Molecule

Leupeptin

AlkaPlorer ID: AK005870

Synonym: None

IUPAC Name: (2S)-2-acetamido-N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methylpentanamide

Structure

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

InChI: InChI=1S/C20H38N6O4/c1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23)/t15-,16-,17-/m0/s1

InChIKey: GDBQQVLCIARPGH-ULQDDVLXSA-N

Reference

Leupeptins Produced by the Marine<i>Alteromonas</i>sp. B-10–31

PubChem CID: 72429

CAS: 103476-89-7

LOTUS: LTS0072987

SuperNatural Ⅲ: SN0102451-03

NPASS: NPC191774

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Streptomyces mobaraensis	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria
Blumea balsamifera	Blumea	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 426.5620000000001

TPSA？: 176.74

MolLogP？: 2.535970000000001

Number of H-Donors: 6

Number of H-Acceptors: 5

RingCount: 0

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bos taurus	Alpha-chymotrypsin	Inhibition	nan	%	10.1016/0960-894X(95)00236-M
Bos taurus	Cathepsin B	IC50	310.0	nM	10.1021/jm00060a016
Bos taurus	Plasminogen	IC50	3700.0	nM	10.1021/jm00060a016
Bos taurus	Thrombin	IC50	12000.0	nM	10.1021/jm00060a016
Bos taurus	Trypsin I	IC50	8100.0	nM	10.1021/jm00060a016
Capra hircus	Cathepsin B	Activity	0.0	%	10.1016/j.ejmech.2014.03.007
Capra hircus	Cathepsin B	Activity	0.067	nmol/min/ml	10.1016/j.bmc.2014.05.037
Capra hircus	Cathepsin B	Activity	1.2	%	10.1016/j.ejmech.2014.03.007
Capra hircus	Cathepsin B	Inhibition	98.8	%	10.1016/j.ejmech.2014.03.007
Capra hircus	Cathepsin B	Ki	0.02	nM	10.1016/j.ejmech.2014.03.007
Capra hircus	Cathepsin B	Ki	12.5	nM	10.1016/j.bmc.2014.05.037
Capra hircus	Cathepsin H	Activity	0.0	%	10.1016/j.ejmech.2014.03.007
Capra hircus	Cathepsin H	Activity	0.241	nmol/min/ml	10.1016/j.bmc.2014.05.037
Capra hircus	Cathepsin H	Activity	48.2	%	10.1016/j.ejmech.2014.03.007
Capra hircus	Cathepsin H	Inhibition	51.8	%	10.1016/j.ejmech.2014.03.007
Carica papaya	Papain	Delta Tm	1.0	degrees C	10.1021/acs.jnatprod.0c00201
Carica papaya	Papain	IC50	2.2	nM	10.1021/acs.jnatprod.0c00201
Homo sapiens	Calpain 1	IC50	300.0	nM	10.1016/0960-894X(95)00041-Q
Homo sapiens	Cathepsin B	IC50	0.0092	ug.mL-1	10.1016/s0960-894x(99)00618-6
Homo sapiens	Cathepsin B	IC50	9.4	nM	10.1021/jm9803065
Homo sapiens	Cathepsin B	IC50	47.0	nM	10.1016/j.ejmech.2008.09.018
Homo sapiens	Cathepsin B	IC50	117.0	nM	10.1016/0960-894X(95)00236-M
Homo sapiens	Cathepsin B	Inhibition	15.0	%	10.1016/s0960-894x(99)00618-6
Homo sapiens	Cathepsin B	Inhibition	25.0	%	10.1016/s0960-894x(99)00618-6
Homo sapiens	Cathepsin B	Inhibition	35.0	%	10.1016/s0960-894x(99)00618-6
Homo sapiens	Cathepsin B	Inhibition	55.0	%	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	82.0	%	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	100.0	%	10.1016/s0960-894x(99)00618-6
Homo sapiens	Cathepsin B	Ki	5.0	nM	10.1016/j.bmc.2013.03.062
Homo sapiens	Cathepsin B	Ki	7.0	nM	10.1016/j.bmc.2014.05.037
Homo sapiens	Cathepsin B	Ki	7.0	nM	10.1016/j.ejmech.2014.03.007
Homo sapiens	Cathepsin B	Ratio	1.66	None	10.1016/0960-894X(95)00236-M
Homo sapiens	Cathepsin H	Ki	9200.0	nM	10.1016/j.bmc.2014.05.037
Homo sapiens	Cathepsin H	Ki	9200.0	nM	10.1016/j.ejmech.2014.03.007
Homo sapiens	Cathepsin K	IC50	0.018	ug.mL-1	10.1016/j.bmcl.2006.09.042
Homo sapiens	Cathepsin K	Ki	24.0	nM	10.1016/j.bmcl.2017.02.007
Homo sapiens	Cathepsin L	IC50	2.5	nM	10.1021/jm9803065
Homo sapiens	Cathepsin L	IC50	6.6	nM	10.1021/jm9803065
Homo sapiens	HeLa	TC50	224.0	uM	10.1016/S0960-894X(96)00537-9
Homo sapiens	Hepatocyte growth factor activator	Ki	188.0	nM	10.1021/ml500254r
Homo sapiens	Matriptase	Ki	696.0	nM	10.1021/ml500254r
Homo sapiens	Matriptase	Ki	1900.0	nM	10.1021/jm100183e
Homo sapiens	Plasma kallikrein	IC50	40000.0	nM	10.1021/jm00060a016
Homo sapiens	Plasminogen	IC50	1200.0	nM	10.1021/np049622e
Homo sapiens	Runt-related transcription factor 1/Core-binding factor subunit beta	Potency	31622.8	nM	None
Homo sapiens	Serine protease hepsin	Ki	61.0	nM	10.1021/ml500254r
Homo sapiens	Transmembrane protease serine 6	Ki	2400.0	nM	10.1021/jm100183e
Homo sapiens	Transmembrane protease serine 6	Ki	4100.0	nM	10.1021/jm100183e
Homo sapiens	Trypsin	IC50	600.0	nM	10.1021/acs.jnatprod.2c00382
Human rhinovirus sp.	Human rhinovirus A protease	Inhibition	57.0	%	10.1016/j.bmc.2007.12.030
Human rhinovirus sp.	Human rhinovirus sp.	IC50	224000.0	nM	10.1016/S0960-894X(96)00537-9
Leishmania donovani	Cysteine protease	IC50	10.0	nM	10.1021/jm0505765
Mus musculus	Mus musculus	Inhibition	87.02	%	10.1021/jm058208o
Plasmodium berghei	Plasmodium berghei	Inhibition	89.06	%	10.1016/j.bmc.2008.02.011
Plasmodium berghei	Plasmodium berghei	Inhibition	89.06	%	10.1016/j.ejmech.2008.08.005
Plasmodium berghei	Plasmodium berghei	Inhibition	91.62	%	10.1016/j.bmc.2011.01.050
Plasmodium falciparum	Cysteine protease falcipain-3	IC50	87.0	nM	10.1128/aac.00057-08
Plasmodium falciparum	Cysteine protease falcipain-3	IC50	98.0	nM	10.1128/aac.00057-08
Plasmodium falciparum	Cysteine protease falcipain-3	Inhibition	nan	%	10.1128/aac.00057-08
Plasmodium falciparum	Falcipain 2	IC50	5.8	nM	10.1021/jm058208o
Plasmodium falciparum	Falcipain 2	IC50	87.0	nM	10.1128/aac.00057-08
Plasmodium falciparum	Falcipain 2	IC50	98.0	nM	10.1128/aac.00057-08
Plasmodium falciparum	Falcipain 2	Inhibition	nan	%	10.1128/aac.00057-08
Plasmodium falciparum	Plasmodium falciparum	Activity	89.75	%	10.1016/j.ejmech.2008.09.044
Plasmodium falciparum	Plasmodium falciparum	Activity	nan	None	10.1128/aac.00057-08
Plasmodium falciparum	Plasmodium falciparum	GI	nan	None	10.1128/aac.00057-08
Plasmodium falciparum	Plasmodium falciparum	IC50	6260.0	nM	10.1021/jm058208o
Plasmodium falciparum	Plasmodium falciparum	IC50	18000.0	nM	10.1128/aac.00057-08
Plasmodium falciparum	Plasmodium falciparum	IC50	74000.0	nM	10.1128/aac.00057-08
Sus scrofa	Calpain 1	IC50	80.0	nM	10.1016/j.bmcl.2005.08.064
Sus scrofa	Trypsin	IC50	200.0	nM	10.1021/np500106w
Sus scrofa	Trypsin	IC50	500.0	nM	10.1021/np500106w
None	ADMET	Inhibition	87.02	%	10.1016/j.ejmech.2007.01.001
None	No relevant target	T1/2	0.01667	hr	10.1021/acs.jmedchem.9b01060
None	No relevant target	T1/2	0.125	hr	10.1021/acs.jmedchem.9b01060
None	Unchecked	Activity	nan	None	10.1074/jbc.m705646200
None	Unchecked	Activity	nan	None	10.1128/aac.00057-08
None	Unchecked	Delta Tm	0.2	degrees C	10.1021/acs.jnatprod.0c00201
None	Unchecked	IC50	70.3	nM	10.1016/0960-894X(95)00236-M
None	Unchecked	IC50	165.0	nM	None
None	Unchecked	IC50	30000.0	nM	10.1021/acs.jnatprod.0c00201
None	Unchecked	IC50	129000.0	nM	10.1016/j.bmc.2020.115756
None	Unchecked	IC50	nan	None	None
None	Unchecked	Inhibition	0.0	%	10.1016/j.bmcl.2005.08.064
None	Unchecked	Inhibition	nan	%	10.1016/j.ejmech.2011.02.061
None	Unchecked	Inhibition	nan	%	10.1128/aac.00057-08
None	Unchecked	Potency	112.2	nM	None
None	Unchecked	Ratio	1.4	None	10.1021/jm9803065
None	Unchecked	Ratio Ki	3.0	None	10.1021/ml500254r