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Record Information
Version1.0
Created at2022-05-11 16:26:40 UTC
Updated at2022-05-11 16:26:40 UTC
NP-MRD IDNP0086634
Secondary Accession NumbersNone
Natural Product Identification
Common NameLithocholic acid glycine conjugate
DescriptionLithocholic acid glycine conjugate, also known as glycolithocholic acid or lithocholylglycine, 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. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. Lithocholic acid glycine conjugate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Is an acyl glycine and a bile acid-glycine conjugate. In humans, lithocholic acid glycine conjugate is involved in the metabolic disorder called familial hypercholanemia (fhca). 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 ). It was first documented in 1975 (PMID: 1097294). Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol (PMID: 16548228) (PMID: 1150035) (PMID: 9518169) (PMID: 1150037).
Structure
Thumb
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 Mass433.6239 Da
Monoisotopic Mass433.31921 Da
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 NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0000698
DrugBank IDNot Available
Phenol Explorer Compound 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
Good Scents IDNot Available
References
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. doi: 10.1016/s0378-4347(97)00443-x. [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 ]