Page last updated: 2024-10-15

5,11-methenyltetrahydrohomofolate

Cross-References

ID SourceID
PubMed CID135407589
CHEMBL ID13659
SCHEMBL ID9688062
MeSH IDM0101213

Synonyms (18)

Synonym
118252-44-1
5,11-methenyltetrahydrohomofolate
5-dacthf
CHEMBL13659 ,
(s)-2-{4-[3-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-propylamino]-benzoylamino}-pentanedioic acid
bdbm50005520
2-{4-[3-(2,4-diamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-propylamino]-benzoylamino}-pentanedioic acid
(2s)-2-[[4-[3-(2,6-diamino-4-oxo-1h-pyrimidin-5-yl)propylamino]benzoyl]amino]pentanedioic acid
l-glutamic acid, n-(4-((3-(2,6-diamino-1,4-dihydro-4-oxo-5-pyrimidinyl)propyl)amino)benzoyl)-
5-deazacyclotetrahydrofolate
SCHEMBL9688062
DTXSID90922646
n-(4-{[3-(6-amino-4-hydroxy-2-imino-1,2-dihydropyrimidin-5-yl)propyl]amino}benzoyl)glutamic acid
CPVRCGLCOADOPV-ZDUSSCGKSA-N ,
n-[4-[3-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propylamino]benzoyl]-l-glutamic acid
(4-((3-(2,6-diamino-4-oxo-1,4-dihydropyrimidin-5-yl)propyl)amino)benzoyl)-l-glutamic acid
(2s)-2-[[4-[3-(2,4-diamino-6-oxo-1h-pyrimidin-5-yl)propylamino]benzoyl]amino]pentanedioic acid
AKOS040746484

Bioavailability

ExcerptReference
" The aim of this study was to evaluate the effects of 5-MTHF in combination with propranolol on HVPG and nitric oxide bioavailability markers in patients with cirrhosis and portal hypertension."( 5-MTHF enhances the portal pressure reduction achieved with propranolol in patients with cirrhosis: A randomized placebo-controlled trial.
Andreone, P; Berzigotti, A; Bosch, J; Di Donato, R; Gitto, S; Renzulli, M; Roncarati, G; Schepis, F; Simoni, P; Villa, E; Vukotic, R, 2023
)
" HVPG and markers of nitric oxide bioavailability (BH4, ADMA and tHcy) were measured again at the end of treatment."( 5-MTHF enhances the portal pressure reduction achieved with propranolol in patients with cirrhosis: A randomized placebo-controlled trial.
Andreone, P; Berzigotti, A; Bosch, J; Di Donato, R; Gitto, S; Renzulli, M; Roncarati, G; Schepis, F; Simoni, P; Villa, E; Vukotic, R, 2023
)
"Groups were similar in terms of baseline clinical and hemodynamic data and nitric oxide bioavailability markers."( 5-MTHF enhances the portal pressure reduction achieved with propranolol in patients with cirrhosis: A randomized placebo-controlled trial.
Andreone, P; Berzigotti, A; Bosch, J; Di Donato, R; Gitto, S; Renzulli, M; Roncarati, G; Schepis, F; Simoni, P; Villa, E; Vukotic, R, 2023
)
" This effect appears to be mediated by improved nitric oxide bioavailability in the hepatic microcirculation."( 5-MTHF enhances the portal pressure reduction achieved with propranolol in patients with cirrhosis: A randomized placebo-controlled trial.
Andreone, P; Berzigotti, A; Bosch, J; Di Donato, R; Gitto, S; Renzulli, M; Roncarati, G; Schepis, F; Simoni, P; Villa, E; Vukotic, R, 2023
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydrofolate reductaseHomo sapiens (human)IC50 (µMol)100.00000.00060.87267.3000AID56808
Thymidylate synthaseHomo sapiens (human)IC50 (µMol)100.00000.00662.06379.5000AID212152
Trifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)IC50 (µMol)3.00000.00580.31223.0000AID72755
Bifunctional purine biosynthesis protein ATICHomo sapiens (human)IC50 (µMol)70.67500.01000.26000.7000AID31286; AID31288; AID31289; AID31302
Bifunctional purine biosynthesis protein ATICMus musculus (house mouse)IC50 (µMol)53.00000.70004.00009.4000AID31293; AID31294; AID31295; AID31296
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Folylpolyglutamate synthase, mitochondrialHomo sapiens (human)Km7.30000.40004.53447.3000AID71220; AID71223
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (51)

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)
brainstem developmentTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
GMP biosynthetic processTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
'de novo' IMP biosynthetic processTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
glycine metabolic processTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
purine ribonucleoside monophosphate biosynthetic processTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
response to organic substanceTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
response to inorganic substanceTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
cerebellum developmentTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
cerebral cortex developmentTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
'de novo' AMP biosynthetic processTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
tetrahydrofolate biosynthetic processTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
'de novo' XMP biosynthetic processTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
purine nucleotide biosynthetic processTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
adenine biosynthetic processTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
brainstem developmentBifunctional purine biosynthesis protein ATICHomo sapiens (human)
nucleobase-containing compound metabolic processBifunctional purine biosynthesis protein ATICHomo sapiens (human)
GMP biosynthetic processBifunctional purine biosynthesis protein ATICHomo sapiens (human)
'de novo' IMP biosynthetic processBifunctional purine biosynthesis protein ATICHomo sapiens (human)
response to inorganic substanceBifunctional purine biosynthesis protein ATICHomo sapiens (human)
cerebellum developmentBifunctional purine biosynthesis protein ATICHomo sapiens (human)
cerebral cortex developmentBifunctional purine biosynthesis protein ATICHomo sapiens (human)
animal organ regenerationBifunctional purine biosynthesis protein ATICHomo sapiens (human)
'de novo' AMP biosynthetic processBifunctional purine biosynthesis protein ATICHomo sapiens (human)
dihydrofolate metabolic processBifunctional purine biosynthesis protein ATICHomo sapiens (human)
tetrahydrofolate biosynthetic processBifunctional purine biosynthesis protein ATICHomo sapiens (human)
'de novo' XMP biosynthetic processBifunctional purine biosynthesis protein ATICHomo sapiens (human)
cellular response to interleukin-7Bifunctional purine biosynthesis protein ATICHomo sapiens (human)
liver developmentFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
nucleobase-containing compound metabolic processFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
glutamate metabolic processFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
one-carbon metabolic processFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
folic acid-containing compound metabolic processFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
animal organ regenerationFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
folic acid metabolic processFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
tetrahydrofolylpolyglutamate biosynthetic processFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (18)

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)
phosphoribosylamine-glycine ligase activityTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
phosphoribosylformylglycinamidine cyclo-ligase activityTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
phosphoribosylglycinamide formyltransferase activityTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
ATP bindingTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
metal ion bindingTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
IMP cyclohydrolase activityBifunctional purine biosynthesis protein ATICHomo sapiens (human)
protein homodimerization activityBifunctional purine biosynthesis protein ATICHomo sapiens (human)
cadherin bindingBifunctional purine biosynthesis protein ATICHomo sapiens (human)
phosphoribosylaminoimidazolecarboxamide formyltransferase activityBifunctional purine biosynthesis protein ATICHomo sapiens (human)
tetrahydrofolylpolyglutamate synthase activityFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
ATP bindingFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
metal ion bindingFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

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)
cytosolTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
cytosolTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
extracellular exosomeTrifunctional purine biosynthetic protein adenosine-3Homo sapiens (human)
cytosolBifunctional purine biosynthesis protein ATICHomo sapiens (human)
plasma membraneBifunctional purine biosynthesis protein ATICHomo sapiens (human)
membraneBifunctional purine biosynthesis protein ATICHomo sapiens (human)
extracellular exosomeBifunctional purine biosynthesis protein ATICHomo sapiens (human)
cytosolBifunctional purine biosynthesis protein ATICHomo sapiens (human)
mitochondrial inner membraneFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
mitochondrial matrixFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
cytosolFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
cytoplasmFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
mitochondrionFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
cytosolFolylpolyglutamate synthase, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (67)

Assay IDTitleYearJournalArticle
AID31293Diglutamyl homologue inhibition activity against the AICAR formyltransferase was determined against L cell1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID105289Antitumor activity on MOLT-4 T-cell acute lymphoblastic leukemia cell lines1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID105287Ability to inhibit [3H]methotrexate transport into MOLT-4 cells in vitro1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Thienyl and thiazolyl acyclic analogues of 5-deazatetrahydrofolic acid.
AID153426Effect on P388 tumor cell growth in mice. The percentage of increased life span was determined administered 5 mg/kg schedule - t.i.d., days 1-41990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID94568Evaluated for reversal of L cell inhibition, where reversal of toxicity was evaluated by the addition of Leucovorin (0.2 uM)1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID72876Ability to inhibit glycinamide ribonucleotide transformylase (GAR-Tfase) in vitro, using hog liver with (6R)-10-formyl-FH4 as cofactor1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Thienyl and thiazolyl acyclic analogues of 5-deazatetrahydrofolic acid.
AID94566Evaluated in vitro for ability to inhibit the L cell lines.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID72754Inhibition of GAR transformylase in hog liver1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.
AID102785In vitro inhibition of growth of MCF-7 human breast adenocarcinoma using 72 hours continuous exposure1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and biological activity of open-chain analogues of 5,6,7,8-tetrahydrofolic acid--potential antitumor agents.
AID103898Antitumor activity on MCF-7 breast adenocarcinoma cell lines1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID71346Apparent Km in uM for its activation for Hog Liver Folyl-polyglutamate synthase was determined1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID31287Diglutamyl homologue inhibition activity against the AICAR formyltransferase was determined against MOLT-4; NT=Not tested1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID31302In vitro inhibitory activity against MOLT-4 T-cell leukemia cell AICAR transformylase1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and biological activity of open-chain analogues of 5,6,7,8-tetrahydrofolic acid--potential antitumor agents.
AID200371Evaluated for inhibitory activity on Serine hydroxymethyl transferase (Lcell) at folate substrate concentration of 160 uM1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID201678Antitumor activity on SW 480 colon adenocarcinoma cell lines1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID73656Inhibition activity against Glycinamide ribotide formyltransferase against L cell1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID31296Triglutamyl homologue inhibition activity against AICAR formyltransferase was determined against L cell1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID94706Evaluated for reversal of L cell inhibition, where reversal of toxicity was evaluated by the addition of Thymidine (20 uM)1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID231102Ratio of app Km to ral Vmax1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID102441Effective dose which is required to inhibit 50% of the cell growth of MCF-7 cells in culture.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.
AID71347Compound was evaluated for the substrate activity for hog liver Folyl-polyglutamate synthase1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.
AID73791Triglutamyl homologue inhibition activity against Glycinamide ribonucleotide transformylase (GAR-TFase)was determined against L cell1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID105644Inhibition of the uptake of [3H]MTX influx into MOLT-4 cells.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.
AID153425Effect on P388 tumor cell growth in mice. The percentage of increased life span was determined administered 10 mg/kg schedule - t.i.d., days 1-41990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID31289Inhibition activity against AICAR formyltransferase determined against MOLT-41990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID71345Vmax of Hog Folyl-polyglutamate synthase relative to aminopterin1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Thienyl and thiazolyl acyclic analogues of 5-deazatetrahydrofolic acid.
AID3139Inhibitory activity against 5,10-methylenetetrahydrofolate dehydrogenase from Escherichia coli at a concentration of 0.1 mM; NT=Not tested1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID71227Percent Vmax of Hog folyl-poly-glutamate synthase in presence relative to aminopterin1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and biological activity of open-chain analogues of 5,6,7,8-tetrahydrofolic acid--potential antitumor agents.
AID73789Inhibition activity against Glycinamide ribonucleotide transformylase (GAR-TFase) against L cell1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID73657Triglutamyl homologue inhibition activity against Glycinamide ribonucleotide transformylase (GAR-TFase)was determined against hog liver; NT=Not tested1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID31294Hexaglutamyl homologue inhibition activity against the AICAR formyltransferase was determined against L cell1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID31295Inhibition activity against AICAR formyltransferase determined against L cell1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID8816Antitumor activity on A-427 lung carcinoma cell lines1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID94567Evaluated for reversal of L cell inhibition, where reversal of toxicity was evaluated by the addition of Hypoxanthine (37 uM)1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID105508Compound was evaluated for inhibition of [3H]methotrexate uptake into MOLT-4 cells1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and biological activity of open-chain analogues of 5,6,7,8-tetrahydrofolic acid--potential antitumor agents.
AID43846Compound was evaluated for reversal of growth inhibition against human lymphoblastic leukemic CCRF-CEM cells at 0.46 uM concentration and with 300 uM of AICA1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
Synthesis and biological activity of acyclic analogues of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid.
AID3143Evaluated for inhibitory activity on 5,10-methylenetetrahydrofolate dehydrogenase(L cell) at folate substrate concentration of 100 uM1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID43845Compound was evaluated for reversal of growth inhibition against human lymphoblastic leukemic CCRF-CEM cells at 0.46 uM concentration and with 100 uM of hypoxanthine1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
Synthesis and biological activity of acyclic analogues of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid.
AID73787Diglutamyl homologue inhibition activity against the Glycinamide ribonucleotide transformylase (GAR-TFase)was determined against L cell1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID56808Inhibition of dihydrofolate reductase (DHFR) in WIL2 cells1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.
AID72755In vitro inhibition of hog liver GAR transformylase with (6R)-10-formyl-FH4 as cofactor1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and biological activity of open-chain analogues of 5,6,7,8-tetrahydrofolic acid--potential antitumor agents.
AID23336Maximum drug concentration (Vmax), relative to a control of 50 uM aminopterin included in each experiment.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.
AID212152Inhibition of thymidylate synthase (TS) in human1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.
AID3083Evaluated for inhibitory activity on 10-formyltetrahydrofolate synthetase(L cell) at folate substrate concentration of 100 uM1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID216454Antitumor activity on WiDr colon adenocarcinoma cell lines1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID73788Hexaglutamyl homologue inhibition activity against the Glycinamide ribonucleotide transformylase (GAR-TFase) was determined against L cell1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID31288Hexaglutamyl homologue inhibition activity against the AICAR formyltransferase was determined against MOLT-41990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID103887Ability to inhibit growth of MCF-7 human breast adenocarcinoma in vitro1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Thienyl and thiazolyl acyclic analogues of 5-deazatetrahydrofolic acid.
AID153427Effect on P388 tumor cell growth in mice. The percentage of increased life span was determined administered 7.5 mg/kg schedule - b.i.d., days 1-31990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID212147Evaluated for inhibitory activity on Thymidylate synthase(calf thymus) at folate substrate concentration of 200 uM1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID58005Evaluated for inhibitory activity on Dihydrofolate reductase(rat liver) at folate substrate concentration of 45 uM1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID56620Evaluated in vitro for ability to inhibit the Detroit 98 cell lines1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID153428Effect on P388 tumor cell growth in mice. The percentage of increased life span was determined administered 75 mg/kg schedule - QD,days1,5,91990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID3138Evaluated for inhibitory activity on 5,10-Methenyl Tetrahydrofolate Cyclohydrolase(L cell) at folate substrate concentration of 100 uM1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID43705Cytotoxicity against human lymphoblastic leukemic CCRF-CEM cell line was evaluated as the concentration required for 50% inhibition of the growth of the control value1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
Synthesis and biological activity of acyclic analogues of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid.
AID43706In vitro antitumor activity was assessed from rate of cell growth of CCRF/CEM cell line1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Thienyl and thiazolyl acyclic analogues of 5-deazatetrahydrofolic acid.
AID71223Km value of Hog folyl-poly-glutamate synthase in presence relative to aminopterin1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Synthesis and biological activity of open-chain analogues of 5,6,7,8-tetrahydrofolic acid--potential antitumor agents.
AID75851Diglutamyl homologue inhibition activity against the Glycinamide ribonucleotide transformylase (GAR-TFase)was determined against hog liver; NT=Not tested1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID43847Compound was evaluated for reversal of growth inhibition against human lymphoblastic leukemic CCRF-CEM cells at 0.46 uM concentration and with 5 uM of Thymidine1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
Synthesis and biological activity of acyclic analogues of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid.
AID71349Relative Vmax for its activation for Hog Liver Folyl-polyglutamate synthase was determined1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID107929Evaluated for inhibitory activity on Methionine synthase(L cell) at folate substrate concentration of 100 uM1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID31286Inhibition of 5-aminoimidazole-4-carboxamide AICAR formyltransferase in MOLT-4 cells1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.
AID43560Antitumor activity on CCRF-CEM T-cell acute lymphoblastic leukemia cell lines1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID94569Evaluated for reversal of L cell inhibition, where reversal of toxicity was evaluated by the addition of Thymidine Hypoxanthine1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID230506Ratio of relative Vmax values to that of apparent Km values.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Synthesis and biological evaluation of 5-deazaisofolic acid, 5-deaza-5,6,7,8-tetrahydroisofolic acid, and their N9-substituted analogues.
AID73660Hexaglutamyl homologue inhibition activity against the Glycinamide ribonucleotide transformylase (GAR-TFase) was determined against hog liver1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Synthesis and biological activity of an acyclic analogue of 5,6,7,8-tetrahydrofolic acid, N-[4-[[3-(2,4-diamino-1,6-dihydro-6-oxo-5- pyrimidinyl)propyl]amino]-benzoyl]-L-glutamic acid.
AID71220Km of Hog Folyl-polyglutamate synthase relative to aminopterin1994Journal of medicinal chemistry, Jun-24, Volume: 37, Issue:13
Thienyl and thiazolyl acyclic analogues of 5-deazatetrahydrofolic acid.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (59)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (6.78)18.7374
1990's12 (20.34)18.2507
2000's26 (44.07)29.6817
2010's13 (22.03)24.3611
2020's4 (6.78)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 (%)
Trials5 (7.94%)5.53%
Reviews6 (9.52%)6.00%
Case Studies1 (1.59%)4.05%
Observational0 (0.00%)0.25%
Other51 (80.95%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]