Glycochenodeoxycholic Acid
Basic information
- CAS
640-79-9- 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]3CC[C@]12C- InChIKey
GHCZAUBVMUEKKP-GYPHWSFCSA-N- Molecular formula
- C26H43NO5
- Average molar mass
- 449.6 g/mol
- Monoisotopic mass
- 449.31412347
Overview
Glycochenodeoxycholic acid is a bile acid glycine conjugate having 3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl as the bile acid component. It has a role as a human metabolite. It is functionally related to a chenodeoxycholic acid. It is a conjugate acid of a glycochenodeoxycholate.
Names & identifiers
- Preferred name
- Glycochenodeoxycholic Acid
- IUPAC
- 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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
- Glycochenodeoxycholic Acid
- Molecular formula
- C26H43NO5
- Molecular weight
- 449.62
Names & synonyms
GLYCOCHENODEOXYCHOLIC ACID640-79-9GlycochenodeoxycholateChenodeoxycholylglycineGCDCAChenodeoxyglycocholateChenodeoxyglycocholic acid451ZNJ667YDTXSID301020165CHEBI:362742-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 acidN-(3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl)-glycine
Show more names
GCDCGlycinodeoxycholic acidglycochenodeoxycholic aciGlycine chenodeoxycholateGlycoanthropodeoxycholic acidGlycochenodeoxycholic-d4 Acid
Glycine, N-((3alpha,5beta,7alpha)-3,7-dihydroxy-24-oxocholan-24-yl)-CHEBI:36252Chenodeoxycholate, GlycineAcid, Glycochenodeoxycholic2-(((4R)-4-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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)-5,9-dihydroxy-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-14-yl)pentanamido)acetic acid2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acidRefChem:143903
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 727
Experimental & physicochemical properties
Chemical ClassesBile Acids -> Quant Bile Acids
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Glycine conjugates [ST0503]
LogP2.12
Solubility0.00315 mg/mL
Physical DescriptionSolid
Collision Cross Section
203.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Bile Acids]
218.8 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
200.7 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
198.85 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Boiling point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H225-H301+H311+H331-H370
- Precautionary statements
- P210-P240-P241-P242-P243-P260-P264-P270-P271-P280-P301+P310-P321-P330-P303+P361+P353-P304+P340-P307+P311-P312-P361+P364-P370+P378-P403+P233-P403+P235-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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 LocationsPlacenta
Cellular LocationsExtracellular
Metabolite Pathways27-Hydroxylase Deficiency
Applications
UsesGlycochenodeoxycholic acid (Chenodeoxycholylglycine) is a relatively toxic bile salt generated in the liver from chenodeoxycholic acid and glycine. Glycochenodeoxycholic acid inhibits Autophagosome formation and impairs lysosomal function by inhibiting lysosomal proteolysis and increasing lysosomal pH in human normal liver cells, leading to the Apoptosis of human hepatocyte cells. Glycochenodeoxycholic acid induces stemness and chemoresistance via activating STAT3 signaling pathway in hepatocellular carcinoma cells (HCC). Glycochenodeoxycholic acid is promising for research in the field of cholestasis desease, hepatocellular carcinoma and primary sclerosing cholangitis (PSC)[1][2][3][4].
Additional notes
DefinitionChEBI: A bile acid glycine conjugate having 3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl as the bile acid component.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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