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Compound Detail

CHEMBL2364628

RICOLINOSTAT
🧪 Phase II
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🧪 Phase II
O=C(CCCCCCNC(=O)c1cnc(N(c2ccccc2)c2ccccc2)nc1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2364628
Name RICOLINOSTAT
Phase Phase II
Structure Type MOL
InChI Key QGZYDVAGYRLSKP-UHFFFAOYSA-N

Known Names

ACY-1215 ACY-63 Ricolinostat
36
Targets
218
Activities
3
Assay Types
14
PK Parameters
20
Publications
3
Known Names
9
Indications
1
Mechanisms

Molecular Properties

433.5
MW (Da)
4.13
ALogP
6
HBA
3
HBD
107.5
PSA (Ų)
0.24
QED
0
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -stat
USAN Year 2013

Extended Properties

Molecular Formula C24H27N5O3
MW 433.51
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.75

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Histone deacetylase 6 inhibitor INHIBITOR Histone deacetylase 6 ✓ ✓

Indications

Diabetic Neuropathies Breast Neoplasms Cholangiocarcinoma Hematologic Neoplasms Klatskin Tumor Leukemia, Lymphocytic, Chronic, B-Cell Lymphoma Multiple Myeloma Peripheral Nervous System Diseases

Activity Summary

IC50 211 meas. best 8.6
Ki 4 meas. best 9.0
EC50 3 meas. best 9.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MM1.S
CHEMBL4296471
 EC50 9.07 9.07 0.8 1
Histone deacetylase 6
CHEMBL1865
 Ki 9.0 9.0 1.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 8.6 8.1194 2.5 49
Histone deacetylase 3
CHEMBL1829
 IC50 7.84 7.3044 14.3 18
Histone deacetylase 1
CHEMBL325
 IC50 7.8 7.1923 16.0 30
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 7.43 7.3367 37.0 3
Histone deacetylase 2
CHEMBL1937
 IC50 7.32 7.1629 48.0 21
Histone deacetylase 1
CHEMBL325
 Ki 7.13 7.13 74.0 1
Histone deacetylase 6
CHEMBL4739666
 IC50 7.05 7.05 90.0 1
Unchecked
CHEMBL612545
 IC50 7.04 6.0588 90.2 8
Histone deacetylase 8
CHEMBL3192
 IC50 7.0 6.852 100.0 15
Histone deacetylase 3
CHEMBL1829
 Ki 6.91 6.91 123.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 6.9 6.47 125.9 3
697
CHEMBL2366253
 IC50 6.7 6.7 201.0 1
Histone deacetylase 2
CHEMBL1937
 Ki 6.69 6.69 204.0 1
MV4-11
CHEMBL613835
 IC50 6.18 6.15 656.0 3
MV4-11
CHEMBL613835
 EC50 6.15 6.15 710.0 1
T47D
CHEMBL614361
 IC50 6.15 6.15 710.0 1
SU-DHL-6
CHEMBL4296496
 IC50 6.08 6.08 830.0 1
MM1.S
CHEMBL4296471
 IC50 6.08 5.89 840.0 2
RPMI-8226
CHEMBL614882
 IC50 5.92 5.4325 1191.0 4
Histone deacetylase 7
CHEMBL2716
 IC50 5.85 5.85 1400.0 7
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.83 5.83 1468.0 1
HL-60
CHEMBL383
 IC50 5.81 5.488 1540.0 5
SEM
CHEMBL4296493
 IC50 5.79 5.79 1610.0 2
HCT-116
CHEMBL394
 IC50 5.73 5.73 1850.0 1
SUP-B15
CHEMBL4296498
 IC50 5.72 5.585 1920.0 2
OPM-2
CHEMBL2366353
 IC50 5.7 5.7 2000.0 1
HAL-01
CHEMBL2366142
 IC50 5.69 5.69 2040.0 1
KM12
CHEMBL614709
 IC50 5.67 5.67 2150.0 1
Jurkat
CHEMBL397
 IC50 5.62 5.62 2420.0 1
K562
CHEMBL385
 IC50 5.59 5.4133 2540.0 3
HEL
CHEMBL613888
 IC50 5.59 5.51 2540.0 2
KCL-22
CHEMBL4296452
 IC50 5.47 5.4433 3380.0 3
U-266
CHEMBL2366315
 IC50 5.45 5.06 3520.0 2
TALL-1
CHEMBL2366254
 IC50 5.41 5.41 3880.0 1
MDA-MB-468
CHEMBL614335
 IC50 5.31 5.31 4919.0 1
Histone deacetylase 5
CHEMBL2563
 IC50 5.3 5.3 5000.0 7
HPBALL
CHEMBL4296435
 IC50 5.17 5.17 6700.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 5.16 5.16 7000.0 7
A549
CHEMBL392
 IC50 5.11 5.11 7700.0 1
HUVEC
CHEMBL613979
 IC50 4.87 4.87 13620.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 622.0 hr.ng/g Mus musculus
AUC 1442.0 hr.ng/g Mus musculus
AUC 2493.0 hr.ng/g Mus musculus
AUC 308.0 hr.ng/g Mus musculus
AUC 342.0 ng.hr.mL-1 Mus musculus
AUC 566.0 ng.hr.mL-1 Mus musculus
CL 29.4 mL.min-1.kg-1 Mus musculus
Cmax 858.11 nM Mus musculus
Cmax 768.15 nM Mus musculus
F 6.0 % Mus musculus
T1/2 2.62 hr Mus musculus
T1/2 7.5 hr Homo sapiens
T1/2 0.372 hr Mus musculus
Tmax 0.25 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MM1.S EC50 = 0.85 nM 9.07 Antiproliferative activity against human MM1.S cells assessed as reduction in ce... 33359604
Histone deacetylase 6 Ki = 1.0 nM 9.0 Binding affinity to recombinant HDAC6 (unknown origin) assessed as inhibition co... 36073117
Histone deacetylase 6 IC50 = 2.5 nM 8.6 Inhibition of recombinant full length human HDAC6 expressed in insect Sf9 cells ... 34101461
Histone deacetylase 6 IC50 = 2.59 nM 8.59 Inhibition of recombinant full length human HDAC6 expressed in SF9 baculovirus u... 32615502
Histone deacetylase 6 IC50 = 2.59 nM 8.59 Inhibition of full length human recombinant HDAC6 expressed in Sf9 baculovirus s... 35119267
Histone deacetylase 6 IC50 = 3.71 nM 8.43 Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi... -
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of recombinant HDAC6 (unknown origin) using Boc-Lys(acetyl)-AMC as su... 33769811
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) using FTS as substrate preincubated for 10 ... 37660484
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) using fluorophore tripeptide substrate prei... 38387692
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of N-terminal GST-tagged full length human HDAC6 expressed in baculov... 36399875
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) 33035922
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) 36208870
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) using FTS as substrate pre-incubated with c... 34619465
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) using fluorescent peptide substrate 34992037
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) using FTS as substrate preincubated for 6 m... 36073117
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) using FTS as substrate preincubated for 10 ... 33523672
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) using FTS as substrate preincubated for 10 ... 33769811
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of full length human recombinant N-terminal GST-tagged HDAC6 expresse... 28038324
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) 29549837
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of full length recombinant human N-terminal GST-tagged HDAC6 expresse... 29304284

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
29304284 10.1021/acs.jmedchem.7b01404 Unchecked 11
30365892 10.1021/acs.jmedchem.8b01487 Histone deacetylase 6 11
37797564 10.1016/j.ejmech.2023.115833 RPMI-8226 9
37797564 10.1016/j.ejmech.2023.115833 ADMET 8
26443078 10.1021/acs.jmedchem.5b01342 NON-PROTEIN TARGET 6
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
33769811 10.1021/acs.jmedchem.0c01940 Mus musculus 6
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
33769811 10.1021/acs.jmedchem.0c01940 No relevant target 5
28218840 10.1021/acs.jmedchem.6b01507 Leukotriene A-4 hydrolase 5
30365892 10.1021/acs.jmedchem.8b01487 Unchecked 5
29940115 10.1021/acs.jmedchem.8b00393 HEL 5
35119267 10.1021/acs.jmedchem.1c01585 Unchecked 4
30525585 10.1021/acs.jmedchem.8b01590 ADMET 4
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
33691794 10.1186/s13148-021-01037-1 A549 4
25734520 10.1021/jm502011f Unchecked 3

Data from ChEMBL 36 via Core Engine