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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:59 UTC
Update Date2020-02-26 21:24:12 UTC
HMDB IDHMDB0002639
Secondary Accession Numbers
  • HMDB02639
Metabolite Identification
Common NameSulfolithocholylglycine
DescriptionSulfolithocholylglycine 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 ). Sulfolithocholylglycine is a sulfated bile acid which has a greater renal clearance rate than lithocholylglycine.
Structure
Data?1582752252
Synonyms
ValueSource
Glycolithocholate 3-sulfateChEBI
Glycolithocholate sulfateChEBI
Glycolithocholic acid 3-sulfateChEBI
Glycolithocholic acid sulfateChEBI
SulfoglycolithocholateChEBI
SulfolithocholylglycineChEBI
Glycolithocholate 3-sulphateGenerator
Glycolithocholic acid 3-sulfuric acidGenerator
Glycolithocholic acid 3-sulphuric acidGenerator
Glycolithocholate sulphateGenerator
Glycolithocholic acid sulfuric acidGenerator
Glycolithocholic acid sulphuric acidGenerator
SulphoglycolithocholateGenerator
Sulphoglycolithocholic acidGenerator
SulpholithocholylglycineGenerator
SulfolithoglycocholineMeSH
3alpha-Hydroxy-5beta-cholanoylglycine 3-sulfateHMDB
3alpha-Hydroxy-5beta-cholanoylglycine 3-sulphateHMDB
3α-Hydroxy-5β-cholanoylglycine 3-sulfateHMDB
3α-Hydroxy-5β-cholanoylglycine 3-sulphateHMDB
Glycolithocholic acid 3-sulphateHMDB
Glycolithocholic acid 3alpha-sulfateHMDB
Glycolithocholic acid 3alpha-sulphateHMDB
Glycolithocholic acid 3α-sulfateHMDB
Glycolithocholic acid 3α-sulphateHMDB
Glycolithocholic acid sulphateHMDB
N-[(3alpha,5beta)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycineHMDB
N-[(3α,5β)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycineHMDB
Sulfoglycolithocholic acidHMDB
Chemical FormulaC26H43NO7S
Average Molecular Weight513.69
Monoisotopic Molecular Weight513.276023903
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
Traditional Name[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
CAS Registry Number15324-64-8
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C26H43NO7S/c1-16(4-9-23(28)27-15-24(29)30)20-7-8-21-19-6-5-17-14-18(34-35(31,32)33)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22H,4-15H2,1-3H3,(H,27,28)(H,29,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1
InChI KeyFHXBAFXQVZOILS-OETIFKLTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives 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
  • Sulfated steroid skeleton
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring 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 Solubility0.00038 g/LALOGPS
logP1.1ALOGPS
logP2.64ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)-1.1ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area130 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.48 m³·mol⁻¹ChemAxon
Polarizability57.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.06 +/- 0.01 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified1.26 +/- 1.24 nmol/g dry fecesNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.0691 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.112 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified0.684 umol/mmol creatinineAdult (>18 years old)Both
Hepatitis
details
UrineDetected and Quantified1.150 (0.044-5.349) umol/mmol creatinineAdult (>18 years old)Both
Hepatitis
details
UrineDetected and Quantified1.771 umol/mmol creatinineAdult (>18 years old)BothCirrhosis details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Hepatitis
  1. Kobayashi N, Katsumata H, Uto Y, Goto J, Niwa T, Kobayashi K, Mizuuchi Y: A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. Steroids. 2002 Sep;67(10):827-33. [PubMed:12231118 ]
Cirrhosis
  1. Kobayashi N, Katsumata H, Uto Y, Goto J, Niwa T, Kobayashi K, Mizuuchi Y: A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. Steroids. 2002 Sep;67(10):827-33. [PubMed:12231118 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023034
KNApSAcK IDNot Available
Chemspider ID65188
KEGG Compound IDC11301
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72222
PDB IDNot Available
ChEBI ID9347
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. Kobayashi N, Katsumata H, Uto Y, Goto J, Niwa T, Kobayashi K, Mizuuchi Y: A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. Steroids. 2002 Sep;67(10):827-33. [PubMed:12231118 ]
  4. Hepner GW, Demers LM: Dynamics of the enterohepatic circulation of the glycine conjugates of cholic, chenodeoxycholic, deoxycholic, and sulfolithocholic acid in man. Gastroenterology. 1977 Mar;72(3):499-501. [PubMed:832799 ]
  5. Kirkpatrick RB, Belsaas RA: Formation and secretion of glycolithocholate-3-sulfate in primary hepatocyte cultures. J Lipid Res. 1985 Dec;26(12):1431-7. [PubMed:4086945 ]
  6. Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. [PubMed:3944741 ]
  7. 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 ]

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