Compounds > N(2)-carbamimidoyl-N-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-D-leucinamide
Page last updated: 2024-12-10

N(2)-carbamimidoyl-N-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-D-leucinamide

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Description

N(2)-carbamimidoyl-N-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1H-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-D-leucinamide : A leucine derivative obtained by fpormal condensation of the secondary amino group of 5-({2,3-dichloro-4-[1-methyl-5-(piperidin-4-yl)-1H-pyrazol-3-yl]phenoxy}methyl)-2-furoic acid and the carboxy group of N-amidino-L-leucylglycine [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5288251
CHEMBL ID429852
CHEBI ID47417
SCHEMBL ID10068448

Synonyms (21)

Synonym
5-[2,3-dichloro-4-(5-{1-[2-(2-guanidino-4-methyl-pentanoylamino)-acetyl]-piperidin-4-yl}-1-methyl-1h-pyrazol-3-yl)-phenoxymethyl]-furan-2-carboxylic acid
n(2)-carbamimidoyl-n-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1h-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-d-leucinamide
DB02581
1PY2
CHEMBL429852 ,
chebi:47417 ,
sp-4206
5-[[2,3-dichloro-4-[5-[1-[2-[[(2r)-2-(diaminomethylideneamino)-4-methylpentanoyl]amino]acetyl]piperidin-4-yl]-1-methylpyrazol-3-yl]phenoxy]methyl]furan-2-carboxylic acid
SP4206 ,
SCHEMBL10068448
compound 13 [pmid:12656598]
gtpl9037
n~2~-carbamimidoyl-n-{2-[4-(3-{4-[(5-carboxyfuran-2-yl)methoxy]-2,3-dichlorophenyl}-1-methyl-1h-pyrazol-5-yl)piperidin-1-yl]-2-oxoethyl}-d-leucinamide
515846-21-6 (free base)
HY-119424
Q27088843
cid 5288251
515846-21-6
CS-0068171
MS-31023
AKOS040738906
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (6)

ClassDescription
guanidinesAny organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas.
furoic acidA monocarboxylic acid that consists of a furan ring having a single carboxylic acid group on any ring position and derivatives thereof.
pyrazolylpiperidine
glycine derivativeA proteinogenic amino acid derivative resulting from reaction of glycine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
dichlorobenzeneAny member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.
D-leucine derivativeA non-proteinogenic amino acid derivative resulting from reaction of D-leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of D-leucine by a heteroatom.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain B, Interleukin-2Homo sapiens (human)IC50 (µMol)0.06000.06000.06000.0600AID977608
Chain A, Interleukin-2Homo sapiens (human)IC50 (µMol)0.06000.06000.06000.0600AID977608
Interleukin-2 receptor subunit alphaMus musculus (house mouse)IC50 (µMol)0.06000.06003.03006.0000AID91894
Interleukin-2Homo sapiens (human)Ki0.06000.06000.06000.0600AID318564
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Interleukin-2 receptor subunit alphaMus musculus (house mouse)EC50 (µMol)0.00300.00300.00300.0030AID107967
Interleukin-2Homo sapiens (human)Kd0.10000.00001.30375.4700AID1774677
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (38)

Processvia Protein(s)Taxonomy
positive regulation of immunoglobulin productionInterleukin-2Homo sapiens (human)
positive regulation of plasma cell differentiationInterleukin-2Homo sapiens (human)
negative regulation of B cell apoptotic processInterleukin-2Homo sapiens (human)
positive regulation of B cell proliferationInterleukin-2Homo sapiens (human)
positive regulation of activated T cell proliferationInterleukin-2Homo sapiens (human)
negative regulation of protein phosphorylationInterleukin-2Homo sapiens (human)
adaptive immune responseInterleukin-2Homo sapiens (human)
leukocyte activation involved in immune responseInterleukin-2Homo sapiens (human)
transcription by RNA polymerase IIInterleukin-2Homo sapiens (human)
immune responseInterleukin-2Homo sapiens (human)
cell adhesionInterleukin-2Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationInterleukin-2Homo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayInterleukin-2Homo sapiens (human)
cell-cell signalingInterleukin-2Homo sapiens (human)
positive regulation of cell population proliferationInterleukin-2Homo sapiens (human)
natural killer cell activationInterleukin-2Homo sapiens (human)
T cell differentiationInterleukin-2Homo sapiens (human)
positive regulation of cell growthInterleukin-2Homo sapiens (human)
positive regulation of type II interferon productionInterleukin-2Homo sapiens (human)
positive regulation of interleukin-17 productionInterleukin-2Homo sapiens (human)
positive regulation of tissue remodelingInterleukin-2Homo sapiens (human)
interleukin-2-mediated signaling pathwayInterleukin-2Homo sapiens (human)
positive regulation of tyrosine phosphorylation of STAT proteinInterleukin-2Homo sapiens (human)
negative regulation of apoptotic processInterleukin-2Homo sapiens (human)
response to ethanolInterleukin-2Homo sapiens (human)
positive regulation of regulatory T cell differentiationInterleukin-2Homo sapiens (human)
positive regulation of transcription by RNA polymerase IIInterleukin-2Homo sapiens (human)
regulation of T cell homeostatic proliferationInterleukin-2Homo sapiens (human)
positive regulation of isotype switching to IgG isotypesInterleukin-2Homo sapiens (human)
negative regulation of lymphocyte proliferationInterleukin-2Homo sapiens (human)
negative regulation of inflammatory responseInterleukin-2Homo sapiens (human)
positive regulation of inflammatory responseInterleukin-2Homo sapiens (human)
activated T cell proliferationInterleukin-2Homo sapiens (human)
positive regulation of dendritic spine developmentInterleukin-2Homo sapiens (human)
extrinsic apoptotic signaling pathway in absence of ligandInterleukin-2Homo sapiens (human)
response to tacrolimusInterleukin-2Homo sapiens (human)
negative regulation of T-helper 17 cell differentiationInterleukin-2Homo sapiens (human)
regulation of CD4-positive, alpha-beta T cell proliferationInterleukin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
cytokine activityInterleukin-2Homo sapiens (human)
interleukin-2 receptor bindingInterleukin-2Homo sapiens (human)
protein bindingInterleukin-2Homo sapiens (human)
growth factor activityInterleukin-2Homo sapiens (human)
kinase activator activityInterleukin-2Homo sapiens (human)
carbohydrate bindingInterleukin-2Homo sapiens (human)
kappa-type opioid receptor bindingInterleukin-2Homo sapiens (human)
glycosphingolipid bindingInterleukin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
extracellular spaceInterleukin-2Homo sapiens (human)
extracellular regionInterleukin-2Homo sapiens (human)
extracellular spaceInterleukin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID91891Inhibition of Interleukin-2 receptor2004Journal of medicinal chemistry, Jul-01, Volume: 47, Issue:14
Fragment-based drug discovery.
AID7867Volume distribution (steady state) of compound was determined in mouse2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Integrating fragment assembly and biophysical methods in the chemical advancement of small-molecule antagonists of IL-2: an approach for inhibiting protein-protein interactions.
AID1774670Inhibition of IL2/IL-2Ralpha (unknown origin) interaction2021Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23
Identification and Validation of New Interleukin-2 Ligands Using DNA-Encoded Libraries.
AID91894Concentration required to inhibit mouse interleukin-2 alpha receptor was determined by SPA assay2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Integrating fragment assembly and biophysical methods in the chemical advancement of small-molecule antagonists of IL-2: an approach for inhibiting protein-protein interactions.
AID241068Inhibitory concentration against interleukin-2 binding2005Bioorganic & medicinal chemistry letters, Feb-15, Volume: 15, Issue:4
Identification of nonpeptidic small-molecule inhibitors of interleukin-2.
AID9563Plasma clearance in mouse2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Integrating fragment assembly and biophysical methods in the chemical advancement of small-molecule antagonists of IL-2: an approach for inhibiting protein-protein interactions.
AID700921Inhibition of IL2 receptor binding to IL2 alpha receptor by scintillation proximity assay2012Bioorganic & medicinal chemistry, Mar-15, Volume: 20, Issue:6
Chemical modulators working at pharmacological interface of target proteins.
AID1674204Antagonist activity at IL-2/IL-2RA (unknown origin) assessed as reduction in IL-2/IL-2RA protein-protein interaction by scintillation proximity assay2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Fragment Linking Strategies for Structure-Based Drug Design.
AID11745Terminal half life of compound was determined in mouse2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Integrating fragment assembly and biophysical methods in the chemical advancement of small-molecule antagonists of IL-2: an approach for inhibiting protein-protein interactions.
AID107967Effective concentration required against phosphorylation of Mammary gland factor/STAT52004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Integrating fragment assembly and biophysical methods in the chemical advancement of small-molecule antagonists of IL-2: an approach for inhibiting protein-protein interactions.
AID318564Binding affinity to IL2 assessed as inhibition of IL2-IL2Ralpha interaction2007Nature, Dec-13, Volume: 450, Issue:7172
Reaching for high-hanging fruit in drug discovery at protein-protein interfaces.
AID1774677Binding affinity to IL2 (unknown origin) by SPR assay2021Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23
Identification and Validation of New Interleukin-2 Ligands Using DNA-Encoded Libraries.
AID1811Experimentally measured binding affinity data derived from PDB2003Journal of the American Chemical Society, Dec-17, Volume: 125, Issue:50
Potent small-molecule binding to a dynamic hot spot on IL-2.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2003Journal of the American Chemical Society, Dec-17, Volume: 125, Issue:50
Potent small-molecule binding to a dynamic hot spot on IL-2.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (62.50)29.6817
2010's1 (12.50)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.33

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 Index12.33 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (50.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (50.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
indole
[no description available]		3.1210indole;
polycyclic heteroarene		Escherichia coli metabolite
tacrine
Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.		4.0920acridines;
aromatic amine		EC 3.1.1.7 (acetylcholinesterase) inhibitor
abt 702
[no description available]		3.1210bipyridines
acetohydroxamic acid
acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.		4.0920acetohydroxamic acids;
carbohydroximic acid		algal metabolite;
EC 3.5.1.5 (urease) inhibitor
benzamidine
benzamidine: RN given refers to parent cpd. benzamidine : A carboxamidine that is benzene carrying an amidino group.		3.3510benzenes;
carboxamidine		serine protease inhibitor
N-[4-(4-morpholinyl)butyl]-2-benzofurancarboxamide
CL82198: a selective inhibitor of MMP13		3.1210benzofurans
n(6),n(6)-dimethyladenine
N(6),N(6)-dimethyladenine : A tertiary amine that is adenine substituted at N-6 by geminal methyl groups.		3.3510tertiary amine
aminosalicylic acid
Aminosalicylic Acid: An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid.. 4-aminosalicylic acid : An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.		4.0920aminobenzoic acid;
phenols		antitubercular agent
4-phenylphenol
4-phenylphenol: RN given refers to cpd without isomeric designation. biphenyl-4-ol : A member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.		4.0920hydroxybiphenyls
quinaldic acid
[no description available]		3.3510quinolinemonocarboxylic acidhuman metabolite;
Saccharomyces cerevisiae metabolite
benzanilide
[no description available]		3.1210
hexanoic acid
hexanoic acid : A C6, straight-chain saturated fatty acid.		3.3510medium-chain fatty acid;
straight-chain saturated fatty acid		human metabolite;
plant metabolite
1,4-benzodioxan
1,4-benzodioxan: structure in first source		3.1210
hadacidin
hadacidin: inhibitor of AMP synthesis; RN given refers to parent cpd; structure. hadacidin : A monocarboxylic acid that is N-hydroxyglycine in which the hydrogen attached to the nitrogen is replaced by a formyl group. It was originally isolated from cultures of Penicillium frequentans.		3.1210aldehyde;
monocarboxylic acid;
N-hydroxy-alpha-amino-acid		antimicrobial agent;
antineoplastic agent;
Penicillium metabolite;
teratogenic agent
4-phenylbenzoic acid
4-phenylbenzoic acid: RN given refers to 4-carboxylic cpd		3.1210
prolinal
[no description available]		3.3510pyrrolidines
5-Chloro-1H-indole-2,3-dione
[no description available]		3.3510indolesanticoronaviral agent
benzo(b)thiophene-2-carboxylic acid
benzo(b)thiophene-2-carboxylic acid: for prevention of osteoporosis; structure given in first source		3.1210
propidium iodide
[no description available]		3.1210organic iodide salt
nsc 23766
[no description available]		3.1310aminopyrimidine;
aminoquinoline;
primary amino compound;
secondary amino compound;
tertiary amino compound		antiviral agent;
apoptosis inducer;
EC 3.6.5.2 (small monomeric GTPase) inhibitor;
muscarinic antagonist
desthiobiotin
desthiobiotin: RN given refers to cpd without isomeric designation; structure. (4R,5S)-dethiobiotin : The (4R,5S)-isomer of dethiobiotin.		3.3510dethiobiotin
gs 4071
GS 4071: The acid form.. oseltamivir acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid which is substituted at positions 3, 4, and 5 by pentan-3-yloxy, acetamido, and amino groups, respectively (the 3R,4R,5S enantiomer). An antiviral drug, it is used as the corresponding ethyl ester prodrug, oseltamivir, to slow the spread of influenza.		3.1210acetate ester;
amino acid;
cyclohexenecarboxylic acid;
primary amino compound		antiviral drug;
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor;
marine xenobiotic metabolite
nbd 556
[no description available]		3.1310
ro26-4550
[no description available]		3.8230
spd-304
SPD-304: structure in first source		3.1310
cp 91149
CP 91149: inhibits liver glycogen phosphorylase; structure in first source		3.1210
abt-737
[no description available]		3.1310aromatic amine;
aryl sulfide;
biphenyls;
C-nitro compound;
monochlorobenzenes;
N-arylpiperazine;
N-sulfonylcarboxamide;
secondary amino compound;
tertiary amino compound		anti-allergic agent;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
B-cell lymphoma 2 inhibitor
nutlin-3a
nutlin 3: an MDM2 antagonist; structure in first source		4.0620stilbenoid
2,3,4,10-tetrahydro-7,10-dimethyl-2,4-dioxobenzo(g)pteridine
[no description available]		3.1710flavin
navitoclax
[no description available]		3.3510aryl sulfide;
monochlorobenzenes;
morpholines;
N-sulfonylcarboxamide;
organofluorine compound;
piperazines;
secondary amino compound;
sulfone;
tertiary amino compound		antineoplastic agent;
apoptosis inducer;
B-cell lymphoma 2 inhibitor
abt-199
venetoclax: A BCL-2 inhibitor with antineoplastic activity that is used in the treatment of CHRONIC LYMPHOCYTIC LEUKEMIA associated with chromosome 17p deletion; structure in first source.. venetoclax : A member of the class of pyrrolopyridines that is a potent inhibitor of the antiapoptotic protein B-cell lymphoma 2. It is used for treamtment of chronic lymphocytic leukemia with 17p deletion.		3.3510aromatic ether;
C-nitro compound;
monochlorobenzenes;
N-alkylpiperazine;
N-arylpiperazine;
N-sulfonylcarboxamide;
oxanes;
pyrrolopyridine		antineoplastic agent;
apoptosis inducer;
B-cell lymphoma 2 inhibitor
5,10-methylenetetrahydrofolic acid
5,10-methylenetetrahydrofolic acid: RN refers to parent cpd(L-Glu)-isomer		3.1210benzamides;
methylenetetrahydrofolic acid
ConditionIndicatedRelationship StrengthStudiesTrials
Degenerative Diseases, Central Nervous System
[description not available]		02.9910
Bacterial Disease
[description not available]		02.9910
Diseases of Immune System
[description not available]		02.9910
Benign Neoplasms
[description not available]		02.9910
Viral Diseases
[description not available]		02.9910
Bacterial Infections
Infections by bacteria, general or unspecified.		02.9910
Immune System Diseases
Disorders caused by abnormal or absent immunologic mechanisms, whether humoral, cell-mediated, or both.		02.9910
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.9910
Virus Diseases
A general term for diseases caused by viruses.		02.9910
Neurodegenerative Diseases
Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.		02.9910