Glycocholic acid

Modify Date: 2025-08-21 22:42:58

Glycocholic acid Structure
Glycocholic acid structure
 Common Name Glycocholic acid
CAS Number 475-31-0 Molecular Weight 465.623
Density 1.4±0.1 g/cm3 Boiling Point 655.3±65.0 °C at 760 mmHg
Molecular Formula C26H43NO6 Melting Point 128°C
MSDS N/A Flash Point 350.1±34.3 °C

 Use of Glycocholic acid


Glycocholic acid is a bile acid with anticancer activity, targeting against pump resistance-related and non-pump resistance-related pathways.

 Names

Name glycocholic acid
Synonym More Synonyms

 Glycocholic acid Biological Activity

Description Glycocholic acid is a bile acid with anticancer activity, targeting against pump resistance-related and non-pump resistance-related pathways.
Related Catalog
Target

Human Endogenous Metabolite

Bax

Bcl-2

MDR1

MRP1

MDR2

In Vitro Glycocholic acid (GC) increases the cytotoxicity of epirubicin, significantly increases the intracellular accumulation of epirubicin in Caco-2 cells and the absorption of epirubicin in rat small intestine, and intensified epirubicin-induced apoptosis. Glycocholic acid and epirubicin significantly reduce mRNA expression levels of human intestinal MDR1, MDR-associated protein (MRP)1, and MRP2; downregulate the MDR1 promoter region; suppress the mRNA expression of Bcl-2; induce the mRNA expression of Bax; and significantly increase the Bax-to-Bcl-2 ratio and the mRNA levels of p53, caspase-9 and -3. A combination of anticancer drugs with Glycocholic acid can control MDR via a mechanism that involves modulating P-gp and MRPs as well as regulating apoptosis-related pathways[1].
References

[1]. Lo YL, et al. Inhibit multidrug resistance and induce apoptosis by using glycocholic acid and epirubicin. Eur J Pharm Sci. 2008 Sep 2;35(1-2):52-67.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 655.3±65.0 °C at 760 mmHg
Melting Point 128°C
Molecular Formula C26H43NO6
Molecular Weight 465.623
Flash Point 350.1±34.3 °C
Exact Mass 465.309052
PSA 127.09000
LogP 2.45
Vapour Pressure 0.0±4.5 mmHg at 25°C
Index of Refraction 1.645
InChIKey RFDAIACWWDREDC-FRVQLJSFSA-N
SMILES CC(CCC(=O)NCC(=O)O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
Storage condition Refrigerator
Water Solubility methanol: 0.1 g/mL, clear, colorless

 Safety Information

Hazard Codes N:Dangerousfortheenvironment;
Risk Phrases R51/53
Safety Phrases S61
RIDADR UN 3077 9/PG 3
WGK Germany 3

 Glycocholic acidBioassay

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Name: Luminescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: mu-type opioid receptor isoform MOR-1 [Homo sapiens]
External Id: OPRM1-OPRD1_AG_LUMI_1536_1X%ACT PRUN
Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN
Name: Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: lu...
Source: 824
External Id: CYP273
Name: TP_TRANSPORTER: inhibition of Ochratoxin A uptake (OTA: 1 uM, GC: 100uM) in Xenopus l...
Source: ChEMBL
Target: Solute carrier organic anion transporter family member 1A1
External Id: CHEMBL2076390
Name: Fluorescence-based cell-based primary high throughput screening assay to identify pos...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_PAM_FLUO8_1536_1X%ACT PRUN
Name: Fluorescence polarization-based biochemical high throughput primary assay to identify...
Source: The Scripps Research Institute Molecular Screening Center
Target: RecName: Full=Sialate O-acetylesterase; AltName: Full=H-Lse; AltName: Full=Sialic acid-specific 9-O-acetylesterase; Flags: Precursor [Homo sapiens]
External Id: SIAE_INH_FP_1536_1X%INH PRUN
Name: p53 small molecule agonists, cell-based qHTS assay: qHTS cell viability counter scree...
Source: 824
Target: N/A
External Id: P53600
Name: p53 small molecule agonists, cell-based qHTS assay with rat liver microsomes: qHTS ce...
Source: 824
Target: N/A
External Id: P53MS958
Name: p53 small molecule agonists, cell-based qHTS assay with rat liver microsomes: Summary
Source: 824
External Id: P53MS482
Name: p53 small molecule agonists, cell-based qHTS assay
Source: 824
External Id: P53344
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 Synonyms

(Z)-N-[(3α,5β,7α,8ξ,12α,20R,24Z)-3,7,12,24-Tetrahydroxycholan-24-ylidene]glycine
N-choloyl-Glycine
Glycocholic Acid Hydrate
3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine
Glycocholic acid
N-[(3α,5β,7α,12α)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine
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
N-Choloylglycine
N-[(3a,5b,7a,12a)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine
EINECS 207-494-9
({(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl}amino)acetic acid
MFCD06408004
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