Synonyms
Status
Molecule Category UNKNOWN
ATC P01AX07
UNII UPN4ITI8T4
EPA CompTox DTXSID3023714

Structure

InChI Key NOYPYLRCIDNJJB-UHFFFAOYSA-N
Smiles COc1cc(NCc2ccc3nc(N)nc(N)c3c2C)cc(OC)c1OC
InChI
InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H23N5O3
Molecular Weight 369.43
AlogP 2.74
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 6.0
Polar Surface Area 117.54
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 27.0
Assay Description Organism Bioactivity Reference
Cytotoxic activity evaluated against A549 tumor cells Homo sapiens 5.3 nM
Cytotoxic Activity was evaluated against D54 tumor cells Homo sapiens 60.0 nM
Inhibition of Pneumocystis carinii dihydrofolate reductase None 42.0 nM
Inhibition of Pneumocystis carinii (pc) Dihydrofolate reductase Pneumocystis carinii 42.0 nM
Inhibitory activity against pneumocystis carinii Dihydrofolate reductase Pneumocystis carinii 10.0 nM
Inhibitory activity against Pneumocystis carinii dihydrofolate reductase. Pneumocystis carinii 42.0 nM
Compound was tested for inhibition activity against pneumocystis carinii (Pneumocystis carinii) Dihydrofolate reductase Pneumocystis carinii 42.0 nM
Concentration inhibiting Pneumocystis carinii dihydrofolate reductase Pneumocystis carinii 42.0 nM
Inhibition of Pneumocystis carinii dihydrofolate reductase Pneumocystis carinii 42.0 nM
In vitro inhibitory concentration against Pneumocystis carinii dihydrofolate reductase Pneumocystis carinii 42.0 nM
Inhibition against Dihydrofolate reductase in Pneumocystis carinii Pneumocystis carinii 42.0 nM
Inhibition of Dihydrofolate reductase of Pneumocystis carinii Pneumocystis carinii 42.0 nM
Concentration required to inhibit the Toxoplasma gondii Dihydrofolate reductase by 50% was determined; Range: 8-30 Toxoplasma gondii 16.0 nM
Inhibition of dihydrofolate reductase from Toxoplasma gondii. None 10.0 nM
Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii Pneumocystis carinii 42.0 nM
Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii (pcDHFR) Pneumocystis carinii 42.0 nM
Inhibition of dihydrofolate reductase DHFR in Pneumocystis carinii. Pneumocystis carinii 42.0 nM
Inhibitory activity against dihydrofolate reductase (DHFR) from Pneumocystis carinii Pneumocystis carinii 42.0 nM
Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii was evaluated using 90 uM dihydrofolic acid as substrate Pneumocystis carinii 42.0 nM
Inhibitory activity against DHFR (Dihydrofolate reductase) from Pneumocystis carinii. Pneumocystis carinii 42.0 nM
Inhibitory activity against Pneumocystis carinii Dihydrofolate reductase Pneumocystis carinii 42.0 nM
Inhibitory activity against Pneumocystis carinii dihydrofolate reductase Pneumocystis carinii 42.0 nM
Inhibitory activity against dihydrofolate reductase in Pneumocystis carinii at 37 centigrade. Pneumocystis carinii 26.0 nM
Inhibitory concentration against Dihydrofolate reductase from Pneumocystis carinii (pc) Pneumocystis carinii 42.0 nM
Inhibitory concentration against Pneumocystis carinii Dihydrofolate reductase Pneumocystis carinii 42.0 nM
Inhibitory concentration against Pneumocystis carinii dihydrofolate reductase Pneumocystis carinii 47.0 nM
Inhibitory concentration against dihydrofolate reductase dihydrofolate reductase from Pneumocystis carinii. Pneumocystis carinii 42.0 nM
Inhibition of dihydrofolate reductase (DHFR) from Pneumocystis carinii(pc) Pneumocystis carinii 42.0 nM
Inhibitory activity against purified dihydrofolate reductase from Pneumocystis carinii. Pneumocystis carinii 42.0 nM
Binding affinity was reported with purified recombinant Pneumocystis carinii Dihydrofolate reductase Pneumocystis carinii 0.71 nM
Inhibitory activity against Pneumocystis carinii dihydrofolate reductase (in 90 uM dihydrofolic acid) Pneumocystis carinii 42.0 nM
Inhibition of Pneumocystis carinii dihydrofolate reductase Pneumocystis carinii 42.0 nM
Inhibition of dihydrofolate reductase in pneumocystis carinii. None 42.0 nM
Cytotoxic activity was evaluated against Daoy tumor cells Homo sapiens 12.0 nM
Inhibitory activity against dihydrofolate reductase from pneumocystis carinii Pneumocystis carinii 42.0 nM
Inhibition of Toxoplasma gondii dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibition of Toxoplasma gondii (tc) Dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibition of dihydrofolate reductase (DHFR) from Toxoplasma gondii(tg) Toxoplasma gondii 10.0 nM
Inhibitory activity against Toxoplasma gondii (tg) Dihydrofolate reductase (DHFR) Toxoplasma gondii 5.1 nM
Inhibitory activity against Toxoplasma gondii dihydrofolate reductase. Toxoplasma gondii 10.0 nM
Compound was tested for inhibition activity against Toxoplasma gondii (Toxoplasma gondii) Dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibitory activity against dihydrofolate reductase from Toxoplasma gondii Toxoplasma gondii 10.0 nM
Concentration inhibiting Toxoplasma gondii dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibition of Toxoplasma gondii dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibitory concentration against Toxoplasma gondii dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibition against Dihydrofolate reductase in Toxoplasma gondii Toxoplasma gondii 10.0 nM
Inhibition of Dihydrofolate reductase of Toxoplasma gondii Toxoplasma gondii 10.0 nM
Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii Toxoplasma gondii 10.0 nM
Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii (tgDHFR) Toxoplasma gondii 10.0 nM
Inhibitory activity against dihydrofolate reductase DHFR in Toxoplasma gondii. Toxoplasma gondii 10.0 nM
Inhibitory activity against dihydrofolate reductase (DHFR) from Toxoplasma gondii Toxoplasma gondii 10.0 nM
Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii was evaluated using 90 uM dihydrofolic acid as substrate Toxoplasma gondii 10.0 nM
Inhibitory activity against DHFR (Dihydrofolate reductase) from Toxoplasma gondii. Toxoplasma gondii 10.0 nM
Inhibitory activity against Toxoplasma gondii Dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibitory activity against Toxoplasma gondii dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibitory concentration against Dihydrofolate reductase from Toxoplasma gondii (tg) Toxoplasma gondii 10.0 nM
Inhibitory concentration against Toxoplasma gondii Dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibitory concentration against Toxoplasma gondii dihydrofolate reductase Toxoplasma gondii 16.0 nM
Inhibitory concentration against dihydrofolate reductase DHFR from Toxoplasma gondii Toxoplasma gondii 10.0 nM
Inhibition of Toxoplasma gondii Dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibitory activity against purified Dihydrofolate reductase from Toxoplasma gondii. Toxoplasma gondii 10.0 nM
Inhibitory activity against Toxoplasma gondii dihydrofolate reductase (in 90 uM dihydrofolic acid) Toxoplasma gondii 10.0 nM
Inhibition of dihydrofolate reductase in Toxoplasma gondii. None 10.0 nM
In vitro inhibition of human dihydrofolate reductase None 1.0 nM
Inhibitory concentration against Dihydrofolate reductase from Mycobacterium avium (Mycobacterium avium) Mycobacterium avium 1.5 nM
Inhibition of Dihydrofolate reductase from Pneumocystis carinii (Pneumocystis carinii) Pneumocystis carinii 42.0 nM
Inhibitory activity against recombinant human Dihydrofolate reductase None 18.0 nM
Inhibitory activity against human dihydrofolate reductase Homo sapiens 90.0 nM
Tested for inhibitory activity against dihydrofolate reductase in human None 1.4 nM
Tested for inhibitory concentration against human dihydrofolate reductase(DHFR) None 12.2 nM
Inhibitory concentration against Dihydrofolate reductase from Toxoplasma gondii (Toxoplasma gondii) Toxoplasma gondii 10.0 nM
Inhibitory concentration against Dihydrofolate reductase from rat liver Rattus norvegicus 3.0 nM
Inhibition of dihydrofolate reductase in Candida albicans (in vitro). Candida albicans 40.0 nM
Inhibition of Dihydrofolate reductase enzyme from Candida albicans Candida albicans 1.9 nM
Inhibition of human recombinant Dihydrofolate reductase enzyme None 1.4 nM
Inhibitory activity against Leu22-Phe mutant human Dihydrofolate reductase None 83.0 nM
Inhibitory activity against recombinant Dihydrofolate reductase from Escherichia coli (ecDHFR) Escherichia coli 10.0 nM
Inhibitory activity against Escherichia coli (ec) Dihydrofolate reductase Escherichia coli 7.0 nM
Inhibitory activity against Dihydrofolate reductase from Lactobacillus casei Lactobacillus casei 27.0 nM
Concentration required to inhibit the Mycobacterium avium Dihydrofolate reductase by 50% was determined; Range: 1.3-1.7 Mycobacterium avium 1.5 nM
Concentration required to inhibit the Pneumocystis carinii Dihydrofolate reductase by 50% was determined; Range: 34-66 Pneumocystis carinii 47.0 nM
Inhibition of dihydrofolate reductase from pneumocystis carinii. None 42.0 nM
Inhibitory activity against Dihydrofolate reductase from Lactobacillus casei (lcDHFR) Lactobacillus casei 260.0 nM
Compound was tested for inhibition activity against rat liver lipophilic Dihydrofolate reductase (DHFR). None 3.0 nM
Inhibitory activity against dihydrofolate reductase from rat liver None 3.0 nM
Concentration inhibiting rat liver dihydrofolate reductase. None 3.0 nM
Concentration required to inhibit the rat liver Dihydrofolate reductase by 50% was determined; Range: 7.0-9.2 None 8.0 nM
Inhibition of rat liver dihydrofolate reductase Rattus norvegicus 3.0 nM
In vitro inhibitory concentration against rat liver dihydrofolate reductase None 3.0 nM
Inhibition against Dihydrofolate reductase in rat liver None 3.0 nM
Inhibition of Dihydrofolate reductase (DHFR) of in rat liver Rattus norvegicus 3.0 nM
Inhibitory activity against Dihydrofolate reductase from rat liver None 3.0 nM
Inhibitory activity against Dihydrofolate reductase from rat liver (rlDHFR) None 3.0 nM
Inhibitory activity against dihydrofolate reductase DHFR in rat liver None 3.0 nM
Inhibition of dihydrofolate reductase from rat liver. None 3.0 nM
Inhibitory activity against dihydrofolate reductase (DHFR) from rat liver None 3.0 nM
Inhibitory activity against Dihydrofolate reductase from rat liver was evaluated using 90 uM dihydrofolic acid as substrate None 3.0 nM
Inhibitory activity against DHFR (Dihydrofolate reductase) from Rat liver None 3.0 nM
Inhibitory activity against rat liver dihydrofolate reductase None 3.0 nM
Inhibitory activity against rat liver dihydrofolate reductase. None 3.0 nM
Inhibitory activity against rat liver dihydrofolate reductase (in 90 uM dihydrofolic acid) None 3.0 nM
Inhibitory activity against rat dihydrofolate reductase None 8.0 nM
Inhibitory activity against rat liver Dihydrofolate reductase None 3.0 nM
Inhibitory concentration against Dihydrofolate reductase from Rat liver (rl) None 3.0 nM
Inhibitory concentration against Rat liver Dihydrofolate reductase None 3.0 nM
Inhibitory concentration against dihydrofolate reductase DHFR from rat liver. None 8.0 nM
Inhibition of rat liver dihydrofolate reductase Rattus norvegicus 3.0 nM
Inhibition of rat liver Dihydrofolate reductase Rattus norvegicus 3.0 nM
Inhibition of Dihydrofolate reductase of rat liver Rattus norvegicus 3.0 nM
Inhibition of rat liver dihydrofolate reductase. None 3.0 nM
Inhibition of dihydrofolate reductase (DHFR) from rat liver (rl) None 3.0 nM
Inhibitory activity against purified dihydrofolate reductase from rat None 3.0 nM
Inhibitory concentration against Mycobacterium avium dihydrofolate reductase Mycobacterium avium 1.5 nM
Activity was evaluated against HCT-8 tumor cells Homo sapiens 1.8 nM
Inhibition of 0.5-0.7 uM of U-46,619 induced [14C]5-HT secretion Homo sapiens 750.0 nM
Cytotoxic activity was evaluated against L tumor cells Mus musculus 4.7 nM
Inhibitory concentration against Lactobacillus casei Lactobacillus casei 27.0 nM
Combined effect of active site mutation F31A and F34A on inhibitory effect for F31A/F34A murine dihydrofolate reductase (DHFR) None 0.43 kcat/Km
Inhibitory constant for F31A/F34A murine dihydrofolate reductase (DHFR) None 0.81 nM
Cytotoxic activity was evaluated against P388D1 tumor cells Mus musculus 2.7 nM
Inhibition of 0.5-0.7 uM of U-46,619 induced human platelet aggregation Homo sapiens 770.0 nM
Tested for inhibitory concentration against human SCC25 cell line Homo sapiens 8.0 nM
Tested for inhibitory concentration against SCC-VII murine squamous carcinoma cell line Mus musculus 6.3 nM
Inhibitory activity against Toxoplasma gondii cell growth(ca denotes calculated value) Toxoplasma gondii 20.0 nM
Cytotoxic activity was evaluated against U87MG tumor cells Homo sapiens 11.0 nM
Cytotoxic activity was evaluated against U373MG tumor cells Homo sapiens 9.6 nM
Cytotoxic Activity was evaluated against Vero tumor cells Chlorocebus sabaeus 16.0 nM
Inhibitory compound against Wild-type human DHFR. None 13.0 nM
Combined effect of active site mutation F31A and F34A on inhibitory effect for murine Wild-type dihydrofolate reductase (DHFR) None 1.58 kcat/Km
Inhibitory constant for murine Wild-type dihydrofolate reductase (DHFR) None 0.06 nM
Selectivity ratio of IC50 for rat liver DHFR to IC50 for Toxoplasma gondii DHFR None 0.3
Inhibition of Pneumocystis carinii DHFR using dihydrofolic acid substrate and NADPH cofactor Pneumocystis carinii 42.0 nM
Inhibition of rat liver DHFR using dihydrofolic acid substrate and NADPH cofactor Rattus norvegicus 3.0 nM
Inhibition of Mycobacterium avium DHFR using dihydrofolic acid substrate and NADPH cofactor Mycobacterium avium 1.5 nM
Antiproliferative activity against human RFC expressing Chinese hamster PC43-10 cells Cricetulus griseus 25.0 nM
Antiproliferative activity against human RFC expressing Chinese hamster R2 cells Cricetulus griseus 6.7 nM
Antiproliferative activity against human FRalpha expressing Chinese hamster RT16 cells Cricetulus griseus 13.0 nM
Antiproliferative activity against human FRalpha expressing Chinese hamster RT16 cells in presence of folic acid Cricetulus griseus 4.1 nM
Antiproliferative activity against human FRbeta expressing Chinese hamster D4 cells Cricetulus griseus 11.0 nM
Antiproliferative activity against human FRbeta expressing Chinese hamster D4 cells in presence of folic acid Cricetulus griseus 6.1 nM
Antiproliferative activity against human RFC and FRalpha expressing human KB cells Homo sapiens 58.0 nM
Antiproliferative activity against human RFC and FRalpha expressing human KB cells in presence of folic acid Homo sapiens 155.0 nM
Antiproliferative activity against human RFC and FRalpha expressing human IGROV1 cells Homo sapiens 12.0 nM
Antiproliferative activity against human RFC and FRalpha expressing human IGROV1 cells in presence of folic acid Homo sapiens 8.6 nM
Inhibition of Pneumocystis carinii dihydrofolate reductase Pneumocystis carinii 42.0 nM
Inhibition of rat liver dihydrofolate reductase Rattus norvegicus 3.0 nM
Inhibition of Toxoplasma gondii dihydrofolate reductase Toxoplasma gondii 10.0 nM
Inhibition of Mycobacterium avium DHFR at 37 degC by spectrophotometry Mycobacterium avium 1.5 nM
Inhibition of Pneumocystis carinii DHFR at 37 degC by spectrophotometry Pneumocystis carinii 42.0 nM
Inhibition of rat liver DHFR at 37 degC by spectrophotometry Rattus norvegicus 3.0 nM
Inhibition of Toxoplasma gondii DHFR at 37 degC by spectrophotometry Toxoplasma gondii 10.0 nM
Inhibition of Trypanosoma cruzi DHFR by spectrophotometric assay Trypanosoma cruzi 20.2 nM Inhibition of Trypanosoma cruzi DHFR by spectrophotometric assay Trypanosoma cruzi 6.6 nM
Inhibition of human DHFR by spectrophotometric assay Homo sapiens 80.9 nM
Antimalarial activity against pyrimethamine-resistant Plasmodium falciparum V1S expressing DHFR quadruple mutant with point mutations at codons 108, 51, 59 and 164 gene by [3H]hypoxanthine incorporation assay Plasmodium falciparum 24.8 nM
Antimalarial activity against pyrimethamine-sensitive Plasmodium falciparum 3D7 expressing wild type DHFR by [3H]hypoxanthine incorporation assay Plasmodium falciparum 1.9 nM
Antimalarial activity against Plasmodium falciparum Kenyan isolates by [3H]hypoxanthine incorporation assay Plasmodium falciparum 30.0 nM
Antimalarial activity against Plasmodium falciparum Kenyan isolates expressing DHFR Ser108Asn and Cys59Arg or Ser108Asn and Asn51Ile double mutant by [3H]hypoxanthine incorporation assay Plasmodium falciparum 40.92 nM
Antimalarial activity against Plasmodium falciparum Kenyan isolates expressing DHFR Ser108Asn, Asn51Ile and Cys59Arg triple mutant by [3H]hypoxanthine incorporation assay Plasmodium falciparum 20.91 nM
Antimalarial activity against Plasmodium falciparum isolate Kil-164 expressing DHFR Ser108Asn, Asn51Ile, Cys59Arg and Ile164Leu quadruple mutant by [3H]hypoxanthine incorporation assay Plasmodium falciparum 44.66 nM
Inhibition of Mycobacterium avium DHFR Mycobacterium avium 1.5 nM
Inhibition of Pneumocystis carinii DHFR Pneumocystis carinii 42.0 nM
Inhibition of rat liver DHFR Rattus norvegicus 3.0 nM
Inhibition of Pneumocystis jirovecii recombinant DHFR Pneumocystis jirovecii 2.1 nM
Inhibition of human recombinant DHFR Homo sapiens 2.6 nM
Inhibition of Pneumocystis jirovecii DHFR expressed in Escherichia coli Rosetta-gami B (DE3) assessed as reduction in consumption of NADPH using 18 uM DHFA as substrate Pneumocystis jirovecii 2.1 nM
Inhibition of recombinant human DHFR assessed as reduction in consumption of NADPH using 18 uM DHFA as substrate Homo sapiens 2.6 nM
Inhibition of Toxoplasma gondii DHFR-TS expressed in Escherichia coli BL21 competent cells using DHF as substrate preincubated for 15 mins followed by substrate and NADPH addition and measured after 60 mins by resazurin dye based diaphorase-coupled assay Toxoplasma gondii 1.35 nM
Inhibition of human DHFR expressed in Escherichia coli BL21 competent cells using DHF as substrate preincubated for 15 mins followed by substrate and NADPH addition and measured after 60 mins by resazurin dye based diaphorase-coupled assay Homo sapiens 4.07 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -0.6 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 58.28 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 58.28 %
Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity of VERO-E6 cells after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 330.0 nM Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity of VERO-E6 cells after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 330.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL119
DrugBank DB01157
DrugCentral 2757
FDA SRS UPN4ITI8T4
Human Metabolome Database HMDB0015288
Guide to Pharmacology 7613
KEGG C11154
PharmGKB PA451790
PubChem 5583
SureChEMBL SCHEMBL3983
ZINC ZINC000000598852