Compounds > 2-desamino-2-methyl-5,8-dideazaisofolic acid
Page last updated: 2024-10-15

2-desamino-2-methyl-5,8-dideazaisofolic acid

Description

2-desamino-2-methyl-5,8-dideazaisofolic acid: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135625340
CHEMBL ID70515
MeSH IDM0185154

Synonyms (13)

Synonym
2-deamino-2-methyl-5,8-dideazaisofolic acid
CHEMBL70515 ,
bdbm50012516
(s)-2-(4-((2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methylamino)benzamido)pentanedioic acid
2-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid
(2s)-2-[[4-[(2-methyl-4-oxo-1h-quinazolin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
2-desamino-2-methyl-5,8-dideazaisofolic acid
ds-m-iahq
l-glutamic acid, n-(4-(((1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)amino)benzoyl)-
112887-79-3
(2s)-2-[[4-[(2-methyl-4-oxo-3h-quinazolin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
DTXSID60920937
n-(4-{[(4-hydroxy-2-methylquinazolin-6-yl)methyl]amino}benzoyl)glutamic acid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate synthaseHomo sapiens (human)IC50 (µMol)4.46680.00662.06379.5000AID477806
Thymidylate synthaseMus musculus (house mouse)IC50 (µMol)4.50000.00041.322610.0000AID212478; AID212486; AID212492
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

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)
[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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID212492In vitro inhibition against L1210 thymidylate synthase (TS)1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Quinazoline antifolate thymidylate synthase inhibitors: bridge modifications and conformationally restricted analogues in the C2-methyl series.
AID100451Tested for the concentration to inhibit 50% of L1210 cell growth in culture.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Quinazoline antifolate thymidylate synthase inhibitors: bridge modifications and conformationally restricted analogues in the C2-methyl series.
AID98129Growth inhibition of L1210 cells in culture.1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: benzoyl ring modifications in the C2-methyl series.
AID212478Inhibition of partially purified thymidylate synthase (TS)1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: benzoyl ring modifications in the C2-methyl series.
AID477806Inhibition of thymidylate synthase2010European journal of medicinal chemistry, Apr, Volume: 45, Issue:4
3D-QSAR studies on quinazoline antifolate thymidylate synthase inhibitors by CoMFA and CoMSIA models.
AID212486Concentration required for in vitro inhibition of thymidylate synthase1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position.
AID101072Concentration required to inhibit 50 percent growth of L1210 mouse leukemia cells1990Journal of medicinal chemistry, Nov, Volume: 33, Issue:11
Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (66.67)18.2507
2000's1 (16.67)29.6817
2010's1 (16.67)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%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		210
thiophenes
Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.		210mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent
quinazolines
Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.		2.3920azaarene;
mancude organic heterobicyclic parent;
ortho-fused heteroarene;
quinazolines
methotrexate
[no description available]		2.3920dicarboxylic 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.		210dicarboxylic acidEC 1.5.1.3 (dihydrofolate reductase) inhibitor;
mutagen
edatrexate
edatrexate: structure given in first source		210glutamic acid derivative
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.		210folic acids;
N-acyl-amino acid		human metabolite;
mouse metabolite;
nutrient
raltitrexed
[no description available]		2.6930N-acyl-amino acid
nolatrexed
nolatrexed: structure given in first source; RN given refers to dihydrochloride		210
ici 198583
ICI 198583: RN & structure given in first source		2.940
lometrexol
lometrexol: RN & structure given in first source;		210
cb 3717
[no description available]		2.4120N-acyl-L-glutamic acid
5,8-dideazaisofolic acid
5,8-dideazaisofolic acid: structure given in first source		6.9710
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		02.6730