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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:05 UTC
HMDB IDHMDB0000698
Secondary Accession Numbers
  • HMDB0002474
  • 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 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
Data?1582752150
Synonyms
ValueSource
GlycolithocholateChEBI
LithocholylglycineChEBI
N-((3-alpha,5-beta)-3-Hydroxy-24-oxocholan-24-yl)glycineChEBI
Glycolithocholic acidKegg
N-((3-a,5-b)-3-Hydroxy-24-oxocholan-24-yl)glycineGenerator
N-((3-Α,5-β)-3-hydroxy-24-oxocholan-24-yl)glycineGenerator
Lithocholate glycine conjugateGenerator
Lithocholic acid glycine conjugic acidGenerator
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 saltHMDB
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-sulfateHMDB
Glycolithocholic acid 3-sulphateHMDB
Glycolithocholic acid 3alpha-sulfateHMDB
Glycolithocholic acid 3alpha-sulphateHMDB
Glycolithocholic acid 3α-sulfateHMDB
Glycolithocholic acid 3α-sulphateHMDB
Glycolithocholic acid sulfateHMDB
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
SulfolithocholylglycineHMDB
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[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
Traditional Name[(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
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
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
  • 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
Physiological effectNot Available
Disposition
Source
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available197.357http://allccs.zhulab.cn/database/detail?ID=AllCCS00000208
[M+H]+Not Available201.431http://allccs.zhulab.cn/database/detail?ID=AllCCS00000208
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP3.71ALOGPS
logP3.92ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity120.48 m³·mol⁻¹ChemAxon
Polarizability51.32 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.65631661259
DarkChem[M-H]-197.27931661259
AllCCS[M+H]+209.57432859911
AllCCS[M-H]-203.18732859911
DeepCCS[M-2H]-240.94630932474
DeepCCS[M+Na]+214.9330932474
AllCCS[M+H]+209.632859911
AllCCS[M+H-H2O]+207.832859911
AllCCS[M+NH4]+211.232859911
AllCCS[M+Na]+211.732859911
AllCCS[M-H]-203.232859911
AllCCS[M+Na-2H]-205.132859911
AllCCS[M+HCOO]-207.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lithocholic acid glycine conjugate[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)=O3923.4Standard polar33892256
Lithocholic acid glycine conjugate[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)=O3492.6Standard non polar33892256
Lithocholic acid glycine conjugate[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)=O3954.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lithocholic acid glycine conjugate,1TMS,isomer #1C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3838.0Semi standard non polar33892256
Lithocholic acid glycine conjugate,1TMS,isomer #2C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3776.5Semi standard non polar33892256
Lithocholic acid glycine conjugate,1TMS,isomer #3C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3830.9Semi standard non polar33892256
Lithocholic acid glycine conjugate,2TMS,isomer #1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3759.0Semi standard non polar33892256
Lithocholic acid glycine conjugate,2TMS,isomer #2C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3803.9Semi standard non polar33892256
Lithocholic acid glycine conjugate,2TMS,isomer #3C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3753.7Semi standard non polar33892256
Lithocholic acid glycine conjugate,3TMS,isomer #1C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3724.0Semi standard non polar33892256
Lithocholic acid glycine conjugate,3TMS,isomer #1C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3763.7Standard non polar33892256
Lithocholic acid glycine conjugate,3TMS,isomer #1C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4223.5Standard polar33892256
Lithocholic acid glycine conjugate,1TBDMS,isomer #1C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4065.3Semi standard non polar33892256
Lithocholic acid glycine conjugate,1TBDMS,isomer #2C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4052.6Semi standard non polar33892256
Lithocholic acid glycine conjugate,1TBDMS,isomer #3C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4058.5Semi standard non polar33892256
Lithocholic acid glycine conjugate,2TBDMS,isomer #1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4253.5Semi standard non polar33892256
Lithocholic acid glycine conjugate,2TBDMS,isomer #2C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4264.7Semi standard non polar33892256
Lithocholic acid glycine conjugate,2TBDMS,isomer #3C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4245.0Semi standard non polar33892256
Lithocholic acid glycine conjugate,3TBDMS,isomer #1C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4435.9Semi standard non polar33892256
Lithocholic acid glycine conjugate,3TBDMS,isomer #1C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4404.7Standard non polar33892256
Lithocholic acid glycine conjugate,3TBDMS,isomer #1C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4432.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pxr-1219800000-b1461cae26afb8277a4b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2011290000-9d901bc0dc4a11f911332017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholic acid glycine conjugate GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 10V, Positive-QTOFsplash10-00di-9003600000-1f7e0c91520f949fb8ec2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 20V, Positive-QTOFsplash10-00di-9002000000-539de7f82b85a471b3382016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 40V, Positive-QTOFsplash10-00di-9001000000-e53d44b83740a1b3b6202016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 10V, Negative-QTOFsplash10-001i-0002900000-60e5b38e213f73a869962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 20V, Negative-QTOFsplash10-06z9-5107900000-ba230e9f34047158250a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 40V, Negative-QTOFsplash10-00dl-9102000000-859c6b8ef80fb6861c552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 10V, Positive-QTOFsplash10-00lr-0002900000-29a47c1e04617905309c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 20V, Positive-QTOFsplash10-001m-4159200000-abff50ceed535345c3782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 40V, Positive-QTOFsplash10-052g-9321000000-54d1ab9b1acc01fa59f12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 10V, Negative-QTOFsplash10-001i-0000900000-5cc587be0f34335a1e1c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 20V, Negative-QTOFsplash10-001i-0004900000-c9cb6871ee09ad0572f82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholic acid glycine conjugate 40V, Negative-QTOFsplash10-00e9-9002400000-076670a1180a04e9a7cc2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Bile
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Gall Bladder
  • Intestine
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified6.68 +/- 18.49 nmol/g dry fecesNot SpecifiedNot Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDHC02193
MarkerDB IDNot Available
Good Scents IDNot Available
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