEBI
3-Epichenodeoxycholic acidChEBI
3beta,7alpha-Dihydroxy-5beta-cholanic acidChEBI
3beta-Chenodeoxycholic acidChEBI
Isochenodeoxycholic acidChEBI
(3b,5b,7a)-3,7-Dihydroxycholan-24-OateGenerator
(3b,5b,7a)-3,7-Dihydroxycholan-24-Oic acidGenerator
(3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-OateGenerator
(3Β,5β,7α)-3,7-dihydroxycholan-24-OateGenerator
(3Β,5β,7α)-3,7-dihydroxycholan-24-Oic acidGenerator
3-Epi-chenodeoxycholateGenerator
3-EpichenodeoxycholateGenerator
3b,7a-Dihydroxy-5b-cholanateGenerator
3b,7a-Dihydroxy-5b-cholanic acidGenerator
3beta,7alpha-Dihydroxy-5beta-cholanateGenerator
3Β,7α-dihydroxy-5β-cholanateGenerator
3Β,7α-dihydroxy-5β-cholanic acidGenerator
3b-ChenodeoxycholateGenerator
3b-Chenodeoxycholic acidGenerator
3beta-ChenodeoxycholateGenerator
3Β-chenodeoxycholateGenerator
3Β-chenodeoxycholic acidGenerator
IsochenodeoxycholateGenerator
3b,7a-Dihydroxy-5b-cholanoateGenerator
3b,7a-Dihydroxy-5b-cholan-24-OateHMDB
3b,7a-Dihydroxy-5b-cholan-24-Oic acidHMDB
Molecular FormulaC24H40O4
Average Mass392.572
Monoisotopic Mass392.292659768
IUPAC Name(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
CAS Registry Number566-24-5
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](O)CC[C@]12C
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-JGFDLHJZSA-N