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cycloguanil

AlkaPlorer ID: AK270385

Synonym: None

IUPAC Name: 1-(4-chlorophenyl)-6,6-dimethyl-1,3,5-triazine-2,4-diamine

Structure

SMILES: CC1(C)NC(=N)NC(=N)N1C1=CC=C(Cl)C=C1

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InChI: InChI=1S/C11H14ClN5/c1-11(2)16-9(13)15-10(14)17(11)8-5-3-7(12)4-6-8/h3-6H,1-2H3,(H4,13,14,15,16)

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InChIKey: QMNFFXRFOJIOKZ-UHFFFAOYSA-N

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Reference

PubChem CID: 9049

CAS: 152-53-4

SuperNatural Ⅲ: SN0309442

NPASS: NPC74760

COCONUT: CNP0108815

Source

Species Genus Family Order Class Phylum Kingdom Domain
Miliusa cuneata Miliusa Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 251.721

TPSA？: 75.0

MolLogP？: 1.9448399999999992

Number of H-Donors: 4

Number of H-Acceptors: 2

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Canis lupus familiaris MDCK CC50 52000.0 nM 10.1016/j.ejmech.2017.04.070
Canis lupus familiaris MDCK MCC 4000.0 nM 10.1016/j.ejmech.2017.04.070
Chlorocebus sabaeus Vero IC50 50000.0 nM 10.1021/jm030165t
Chlorocebus sabaeus Vero MCC 100000.0 nM 10.1016/j.ejmech.2017.04.070
Chlorocebus sabaeus Vero Safety ratio 13.0 None 10.1021/jm030165t
Chlorocebus sabaeus Vero Safety ratio 1250.0 None 10.1021/jm030165t
Coxsackievirus B4 Coxsackievirus B4 EC50 100000.0 nM 10.1016/j.ejmech.2017.04.070
Enterococcus faecium Enterococcus faecium IC50 17.0 nM 10.1021/jm00212a010
Enterococcus faecium Enterococcus faecium IC50 3300000.0 nM 10.1021/jm00212a010
Enterococcus faecium Enterococcus faecium Inhibition nan % 10.1021/jm00212a010
Enterococcus faecium Enterococcus faecium Ratio IC50 194000.0 None 10.1021/jm00212a010
Escherichia coli Dihydrofolate reductase Delta Tm 12.25 degrees C 10.1016/j.ejmech.2015.08.021
Escherichia coli Dihydrofolate reductase IC50 20910.0 nM 10.1016/j.ejmech.2015.08.021
Escherichia coli Dihydrofolate reductase Kd 11770.0 nM 10.1016/j.ejmech.2015.08.021
Escherichia coli Dihydrofolate reductase Ki 1020.0 nM 10.1016/j.ejmech.2015.08.021
Escherichia coli Dihydrofolate reductase type 1 Log 1/C 6.4 None 10.1021/jm00381a013
Escherichia coli Escherichia coli IC50 3470000.0 nM 10.1021/jm00212a010
Escherichia coli Escherichia coli Log 1/C 2.47 None 10.1021/jm00150a026
Escherichia coli Escherichia coli Log 1/C 2.5 None 10.1021/jm00150a026
Gallus gallus Dihydrofolate reductase Ki 112.2 nM 10.1021/jm00368a006
Homo sapiens Calu-3 MCC 100000.0 nM 10.1016/j.ejmech.2017.04.070
Homo sapiens Dihydrofolate reductase Ki 55.6 nM 10.1128/aac.01526-09
Homo sapiens Dihydrofolate reductase Ki 410.0 nM 10.1016/j.ejmech.2017.04.070
Homo sapiens Dihydrofolate reductase Ki 43000.0 nM 10.1016/j.ejmech.2017.04.070
Homo sapiens Dihydrofolate reductase Log 1/Ki app 6.2 None 10.1021/jm00368a007
Homo sapiens HeLa MCC 100000.0 nM 10.1016/j.ejmech.2017.04.070
Homo sapiens HepG2-CD81 HEPG2TOX ASSAY - CC50 0.341 uM 10.1126/science.aat9446
Homo sapiens HepG2-CD81 HEPG2TOX ASSAY - CC90 0.341 uM 10.1126/science.aat9446
Homo sapiens KB IC50 41000.0 nM 10.1021/jm030165t
Homo sapiens KB Safety ratio 0.4 None 10.1021/jm030165t
Homo sapiens KB Safety ratio 1.1 None 10.1021/jm030165t
Homo sapiens KB Safety ratio 1025.0 None 10.1021/jm030165t
Homo sapiens Trace amine-associated receptor 1 Activity nan None 10.1016/j.ejmech.2016.10.058
Human respirovirus 3 Human respirovirus 3 EC50 100000.0 nM 10.1016/j.ejmech.2017.04.070
Influenza A virus Influenza A virus EC50 29000.0 nM 10.1016/j.ejmech.2017.04.070
Influenza A virus Influenza A virus EC50 33000.0 nM 10.1016/j.ejmech.2017.04.070
Influenza B virus Influenza B virus EC50 2200.0 nM 10.1016/j.ejmech.2017.04.070
Lacticaseibacillus casei Lacticaseibacillus casei IC50 16300.0 nM 10.1021/jm00212a010
Lacticaseibacillus casei Lacticaseibacillus casei IC50 2400000.0 nM 10.1021/jm00212a010
Lacticaseibacillus casei Lacticaseibacillus casei Inhibition nan % 10.1021/jm00212a010
Lacticaseibacillus casei Lacticaseibacillus casei Ratio IC50 147.0 None 10.1021/jm00212a010
Lactobacillus casei Dihydrofolate reductase Ki 17378.01 nM 10.1021/jm00368a006
Mammalian orthoreovirus 1 Mammalian orthoreovirus 1 EC50 100000.0 nM 10.1016/j.ejmech.2017.04.070
Mus musculus Dihydrofolate reductase Log 1/C 4.84 None 10.1021/jm00369a019
Mus musculus Dihydrofolate reductase Log 1/C 8.27 None 10.1021/jm00369a019
Mus musculus Mus musculus MST nan None 10.1021/jm00134a002
Mus musculus Mus musculus No. of toxic deaths 5.0 None 10.1021/jm00134a002
Mus musculus Trace amine-associated receptor 1 Activity nan None 10.1016/j.ejmech.2016.10.058
Mus musculus Trace amine-associated receptor 5 EC50 10000.0 nM 10.1016/j.ejmech.2016.10.058
Plasmodium berghei Plasmodium berghei LUCIFERASE EXPRESSION CONTROL - IC50 1.58 uM 10.1126/science.aat9446
Plasmodium berghei Plasmodium berghei LUCIFERASE EXPRESSION CONTROL - IC90 1.58 uM 10.1126/science.aat9446
Plasmodium berghei Plasmodium berghei LUCIFERASE INFECTION ASSAY - IC50 0.341 uM 10.1126/science.aat9446
Plasmodium berghei Plasmodium berghei LUCIFERASE INFECTION ASSAY - IC90 0.515 uM 10.1126/science.aat9446
Plasmodium berghei Plasmodium berghei MCD 40.0 mg kg-1 10.1021/jm00212a010
Plasmodium berghei Plasmodium berghei MED 20.0 mg kg-1 10.1021/jm00212a010
Plasmodium berghei Plasmodium berghei MST 7.9 day 10.1021/jm00134a002
Plasmodium berghei Plasmodium berghei MST 8.1 day 10.1021/jm00134a002
Plasmodium berghei Plasmodium berghei MST 13.4 day 10.1021/jm00134a002
Plasmodium berghei Plasmodium berghei MST 21.6 day 10.1021/jm00134a002
Plasmodium berghei Plasmodium berghei MST 21.9 day 10.1021/jm00134a002
Plasmodium berghei Plasmodium berghei MST nan None 10.1021/jm00134a002
Plasmodium falciparum Plasmodium falciparum EC50 38.0 nM 10.1016/j.bmcl.2013.03.067
Plasmodium falciparum Plasmodium falciparum FC 18.0 None 10.1128/aac.00282-08
Plasmodium falciparum Plasmodium falciparum IC50 0.000328 ug.mL-1 10.1021/jm049683+
Plasmodium falciparum Plasmodium falciparum IC50 0.0005 ug.mL-1 10.1021/jm010089z
Plasmodium falciparum Plasmodium falciparum IC50 0.0025 ug.mL-1 10.1021/jm049683+
Plasmodium falciparum Plasmodium falciparum IC50 0.118 nM 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum IC50 0.429 nM 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum IC50 0.587 nM 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum IC50 0.81 nM 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum IC50 1.699 nM 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum IC50 2.77 nM 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum IC50 7.5 nM 10.1016/s0960-894x(01)00798-3
Plasmodium falciparum Plasmodium falciparum IC50 10.0 nM 10.1021/acs.jnatprod.7b00876
Plasmodium falciparum Plasmodium falciparum IC50 37.0 nM 10.1016/j.ejmech.2020.112263
Plasmodium falciparum Plasmodium falciparum IC50 40.0 nM 10.1021/acs.jnatprod.5b01054
Plasmodium falciparum Plasmodium falciparum IC50 40.0 nM 10.1021/jm0009181
Plasmodium falciparum Plasmodium falciparum IC50 116.4 nM 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum IC50 250.0 nM 10.1128/aac.00282-08
Plasmodium falciparum Plasmodium falciparum IC50 320.0 nM 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum IC50 540.0 nM 10.1021/acs.jnatprod.7b00876
Plasmodium falciparum Plasmodium falciparum IC50 2200.0 nM 10.1016/s0960-894x(00)00684-3
Plasmodium falciparum Plasmodium falciparum IC50 2200.0 nM 10.1016/s0960-894x(01)00798-3
Plasmodium falciparum Plasmodium falciparum IC50 2200.0 nM 10.1016/s0960-894x(02)00555-3
Plasmodium falciparum Plasmodium falciparum IC50 2200.0 nM 10.1016/s0960-894x(02)01003-x
Plasmodium falciparum Plasmodium falciparum IC50 2200.0 nM 10.1016/s0960-894x(03)00179-3
Plasmodium falciparum Plasmodium falciparum IC50 2200.0 nM 10.1016/s0960-894x(03)00353-6
Plasmodium falciparum Plasmodium falciparum IC50 2400.0 nM 10.1016/j.ejmech.2020.112263
Plasmodium falciparum Plasmodium falciparum IC50 2430.0 nM 10.1021/jm0009181
Plasmodium falciparum Plasmodium falciparum IC50 3000.0 nM 10.1016/j.bmc.2010.01.068
Plasmodium falciparum Plasmodium falciparum IC50 3200.0 nM 10.1021/acs.jnatprod.5b01054
Plasmodium falciparum Plasmodium falciparum IC50 3700.0 nM 10.1016/j.ejmech.2020.112263
Plasmodium falciparum Plasmodium falciparum IC50 4995.0 nM 10.1016/j.ejmech.2011.02.054
Plasmodium falciparum Plasmodium falciparum IC50 6080.0 nM 10.1016/j.ejmech.2020.112263
Plasmodium falciparum Plasmodium falciparum IC50 37900.0 nM 10.1016/j.ejmech.2020.112263
Plasmodium falciparum Plasmodium falciparum IC50 100000.0 nM 10.1016/j.ejmech.2020.112263
Plasmodium falciparum Plasmodium falciparum IC90 0.152 ug.mL-1 10.1021/jm010089z
Plasmodium falciparum Plasmodium falciparum MIC 64.0 ug.mL-1 10.1016/j.bmcl.2004.11.052
Plasmodium falciparum Plasmodium falciparum MIC 64.0 ug.mL-1 10.1016/j.bmcl.2005.08.023
Plasmodium falciparum Plasmodium falciparum Ratio IC50 1.0 None 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum Ratio IC50 2.0 None 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum Ratio IC50 4.0 None 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum Ratio IC50 6.0 None 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum Ratio IC50 50.0 None 10.1128/aac.00628-10
Plasmodium falciparum Plasmodium falciparum Ratio IC50 746.0 None 10.1128/aac.00628-10
Plasmodium falciparum K1 Dihydrofolate reductase IC50 40.0 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase IC50 2400.0 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase IC50 3700.0 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase IC50 5800.0 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase IC50 37900.0 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase IC50 100000.0 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase IC50 ratio 60.75 None 10.1021/jm0009181
Plasmodium falciparum K1 Dihydrofolate reductase Ki 1.1 nM 10.1021/jm040769c
Plasmodium falciparum K1 Dihydrofolate reductase Ki 1.5 nM 10.1021/jm0009181
Plasmodium falciparum K1 Dihydrofolate reductase Ki 1.5 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase Ki 1.6 nM 10.1021/jm030781p
Plasmodium falciparum K1 Dihydrofolate reductase Ki 2.6 nM 10.1021/jm030781p
Plasmodium falciparum K1 Dihydrofolate reductase Ki 2.6 nM 10.1021/jm970845u
Plasmodium falciparum K1 Dihydrofolate reductase Ki 31.4 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase Ki 82.1 nM 10.1021/jm970845u
Plasmodium falciparum K1 Dihydrofolate reductase Ki 285.0 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase Ki 420.0 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase Ki 570.0 nM 10.1021/jm030781p
Plasmodium falciparum K1 Dihydrofolate reductase Ki 730.0 nM 10.1021/jm030781p
Plasmodium falciparum K1 Dihydrofolate reductase Ki 1140.0 nM 10.1021/jm030781p
Plasmodium falciparum K1 Dihydrofolate reductase Ki 1314.0 nM 10.1021/jm0009181
Plasmodium falciparum K1 Dihydrofolate reductase Ki 1314.0 nM 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase Ki 2130.0 nM 10.1021/jm030781p
Plasmodium falciparum K1 Dihydrofolate reductase Ratio 20.9 None 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase Ratio 190.0 None 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase Ratio 280.0 None 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase Ratio 876.0 None 10.1021/jm0009181
Plasmodium falciparum K1 Dihydrofolate reductase Ratio 876.0 None 10.1021/jm030165t
Plasmodium falciparum K1 Dihydrofolate reductase Relative activity 1.0 None 10.1021/jm0009181
Pneumocystis carinii Dihydrofolate reductase IC50 450.0 nM 10.1021/jm00024a001
Pneumocystis carinii Dihydrofolate reductase Ki 23.3 nM 10.1021/jm00024a001
Pneumocystis carinii Dihydrofolate reductase Ki 109.65 nM 10.1021/jm00006a016
Pneumocystis carinii Dihydrofolate reductase Ki 109000.0 nM 10.1016/j.ejmech.2017.04.070
Punta Toro virus Punta Toro virus EC50 100000.0 nM 10.1016/j.ejmech.2017.04.070
Rattus norvegicus Dihydrofolate reductase IC50 110.0 nM 10.1021/jm00024a001
Respiratory syncytial virus Respiratory syncytial virus EC50 550.0 nM 10.1016/j.ejmech.2017.04.070
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Sindbis virus Sindbis virus EC50 100000.0 nM 10.1016/j.ejmech.2017.04.070
Vesicular stomatitis virus Vesicular stomatitis virus EC50 100000.0 nM 10.1016/j.ejmech.2017.04.070
Yellow fever virus Yellow fever virus EC50 100000.0 nM 10.1016/j.ejmech.2017.04.070
None BC IC50 50000.0 nM 10.1021/jm030165t
None BC Safety ratio 1.3 None 10.1021/jm030165t
None BC Safety ratio 1250.0 None 10.1021/jm030165t
None NON-PROTEIN TARGET IC50 35000.0 nM 10.1021/jm00212a010
None NON-PROTEIN TARGET IC50 900000.0 nM 10.1021/jm00212a010
None NON-PROTEIN TARGET Inhibition nan % 10.1021/jm00212a010
None NON-PROTEIN TARGET Ratio 2.1 None 10.1021/jm00134a002
None NON-PROTEIN TARGET Ratio nan None 10.1021/jm00134a002
None No relevant target LogP 2.94 None 10.1016/j.bmcl.2004.11.052
None No relevant target PKa 3.82 None 10.1016/j.bmcl.2004.11.052
None Unchecked EC50 1100.0 nM 10.1016/j.ejmech.2017.04.070
None Unchecked EC50 17000.0 nM 10.1016/j.ejmech.2017.04.070
None Unchecked EC50 28000.0 nM 10.1016/j.ejmech.2017.04.070
None Unchecked IC50 5000.0 nM 10.1016/j.ejmech.2015.03.011
None Unchecked Ki 1.5 nM 10.1016/j.ejmech.2020.112263
None Unchecked Ki 1.51 nM 10.1128/aac.01526-09
None Unchecked Ki 31.4 nM 10.1016/j.ejmech.2020.112263
None Unchecked Ki 43.2 nM 10.1016/j.ejmech.2020.112263
None Unchecked Ki 285.0 nM 10.1016/j.ejmech.2020.112263
None Unchecked Ki 421.0 nM 10.1016/j.ejmech.2020.112263
None Unchecked Ki 454.0 nM 10.1128/aac.01526-09
None Unchecked Ki 1314.0 nM 10.1016/j.ejmech.2020.112263
None Unchecked Ratio 31.5 None 10.1021/jm970845u
None Unchecked Ratio EC50 15.0 None 10.1016/j.ejmech.2017.04.070
None Unchecked Ratio IC50 26.0 None 10.1021/jm00212a010
None Unchecked Ratio Ki 37.0 None 10.1128/aac.01526-09
None Unchecked Ratio Ki 300.0 None 10.1128/aac.01526-09

Metabolism Information