You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 18:15:30 UTC
HMDB IDHMDB0000698
Secondary Accession Numbers
  • HMDB00698
  • HMDB02474
Metabolite Identification
Common NameLithocholic acid glycine conjugate
DescriptionLithocholic 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
Thumb
Synonyms
ValueSource
GlycolithocholateChEBI
LithocholylglycineChEBI
N-((3-alpha,5-beta)-3-Hydroxy-24-oxocholan-24-yl)glycineChEBI
Glycolithocholic acidGenerator
Lithocholate glycine conjugateGenerator
Lithocholic acid glycine conjugic acidGenerator
N-((3-a,5-b)-3-Hydroxy-24-oxocholan-24-yl)glycineGenerator
N-((3-α,5-β)-3-hydroxy-24-oxocholan-24-yl)glycineGenerator
3a-Hydroxy-5b-cholanic acid glycine esterHMDB
3a-Hydroxy-5b-cholanoylglycineHMDB
3a-Hydroxy-N-(carboxymethyl)-5b-cholan-24-amideHMDB
3alpha-Hydroxy-5beta-cholan-24-OateHMDB
3alpha-Hydroxy-5beta-cholan-24-Oic acidHMDB
3alpha-Hydroxy-5beta-cholan-24-Oic acid N-(carboxymethyl)amideHMDB
LithocholoyglycineHMDB
N-(3a-Hydroxy-5b-cholan-24-oyl)-glycineHMDB
N-(3a-Hydroxy-5b-cholanoyl)glycineHMDB
N-(Carboxymethyl)-3a-hydroxy-5b-cholan-24-amideHMDB
Glycolithocholic acid, monosodium saltMeSH
Chemical FormulaC26H43NO4
Average Molecular Weight433.6239
Monoisotopic Molecular Weight433.319208869
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid
Traditional Nameglycolithocholic acid
CAS Registry Number474-74-8
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 KeyXBSQTYHEGZTYJE-OETIFKLTSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycinated bile acids and derivatives. These are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentGlycinated bile acids and derivatives
Alternative Parents
Substituents
  • Glycinated bile acid
  • Hydroxy bile acid, alcohol, or derivatives
  • Monohydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP3.71ALOGPS
logP3.92ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity120.48 m³·mol⁻¹ChemAxon
Polarizability51.3 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pxr-1219800000-b1461cae26afb8277a4bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2011290000-9d901bc0dc4a11f91133View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9003600000-1f7e0c91520f949fb8ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9002000000-539de7f82b85a471b338View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9001000000-e53d44b83740a1b3b620View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0002900000-60e5b38e213f73a86996View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06z9-5107900000-ba230e9f34047158250aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9102000000-859c6b8ef80fb6861c55View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Bile
  • Blood
  • Feces
Tissue Location
  • Gall Bladder
  • Intestine
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
27-Hydroxylase DeficiencyPw000697Pw000697 greyscalePw000697 simpleNot Available
Bile Acid BiosynthesisPw000145Pw000145 greyscalePw000145 simpleMap00120
Cerebrotendinous Xanthomatosis (CTX)Pw000196Pw000196 greyscalePw000196 simpleNot Available
Congenital Bile Acid Synthesis Defect Type IIPw000192Pw000192 greyscalePw000192 simpleNot Available
Congenital Bile Acid Synthesis Defect Type IIIPw000193Pw000193 greyscalePw000193 simpleNot Available
Displaying entries 1 - 5 of 7 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BileDetected and Quantified620 (590-650) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.009 (0.005-0.015) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected and Quantified6.68 +/- 18.49 nmol/g of fecesNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022187
KNApSAcK IDNot Available
Chemspider ID103116
KEGG Compound IDC15557
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5666
PubChem Compound115245
PDB IDNot Available
ChEBI ID37998
References
Synthesis ReferenceMomose, 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. Epub 2006 Sep 1. [PubMed:16949895 ]
  7. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
  8. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
  9. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
  10. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Molecular weight:
33779.57
Reactions
Phosphoadenosine phosphosulfate + Lithocholic acid glycine conjugate → Adenosine 3',5'-diphosphate + Sulfolithocholylglycinedetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:
GLYATL3
Uniprot ID:
Q5SZD4
Molecular weight:
32703.3