Basic information
- CAS
475-31-0- Standard SMILES
C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C- InChIKey
RFDAIACWWDREDC-FRVQLJSFSA-N- Molecular formula
- C26H43NO6
- Average molar mass
- 465.6 g/mol
- Monoisotopic mass
- 465.30903809
Overview
Glycocholic acid is a bile acid glycine conjugate having cholic acid as the bile acid component. It has a role as a human metabolite. It is functionally related to a cholic acid and a glycochenodeoxycholic acid. It is a conjugate acid of a glycocholate.
Names & identifiers
- Preferred name
- Glycocholic Acid
- IUPAC
- 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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
- Glycocholic acid
- Molecular formula
- C26H43NO6
- Molecular weight
- 465.63
Names & synonyms
Glycocholic acid475-31-0CholylglycineN-CholoylglycineDTXSID2047436G59NX3I3RT2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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 acidDTXCID0027436CHEBI:17687N-(3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholan-24-oyl)-glycineN-((3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl)glycineGlycine, N-((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)-
Show more names
GLYCITINGLYCOCHOLIC ACID HYDRATEN-CholylglycineCholylglycinate[(3,7,12-Trihydroxy-24-oxocholan-24-yl)amino]acetic acidGLYCOCHOLICN-cholyglycineglycocholicaci
N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid2-(((4R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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 acid2-((4R)-4-((1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-14-yl)pentanamido)acetic acidRefChem:389020Glycine, N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]-207-494-9glycocholate
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 127 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 759
Experimental & physicochemical properties
Chemical Classes
Bile Acids -> Quant Bile Acids
Biological Agents -> Other Biomolecules
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Glycine conjugates [ST0503]
LogP
1.65
1.65
Food AdditivesPH CONTROL AGENT -> FDA Substance added to food
Solubility0.0033 mg/mL
Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point170 °C
Physical Description
Dihydrate: Solid; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
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
Regulatory InformationGlycocholic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- ridadr
- UN 3077 9/PG 3
- risk_code
- 51/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- N
- safety_code
- 61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332
- Precautionary statements
- P280
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic).
Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties.
Tissue LocationsFibroblasts
Cellular LocationsExtracellular
Metabolite Pathways27-Hydroxylase Deficiency
Uses & manufacturing
UsesMain constituent of the bile of herbivorous animals; [Merck Index] Functions as a detergent to solubilize fats for absorption and is absorbed itself; [ChemIDplus] Used as a Ph control agent for foods; [FDA]
Applications
DescriptionN-Cholylglycine. Bile salt, conjugate of cholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic.
DescriptionGlycocholic acid is a glycine-conjugated form of the primary bile acid cholic acid and has roles in the emulsification of fats. It reduces expression of the gene encoding the farnesoid X receptor (FXR) and increases expression of the genes encoding the bile acid receptors TGR5 and S1PR2 in SNU-245 cells when used at a concentration of 1.6 μmol/ml. Glycocholic acid (250 μM) increases the intracellular accumulation and cytotoxicity of epirubicin in Caco-2 cells, as well as decreases expression of the genes encoding multidrug resistance protein 1 (MDR1), MDR-associated protein 1 (MRP1), and MRP2 when used alone or in combination with epirubicin. It increases absorption of epirubicin into everted sacs of rat ileum and jejunum when used at a concentration of 250 μM. The bile acid composition ratio of glycocholic acid is elevated in bile of patients with cholangiocarcinoma compared with patients with pancreatic cancer or benign biliary diseases. Serum levels of glycocholic acid are elevated in patients with hepatocellular carcinoma compared with healthy individuals.
Related reactions
0 records
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Compound notes
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