Compounds > n-(4-(n-((2,4-diaminofuro(2,3-d)pyrimidin-5-yl)methyl)amino)benzoyl)glutamic acid
Page last updated: 2024-12-08

n-(4-(n-((2,4-diaminofuro(2,3-d)pyrimidin-5-yl)methyl)amino)benzoyl)glutamic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

N-(4-(N-((2,4-diaminofuro(2,3-d)pyrimidin-5-yl)methyl)amino)benzoyl)glutamic acid: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID158351
CHEMBL ID106628
MeSH IDM0230292

Synonyms (12)

Synonym
(s)-2-{4-[(2,4-diamino-furo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoylamino}-pentanedioic acid
(s)-2-(4-((2,4-diaminofuro[2,3-d]pyrimidin-5-yl)methylamino)benzamido)pentanedioic acid
bdbm50030820
(2s)-2-[[4-[(2,4-diaminofuro[2,3-d]pyrimidin-5-yl)methylamino]benzoyl]amino]pentanedioic acid
2-[(1-{4-[(2,4-diamino-furo[2,3-d]pyrimidin-5-ylmethyl)-amino]-phenyl}-methanoyl)-amino]-l-glutamic acid
CHEMBL106628 ,
156595-84-5
dpmabg
n-(4-(n-((2,4-diaminofuro(2,3-d)pyrimidin-5-yl)methyl)amino)benzoyl)glutamic acid
l-glutamic acid, n-(4-(((2,4-diaminofuro(2,3-d)pyrimidin-5-yl)methyl)amino)benzoyl)-
n-(4-{[(4-amino-2-imino-2,3-dihydrofuro[2,3-d]pyrimidin-5-yl)methyl]amino}benzoyl)glutamic acid
DTXSID60935480
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydrofolate reductaseHomo sapiens (human)IC50 (µMol)0.39250.00060.87267.3000AID457195; AID56977; AID56979; AID56981
Dihydrofolate reductaseLacticaseibacillus caseiIC50 (µMol)0.56000.00130.26964.9000AID57758; AID57763
Thymidylate synthaseLacticaseibacillus caseiIC50 (µMol)200.00000.00901.93248.8000AID211798; AID211800
Thymidylate synthaseHomo sapiens (human)IC50 (µMol)200.00000.00662.06379.5000AID212299; AID212302; AID212304; AID457192
Bifunctional dihydrofolate reductase-thymidylate synthaseToxoplasma gondiiIC50 (µMol)0.70000.00061.042810.0000AID56320
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (31)

Processvia Protein(s)Taxonomy
tetrahydrobiopterin biosynthetic processDihydrofolate reductaseHomo sapiens (human)
one-carbon metabolic processDihydrofolate reductaseHomo sapiens (human)
negative regulation of translationDihydrofolate reductaseHomo sapiens (human)
axon regenerationDihydrofolate reductaseHomo sapiens (human)
response to methotrexateDihydrofolate reductaseHomo sapiens (human)
dihydrofolate metabolic processDihydrofolate reductaseHomo sapiens (human)
tetrahydrofolate metabolic processDihydrofolate reductaseHomo sapiens (human)
tetrahydrofolate biosynthetic processDihydrofolate reductaseHomo sapiens (human)
folic acid metabolic processDihydrofolate reductaseHomo sapiens (human)
positive regulation of nitric-oxide synthase activityDihydrofolate reductaseHomo sapiens (human)
regulation of removal of superoxide radicalsDihydrofolate reductaseHomo sapiens (human)
dTMP biosynthetic processThymidylate synthaseHomo sapiens (human)
dTTP biosynthetic processThymidylate synthaseHomo sapiens (human)
circadian rhythmThymidylate synthaseHomo sapiens (human)
response to xenobiotic stimulusThymidylate synthaseHomo sapiens (human)
response to toxic substanceThymidylate synthaseHomo sapiens (human)
negative regulation of translationThymidylate synthaseHomo sapiens (human)
uracil metabolic processThymidylate synthaseHomo sapiens (human)
methylationThymidylate synthaseHomo sapiens (human)
response to progesteroneThymidylate synthaseHomo sapiens (human)
response to vitamin AThymidylate synthaseHomo sapiens (human)
response to cytokineThymidylate synthaseHomo sapiens (human)
tetrahydrofolate interconversionThymidylate synthaseHomo sapiens (human)
response to ethanolThymidylate synthaseHomo sapiens (human)
response to organophosphorusThymidylate synthaseHomo sapiens (human)
developmental growthThymidylate synthaseHomo sapiens (human)
cartilage developmentThymidylate synthaseHomo sapiens (human)
response to glucocorticoidThymidylate synthaseHomo sapiens (human)
response to folic acidThymidylate synthaseHomo sapiens (human)
intestinal epithelial cell maturationThymidylate synthaseHomo sapiens (human)
DNA biosynthetic processThymidylate synthaseHomo sapiens (human)
liver regenerationThymidylate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
mRNA regulatory element binding translation repressor activityDihydrofolate reductaseHomo sapiens (human)
mRNA bindingDihydrofolate reductaseHomo sapiens (human)
dihydrofolate reductase activityDihydrofolate reductaseHomo sapiens (human)
folic acid bindingDihydrofolate reductaseHomo sapiens (human)
NADPH bindingDihydrofolate reductaseHomo sapiens (human)
sequence-specific mRNA bindingDihydrofolate reductaseHomo sapiens (human)
NADP bindingDihydrofolate reductaseHomo sapiens (human)
mRNA regulatory element binding translation repressor activityThymidylate synthaseHomo sapiens (human)
thymidylate synthase activityThymidylate synthaseHomo sapiens (human)
folic acid bindingThymidylate synthaseHomo sapiens (human)
protein homodimerization activityThymidylate synthaseHomo sapiens (human)
sequence-specific mRNA bindingThymidylate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
mitochondrionDihydrofolate reductaseHomo sapiens (human)
cytosolDihydrofolate reductaseHomo sapiens (human)
mitochondrionDihydrofolate reductaseHomo sapiens (human)
nucleusThymidylate synthaseHomo sapiens (human)
cytoplasmThymidylate synthaseHomo sapiens (human)
mitochondrionThymidylate synthaseHomo sapiens (human)
mitochondrial inner membraneThymidylate synthaseHomo sapiens (human)
mitochondrial matrixThymidylate synthaseHomo sapiens (human)
cytosolThymidylate synthaseHomo sapiens (human)
mitochondrionThymidylate synthaseHomo sapiens (human)
cytosolThymidylate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID212299Inhibitory concentration against human TS2000Journal of medicinal chemistry, Oct-19, Volume: 43, Issue:21
Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent.
AID212811Inhibitory concentration against rat Thymidylate synthase (TS); ND means not determined2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID72337Growth inhibition of human squamous cell carcinoma FaDu in culture2000Journal of medicinal chemistry, Oct-19, Volume: 43, Issue:21
Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent.
AID72336Growth inhibition of human squamous cell carcinoma FaDu cells during continuous Exposure (0-12 h)2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID57763inhibitory concentration against Lactobacillus casei DHFR(Dihydro folate reductase).1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
Effect of bridge region variation on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID457192Inhibition of human thymidylate synthase at 30 degC under pH 7.4 by spectrophotometry2010Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2
2,4-Diamino-5-methyl-6-substituted arylthio-furo[2,3-d]pyrimidines as novel classical and nonclassical antifolates as potential dual thymidylate synthase and dihydrofolate reductase inhibitors.
AID211800Inhibitory concentration against Lactobacillus casei TS (Thymidylate synthase).1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
Effect of bridge region variation on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID57242Inhibitory concentration against Escherichia coli Dihydrofolate reductase; ND means not determined2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID44007Growth inhibition of human T-lymphoblastic leukemia cell line CCRF-CEM in culture2000Journal of medicinal chemistry, Oct-19, Volume: 43, Issue:21
Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent.
AID105921Growth inhibition of MTX-resistant R1 sublines.2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID105928Growth inhibition of MTX-resistant R30dm sublines.2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID57758Inhibitory concentration against Lactobacillus casei Dihydrofolate reductase2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID31290Inhibition against 50 aminoimidazole-4-carboxamide ribonucleotide formyltransferase (AICAR formyltransferase); In active2000Journal of medicinal chemistry, Oct-19, Volume: 43, Issue:21
Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent.
AID212302Inhibitory concentration against recombinant human (rh) Thymidylate synthase (TS)2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID56979Inhibitory concentration against recombinant human (rh) Dihydrofolate reductase2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID44340Growth inhibition of CCRF-CEM human leukemia cells.2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID212304Inhibitory concentration against recombinant human TS (Thymidylate synthase).1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
Effect of bridge region variation on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID72756Inhibition against GAR transformylase; In active2000Journal of medicinal chemistry, Oct-19, Volume: 43, Issue:21
Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent.
AID457195Inhibition of human DHFR at 30 degC under pH 7.4 by spectrophotometry2010Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2
2,4-Diamino-5-methyl-6-substituted arylthio-furo[2,3-d]pyrimidines as novel classical and nonclassical antifolates as potential dual thymidylate synthase and dihydrofolate reductase inhibitors.
AID56320Inhibitory concentration against Toxoplasma gondii Dihydrofolate reductase2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID56977Inhibitory concentration against human dihydrofolate reductase (DHFR),2000Journal of medicinal chemistry, Oct-19, Volume: 43, Issue:21
Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent.
AID9815Growth inhibition of human squamous cell carcinoma A253 cells during continuous Exposure (0-12 h); ND means not determined2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID105926Growth inhibition of MTX-resistant R2(Bos) sublines;ND means not determined2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID211798Inhibitory concentration against Lactobacillus casei Thymidylate synthase (TS).2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID56981Inhibitory concentration against recombinant human DHFR(Dihydro folate reductase).1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
Effect of bridge region variation on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
AID211445Inhibitory concentration against Escherichia coli Thymidylate synthase (TS); ND means not determined2000Journal of medicinal chemistry, Aug-10, Volume: 43, Issue:16
Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (40.00)18.2507
2000's2 (40.00)29.6817
2010's1 (20.00)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: 12.40

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 Index12.40 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.20 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.40)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
trimethoprim
Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.		2.0510aminopyrimidine;
methoxybenzenes		antibacterial drug;
diuretic;
drug allergen;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
environmental contaminant;
xenobiotic
trimetrexate
Trimetrexate: A nonclassical folic acid inhibitor through its inhibition of the enzyme dihydrofolate reductase. It is being tested for efficacy as an antineoplastic agent and as an antiparasitic agent against PNEUMOCYSTIS PNEUMONIA in AIDS patients. Myelosuppression is its dose-limiting toxic effect.		2.0510
methotrexate
[no description available]		3.150dicarboxylic acid;
monocarboxylic acid amide;
pteridines		abortifacient;
antimetabolite;
antineoplastic agent;
antirheumatic drug;
dermatologic drug;
DNA synthesis inhibitor;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
immunosuppressive agent
aminopterin
Aminopterin: A folic acid derivative used as a rodenticide that has been shown to be teratogenic.		2.6930dicarboxylic acidEC 1.5.1.3 (dihydrofolate reductase) inhibitor;
mutagen
folic acid
folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.		1.9810folic acids;
N-acyl-amino acid		human metabolite;
mouse metabolite;
nutrient
raltitrexed
[no description available]		2.4320N-acyl-amino acid
n-(4(n-((2-amino-4-hydroxy-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-l-glutamic acid
[no description available]		210
pemetrexed
pemetrexed disodium : An organic sodium salt that is the disodium salt of N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT).		2.4320N-acyl-L-glutamic acid;
pyrrolopyrimidine		antimetabolite;
antineoplastic agent;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
EC 2.1.1.45 (thymidylate synthase) inhibitor;
EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor
cb 3717
[no description available]		210N-acyl-L-glutamic acid
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Lymphoid Leukemia
[description not available]		01.9810
Precursor Cell Lymphoblastic Leukemia-Lymphoma
A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.		01.9810
Benign Neoplasms
[description not available]		01.9810
AIDS-Related Opportunistic Infections
Opportunistic infections found in patients who test positive for human immunodeficiency virus (HIV). The most common include PNEUMOCYSTIS PNEUMONIA, Kaposi's sarcoma, cryptosporidiosis, herpes simplex, toxoplasmosis, cryptococcosis, and infections with Mycobacterium avium complex, Microsporidium, and Cytomegalovirus.		01.9810
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.		01.9810