Structure

InChI Key VAOCPAMSLUNLGC-UHFFFAOYSA-N
Smiles Cc1ncc([N+](=O)[O-])n1CCO
InChI
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C6H9N3O3
Molecular Weight 171.16
AlogP 0.09
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 81.19
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 12.0

Bioactivity

Mechanism of Action Action Reference
DNA inhibitor INHIBITOR FDA Wikipedia
Assay Description Organism Bioactivity Reference
In vitro antiamnesic activity was evaluated against HK-9 strain of Entamoeba histolytica Entamoeba histolytica 0.22 ug.mL-1
In vitro antiprotozoal activity against Entamoeba histolytica Entamoeba histolytica 350.0 nM
Tested for antiamnesic activity against HK-9 strain of Entamoeba histolytica Entamoeba histolytica 0.33 ug.mL-1
The compound was tested in vitro against the protozoa Entamoeba histolytica, for the inhibition of tubulin polymerization in rat brain Entamoeba histolytica 350.0 nM
Antiprotozoal activity against Trichomonas vaginalis Trichomonas vaginalis 286.0 nM
Antiprotozoal activity against Entamoeba histolytica Entamoeba histolytica 771.0 nM
Antiprotozoal activity against Entamoeba histolytica HM-1:IMSS trophozoites after 48 hrs by MTT/PMS assay Entamoeba histolytica HM-1:IMSS 0.04 ug.mL-1
Antiprotozoal activity against Giardia lamblia IMSS:0989:1 after 48 hrs by MTT/PMS assay Giardia intestinalis 0.21 ug.mL-1
Antifungal activity against Giardia intestinalis ATCC 30888 after 48 hrs by XTT assay Giardia intestinalis 0.1 ug.mL-1
Antiprotozoal activity against axenically grown trophozoites of Giardia lamblia IMSS:0989:1 after 48 hrs by MTT method Giardia intestinalis 0.21 ug.mL-1
Antiprotozoal activity against axenically grown trophozoites of Entamoeba histolytica HM1-IMSS after 48 hrs by MTT method Entamoeba histolytica 0.04 ug.mL-1
Antiprotozoal activity against Trichomonas vaginalis GT3 trophozoites after 48 hrs Trichomonas vaginalis 236.0 nM
Antiparasitic activity against Trichomonas vaginalis GT3 trophozoites after 48 hrs by Hill culture method Trichomonas vaginalis 290.0 nM
Antiamnesic activity against Entamoeba histolytica HM-1:IMSS trophozoites after 48 hrs by Hill culture method Entamoeba histolytica HM-1:IMSS 770.0 nM
Antigiardial activity against Giardia lamblia WB (ATCC 30957) trophozoites after 24 hrs by trypan blue assay Giardia intestinalis 2.88 ug.mL-1
Antiprotozoal activity against Entamoeba histolytica HM-1:IMSS after 48 hrs Entamoeba histolytica HM-1:IMSS 350.0 nM
Antiprotozoal activity against Trichomonas vaginalis G3 after 48 hrs Trichomonas vaginalis G3 216.0 nM
Antiparasitic activity against Trichomonas vaginalis T1 after 24 hrs by hemocytometric analysis Trichomonas vaginalis 720.0 nM
Antiparasitic activity against Trichomonas vaginalis G3 after 24 hrs by hemocytometric analysis Trichomonas vaginalis G3 770.0 nM
Antimicrobial activity against Trichomonas vaginalis GT3 after 48 hrs Trichomonas vaginalis 290.0 nM
Antimicrobial activity against Entamoeba histolytica HM-1:IMSS after 48 hrs Entamoeba histolytica HM-1:IMSS 770.0 nM
Inhibition of Helicobacter pylori invasion into human AGS cells at 2.5 uM after 6 hrs Helicobacter pylori 20.0 %
Inhibition of Helicobacter pylori-induced inflammation in human AGS cells assessed as reduction of IL-8 production at 10 uM by ELISA Helicobacter pylori 81.9 %
Antitrypanosomal activity against Trichomonas vaginalis T1 Trichomonas vaginalis 720.0 nM Antitrypanosomal activity against Trichomonas vaginalis T1 Trichomonas vaginalis 0.12 ug.mL-1
Antimicrobial activity against Escherichia coli JM109 transformed with empty vector PQE30 after 16 hrs Escherichia coli 25.0 ug.mL-1
Antimicrobial activity against Escherichia coli JM109 transformed with Entamoeba histolytica NTR1 after 16 hrs Escherichia coli 7.0 ug.mL-1
Antimicrobial activity against Escherichia coli JM109 transformed with Entamoeba histolytica NTR2 after 16 hrs Escherichia coli 8.0 ug.mL-1
Antimicrobial activity against Escherichia coli JM109 transformed with Entamoeba histolytica nim1 after 16 hrs Escherichia coli 750.0 ug.mL-1
Antimicrobial activity against Escherichia coli JM109 transformed with Trichomonas vaginalis nim1 after 16 hrs Escherichia coli 500.0 ug.mL-1
Antiprotozoan activity against Trichomonas vaginalis GT3 trophozoites after 48 hrs Trichomonas vaginalis 290.0 nM
Antiprotozoan activity against Entamoeba histolytica HM1-IMSS trophozoites after 48 hrs Entamoeba histolytica 770.0 nM
Antiprotozoan activity against Trichomonas vaginalis GT3 trophozoites compound treated for 48 hrs measured after 48 hrs washout period Trichomonas vaginalis 236.0 nM
Antiprotozoan activity against Entamoeba histolytica HM1-IMSS trophozoites compound treated for 48 hrs measured after 48 hrs washout period Entamoeba histolytica 350.0 nM
Growth inhibition of Trichomonas vaginalis T1 after 24 hrs by hemocytometry Trichomonas vaginalis 720.0 nM
Growth inhibition of mtronidazole-resistant Trichomonas vaginalis after 24 hrs by hemocytometry Trichomonas vaginalis 210.0 nM
Inhibition of Helicobacter pylori invasion to human AGS cells at 20 ug/ml after 6 hrs by gentamicin assay relative to control Helicobacter pylori 20.0 %
Inhibition of Helicobacter pylori adhesion to human AGS cells at 20 ug/ml after 6 hrs by gentamicin assay relative to control Helicobacter pylori 20.0 %
Antibacterial activity against Trichomonas vaginalis G3 after 24 hrs by hemocytometry Trichomonas vaginalis G3 720.0 nM
Antiprotozoal activity against trophozoite stage of Entamoeba histolytica HM-1:IMSS assessed as growth inhibition after 48 hrs by haemocytometric analysis Entamoeba histolytica HM-1:IMSS 379.8 nM
Antiprotozoal activity against trophozoite stage of Trichomonas vaginalis GT3 assessed as growth inhibition after 48 hrs by haemocytometric analysis Trichomonas vaginalis 236.0 nM
Antiprotozoal activity against clinical isolates of Giardia lamblia IMSS:8901:1 Giardia intestinalis 0.21 ug.mL-1
Antiprotozoal activity against clinical isolates of Entamoeba histolytica HM-1:IMSS Entamoeba histolytica HM-1:IMSS 0.04 ug.mL-1
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 102.59 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 98.27 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control Homo sapiens 17.0 %
Antiprotozoal activity against Entamoeba histolytica HM-1:IMSS Entamoeba histolytica HM-1:IMSS 230.0 nM
Antimicrobial activity against Trichomonas vaginalis GT3 incubated for 48 hrs followed by compound washout measured after 48 hrs Trichomonas vaginalis 316.23 nM Antimicrobial activity against Trichomonas vaginalis GT3 incubated for 48 hrs followed by compound washout measured after 48 hrs Trichomonas vaginalis 290.0 nM
Antiprotozoal activity against trophozoite stage of Trichomonas vaginalis GT3 assessed as growth inhibition Trichomonas vaginalis 0.037 ug.mL-1
Antiprotozoal activity against trophozoite stage of Giardia lamblia IMSS:8909:1 assessed as growth inhibition after 48 hrs Giardia intestinalis 1.22 ug.mL-1
Antiprotozoal activity against trophozoite stage of Entamoeba histolytica HM-1:IMSS assessed as growth inhibition after 48 hrs Entamoeba histolytica HM-1:IMSS 0.23 ug.mL-1
Antimicrobial activity against Trichomonas vaginalis G3 assessed as growth inhibition after 24 hrs by hemocytometry Trichomonas vaginalis G3 720.0 nM
Antiprotozoal activity against Giardia lamblia assessed as growth inhibition Giardia intestinalis 580.0 nM
Antiprotozoan activity against Giardia lamblia G1 Giardia intestinalis 580.0 nM
Antiprotozoal activity against Entamoeba histolytica HM-1:IMSS trophozoites assessed as growth inhibition compound treated for 48 hrs measured 48 hrs post wash-out by MTT assay Entamoeba histolytica HM-1:IMSS 0.04 ug.mL-1
Antiprotozoal activity against Giardia lamblia IMSS: 8909:1 trophozoites assessed as growth inhibition compound treated for 48 hrs measured 48 hrs post wash-out by MTT assay Giardia intestinalis 0.21 ug.mL-1
Trichomonicidal activity against Trichomonas vaginalis GT3 compound treated for 48 hrs followed by incubation for 48 hrs in compound-free medium by cell counting Trichomonas vaginalis 290.0 nM
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 1 hr relative to control Rattus norvegicus 66.3 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 2 hrs relative to control Rattus norvegicus 66.3 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 3 hrs relative to control Rattus norvegicus 60.8 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 4 hrs relative to control Rattus norvegicus 58.9 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 24 hrs relative to control Rattus norvegicus 0.0 %
Trichomonicidal activity against Trichomonas vaginalis JH31A#4 trophozite assessed as inhibition of parasite growth at 300 uM after 24 hrs by resazurin redox dye based fluorimetric microtiter method Trichomonas vaginalis 100.0 %
Trichomonicidal activity against Trichomonas vaginalis JH31A#4 trophozite assessed as inhibition of parasite growth at 150 uM after 24 hrs by resazurin redox dye based fluorimetric microtiter method Trichomonas vaginalis 100.0 %
Trichomonicidal activity against Trichomonas vaginalis JH31A#4 trophozite assessed as inhibition of parasite growth at 75 uM after 24 hrs by resazurin redox dye based fluorimetric microtiter method Trichomonas vaginalis 100.0 %
Trichomonicidal activity against Trichomonas vaginalis JH31A#4 trophozite assessed as inhibition of parasite growth at 37.5 uM after 24 hrs by resazurin redox dye based fluorimetric microtiter method Trichomonas vaginalis 99.37 %
Trichomonicidal activity against Trichomonas vaginalis JH31A#4 trophozite assessed as inhibition of parasite growth at 18.75 uM after 24 hrs by resazurin redox dye based fluorimetric microtiter method Trichomonas vaginalis 95.98 %
Trichomonicidal activity against Trichomonas vaginalis JH31A#4 trophozite assessed as inhibition of parasite growth at 9.37 uM after 24 hrs by resazurin redox dye based fluorimetric microtiter method Trichomonas vaginalis 82.69 %
Trichomonicidal activity against Trichomonas vaginalis C-1:NIH trophozoites infected in NMRI mouse assessed as reduction of pathogenicity at 25 mg/kg/day, po administered for 7 days from day 3 to day 10 post-infection measured at day 15 post-infection Trichomonas vaginalis 93.96 %
Antiprotozoal activity against Entamoeba histolytica HM-1:IMSS Entamoeba histolytica HM-1:IMSS 230.0 nM
Antiparasitic activity against metronidazole sensitive Trichomonas vaginalis F1623 trophozoites after 24 to 48 hrs under anaerobic conditions by Celltiter-Glo assay Trichomonas vaginalis 800.0 nM Antiparasitic activity against metronidazole sensitive Trichomonas vaginalis F1623 trophozoites after 24 to 48 hrs under anaerobic conditions by Celltiter-Glo assay Trichomonas vaginalis 794.33 nM
Antiprotozoal activity against Trichomonas vaginalis GT3 trophozoites incubated for 48 hrs Trichomonas vaginalis 290.0 nM
Antiparasitic activity against trophozoite stage of Trichomonas vaginalis CNCD 147 after 48 hrs Trichomonas vaginalis 236.0 nM
Antiparasitic activity against trophozoite stage of Entamoeba histolytica HM-1:IMSS after 48 hrs Entamoeba histolytica HM-1:IMSS 379.8 nM
Inhibition of Bacillus pasteurii urease using urea as substrate measured after 20 mins by phenol reagent based assay relative to control Sporosarcina pasteurii 13.0 %
Antiparasitic activity against Trichomonas vaginalis assessed as parasite growth inhibition after 24 hrs by hemacytometer Trichomonas vaginalis 720.0 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 17.23 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 2.82 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 13.91 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 12.01 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 26.53 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 1.89 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -8.47 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 3.8 %
Cytotoxicity against human HT-29 cells after 24 hrs by MTT assay Homo sapiens 278.08 ug.mL-1
Cytotoxicity against human A549 cells after 24 hrs by MTT assay Homo sapiens 223.78 ug.mL-1
Cytotoxicity against human MCF7 cells after 24 hrs by MTT assay Homo sapiens 347.96 ug.mL-1
Antiparasitic activity against Entamoeba histolytica HM1-IMSS trophozoites assessed as inhibition of parasitic growth treated for 48 hrs followed by compound washout and measured after 48 hrs by MTT/PMS dye based colorimetric method Entamoeba histolytica 200.0 nM
Antileishmanial activity against Leishmania donovani MHOM/IN/80/Dd8 promastigotes harboring luciferase reporter gene at 50 uM after 48 hrs by Steady-Glo luminescence assay relative to control Leishmania donovani 62.2 %
Antileishmanial activity against Leishmania donovani MHOM/IN/80/Dd8 promastigotes harboring luciferase reporter gene at 25 uM after 48 hrs by Steady-Glo luminescence assay relative to control Leishmania donovani 41.3 %
Antileishmanial activity against Leishmania donovani MHOM/IN/80/Dd8 amastigotes harboring luciferase reporter gene infected in mouse J774 cells at 50 uM after 48 hrs by Steady-Glo luminescence assay relative to control Leishmania donovani 68.1 %
Antileishmanial activity against Leishmania donovani MHOM/IN/80/Dd8 amastigotes harboring luciferase reporter gene infected in mouse J774 cells at 25 uM after 48 hrs by Steady-Glo luminescence assay relative to control Leishmania donovani 31.2 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 18.14 %
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 -0.2 % 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 -0.2 %
Antigiardial activity against Giardia duodenalis GS/M-83-H7 (ATCC 50581) incubated for 3 days by fluorescence method Giardia intestinalis 500.0 nM
Antigiardial activity against Giardia duodenalis WB (ATCC 30957) incubated for 3 days by fluorescence method Giardia intestinalis 500.0 nM
Antigiardial activity against Giardia duodenalis G1 incubated for 3 days by fluorescence method Giardia intestinalis 500.0 nM
Antigiardial activity against Giardia duodenalis Ah1 incubated for 3 days by fluorescence method Giardia intestinalis 500.0 nM
Antigiardial activity against Giardia duodenalis Ah2 incubated for 3 days by fluorescence method Giardia intestinalis 500.0 nM
Antigiardial activity against Giardia duodenalis Ac1 incubated for 3 days by fluorescence method Giardia intestinalis 500.0 nM
Antigiardial activity against Giardia duodenalis Ac2 incubated for 3 days by fluorescence method Giardia intestinalis 500.0 nM
Antigiardial activity against Giardia duodenalis Ec1 incubated for 3 days by fluorescence method Giardia intestinalis 500.0 nM
Antigiardial activity against Giardia duodenalis Ec2 incubated for 3 days by fluorescence method Giardia intestinalis 500.0 nM
Antigiardial activity against Giardia lamblia WB (ATCC 30957) incubated for 3 days by [3H]thymidine incorporation based assay Giardia intestinalis 500.0 nM
Anti-trichomonas activity against Trichomonas vaginalis JT incubated for 48 hrs by hemocytometer based eosin exclusion assay Trichomonas vaginalis 68.0 nM
Anti-trichomonas activity against Trichomonas vaginalis CDC 085 incubated for 48 hrs by hemocytometer based eosin exclusion assay Trichomonas vaginalis 490.0 nM
Anti-trichomonas activity against Trichomonas vaginalis GT3 incubated for 48 hrs Trichomonas vaginalis 930.0 nM

Related Entries

Environmental Exposure

Countries
Bangladesch
Croatia
Hungary
Romania

Cross References

Resources Reference
ChEBI 6909
ChEMBL CHEMBL137
DrugBank DB00916
DrugCentral 1790
FDA SRS 140QMO216E
Human Metabolome Database HMDB0015052
Guide to Pharmacology 10914
KEGG C07203
PDB 2MN
PharmGKB PA450484
PubChem 4173
SureChEMBL SCHEMBL23042
ZINC ZINC000000113442