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Compound Detail

CHEMBL2169919

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CC(C)N(CCCNC(=O)Nc1ccc(C(C)(C)C)cc1)C[C@H]1O[C@@H](n2ccc3c(N)ncnc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2169919
Phase Preclinical
Structure Type MOL
InChI Key WXRGFPHDRFQODR-ICLZECGLSA-N
8
Targets
32
Activities
4
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

539.7
MW (Da)
2.85
ALogP
9
HBA
5
HBD
150.8
PSA (Ų)
0.26
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C28H41N7O4
MW 539.68
Aromatic Rings 3
Heavy Atoms 39
NP-Likeness -0.67

Activity Summary

IC50 15 meas. best 9.4
Ki 7 meas. best 6.52
EC50 6 meas. best 8.4
Kd 4 meas. best 9.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone-lysine N-methyltransferase, H3 lysine-79 specific
CHEMBL1795117
 Kd 9.6 9.6 0.2 3
Histone-lysine N-methyltransferase, H3 lysine-79 specific
CHEMBL1795117
 IC50 9.4 8.3744 0.4 9
MOLM-13
CHEMBL3706572
 EC50 8.4 8.4 4.0 1
MV4-11
CHEMBL613835
 EC50 8.4 8.4 4.0 1
THP-1
CHEMBL614245
 EC50 8.4 8.4 4.0 1
Histone-lysine N-methyltransferase, H3 lysine-79 specific
CHEMBL1795117
 EC50 8.05 8.05 9.0 1
Unchecked
CHEMBL612545
 IC50 7.08 6.01 84.0 3
Histone-lysine N-methyltransferase, H3 lysine-79 specific
CHEMBL1795117
 Ki 6.52 6.52 300.0 1
Protein arginine N-methyltransferase 5
CHEMBL1795116
 IC50 6.3 6.3 500.0 1
Unchecked
CHEMBL612545
 EC50 6.16 6.16 700.0 2
Protein arginine N-methyltransferase 7
CHEMBL3562175
 IC50 5.12 5.12 7500.0 1
Unchecked
CHEMBL612545
 Kd 4.75 4.75 18000.0 1
Zika virus
CHEMBL4296612
 IC50 4.45 4.45 35190.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 33.88 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 150.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone-lysine N-methyltransferase, H3 lysine-79 specific Kd = 0.253 nM 9.6 Binding affinity to recombinant N-terminal DOT1L (1 to 420 residues) (unknown or... 23250418
Histone-lysine N-methyltransferase, H3 lysine-79 specific Kd = 0.25 nM 9.6 Binding affinity to recombinant N-terminal DOT1L (1 to 420 residues) (unknown or... 23250418
Histone-lysine N-methyltransferase, H3 lysine-79 specific Kd = 0.25 nM 9.6 Binding affinity to DOT1L (unknown origin) by surface plasmon resonance analysis 25406853
Histone-lysine N-methyltransferase, H3 lysine-79 specific IC50 = 0.4 nM 9.4 Inhibition of human recombinant DOT1L using [3H]-SAM as substrate after 30 mins 22975593
Histone-lysine N-methyltransferase, H3 lysine-79 specific IC50 = 0.4 nM 9.4 Competitive inhibition of human recombinant DOT1L (1 to 416 amino acid residues)... 23433670
Histone-lysine N-methyltransferase, H3 lysine-79 specific IC50 = 0.4 nM 9.4 Inhibition of recombinant human DOT1L using chicken erythrocyte oligonucleosomes... -
Histone-lysine N-methyltransferase, H3 lysine-79 specific IC50 = 0.4 nM 9.4 Inhibition of recombinant human DOT1L (1 to 416) using [3H]-SAM, SAM and nucleos... 25406853
Histone-lysine N-methyltransferase, H3 lysine-79 specific IC50 = 0.5 nM 9.3 Inhibition of recombinant N-terminal DOT1L (1 to 420 residues) (unknown origin) ... 23250418
Histone-lysine N-methyltransferase, H3 lysine-79 specific IC50 = 0.86 nM 9.07 Inhibition of recombinant human N-terminal GST-tagged DOT1L (1 to 420 residues) ... 31978781
THP-1 EC50 = 4.0 nM 8.4 Antiproliferative activity against human THP1 cells containing MLL-AF9 23879463
MOLM-13 EC50 = 4.0 nM 8.4 Antiproliferative activity against human MOLM13 cells containing MLL-AF9 23879463
MV4-11 EC50 = 4.0 nM 8.4 Antiproliferative activity against human MV4-11 cells containing MLL-AF4 23879463
Histone-lysine N-methyltransferase, H3 lysine-79 specific EC50 = 9.0 nM 8.05 Inhibition of DOT1L (unknown origin)-mediated H3K79 methylation by cell based as... 23879463
Unchecked IC50 = 84.0 nM 7.08 Downregulation of H3K79 methylation in human MCF-10A cells by fluorescence micro... 23250418
Histone-lysine N-methyltransferase, H3 lysine-79 specific IC50 = 84.0 nM 7.08 Inhibition of DOT1L in human MCF10A cells assessed as reduction of H3K79 level 25406853
Unchecked IC50 = 264.0 nM 6.58 Downregulation of H3K79 methylation in human A-431 cells incubated for 3 to 4 da... 23250418
Histone-lysine N-methyltransferase, H3 lysine-79 specific Ki = 300.0 nM 6.52 Inhibition of human recombinant DOT1L using [3H]-SAM as substrate after 30 mins 22975593
Protein arginine N-methyltransferase 5 IC50 = 500.0 nM 6.3 Inhibition of human PRMT5 23250418
Histone-lysine N-methyltransferase, H3 lysine-79 specific IC50 = 700.0 nM 6.16 Inhibition of DOT1L in human MV4-11 cells assessed as downregulation of HOXA9/ME... -
Histone-lysine N-methyltransferase, H3 lysine-79 specific IC50 = 700.0 nM 6.16 Inhibition of DOT1L in human MOLM13 cells assessed as downregulation of HOXA9/ME... -

Literature References

PubMed DOI Target Context # Activities
22975593 10.1016/j.ejmech.2012.08.010 Unchecked 9
25406853 10.1021/jm501234a Unchecked 9
23250418 10.1038/ncomms2304 Unchecked 6
23250418 10.1038/ncomms2304 Histone-lysine N-methyltransferase, H3 lysine-79 specific 5
25406853 10.1021/jm501234a Histone-lysine N-methyltransferase, H3 lysine-79 specific 5
33691794 10.1186/s13148-021-01037-1 A549 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL3301361 ADMET 3
- 10.1039/C1MD00199J Histone-lysine N-methyltransferase, H3 lysine-79 specific 3
25893041 10.1021/ml500467h PRMT5/MEP50 complex 2
30170321 10.1016/j.ejmech.2018.08.057 Unchecked 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
25406853 10.1021/jm501234a NON-PROTEIN TARGET 2
31978781 10.1016/j.ejmech.2019.112023 Histone-lysine N-methyltransferase, H3 lysine-79 specific 2
23879463 10.1021/jm4007752 Histone-lysine N-methyltransferase, H3 lysine-79 specific 2
23879463 10.1021/jm4007752 Unchecked 2
23879463 10.1021/jm4007752 MV4-11 2
23879463 10.1021/jm4007752 MOLM-13 2
22975593 10.1016/j.ejmech.2012.08.010 Histone-lysine N-methyltransferase, H3 lysine-79 specific 2

Data from ChEMBL 36 via Core Engine