Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:36:12 UTC
Update Date2024-04-30 19:31:55 UTC
Metabolite IDMMDBc0000365
Metabolite Identification
Common NameGlycoursodeoxycholic acid
DescriptionGlycoursodeoxycholic acid 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 ). 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
3alpha,7beta-Dihydroxy-5beta-cholanoylglycineChEBI
Glycine ursodeoxycholic acidChEBI
Glycylursodeoxycholic acidChEBI
GUDCAChEBI
N-(3alpha,7beta-Dihydroxy-5beta-cholan-24-oyl)glycineChEBI
N-[(3alpha,5beta,7beta)-3,7-Dihydroxy-24-oxocholan-24-yl]glycineChEBI
UrsodeoxycholylglycineChEBI
3a,7b-Dihydroxy-5b-cholanoylglycineGenerator
3Α,7β-dihydroxy-5β-cholanoylglycineGenerator
Glycine ursodeoxycholateGenerator
GlycylursodeoxycholateGenerator
N-(3a,7b-Dihydroxy-5b-cholan-24-oyl)glycineGenerator
N-(3Α,7β-dihydroxy-5β-cholan-24-oyl)glycineGenerator
N-[(3a,5b,7b)-3,7-Dihydroxy-24-oxocholan-24-yl]glycineGenerator
N-[(3Α,5β,7β)-3,7-dihydroxy-24-oxocholan-24-yl]glycineGenerator
GlycoursodeoxycholateGenerator
(3beta,5beta,7beta)-3,7-Dihydroxycholan-24-oic acidHMDB
(3β,5β,7β)-3,7-Dihydroxycholan-24-oic acidHMDB
3beta,7beta-Dihydroxy-5beta-cholan-24-oic acidHMDB
3beta,7beta-Dihydroxy-5beta-cholanic acidHMDB
3beta,7beta-Dihydroxy-5beta-cholanoic acidHMDB
3beta-Ursodeoxycholic acidHMDB
3β,7β-Dihydroxy-5β-cholan-24-oic acidHMDB
3β,7β-Dihydroxy-5β-cholanic acidHMDB
3β,7β-Dihydroxy-5β-cholanoic acidHMDB
3β-Ursodeoxycholic acidHMDB
Isoursodeoxycholic acidHMDB
Molecular FormulaC26H43NO5
Average Mass449.6233
Monoisotopic Mass449.314123491
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
Traditional Name[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
CAS Registry NumberNot Available
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)NCC(O)=O
InChI Identifier
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1
InChI KeyGHCZAUBVMUEKKP-XROMFQGDSA-N