| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:09:07 -0700 |
| HMDB ID |
HMDB00698 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
|---|
| Common Name |
Lithocholic acid glycine conjugate |
| Description |
Lithocholic acid glycine conjugate is an acyl glycine and a bile acid-glycine conjugate. 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 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 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 3a-Hydroxy-5b-cholanic acid glycine ester
- 3a-Hydroxy-5b-cholanoylglycine
- 3a-Hydroxy-N-(carboxymethyl)-5b-cholan-24-amide
- 3alpha-hydroxy-5beta-cholan-24-oate
- 3alpha-hydroxy-5beta-cholan-24-oic acid
- 3alpha-hydroxy-5beta-cholan-24-oic acid N-(carboxymethyl)amide
- Glycolithocholate
- Glycolithocholic acid
- Lithocholic acid glycine conjugate
- Lithocholic acid glycine conjugic acid
- Lithocholoyglycine
- Lithocholylglycine
- N-(3a-Hydroxy-5b-cholan-24-oyl)-Glycine
- N-(3a-Hydroxy-5b-cholanoyl)glycine
- N-(Carboxymethyl)-3a-hydroxy-5b-Cholan-24-amide
|
| Chemical Formula |
C26H43NO4 |
| Average Molecular Weight |
433.6239 |
| Monoisotopic Molecular Weight |
433.319208869 |
| IUPAC Name |
2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid |
| Traditional IUPAC Name |
glycolithocholic acid |
| CAS Registry Number |
474-74-8 |
| SMILES |
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[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/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1 |
| InChI Key |
XBSQTYHEGZTYJE-OETIFKLTSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Steroids and Steroid Derivatives |
| Sub Class |
Bile Acids, Alcohols and Derivatives |
| Other Descriptors |
- Aliphatic Homopolycyclic Compounds
- Glycine conjugates(Lipidmaps)
- Organic Compounds
- bile acid glycine conjugate(ChEBI)
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| Substituents |
- 24 Keto Steroid
- 3 Hydroxy Steroid
- Alpha Amino Acid Or Derivative
- Bicyclohexane
- Carboxamide Group
- Carboxylic Acid
- Cyclic Alcohol
- Cyclohexane
- Decaline
- Hydroxy Bile Acid, Alcohol, Or Derivative
- Monohydroxy Bile Acid, Alcohol, Or Derivative
- N Acyl Alpha Amino Acid
- N Acylglycine
- N Substituted Alpha Amino Acid
- Secondary Alcohol
- Secondary Carboxylic Acid Amide
- Sesterterpene
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| Direct Parent |
Glycinated Bile Acids and Derivatives |
| Ontology |
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| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
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| Tissue Location |
- Intestine
- Kidney
- Liver
- Gall Bladder
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| Pathways |
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| Normal Concentrations |
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| Bile |
Detected and Quantified |
|
620 (590-650) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.009 (0.005-0.015) uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
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| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022187 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
103116 |
| KEGG Compound ID |
C15557 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB00698 |
| Metagene Link |
HMDB00698 |
| METLIN ID |
5666 |
| PubChem Compound |
115245 |
| PDB ID |
Not Available |
| ChEBI ID |
37998 |
| References |
|---|
| Synthesis Reference |
Momose, Toshiaki; Tsubaki, Takayuki; Iida, Takashi; Nambara, Toshio. An improved synthesis of taurine- and glycine-conjugated bile acids. Lipids (1997), 32(7), 775-778. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Cowen AE, Korman MG, Hofmann AF, Cass OW, Coffin SB: Metabolism of lithocholate in healthy man. II. Enterohepatic circulation. Gastroenterology. 1975 Jul;69(1):67-76.
Pubmed: 1097294
- Cowen AE, Korman MG, Hofmann AF, Cass OW: Metabolism of lethocholate in healthy man. I. Biotransformation and biliary excretion of intravenously administered lithocholate, lithocholylglycine, and their sulfates. Gastroenterology. 1975 Jul;69(1):59-66.
Pubmed: 1150035
- Lee BL, New AL, Ong CN: Comparative analysis of conjugated bile acids in human serum using high-performance liquid chromatography and capillary electrophoresis. J Chromatogr B Biomed Sci Appl. 1997 Dec 19;704(1-2):35-42.
Pubmed: 9518169
- Cowen AE, Korman MG, Hofmann AF, Thomas PJ: Metabolism of lithocholate in healthy man. III. Plasma disappearance of radioactivity after intravenous injection of labeled lithocholate and its derivatives. Gastroenterology. 1975 Jul;69(1):77-82.
Pubmed: 1150037
- Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10.
Pubmed: 16548228
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