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Compound Detail

CHEMBL356769

TUBACIN
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O=C(CCCCCCC(=O)Nc1ccc([C@H]2O[C@@H](CSc3nc(-c4ccccc4)c(-c4ccccc4)o3)C[C@@H](c3ccc(CO)cc3)O2)cc1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL356769
Name TUBACIN
Phase Preclinical
Structure Type MOL
InChI Key BHUZLJOUHMBZQY-YXQOSMAKSA-N
17
Targets
141
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

721.9
MW (Da)
8.62
ALogP
9
HBA
4
HBD
143.2
PSA (Ų)
0.03
QED
2
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C41H43N3O7S
MW 721.88
Aromatic Rings 5
Heavy Atoms 52
NP-Likeness -0.30

Activity Summary

IC50 113 meas. best 8.4
Ki 22 meas. best 9.05
EC50 6 meas. best 5.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 Ki 9.05 7.9 0.9 3
Histone deacetylase 6
CHEMBL1865
 IC50 8.4 7.93 4.0 25
Histone deacetylase 1
CHEMBL325
 Ki 7.55 6.68 28.0 3
Histone deacetylase 2
CHEMBL1937
 Ki 7.38 6.655 42.0 2
Histone deacetylase 8
CHEMBL3192
 Ki 6.84 6.805 143.1 2
Histone deacetylase 3
CHEMBL1829
 IC50 6.75 6.0438 180.0 8
Histone deacetylase 1
CHEMBL325
 IC50 6.62 5.84 240.0 14
Histone deacetylase 2
CHEMBL1937
 IC50 6.58 5.38 260.0 11
Histone deacetylase 3
CHEMBL1829
 Ki 6.56 6.41 275.0 2
Polyamine deacetylase HDAC10
CHEMBL5103
 Ki 6.43 6.43 373.7 1
Unchecked
CHEMBL612545
 IC50 6.35 6.18 450.0 2
Histone deacetylase 9
CHEMBL4145
 Ki 6.29 5.745 509.3 2
Histone deacetylase 8
CHEMBL3192
 IC50 6.16 5.8845 695.0 11
Histone deacetylase 11
CHEMBL3310
 Ki 6.14 6.14 718.7 1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 5.9 5.9 1270.0 3
Histone deacetylase 5
CHEMBL2563
 Ki 5.82 5.77 1500.0 2
Histone deacetylase HD2
CHEMBL4919
 IC50 5.7 5.7 2000.0 1
Histone deacetylase 6
CHEMBL1865
 EC50 5.6 5.56 2500.0 3
T-24
CHEMBL614774
 EC50 5.54 5.54 2900.0 1
Trypanosoma brucei brucei
CHEMBL612851
 EC50 5.47 5.47 3379.0 1
Histone deacetylase 5
CHEMBL2563
 IC50 5.47 5.47 3350.0 6
Aspartyl/asparaginyl beta-hydroxylase
CHEMBL4680030
 IC50 5.45 5.3475 3570.0 4
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 5.43 5.43 3710.0 6
Histone deacetylase 11
CHEMBL3310
 IC50 5.42 5.42 3790.0 6
Histone deacetylase 9
CHEMBL4145
 IC50 5.37 5.37 4310.0 4
Histone deacetylase 7
CHEMBL2716
 Ki 5.26 5.165 5426.9 2
Histone deacetylase 4
CHEMBL3524
 Ki 5.04 4.905 9124.2 2
Histone deacetylase 7
CHEMBL2716
 IC50 5.01 5.01 9700.0 6
Histone deacetylase 4
CHEMBL3524
 IC50 4.76 4.76 17300.0 6

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 Ki = 0.9 nM 9.05 Inhibition of human HDAC6 25637120
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of recombinant human HDAC6 using RHKKAc fluorogenic peptide substrate 30645113
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of recombinant human HDAC6 using fluorogenic RHKKAc peptide as substr... 20614936
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of HDAC6 (unknown origin) 37797564
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of human recombinant HDAC6 using RHKKAc (379 to 382 residues) as subs... 37902787
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of N-terminal GST-tagged full length human HDAC6 expressed in baculov... 36399875
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of HDAC6 (unknown origin) 27318122
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of human recombinant HDAC6 using ZMAL (Z-(Ac)Lys-AMC) as fluorogenic ... 34251197
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of HDAC6 (unknown origin) 34619465
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of HDAC6 (unknown origin) 35148101
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of HDAC6 (unknown origin) 33992929
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of human HDAC6 using (Z-(Ac)Lys-AMC) as substrate after 90 mins by fl... 30448419
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of human recombinant HDAC6 protein using RHKKAc from p53 as substrate 23627282
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of human recombinant HDAC6 using RHKKAc as substrate 23964961
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of recombinant N-GST-tagged HDAC6 (unknown origin) assessed as reduct... 25454270
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of HADC6 (unknown origin) 31415174
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of HDAC6 (unknown origin) 29549837
Histone deacetylase 6 IC50 = 7.0 nM 8.15 Inhibition of recombinant N-terminal GST-tagged human HDAC6 expressed in baculov... 30645113
Histone deacetylase 6 IC50 = 8.5 nM 8.07 Inhibition of recombinant human HDAC6 using Boc-Lys(Ac)-AMC as substrate pre-inc... 33570940
Histone deacetylase 6 IC50 = 13.0 nM 7.89 Inhibition of HDAC6 20472442

Literature References

PubMed DOI Target Context # Activities
33069066 10.1016/j.bmc.2020.115675 Aspartyl/asparaginyl beta-hydroxylase 5
28218840 10.1021/acs.jmedchem.6b01507 Leukotriene A-4 hydrolase 5
15857140 10.1021/jm049002a Unchecked 3
33488962 10.1021/acsmedchemlett.0c00369 HL-60 3
- 10.6019/CHEMBL5724709 U2OS 2
23964961 10.1021/jm400385r Histone deacetylase 6 2
- 10.1039/C1MD00199J Histone deacetylase 6 2
34251197 10.1021/acs.jmedchem.1c00184 No relevant target 2
25454270 10.1016/j.bmcl.2014.10.022 Histone deacetylase 6 2
30645113 10.1021/acs.jmedchem.8b01090 Histone deacetylase 6 2
- 10.6019/CHEMBL5724709 HEK-293T 2
37611334 10.1016/j.bmc.2023.117444 Histone deacetylase 1 2
37611334 10.1016/j.bmc.2023.117444 Histone deacetylase 6 2
19111466 10.1016/j.bmcl.2008.12.045 T-24 2
20614936 10.1021/ja102758v Unchecked 2
- 10.6019/CHEMBL5724709 Fibroblast 2
15857140 10.1021/jm049002a Histone deacetylase HD2 2
30645113 10.1021/acs.jmedchem.8b01090 Histone deacetylase 1 2
20472442 10.1016/j.bmc.2010.03.080 Histone deacetylase 3 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1

Data from ChEMBL 36 via Core Engine