Page last updated: 2024-10-15

(5)n,(8)n-deaza-(10)-n-methylfolate

Description

(5)N,(8)N-deaza-(10)-N-methylfolate: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135777640
CHEMBL ID347223
SCHEMBL ID6337570
MeSH IDM0050284
PubMed CID135443603
CHEMBL ID343140
MeSH IDM0050284

Synonyms (15)

Synonym
CHEMBL347223 ,
bdbm50023904
(5)n,(8)n-deaza-(10)-n-methylfolate
10-mddf
nsc 178256
10-methyl-5,8-dideazafolate
l-glutamic acid, n-(4-(((2-amino-1,4-dihydro-4-oxo-6-quinazolinyl)methyl)methylamino)benzoyl)-
SCHEMBL6337570
nsc-178256
nsc178256
5854-12-6
CHEMBL343140 ,
2-{4-[(2-amino-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid
2-{4-[(2-amino-4-hydroxy-quinazolin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid
bdbm50017872
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydrofolate reductaseEnterococcus faeciumIC50 (µMol)0.43000.00140.67711.6000AID1134002
Thymidylate synthaseHomo sapiens (human)IC50 (µMol)0.29000.00662.06379.5000AID212156
Cytochrome P450 11B1, mitochondrial Bos taurus (cattle)IC50 (µMol)0.27280.00101.06087.8300AID1134001; AID1134002
Histidine decarboxylaseRattus norvegicus (Norway rat)IC50 (µMol)0.43000.00140.67711.6000AID1134002
Dihydrofolate reductaseRattus norvegicus (Norway rat)IC50 (µMol)0.03700.00060.35076.2000AID1134001
Dihydrofolate reductaseHomo sapiens (human)IC50 (µMol)0.08300.00060.87267.3000AID56813
Thymidylate synthaseMus musculus (house mouse)IC50 (µMol)0.24500.00041.322610.0000AID212475; AID212640
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (32)

Processvia Protein(s)Taxonomy
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)
glucocorticoid biosynthetic processCytochrome P450 11B1, mitochondrial Bos taurus (cattle)
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
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)
iron ion bindingCytochrome P450 11B1, mitochondrial Bos taurus (cattle)
heme bindingCytochrome P450 11B1, mitochondrial Bos taurus (cattle)
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
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)
mitochondrionDihydrofolate reductaseHomo sapiens (human)
cytosolDihydrofolate reductaseHomo sapiens (human)
mitochondrionDihydrofolate reductaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1147641Inhibition of Lactobacillus casei thymidylate synthetase at 1.7 x 10'-6 M relative to control1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Diastereoisomers of 5,10-methylene-5,6,7,8-tetrahydropteroyl-D-glutamic acid.
AID1134001Inhibition of rat liver dihydrofolate reductase using dihydrofolate as substrate1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Quinazolines as inhibitors of dihydrofolate reductase. 4. Classical analogues of folic and isofolic acids.
AID212156Ability to inhibit thymidylate synthase derived from human leukemia K562 cells1987Journal of medicinal chemistry, Apr, Volume: 30, Issue:4
Folate analogues as inhibitors of thymidylate synthase.
AID1134002Inhibition of Streptococcus faecium dihydrofolate reductase using dihydrofolate as substrate1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Quinazolines as inhibitors of dihydrofolate reductase. 4. Classical analogues of folic and isofolic acids.
AID1123093Inhibition of dihydrofolate reductase in human acute lymphocytic leukemia cells1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Multivariate analysis and quantitative structure-activity relationships. Inhibition of dihydrofolate reductase and thymidylate synthetase by quinazolines.
AID1123091Inhibition of thymidylate synthetase in mouse L1210S cells1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Multivariate analysis and quantitative structure-activity relationships. Inhibition of dihydrofolate reductase and thymidylate synthetase by quinazolines.
AID212640Inhibitory concentration of compound to inhibit Thymidylate synthase (TS) in L1210 cells at conc. of 200 uM1989Journal of medicinal chemistry, Apr, Volume: 32, Issue:4
Quinazoline antifolates inhibiting thymidylate synthase: 2-desamino derivatives with enhanced solubility and potency.
AID56813Inhibitory activity against dihydrofolate reductase (DHFR) obtained from human WIL2 cells1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Inhibition of murine thymidylate synthase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin.
AID1123092Inhibition of thymidylate synthetase in Lactobacillus casei1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Multivariate analysis and quantitative structure-activity relationships. Inhibition of dihydrofolate reductase and thymidylate synthetase by quinazolines.
AID56148Binding energy to Streptococcus faecium dihydrofolate reductase1982Journal of medicinal chemistry, Aug, Volume: 25, Issue:8
Quantitative structure-activity relationship by distance geometry: quinazolines as dihydrofolate reductase inhibitors.
AID98530Compound was evaluated for inhibition dose required to inhibit the growth of L1210 cells in culture.1989Journal of medicinal chemistry, Apr, Volume: 32, Issue:4
Quinazoline antifolates inhibiting thymidylate synthase: 2-desamino derivatives with enhanced solubility and potency.
AID212475Inhibitory activity against thymidylate synthase isolated from L1210 leukemia cells1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Inhibition of murine thymidylate synthase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin.
AID56152Binding energy against Streptococcus faecium dihydrofolate reductase1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Quantitative structure-activity relationships by distance geometry: systematic analysis of dihydrofolate reductase inhibitors.
AID1146760Inhibition of Streptococcus faecium dihydrofolate reductase using dihydrofolate as substrate1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Quantitative structure-activity relationships of antimalarial and dihydrofolate reductase inhibition by quinazolines and 5-substituted benzyl-2,4-diaminopyrimidines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (90.91)18.7374
1990's1 (9.09)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]