Glycolithocholic Acid
Basic information
- CAS
474-74-8- Standard SMILES
C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
XBSQTYHEGZTYJE-OETIFKLTSA-N- Molecular formula
- C26H43NO4
- Average molar mass
- 433.6 g/mol
- Monoisotopic mass
- 433.31920885
Overview
Glycolithocholic acid is the glycine conjugate of lithocholic acid. It is a N-acylglycine and a bile acid glycine conjugate. It is functionally related to a lithocholic acid. It is a conjugate acid of a glycolithocholate.
Names & identifiers
- Preferred name
- Glycolithocholic Acid
- IUPAC
- 2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
- English name
- N-[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]-(9CI) Glycine
- Molecular formula
- C26H43NO4
- Molecular weight
- 433.63
Names & synonyms
Glycolithocholic acidLithocholylglycine474-74-8Lithocholic acid glycine conjugateQ53GV75CJGN-((3-alpha,5-beta)-3-Hydroxy-24-oxocholan-24-yl)glycineCHEBI:37998DTXSID009638283a-Hydroxy-5b-cholanic acid glycine esterGlycine, N-((3alpha,5beta)-3-hydroxy-24-oxocholan-24-yl)-N-(3alpha-hydroxy-5beta-cholan-24-oyl)-glycineRefChem:922360
Show more names
Glycolithocholic-d4 AcidGlycine gallateGlycinocholic acidUrsodeoxycholic Impurity 13Glycolithocholic acid (Standard)Urosodeoxycholic Acid Impurity 13Glycolithocholic Acid in MethanolGlycolithocholic acid, 10 mM in DMSO
DTXCID901391558Glycine, N-[(3a,5b)-3-hydroxy-24-oxocholan-24-yl]-CHEMBL258818C26H43NO42-((R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)acetic acidlithocholoyglycineGlykolithocholsaureLITHOGLYCOCHOLATE
Properties
Computed structural properties
- XLogP
- 5.6
- Topological polar surface area
- 86.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 695
Experimental & physicochemical properties
Chemical ClassesBile Acids -> Quant Bile Acids
LipidsLipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Glycine conjugates [ST0503]
Physical DescriptionSolid
Collision Cross Section
205.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]
211.8 Ų [M+Na-H+Cl]- [CCS Type: DT; Method: single field calibrated]
200.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
218.9 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
Physicochemical properties
- Melting point
- 212 · 212-214 °C
- Boiling point
- 546.95 °C · 546.95°C (rough estimate)
- Density
- 1.0738 · 1.0738 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- Refrigerator
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS08
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsGall Bladder
Cellular LocationsExtracellular
Metabolite Pathways27-Hydroxylase Deficiency
Applications
DescriptionGlycolithocholic acid is a glycine-conjugated form of the secondary bile acid lithocholic acid . It is increased in the liver of mice fed a diet supplemented with ursodeoxycholic acid . Glycolithocholic acid levels are decreased in the plasma following subcutaneous administration of PEG-obestatin(Cys10, Cys13), a modified peptide hormone, in lean or diet-induced obese mice. Serum glycolithocholic acid levels increase with age in children.
UsesA metabolite in human hepatic bile. A lithocholic acid analog that inhibit sialyltransferase.
Additional notes
DefinitionChEBI: The glycine conjugate of lithocholic acid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…