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Showing Compound Lithocholic acid glycine conjugate (FDB022187)

Record Information
Version1.0
Creation date2011-09-21 00:09:48 UTC
Update date2015-07-21 06:57:02 UTC
Primary IDFDB022187
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number474-74-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
3alpha-hydroxy-5beta-cholan-24-oatehmdb
3alpha-hydroxy-5beta-cholan-24-oic acidhmdb
3alpha-hydroxy-5beta-cholan-24-oic acid N-(carboxymethyl)amidehmdb
glycolithocholatehmdb
Lithocholic acid glycine conjugatehmdb
lithocholoyglycinehmdb
N-((3-α,5-β)-3-hydroxy-24-oxocholan-24-yl)glycineGenerator
N-(3a-hydroxy-5b-cholan-24-oyl)-Glycinehmdb
N-(carboxymethyl)-3a-hydroxy-5b-Cholan-24-amidehmdb
Predicted 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
Chemical FormulaC26H43NO4
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight433.6239
Monoisotopic Molecular Weight433.319208869
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLithocholic acid glycine conjugate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pxr-1219800000-b1461cae26afb8277a4bSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2011290000-9d901bc0dc4a11f91133Spectrum
Predicted GC-MSLithocholic acid glycine conjugate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSLithocholic acid glycine conjugate, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9003600000-1f7e0c91520f949fb8ec2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9002000000-539de7f82b85a471b3382016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9001000000-e53d44b83740a1b3b6202016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0002900000-60e5b38e213f73a869962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06z9-5107900000-ba230e9f34047158250a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9102000000-859c6b8ef80fb6861c552016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0002900000-29a47c1e04617905309c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001m-4159200000-abff50ceed535345c3782021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-9321000000-54d1ab9b1acc01fa59f12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-5cc587be0f34335a1e1c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0004900000-c9cb6871ee09ad0572f82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9002400000-076670a1180a04e9a7cc2021-09-24View Spectrum
NMRNot Available
ChemSpider ID103116
ChEMBL IDCHEMBL258818
KEGG Compound IDC15557
Pubchem Compound ID115245
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00698
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
Glycine N-acyltransferase-like protein 3GLYATL3Q5SZD4
Bile salt sulfotransferaseSULT2A1Q06520
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference