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name Structure Reference Source Properties Activities Metabolism

3-({1-[(4-carbamimidamidobutyl)carbamoyl]-3-methylbutyl}carbamoyl)oxirane-2-carboxylic acid

AlkaPlorer ID: AK022715

Synonym: None

IUPAC Name: (2S,3S)-3-[[(2S)-1-[4-(diaminomethylideneamino)butylamino]-4-methyl-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylic acid

Structure

SMILES: CC(C)C[C@H](N=C(O)[C@H]1O[C@@H]1C(=O)O)C(O)=NCCCCNC(=N)N

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InChI: InChI=1S/C15H27N5O5/c1-8(2)7-9(20-13(22)10-11(25-10)14(23)24)12(21)18-5-3-4-6-19-15(16)17/h8-11H,3-7H2,1-2H3,(H,18,21)(H,20,22)(H,23,24)(H4,16,17,19)/t9-,10-,11-/m0/s1

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InChIKey: LTLYEAJONXGNFG-DCAQKATOSA-N

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Reference

PubChem CID: 123985

NPASS: NPC483965

Source

Species Genus Family Order Class Phylum Kingdom Domain
Metrodorea stipularis Metrodorea Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 357.4110000000001

TPSA？: 176.91000000000005

MolLogP？: 0.4293700000000024

Number of H-Donors: 6

Number of H-Acceptors: 5

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Carica papaya Papain IC50 2.0 nM 10.1016/j.bmc.2011.10.018
Carica papaya Papain IC50 7.0 nM 10.1016/j.ejmech.2013.08.037
Carica papaya Papain IC50 47.0 nM 10.1016/j.ejmech.2008.09.018
Carica papaya Papain IC50 120.0 nM 10.1039/C2MD20011B
Carica papaya Papain Inhibition nan % 10.1016/j.ejmech.2008.09.018
Carica papaya Papain Ki 5080.0 nM 10.1021/jm4006719
Electrophorus electricus Acetylcholinesterase Inhibition -7.43 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 12.05 % 10.1016/j.bmc.2012.09.040
Homo sapiens Calpain 1 IC50 100.0 nM 10.1021/jm4006719
Homo sapiens Calpain 1 K 4700.0 M-1 s-1 10.1021/jm970197e
Homo sapiens Calpain 1 k obs / 1 2500.0 M-1 s-1 10.1016/0960-894X(95)00042-R
Homo sapiens Calpain 1 k obs / 1 7500.0 M-1 s-1 10.1016/0960-894X(95)00042-R
Homo sapiens Calpain 1 K obs / 1 4700.0 M-1 s-1 10.1016/0960-894X(96)00209-0
Homo sapiens Calpain-9 IC50 11580.0 nM None
Homo sapiens Cathepsin B IC50 0.0049 ug.mL-1 10.1016/s0960-894x(99)00618-6
Homo sapiens Cathepsin B IC50 4.6 nM 10.1039/d1md00316j
Homo sapiens Cathepsin B IC50 5.0 nM 10.1039/C1MD00129A
Homo sapiens Cathepsin B IC50 10.0 nM 10.1074/jbc.m702615200
Homo sapiens Cathepsin B IC50 16.0 nM 10.1021/jm9803065
Homo sapiens Cathepsin B IC50 40.0 nM 10.1021/np500453x
Homo sapiens Cathepsin B Inhibition 24.0 % 10.1016/s0960-894x(99)00618-6
Homo sapiens Cathepsin B Inhibition 29.0 % 10.1016/s0960-894x(99)00618-6
Homo sapiens Cathepsin B Inhibition 52.0 % 10.1016/s0960-894x(99)00618-6
Homo sapiens Cathepsin B Inhibition 75.0 % 10.1016/s0960-894x(99)00618-6
Homo sapiens Cathepsin B Inhibition 75.0 % 10.1021/jm100089e
Homo sapiens Cathepsin B Inhibition 90.0 % 10.1016/s0960-894x(99)00618-6
Homo sapiens Cathepsin B Inhibition 95.0 % 10.1016/s0960-894x(99)00618-6
Homo sapiens Cathepsin B Inhibition 98.0 % 10.1016/s0960-894x(99)00618-6
Homo sapiens Cathepsin B Inhibition 100.0 % 10.1016/s0960-894x(99)00618-6
Homo sapiens Cathepsin B Inhibition nan % 10.1039/d1md00316j
Homo sapiens Cathepsin B Ki 16000.0 nM 10.1016/j.bmc.2009.08.013
Homo sapiens Cathepsin D Inhibition 60.0 % 10.1021/acs.jnatprod.7b00551
Homo sapiens Cathepsin H IC50 190.0 nM 10.1074/jbc.m702615200
Homo sapiens Cathepsin K IC50 4.0 nM 10.1039/C1MD00129A
Homo sapiens Cathepsin L IC50 2.3 nM 10.1039/d1md00316j
Homo sapiens Cathepsin L IC50 13.0 nM 10.1074/jbc.m702615200
Homo sapiens Cathepsin L IC50 16.0 nM 10.1039/C1MD00129A
Homo sapiens Cathepsin L IC50 30.0 nM 10.1021/np500453x
Homo sapiens Cathepsin L IC50 47.0 nM 10.1016/j.bmc.2009.08.013
Homo sapiens Cathepsin L IC50 47.0 nM 10.1021/jm9803065
Homo sapiens Cathepsin L Inhibition -1.3 % 10.1021/jm100089e
Homo sapiens Cathepsin L Inhibition nan % 10.1039/d1md00316j
Homo sapiens Cathepsin L K 110.0 10'3/M/min 10.1021/acs.jmedchem.7b00405
Homo sapiens Cathepsin L Ki 30.0 nM 10.1021/acs.jmedchem.7b00405
Homo sapiens Cathepsin L Kinact 0.0032 /min 10.1021/acs.jmedchem.7b00405
Homo sapiens Cathepsin S IC50 7.0 nM 10.1074/jbc.m702615200
Homo sapiens Cathepsin S Inhibition 99.9 % 10.1016/j.ejmech.2019.06.062
Homo sapiens Dipeptidyl peptidase I IC50 770.0 nM 10.1074/jbc.m702615200
Homo sapiens DNA polymerase kappa Potency 29934.9 nM None
Homo sapiens HEK-293T IC50 nan None 10.1016/j.ejmech.2013.08.037
Homo sapiens HUVEC Inhibition 80.0 % 10.1016/j.bmc.2019.03.032
Homo sapiens Leukocyte elastase IC50 300000.0 nM 10.1128/aac.00968-06
Homo sapiens Lysosomal protective protein IC50 300000.0 nM 10.1128/aac.00968-06
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 5011.9 nM None
Leishmania amazonensis Leishmania amazonensis IC50 nan None 10.1016/j.ejmech.2015.06.005
Mus musculus NIH3T3 IC50 nan None 10.1016/j.ejmech.2013.08.037
Plasmodium falciparum Cysteine protease falcipain-3 IC50 35.0 nM 10.1021/jm0493717
Plasmodium falciparum Cysteine protease falcipain-3 IC50 75.0 nM 10.1021/jm0505765
Plasmodium falciparum Cysteine protease falcipain-3 IC50 481.5 nM 10.1016/j.ejmech.2011.01.008
Plasmodium falciparum Cysteine protease falcipain-3 Inhibition nan % 10.1016/j.bmc.2019.115155
Plasmodium falciparum Falcipain 2 Activity nan None 10.1021/jm070735f
Plasmodium falciparum Falcipain 2 IC50 15.0 nM 10.1021/jm0493717
Plasmodium falciparum Falcipain 2 IC50 15.0 nM 10.1021/jm0505765
Plasmodium falciparum Falcipain 2 IC50 20.0 nM 10.1007/s00044-011-9854-3
Plasmodium falciparum Falcipain 2 IC50 47.0 nM 10.1016/j.bmcl.2009.12.062
Plasmodium falciparum Falcipain 2 IC50 58.0 nM 10.1021/jm058208o
Plasmodium falciparum Falcipain 2 IC50 111.7 nM 10.1016/j.ejmech.2011.01.008
Plasmodium falciparum Falcipain 2 IC50 250.0 nM 10.1021/acs.jmedchem.7b00405
Plasmodium falciparum Falcipain 2 Inhibition 92.0 % 10.1007/s00044-011-9854-3
Plasmodium falciparum Falcipain 2 Inhibition nan % 10.1016/j.bmc.2019.115155
Plasmodium falciparum Falcipain 2 Ka 12.28 10^3/M/s 10.1021/jm701141u
Plasmodium falciparum Falcipain 2 Ki 290.0 nM 10.1016/j.bmc.2010.06.010
Plasmodium falciparum Falcipain 2 Ki 290.0 nM 10.1021/jm701141u
Plasmodium falciparum Falcipain 2 Ki 40300.0 nM 10.1016/j.ejmech.2010.04.003
Plasmodium falciparum Falcipain 2 Kinact 0.46 /min 10.1021/jm701141u
Plasmodium falciparum Falcipain 2 Ratio 1586000.0 None 10.1016/j.bmc.2010.06.010
Plasmodium falciparum Plasmodium falciparum Activity 0.39 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 0.45 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 0.5 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 0.55 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 0.67 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 0.76 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 0.8 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 0.91 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.06 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.15 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.2 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.22 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.25 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.32 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.33 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.4 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.44 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.45 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.69 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 1.78 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 2.05 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 2.07 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 2.1 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 2.11 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 3.0 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 3.15 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity 3.85 None 10.1021/jm5009693
Plasmodium falciparum Plasmodium falciparum Activity nan None 10.1016/j.bmc.2019.115155
Plasmodium falciparum Plasmodium falciparum EC50 2900.0 nM 10.1128/aac.00840-06
Plasmodium falciparum Plasmodium falciparum EC50 nan None 10.1128/aac.00840-06
Plasmodium falciparum Plasmodium falciparum IC50 1940.0 nM 10.1016/j.bmc.2011.10.018
Plasmodium falciparum Plasmodium falciparum IC50 1940.0 nM 10.1016/j.ejmech.2011.01.008
Plasmodium falciparum Plasmodium falciparum IC50 1940.0 nM 10.1016/j.ejmech.2013.08.037
Plasmodium falciparum Plasmodium falciparum IC50 1940.0 nM 10.1039/C2MD20011B
Plasmodium falciparum Plasmodium falciparum IC50 1955.0 nM 10.1016/j.bmcl.2009.04.100
Plasmodium falciparum Plasmodium falciparum IC50 2500.0 nM 10.1021/jm058208o
Plasmodium falciparum Plasmodium falciparum IC50 2511.89 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 3162.28 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 3200.0 nM 10.1021/jm900946n
Plasmodium falciparum Plasmodium falciparum IC50 3690.0 nM 10.1128/aac.00057-08
Plasmodium falciparum Plasmodium falciparum IC50 3981.07 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 5300.0 nM 10.1016/j.bmc.2009.08.013
Plasmodium falciparum Plasmodium falciparum IC50 5300.0 nM 10.1021/jm701141u
Plasmodium falciparum Plasmodium falciparum IC50 5300.0 nM 10.1021/jm900629w
Plasmodium falciparum Plasmodium falciparum IC50 5880.0 nM 10.1128/aac.00057-08
Plasmodium falciparum Plasmodium falciparum IC50 6309.57 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 9300.0 nM 10.1016/j.ejmech.2010.04.003
Plasmodium falciparum Plasmodium falciparum IC50 nan None 10.1016/j.bmcl.2009.12.062
Plasmodium falciparum Plasmodium falciparum IC50 nan None 10.1016/j.ejmech.2012.05.022
Plasmodium falciparum Plasmodium falciparum Inhibition nan % 10.1021/jm5009693
Rattus norvegicus Calpain 1 Activity nan None 10.1021/jm4006719
Rattus norvegicus Cathepsin B Inhibition 99.1 % 10.1016/j.ejmech.2019.06.062
Rattus norvegicus Cathepsin B Inhibition 100.1 % 10.1016/j.ejmech.2019.06.062
Rattus norvegicus Rattus norvegicus Control 24.0 % 10.1021/jm00038a012
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 10.6 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition nan % 10.1021/acs.jnatprod.2c00521
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 relative nan None 10.6019/EOS300033
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.3 % 10.6019/CHEMBL4495565
Sus scrofa Calpain 1 FC 1.0 None 10.1021/jm4006719
Sus scrofa Calpain 1 Ki 3960.0 nM 10.1021/jm4006719
Sus scrofa Carboxylesterase IC50 300000.0 nM 10.1128/aac.00968-06
Toxoplasma gondii Toxoplasma gondii Activity nan None 10.1128/aac.01059-06
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 nan None 10.1021/jm900946n
Trypanosoma brucei rhodesiense Rhodesain IC50 3.1 nM 10.1016/j.bmc.2021.116213
Trypanosoma brucei rhodesiense Rhodesain Inhibition 7.0 % 10.1016/j.bmc.2021.116213
Trypanosoma brucei rhodesiense Rhodesain Inhibition 36.0 % 10.1016/j.ejmech.2019.06.062
Trypanosoma brucei rhodesiense Rhodesain Inhibition 95.0 % 10.1016/j.bmc.2021.116213
Trypanosoma brucei rhodesiense Rhodesain Inhibition 99.0 % 10.1016/j.bmc.2021.116213
Trypanosoma brucei rhodesiense Rhodesain Inhibition 100.0 % 10.1016/j.bmcl.2020.127217
Trypanosoma brucei rhodesiense Rhodesain Inhibition 100.0 % 10.1016/j.ejmech.2019.06.062
Trypanosoma brucei rhodesiense Rhodesain Inhibition nan % 10.1016/j.bmc.2021.116213
Trypanosoma brucei rhodesiense Rhodesain K 261.0 10'3/M/min 10.1021/acs.jmedchem.7b00405
Trypanosoma brucei rhodesiense Rhodesain Ki 35.0 nM 10.1021/acs.jmedchem.7b00405
Trypanosoma brucei rhodesiense Rhodesain Ki nan None 10.1021/jm900946n
Trypanosoma brucei rhodesiense Rhodesain Kinact 0.009 /min 10.1021/acs.jmedchem.7b00405
Trypanosoma cruzi Cruzipain IC50 20.0 nM 10.1016/j.bmc.2021.116213
Trypanosoma cruzi Cruzipain IC50 400.0 nM 10.1016/j.bmc.2016.07.013
Trypanosoma cruzi Cruzipain Inhibition 32.0 % 10.1016/j.ejmech.2019.06.062
Trypanosoma cruzi Cruzipain Inhibition 62.0 % 10.1016/j.ejmech.2012.07.013
Trypanosoma cruzi Cruzipain Inhibition 92.4 % 10.1016/j.ejmech.2019.06.062
Trypanosoma cruzi Cruzipain Inhibition 94.3 % 10.1016/j.ejmech.2019.06.062
Trypanosoma cruzi Cruzipain Inhibition 96.0 % 10.1016/j.ejmech.2019.06.062
Trypanosoma cruzi Cruzipain Inhibition 99.0 % 10.1016/j.bmc.2021.116213
Trypanosoma cruzi Cruzipain Inhibition 100.0 % 10.1016/j.bmc.2016.07.013
Trypanosoma cruzi Cruzipain Inhibition 100.0 % 10.1016/j.ejmech.2019.06.062
Trypanosoma cruzi Cruzipain Inhibition 100.0 % 10.1021/jm070604e
Trypanosoma cruzi Cruzipain Inhibition nan % 10.1016/j.bmc.2016.07.013
Trypanosoma cruzi Cruzipain Inhibition nan % 10.1016/j.ejmech.2019.06.062
None ADMET CC50 nan None 10.1016/j.ejmech.2015.06.005
None ADMET Inhibition 90.0 % 10.1021/jm990412m
None Heme Inhibition nan % 10.1016/j.ejmech.2012.05.022
None Unchecked Activity nan None 10.1021/jm801622x
None Unchecked Activity nan None 10.1074/jbc.m703643200
None Unchecked IC50 9.0 nM 10.1016/j.bmcl.2009.04.100
None Unchecked IC50 17.0 nM 10.1016/j.bmcl.2011.12.011
None Unchecked IC50 17.0 nM 10.1016/j.bmcl.2014.01.074
None Unchecked IC50 17.0 nM 10.1021/jm801622x
None Unchecked IC50 20.0 nM 10.1016/j.bmc.2012.09.008
None Unchecked IC50 24.6 nM 10.1016/j.ejmech.2012.05.022
None Unchecked IC50 30.0 nM 10.1039/C1MD00129A
None Unchecked IC50 47.33 nM 10.1016/j.bmcl.2011.02.008
None Unchecked IC50 55.0 nM 10.1021/jm200149e
None Unchecked IC50 60.0 nM 10.1016/j.ejmech.2013.08.037
None Unchecked IC50 60.0 nM 10.1039/C2MD20011B
None Unchecked IC50 84.0 nM 10.1016/j.bmcl.2009.04.100
None Unchecked IC50 110.0 nM 10.1016/j.bmc.2011.10.018
None Unchecked IC50 125.0 nM 10.1016/j.ejmech.2015.06.005
None Unchecked IC50 300000.0 nM 10.1128/aac.00968-06
None Unchecked IC50 nan None 10.1016/j.ejmech.2012.05.022
None Unchecked Inhibition 36.0 % 10.1016/j.bmc.2008.09.057
None Unchecked Inhibition 92.0 % 10.1016/j.bmc.2012.09.008
None Unchecked Inhibition 97.4 % 10.1016/j.bmcl.2011.12.011
None Unchecked Inhibition 97.4 % 10.1021/jm801622x
None Unchecked Inhibition nan % 10.1016/j.ejmech.2011.02.061
None Unchecked Inhibition nan % 10.1021/jm900629w
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Ki 25.0 nM 10.1021/jm900946n
None Unchecked Ki 220.0 nM 10.1021/jm900946n
None Unchecked Ki 290.0 nM 10.1016/j.bmc.2009.08.013
None Unchecked Ki 290.0 nM 10.1021/jm900047j
None Unchecked Ki 290.0 nM 10.1021/jm900629w
None Unchecked Potency 35481.3 nM None
None Unchecked Ratio 0.33 None 10.1021/jm9803065
None Unchecked Ratio CC50/IC50 nan None 10.1016/j.ejmech.2015.06.005
None Unchecked Ratio IC50 nan None 10.1016/j.ejmech.2013.08.037

Metabolism Information