Compounds > crx-526
Page last updated: 2024-11-13

crx-526

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Description

CRX-526: aminoalkyl-glucosaminide-phosphate; lipid A-mimetic with anti-inflammatory properties; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID24849153
CHEMBL ID505526
MeSH IDM0486521

Synonyms (13)

Synonym
bdbm50275658
(s)-2-((r)-3-(hexanoyloxy)tetradecanamido)-3-((2r,3r,4r,5s,6r)-3-((r)-3-(hexanoyloxy)tetradecanamido)-4-((r)-3-(hexanoyloxy)tetradecanoyloxy)-6-(hydroxymethyl)-5-(phosphonooxy)tetrahydro-2h-pyran-2-yloxy)propanoic acid
CHEMBL505526 ,
crx-526
hexanoic acid, (1r)-1-(2-(((1s)-1-carboxy-2-((2-deoxy-3-o-((3r)-1-oxo-3-((1-oxohexyl)oxy)tetradecyl)-2-(((3r)-1-oxo-3-((1-oxohexyl)oxy)tetradecyl)amino)-4-o-phosphono-.beta.-d-glucopyranosyl)oxy)ethyl)amino)-2-oxoethyl)dodecyl ester
854916-69-1
unii-8nlo017hha
245515-64-4
8nlo017hha ,
hexanoic acid, (1r)-1-(2-(((1s)-1-carboxy-2-((2-deoxy-3-o-((3r)-1-oxo-3-((1-oxohexyl)oxy)tetradecyl)-2-(((3r)-1-oxo-3-((1-oxohexyl)oxy)tetradecyl)amino)-4-o-phosphono-beta-d-glucopyranosyl)oxy)ethyl)amino)-2-oxoethyl)dodecyl ester
Q27270793
(2s)-2-[[(3r)-3-hexanoyloxytetradecanoyl]amino]-3-[(2r,3r,4r,5s,6r)-3-[[(3r)-3-hexanoyloxytetradecanoyl]amino]-4-[(3r)-3-hexanoyloxytetradecanoyl]oxy-6-(hydroxymethyl)-5-phosphonooxyoxan-2-yl]oxypropanoic acid
AKOS040748187
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Toll-like receptor 4Homo sapiens (human)IC50 (µMol)0.00240.00240.78061.4000AID344746
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (86)

Processvia Protein(s)Taxonomy
lipopolysaccharide-mediated signaling pathwayToll-like receptor 4Homo sapiens (human)
positive regulation of MAP kinase activityToll-like receptor 4Homo sapiens (human)
positive regulation of NF-kappaB transcription factor activityToll-like receptor 4Homo sapiens (human)
lipopolysaccharide-mediated signaling pathwayToll-like receptor 4Homo sapiens (human)
response to lipopolysaccharideToll-like receptor 4Homo sapiens (human)
positive regulation of NF-kappaB transcription factor activityToll-like receptor 4Homo sapiens (human)
toll-like receptor signaling pathwayToll-like receptor 4Homo sapiens (human)
wound healing involved in inflammatory responseToll-like receptor 4Homo sapiens (human)
B cell proliferation involved in immune responseToll-like receptor 4Homo sapiens (human)
nitric oxide production involved in inflammatory responseToll-like receptor 4Homo sapiens (human)
regulation of dendritic cell cytokine productionToll-like receptor 4Homo sapiens (human)
MyD88-dependent toll-like receptor signaling pathwayToll-like receptor 4Homo sapiens (human)
nitric oxide biosynthetic processToll-like receptor 4Homo sapiens (human)
phagocytosisToll-like receptor 4Homo sapiens (human)
immune responseToll-like receptor 4Homo sapiens (human)
I-kappaB phosphorylationToll-like receptor 4Homo sapiens (human)
JNK cascadeToll-like receptor 4Homo sapiens (human)
gene expressionToll-like receptor 4Homo sapiens (human)
positive regulation of platelet activationToll-like receptor 4Homo sapiens (human)
positive regulation of gene expressionToll-like receptor 4Homo sapiens (human)
astrocyte developmentToll-like receptor 4Homo sapiens (human)
microglia differentiationToll-like receptor 4Homo sapiens (human)
positive regulation of smooth muscle cell migrationToll-like receptor 4Homo sapiens (human)
detection of fungusToll-like receptor 4Homo sapiens (human)
positive regulation of B cell proliferationToll-like receptor 4Homo sapiens (human)
response to lipopolysaccharideToll-like receptor 4Homo sapiens (human)
detection of lipopolysaccharideToll-like receptor 4Homo sapiens (human)
negative regulation of type II interferon productionToll-like receptor 4Homo sapiens (human)
negative regulation of interleukin-17 productionToll-like receptor 4Homo sapiens (human)
negative regulation of interleukin-23 productionToll-like receptor 4Homo sapiens (human)
negative regulation of interleukin-6 productionToll-like receptor 4Homo sapiens (human)
negative regulation of tumor necrosis factor productionToll-like receptor 4Homo sapiens (human)
positive regulation of chemokine productionToll-like receptor 4Homo sapiens (human)
positive regulation of interferon-alpha productionToll-like receptor 4Homo sapiens (human)
positive regulation of interferon-beta productionToll-like receptor 4Homo sapiens (human)
positive regulation of type II interferon productionToll-like receptor 4Homo sapiens (human)
positive regulation of interleukin-1 beta productionToll-like receptor 4Homo sapiens (human)
positive regulation of interleukin-1 productionToll-like receptor 4Homo sapiens (human)
positive regulation of interleukin-10 productionToll-like receptor 4Homo sapiens (human)
positive regulation of interleukin-12 productionToll-like receptor 4Homo sapiens (human)
positive regulation of interleukin-6 productionToll-like receptor 4Homo sapiens (human)
positive regulation of interleukin-8 productionToll-like receptor 4Homo sapiens (human)
positive regulation of tumor necrosis factor productionToll-like receptor 4Homo sapiens (human)
positive regulation of stress-activated MAPK cascadeToll-like receptor 4Homo sapiens (human)
toll-like receptor 4 signaling pathwayToll-like receptor 4Homo sapiens (human)
TRIF-dependent toll-like receptor signaling pathwayToll-like receptor 4Homo sapiens (human)
cellular response to platelet-derived growth factor stimulusToll-like receptor 4Homo sapiens (human)
T-helper 1 type immune responseToll-like receptor 4Homo sapiens (human)
macrophage activationToll-like receptor 4Homo sapiens (human)
defense response to bacteriumToll-like receptor 4Homo sapiens (human)
positive regulation of macrophage activationToll-like receptor 4Homo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionToll-like receptor 4Homo sapiens (human)
innate immune responseToll-like receptor 4Homo sapiens (human)
MHC class II biosynthetic processToll-like receptor 4Homo sapiens (human)
positive regulation of MHC class II biosynthetic processToll-like receptor 4Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processToll-like receptor 4Homo sapiens (human)
negative regulation of osteoclast differentiationToll-like receptor 4Homo sapiens (human)
positive regulation of transcription by RNA polymerase IIToll-like receptor 4Homo sapiens (human)
positive regulation of JNK cascadeToll-like receptor 4Homo sapiens (human)
positive regulation of smooth muscle cell proliferationToll-like receptor 4Homo sapiens (human)
positive regulation of inflammatory responseToll-like receptor 4Homo sapiens (human)
defense response to Gram-negative bacteriumToll-like receptor 4Homo sapiens (human)
positive regulation of NF-kappaB transcription factor activityToll-like receptor 4Homo sapiens (human)
stress-activated MAPK cascadeToll-like receptor 4Homo sapiens (human)
positive regulation of nitric-oxide synthase biosynthetic processToll-like receptor 4Homo sapiens (human)
intestinal epithelial structure maintenanceToll-like receptor 4Homo sapiens (human)
positive regulation of macrophage cytokine productionToll-like receptor 4Homo sapiens (human)
ERK1 and ERK2 cascadeToll-like receptor 4Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeToll-like receptor 4Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeToll-like receptor 4Homo sapiens (human)
nucleotide-binding oligomerization domain containing 1 signaling pathwayToll-like receptor 4Homo sapiens (human)
positive regulation of nucleotide-binding oligomerization domain containing 1 signaling pathwayToll-like receptor 4Homo sapiens (human)
nucleotide-binding oligomerization domain containing 2 signaling pathwayToll-like receptor 4Homo sapiens (human)
positive regulation of nucleotide-binding oligomerization domain containing 2 signaling pathwayToll-like receptor 4Homo sapiens (human)
cellular response to lipopolysaccharideToll-like receptor 4Homo sapiens (human)
cellular response to lipoteichoic acidToll-like receptor 4Homo sapiens (human)
cellular response to mechanical stimulusToll-like receptor 4Homo sapiens (human)
cellular response to type II interferonToll-like receptor 4Homo sapiens (human)
negative regulation of cold-induced thermogenesisToll-like receptor 4Homo sapiens (human)
cellular response to oxidised low-density lipoprotein particle stimulusToll-like receptor 4Homo sapiens (human)
positive regulation of cytokine production involved in inflammatory responseToll-like receptor 4Homo sapiens (human)
positive regulation of NLRP3 inflammasome complex assemblyToll-like receptor 4Homo sapiens (human)
positive regulation of non-canonical NF-kappaB signal transductionToll-like receptor 4Homo sapiens (human)
positive regulation of reactive oxygen species biosynthetic processToll-like receptor 4Homo sapiens (human)
positive regulation of cellular response to macrophage colony-stimulating factor stimulusToll-like receptor 4Homo sapiens (human)
positive regulation of matrix metallopeptidase secretionToll-like receptor 4Homo sapiens (human)
cellular response to amyloid-betaToll-like receptor 4Homo sapiens (human)
positive regulation of chemokine (C-X-C motif) ligand 2 productionToll-like receptor 4Homo sapiens (human)
positive regulation of extrinsic apoptotic signaling pathwayToll-like receptor 4Homo sapiens (human)
inflammatory responseToll-like receptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
lipopolysaccharide bindingToll-like receptor 4Homo sapiens (human)
amyloid-beta bindingToll-like receptor 4Homo sapiens (human)
lipopolysaccharide immune receptor activityToll-like receptor 4Homo sapiens (human)
transmembrane signaling receptor activityToll-like receptor 4Homo sapiens (human)
signaling receptor bindingToll-like receptor 4Homo sapiens (human)
protein bindingToll-like receptor 4Homo sapiens (human)
signaling receptor activityToll-like receptor 4Homo sapiens (human)
identical protein bindingToll-like receptor 4Homo sapiens (human)
protein heterodimerization activityToll-like receptor 4Homo sapiens (human)
NAD+ nucleotidase, cyclic ADP-ribose generatingToll-like receptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
plasma membraneToll-like receptor 4Homo sapiens (human)
endosome membraneToll-like receptor 4Homo sapiens (human)
ruffleToll-like receptor 4Homo sapiens (human)
phagocytic cupToll-like receptor 4Homo sapiens (human)
cytoplasmToll-like receptor 4Homo sapiens (human)
early endosomeToll-like receptor 4Homo sapiens (human)
plasma membraneToll-like receptor 4Homo sapiens (human)
external side of plasma membraneToll-like receptor 4Homo sapiens (human)
cell surfaceToll-like receptor 4Homo sapiens (human)
endosome membraneToll-like receptor 4Homo sapiens (human)
receptor complexToll-like receptor 4Homo sapiens (human)
perinuclear region of cytoplasmToll-like receptor 4Homo sapiens (human)
lipopolysaccharide receptor complexToll-like receptor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID344746Antagonist activity at TLR4 in human PBMC assessed as inhibition of LPS-stimulated TNFalpha production pre-incubated for 30 mins before LPS challenge measured after 18 hrs by ELISA2008Bioorganic & medicinal chemistry letters, Oct-15, Volume: 18, Issue:20
The 'Ethereal' nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics.
AID344753Inhibition of LPS-induced serum TNFalpha production in iv dosed BALB/c mouse after 1.5 hrs by ELISA2008Bioorganic & medicinal chemistry letters, Oct-15, Volume: 18, Issue:20
The 'Ethereal' nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics.
AID344747Agonist activity at TLR4 in human PBMC assessed as induction of TNFalpha production after 18 hrs by sandwich ELISA2008Bioorganic & medicinal chemistry letters, Oct-15, Volume: 18, Issue:20
The 'Ethereal' nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics.
AID344754Inhibition of CRX-527-mediated protection against Listeria monocytogenes infected iv dosed BALB/c mouse administered 2 days prior to bacterial challenge measured after 2 days2008Bioorganic & medicinal chemistry letters, Oct-15, Volume: 18, Issue:20
The 'Ethereal' nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (42.86)29.6817
2010's4 (57.14)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.51

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.51 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
glucosamine
D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.		3.4670D-glucosamineEscherichia coli metabolite;
geroprotector;
mouse metabolite
b 1287
E5564: structure in first source. eritoran tetrasodium : An organic sodium salt which is the tetrasodium salt of eritoran.		2.1710organic sodium salt
lipid a
Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).		2.7530dodecanoate ester;
lipid A;
tetradecanoate ester		Escherichia coli metabolite
glycolipids
[no description available]		2.0410
transforming growth factor beta
Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.		2.0810
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.5420
Diabetes Mellitus
A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.		02.1710
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.5420
Disease Exacerbation
[description not available]		02.0810
Alloxan Diabetes
[description not available]		02.0810
Diabetic Glomerulosclerosis
[description not available]		02.0810
Albuminuria
The presence of albumin in the urine, an indicator of KIDNEY DISEASES.		02.0810
Diabetic Nephropathies
KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.		02.0810
Cancer of Colon
[description not available]		02.110
Colonic Neoplasms
Tumors or cancer of the COLON.		02.110
Blood Poisoning
[description not available]		02.1110
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.4620
Sepsis
Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.		02.1110
Endotoxemia
A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.		02.1110
Edema, Pulmonary
[description not available]		02.0510
Injury, Ischemia-Reperfusion
[description not available]		02.0510
Pulmonary Edema
Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.		02.0510
Reperfusion Injury
Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.		02.0510
Bowel Diseases, Inflammatory
[description not available]		02.0210
Colitis
Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.		02.0210
Inflammatory Bowel Diseases
Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.		02.0210