Compound Detail

CHEMBL29292

UBENIMEX

🧪 Phase II

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🧪 Phase II

CC(C)C[C@H](NC(=O)[C@@H](O)[C@H](N)Cc1ccccc1)C(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL29292
Name	UBENIMEX
Phase	Phase II
Structure Type	MOL
InChI Key	VGGGPCQERPFHOB-RDBSUJKOSA-N

Known Names

(-)-bestatin Bestatin NK-421 NSC-265489 Ubenimex

Targets

196

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

308.4

MW (Da)

0.53

ALogP

HBA

HBD

112.7

PSA (Å²)

0.56

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-imex

Extended Properties

Molecular Formula	C16H24N2O4
MW	308.38
Aromatic Rings	1
Heavy Atoms	22
NP-Likeness	0.36

Indications

Hypertension, Pulmonary Lymphedema

Activity Summary

IC50 164 meas. best 9.3

Ki 26 meas. best 9.3

EC50 3 meas. best 6.05

Kd 3 meas. best 5.69

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cytosol aminopeptidase CHEMBL1671610	IC50	9.3	9.3	0.5	1
Cytosol aminopeptidase CHEMBL3965	IC50	9.3	7.125	0.5	2
Aminopeptidase N CHEMBL2590	Ki	9.3	6.196	0.5	5
Cytosol aminopeptidase CHEMBL3965	Ki	9.22	8.46	0.6	2
Unchecked CHEMBL612545	Ki	8.8	6.7733	1.6	6
Unchecked CHEMBL612545	IC50	8.8	5.6982	1.6	11
Bacterial leucyl aminopeptidase CHEMBL3750	Ki	8.8	8.8	1.6	1
Aminopeptidase N CHEMBL2590	IC50	8.3	5.4108	5.0	38
Plasmodium falciparum CHEMBL364	IC50	8.1	5.49	8.0	7
Aminopeptidase B CHEMBL2452	Ki	7.85	7.535	14.0	2
Leucyl-cystinyl aminopeptidase CHEMBL3712	Ki	7.7	6.53	20.0	2
Aminopeptidase N CHEMBL4117	Ki	6.72	6.72	190.0	1
Leukotriene A-4 hydrolase CHEMBL4618	IC50	6.7	5.78	200.0	9
Aminopeptidase N CHEMBL4117	IC50	6.55	6.55	284.0	1
Leukotriene A-4 hydrolase CHEMBL4618	Ki	6.5	6.5	320.0	1
Cytosol aminopeptidase CHEMBL1671610	Ki	6.3	6.3	500.0	1
Aminopeptidase N CHEMBL1907	IC50	6.1	4.93	800.0	27
Plasmodium falciparum CHEMBL364	EC50	6.05	5.6967	900.0	3
Leukotriene A-4 hydrolase CHEMBL4618	Kd	5.69	5.4367	2050.0	3
Aminopeptidase N CHEMBL1907	Ki	5.62	5.62	2370.0	1
Aminopeptidase N CHEMBL2189140	Ki	5.52	5.52	3030.0	1
72 kDa type IV collagenase CHEMBL333	IC50	5.47	4.786	3400.0	5
Puromycin-sensitive aminopeptidase CHEMBL2264	IC50	5.46	5.46	3500.0	2
Cytosol aminopeptidase CHEMBL5624	IC50	5.28	5.115	5200.0	2
Aminopeptidase B CHEMBL2452	IC50	5.22	5.22	6000.0	1
Aminopeptidase B CHEMBL2836	IC50	5.22	5.22	6000.0	1
U-937 CHEMBL612794	IC50	5.02	5.02	9560.0	1
Endoplasmic reticulum aminopeptidase 1 CHEMBL5939	IC50	4.96	4.5367	11000.0	3
HepG2 CHEMBL395	IC50	4.84	4.84	14520.0	1
A549 CHEMBL392	IC50	4.8	4.8	15930.0	1
Solute carrier family 15 member 2 CHEMBL3325	Ki	4.75	4.75	18000.0	1
Aminopeptidase N CHEMBL3259	IC50	4.71	4.71	19400.0	1
PLC-PRF-5 CHEMBL1075561	IC50	4.64	4.64	22810.0	1
Aminopeptidase N CHEMBL2189140	IC50	4.63	4.63	23200.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.37	4.165	42540.0	4
HCT-116 CHEMBL394	IC50	4.36	4.36	44060.0	1
U-266 CHEMBL2366315	IC50	4.36	4.36	43480.0	1
MDA-MB-231 CHEMBL400	IC50	4.3	4.3	50600.0	2
HL-60 CHEMBL383	IC50	4.06	4.06	86400.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	11499.0	ng.hr.mL-1	Rattus norvegicus
CL	115.95	mL.min-1.kg-1	Rattus norvegicus
Cmax	7458.33	nM	Rattus norvegicus
MRT	3.436	hr	Rattus norvegicus
T1/2	3.404	hr	Rattus norvegicus
Vd	34.18	L.kg-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aminopeptidase N	Ki	=	0.5	nM	9.3	Competitive inhibition of pig APN using L-leucine-p-nitroanilide as substrate by...	22796349
Cytosol aminopeptidase	IC50	=	0.5	nM	9.3	Inhibition of bovine lens cytosolic leucine aminopeptidase by Dixon plot analysi...	21292493
Cytosol aminopeptidase	IC50	=	0.5	nM	9.3	Inhibition of human recombinant Leucine aminopeptidase 3	39011823
Cytosol aminopeptidase	Ki	=	0.6	nM	9.22	Binding affinity for cytosolic leucine aminopeptidase (LAP) from porcine kidney	12801228
Unchecked	IC50	=	1.6	nM	8.8	Inhibition of Aeromonas proteolytica aminopeptidase by Dixon plot analysis	21292493
Bacterial leucyl aminopeptidase	Ki	=	1.6	nM	8.8	Inhibition of Aeromonas proteolytica leucyl aminopeptidase using L-leucine para-...	24055078
Unchecked	Ki	=	1.6	nM	8.8	Inhibition of recombinant Plasmodium falciparum A-M1 assessed as inhibition cons...	33534577
Aminopeptidase N	IC50	=	5.0	nM	8.3	Inhibitory activity against rabbit kidney aminopeptidase using 10 nM of [3H]Leu-...	3897541
Plasmodium falciparum	IC50	=	8.0	nM	8.1	Antimalarial activity against Plasmodium falciparum 3D7 infected in human O posi...	23176597
Aminopeptidase B	Ki	=	14.0	nM	7.85	Inhibition of aminopeptidase B or arginyl aminopeptidase purified from rat liver	2566685
Cytosol aminopeptidase	Ki	=	20.0	nM	7.7	Inhibitory activity against Leucine aminopeptidase	3184126
Leucyl-cystinyl aminopeptidase	Ki	=	20.0	nM	7.7	Inhibition of leucine aminopeptidase	2566685
Unchecked	Ki	=	25.0	nM	7.6	Inhibition of recombinant Plasmodium falciparum A-M17 assessed as inhibition con...	33534577
Aminopeptidase B	Ki	=	60.0	nM	7.22	Inhibitory activity against aminopeptidase B	3184126
Unchecked	IC50	=	170.0	nM	6.77	Inhibition of partially purified soluble aminopeptidase from rat brain	3184127
Aminopeptidase N	Ki	=	190.0	nM	6.72	Inhibition of Plasmodium falciparum recombinant M1-aminopeptidase expressed in E...	21366301
Leukotriene A-4 hydrolase	IC50	=	200.0	nM	6.7	Inhibition of full length human recombinant Leukotriene A-4 hydrolase expressed ...	39011823
Leukotriene A-4 hydrolase	IC50	=	266.0	nM	6.58	Inhibition of recombinant human full length C-terminal His6-tagged LTA4H express...	32551007
Aminopeptidase N	IC50	=	284.0	nM	6.55	Inhibitory activity for Plasmodium falciparum Zinc aminopeptidase	12873488
Leukotriene A-4 hydrolase	IC50	=	300.0	nM	6.52	Inhibition of human C-terminal his6-tagged/N-terminal T7 gene leader sequence-ta...	27651294

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	455
29202398	10.1016/j.ejmech.2017.11.074	PLC-PRF-5	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
-	10.6019/CHEMBL5303304	Fibroblast	7
29202398	10.1016/j.ejmech.2017.11.074	Rattus norvegicus	7
-	10.6019/CHEMBL5303304	HEK-293T	7
27651294	10.1016/j.bmc.2016.08.047	Leukotriene A-4 hydrolase	7
22901392	10.1016/j.bmcl.2012.07.086	MDA-MB-231	7
1347791	10.1021/jm00083a013	Mus musculus	6
33534577	10.1021/acs.jmedchem.0c01721	Unchecked	6
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
-	10.6019/CHEMBL5303304	U2OS	5
28728898	10.1016/j.bmc.2017.06.047	Unchecked	5
18458130	10.1128/aac.01327-07	Leucine aminopeptidase	5
27253989	10.1021/acs.jmedchem.6b00190	MCF7	5
30737134	10.1016/j.bmc.2019.01.041	Unchecked	4
22901392	10.1016/j.bmcl.2012.07.086	Aminopeptidase N	4
24900417	10.1021/ml3000758	Aminopeptidase N	4
29202398	10.1016/j.ejmech.2017.11.074	Unchecked	4

Data from ChEMBL 36 via Core Engine