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Compound Detail

CHEMBL2169920

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O=C1COc2c(CCNCCN(C(=O)CCNCCc3ccc(Cl)c(Cl)c3)C3CCCCC3)ccc(O)c2N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2169920
Phase Preclinical
Structure Type MOL
InChI Key LIBVHXXKHSODII-UHFFFAOYSA-N
2
Targets
17
Activities
3
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

577.5
MW (Da)
4.55
ALogP
6
HBA
4
HBD
102.9
PSA (Ų)
0.21
QED
1
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H38Cl2N4O4
MW 577.55
Aromatic Rings 2
Heavy Atoms 39
NP-Likeness -0.82

Activity Summary

IC50 13 meas. best 7.29
Kd 3 meas. best 6.3
Ki 1 meas. best 6.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
N-lysine methyltransferase SMYD2
CHEMBL2169716
 IC50 7.29 6.3867 51.0 12
N-lysine methyltransferase SMYD2
CHEMBL2169716
 Ki 6.52 6.52 300.0 1
N-lysine methyltransferase SMYD2
CHEMBL2169716
 Kd 6.3 6.3 500.0 2
MDA-MB-231
CHEMBL400
 IC50 4.88 4.88 13100.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 22.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 38.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
N-lysine methyltransferase SMYD2 IC50 = 51.0 nM 7.29 Inhibition of SMYD2 (unknown origin) using N-terminal GST-tagged MAP3K2 and 3H-S... 29856759
N-lysine methyltransferase SMYD2 IC50 = 120.0 nM 6.92 Inhibition of full length human SMYD2 amino acid 1 to 433 expressed in Escherich... 22975593
N-lysine methyltransferase SMYD2 IC50 = 120.0 nM 6.92 Inhibition of recombinant human full-length SMYD2 (1 to 433) using biotin-aminoh... 25406853
N-lysine methyltransferase SMYD2 IC50 = 120.0 nM 6.92 Inhibition of recombinant full-length human SMYD2 (1 to 433) expressed in Escher... 26101576
N-lysine methyltransferase SMYD2 IC50 = 120.0 nM 6.92 Inhibition of SMYD2 (unknown origin) expressed in Escherichia coli BL21 (DE3) us... 27075367
N-lysine methyltransferase SMYD2 IC50 = 120.0 nM 6.92 Inhibition of full length human SMYD2 (1 to 433 residues) expressed in Escherich... 35914250
N-lysine methyltransferase SMYD2 IC50 = 120.0 nM 6.92 Inhibition of SMYD2 (unknown origin) using 3H-SAM as substrate incubated for 1 h... 34656041
N-lysine methyltransferase SMYD2 IC50 = 230.0 nM 6.64 Inhibition of SMYD2 (unknown origin) using biotinylated GSRAHSSHLKSKKGQSTSRH as ... 26101576
N-lysine methyltransferase SMYD2 Ki = 300.0 nM 6.52 Competitive binding affinity to full length human SMYD2 amino acid 1 to 433 expr... 22975593
N-lysine methyltransferase SMYD2 Kd = 500.0 nM 6.3 Binding affinity to recombinant human full-length SMYD2 (1 to 433) by ITC analys... 25406853
N-lysine methyltransferase SMYD2 Kd = 500.0 nM 6.3 Binding affinity to full length human SMYD2 (1 to 433 residues) expressed in Esc... 35914250
N-lysine methyltransferase SMYD2 IC50 = 812.0 nM 6.09 Inhibition of full length 6xHis-tagged SMYD2 (unknown origin) expressed in Esche... 27075367
N-lysine methyltransferase SMYD2 IC50 = 2900.0 nM 5.54 Inhibition of N-terminal 2xc-myc-tagged human SMYD2 transfected in human MDA-MB-... 27075367
MDA-MB-231 IC50 = 13100.0 nM 4.88 Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition... 34656041
N-lysine methyltransferase SMYD2 IC50 = 13900.0 nM 4.86 Inhibition of SMYD2 in human HEK293T cells assessed as BTF3me1 levels by Western... 29856759
N-lysine methyltransferase SMYD2 IC50 = 20000.0 nM 4.7 Inhibition of human SMYD2 by western blot assay 33650861

Literature References

PubMed DOI Target Context # Activities
22975593 10.1016/j.ejmech.2012.08.010 Unchecked 6
25406853 10.1021/jm501234a Unchecked 6
26101576 10.1021/acsmedchemlett.5b00124 Unchecked 6
- 10.6019/CHEMBL3301361 ADMET 5
26101576 10.1021/acsmedchemlett.5b00124 N-lysine methyltransferase SMYD2 5
27075367 10.1021/acs.jmedchem.5b01890 N-lysine methyltransferase SMYD2 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
32988975 10.1242/dev.190678 Unchecked 3
31106145 10.3389/fonc.2019.00306 Unchecked 3
35914250 10.1021/acs.jmedchem.2c00325 N-lysine methyltransferase SMYD2 3
29856759 10.1371/journal.pone.0197372 N-lysine methyltransferase SMYD2 2
22975593 10.1016/j.ejmech.2012.08.010 N-lysine methyltransferase SMYD2 2
31106145 10.3389/fonc.2019.00306 NCI-H460 2
32988975 10.1242/dev.190678 N-lysine methyltransferase SMYD2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
25406853 10.1021/jm501234a N-lysine methyltransferase SMYD2 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
34656041 10.1016/j.ejmech.2021.113880 N-lysine methyltransferase SMYD2 1
34656041 10.1016/j.ejmech.2021.113880 MDA-MB-231 1

Data from ChEMBL 36 via Core Engine