Compound Detail

CHEMBL2018302

TUBASTATIN A

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CN1CCc2c(c3ccccc3n2Cc2ccc(C(=O)NO)cc2)C1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2018302
Name	TUBASTATIN A
Phase	Preclinical
Structure Type	MOL
InChI Key	GOVYBPLHWIEHEJ-UHFFFAOYSA-N

Targets

337

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

335.4

MW (Da)

2.80

ALogP

HBA

HBD

57.5

PSA (Å²)

0.57

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula	C20H21N3O2
MW	335.41
Aromatic Rings	3
Heavy Atoms	25
NP-Likeness	-0.78

Activity Summary

IC50 316 meas. best 8.72

Ki 16 meas. best 8.71

EC50 5 meas. best 6.84

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histone deacetylase 6 CHEMBL1865	IC50	8.72	7.7826	1.9	100
Histone deacetylase 6 CHEMBL1865	Ki	8.71	8.3617	2.0	6
Histone deacetylase 6 CHEMBL2878	IC50	8.36	8.36	4.4	1
Polyamine deacetylase HDAC10 CHEMBL5103	IC50	7.9	5.8783	12.6	6
Histone deacetylase 8 CHEMBL3192	Ki	7.02	5.9	96.2	3
Unchecked CHEMBL612545	IC50	6.91	5.3	122.1	6
Histone deacetylase 1 CHEMBL325	IC50	6.84	5.2387	144.0	71
Histone deacetylase 6 CHEMBL2878	EC50	6.84	6.84	145.0	1
Histone deacetylase 3 CHEMBL1829	IC50	6.81	5.504	155.0	5
Polyamine deacetylase HDAC10 CHEMBL4802002	IC50	6.66	6.66	220.0	1
Hepatitis C virus CHEMBL379	EC50	6.52	6.52	300.0	1
Histone deacetylase 7 CHEMBL2716	IC50	6.51	5.8833	306.0	6
Histone deacetylase 8 CHEMBL3192	IC50	6.48	6.0722	330.0	37
Histone deacetylase 2 CHEMBL1937	IC50	6.44	5.27	360.0	13
Histone deacetylase 9 CHEMBL4145	IC50	6.21	5.814	621.0	5
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) CHEMBL2111363	IC50	6.11	5.6386	770.0	7
Histone deacetylase 5 CHEMBL2563	IC50	6.0	5.644	1000.0	5
Histone deacetylase 2 CHEMBL1937	Ki	5.98	5.61	1040.0	2
Histone deacetylase 6 CHEMBL1865	EC50	5.96	5.96	1090.0	1
Histone deacetylase 4 CHEMBL3524	IC50	5.96	5.4143	1100.0	7
Histone deacetylase 1 CHEMBL325	Ki	5.89	5.69	1280.0	3
Histone deacetylase 8 CHEMBL3797017	IC50	5.83	5.83	1479.1	1
Histone deacetylase 3 CHEMBL1829	Ki	5.71	5.71	1957.0	1
697 CHEMBL2366253	IC50	5.7	5.7	2006.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.7	5.295	2000.0	4
HCT-116 CHEMBL394	IC50	5.7	5.7	2000.0	2
K562 CHEMBL385	IC50	5.68	5.5667	2070.0	3
HEL CHEMBL613888	IC50	5.59	5.37	2540.0	3
HL-60 CHEMBL383	IC50	5.59	5.47	2540.0	3
Trypanosoma brucei brucei CHEMBL612851	EC50	5.56	5.56	2751.0	1
SH-SY5Y CHEMBL614910	IC50	5.5	5.5	3150.0	1
Jurkat CHEMBL397	IC50	5.47	5.155	3380.0	2
MCF7 CHEMBL387	IC50	5.43	5.43	3700.0	2
Histone deacetylase 11 CHEMBL3310	IC50	5.42	4.998	3790.0	5
CAL-27 CHEMBL1075408	IC50	5.34	5.34	4600.0	1
Histone deacetylase 4 CHEMBL3524	Ki	5.27	5.27	5380.0	1
Histone deacetylase 1 CHEMBL4001	IC50	5.09	5.09	8100.0	1
PC-3 CHEMBL390	IC50	5.07	5.07	8600.0	2
KG-1 CHEMBL612264	IC50	5.05	5.05	8820.0	1
MM1.S CHEMBL4296471	IC50	5.03	5.03	9450.0	1
U-266 CHEMBL2366315	IC50	5.03	5.03	9450.0	1
RPMI-8226 CHEMBL614882	IC50	5.03	5.03	9450.0	1
Histone deacetylase CHEMBL2093865	IC50	5.0	5.0	9900.0	1
MDA-MB-231 CHEMBL400	IC50	4.98	4.98	10400.0	2
LNCaP CHEMBL612518	IC50	4.96	4.96	10880.0	1
No relevant target CHEMBL2362975	IC50	4.92	4.735	12100.0	2
KB CHEMBL398	IC50	4.83	4.83	14810.0	1
NCI-H929 CHEMBL4296391	IC50	4.81	4.81	15420.0	1
HUVEC CHEMBL613979	IC50	4.54	4.35	29170.0	2
U-937 CHEMBL612794	EC50	4.08	4.08	83000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	227.0	ng.hr.mL-1	Mus musculus
AUC	134.0	ng.hr.mL-1	Mus musculus
AUC	227.0	ng.hr.mL-1	Mus musculus
AUC	134.0	ng.hr.mL-1	Mus musculus
CL	222.0	mL.min-1.kg-1	Mus musculus
Cmax	3711.88	nM	Mus musculus
Cmax	402.49	nM	Mus musculus
F	5.9	%	Mus musculus
F	5.9	%	Mus musculus
T1/2	0.5	hr	Mus musculus
T1/2	1.0	hr	Mus musculus
T1/2	0.35	hr	Mus musculus
T1/2	0.86	hr	Mus musculus
T1/2	1.0	hr	Mus musculus
T1/2	0.35	hr	Mus musculus
T1/2	0.86	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histone deacetylase 6	IC50	=	1.9	nM	8.72	Inhibition of human HDAC6 pre-incubated for 5 mins before substrate addition and...	33356256
Histone deacetylase 6	Ki	=	1.97	nM	8.71	Inhibition of purified recombinant human HDAC6 assessed as inhibition constant u...	39067437
Histone deacetylase 6	IC50	=	2.0	nM	8.7	Inhibition of HDAC6 (unknown origin) assessed as fluorescence intensity measured...	23368884
Histone deacetylase 6	Ki	=	3.3	nM	8.48	Inhibition of human HDAC6	25637120
Histone deacetylase 6	Ki	=	3.43	nM	8.46	Inhibition of human full-length recombinant HDAC6 expressed in baculovirus infec...	30525585
Histone deacetylase 6	IC50	=	3.5	nM	8.46	Inhibition of full length human recombinant N-terminal GST-tagged HDAC6 (1 to 12...	27541357
Histone deacetylase 6	IC50	=	3.5	nM	8.46	Inhibition of N-terminal GST tagged human HDAC6 (1 to 1215 residues) expressed i...	28953386
Histone deacetylase 6	IC50	=	3.5	nM	8.46	Inhibition of human HDAC6 using p53 (379 to 382 residues) derived fluorogenic pe...	29945795
Histone deacetylase 6	IC50	=	4.0	nM	8.4	HDAC Activity Assay: HDAC assay is performed using fluorescently-labeled acetyla...	-
Histone deacetylase 6	IC50	=	4.0	nM	8.4	Inhibition of human HDAC6	33035922
Histone deacetylase 6	IC50	=	4.0	nM	8.4	Inhibition of human full length recombinant HDAC6 using p53 (379 to 382 residues...	32608981
Histone deacetylase 6	Ki	=	4.0	nM	8.4	Binding affinity to recombinant HDAC6 (unknown origin) assessed as inhibition co...	36073117
Histone deacetylase 6	IC50	=	4.4	nM	8.36	Inhibition of HDAC6 in mouse N2A cells	32435374
Histone deacetylase 6	IC50	=	4.4	nM	8.36	Inhibition of HDAC6 (unknown origin)	32815366
Histone deacetylase 6	IC50	=	4.4	nM	8.36	Inhibition of human recombinant HDAC6 using AMC-K(Ac)GL as substrate pre-incubat...	37708798
Histone deacetylase 6	IC50	=	6.0	nM	8.22	HDAC Enzyme Activity Inhibition Assay (In Vitro): The effectiveness, or potency,...	-
Histone deacetylase 6	IC50	=	7.0	nM	8.15	Inhibition of recombinant HDAC6 (unknown origin) using RHKK-Ac-AMC as substrate	37633202
Histone deacetylase 6	IC50	=	7.441	nM	8.13	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
Histone deacetylase 6	Ki	=	7.56	nM	8.12	Inhibition of full length recombinant human N-terminal GST-tagged HDAC6 expresse...	29589441
Histone deacetylase 6	IC50	=	9.4	nM	8.03	Inhibition of HDAC6 (unknown origin) measured by fluorescence based assay	36182802

Literature References

PubMed	DOI	Target Context	# Activities
32435374	10.1021/acsmedchemlett.9b00560	ADMET	28
33356256	10.1021/acs.jmedchem.0c01763	Candida albicans	17
28109947	10.1016/j.ejmech.2016.12.032	Unchecked	12
30385227	10.1016/j.bmc.2018.10.022	PC-12	12
36073117	10.1021/acs.jmedchem.2c00853	Histone deacetylase 6	10
29133060	10.1016/j.ejmech.2017.10.040	Unchecked	10
29549837	10.1016/j.ejmech.2018.03.005	Unchecked	9
29150330	10.1016/j.ejmech.2017.10.076	U-937	8
-	10.6019/CHEMBL4689842	Fibroblast	8
-	10.6019/CHEMBL4689842	U2OS	8
29549837	10.1016/j.ejmech.2018.03.005	Histone deacetylase 6	7
27541357	10.1021/acs.jmedchem.6b00157	NON-PROTEIN TARGET	7
30092367	10.1016/j.ejmech.2018.07.069	Unchecked	7
27060764	10.1016/j.ejmech.2016.03.046	Histone deacetylase 6	7
30092367	10.1016/j.ejmech.2018.07.069	Histone deacetylase 6	7
36073117	10.1021/acs.jmedchem.2c00853	ADMET	7
29150330	10.1016/j.ejmech.2017.10.076	Unchecked	6
28337317	10.1021/acsmedchemlett.6b00124	Unchecked	6
29150330	10.1016/j.ejmech.2017.10.076	Histone deacetylase	6
32435374	10.1021/acsmedchemlett.9b00560	Histone deacetylase 6	6

Data from ChEMBL 36 via Core Engine