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Compound Detail

CHEMBL3344081

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CC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)NCc1ccc(-c2scnc2C)cc1)C(C)(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3344081
Phase Preclinical
Structure Type MOL
InChI Key GFVIEZBZIUKYOG-SVFBPWRDSA-N
4
Targets
24
Activities
2
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

472.6
MW (Da)
2.25
ALogP
6
HBA
3
HBD
111.6
PSA (Ų)
0.60
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H32N4O4S
MW 472.61
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness -0.51

Activity Summary

IC50 12 meas. best 6.73
Kd 12 meas. best 6.97

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Von Hippel-Lindau disease tumor suppressor/Elongin B/Elongin C
CHEMBL3301400
 Kd 6.97 6.8575 107.0 4
von Hippel-Lindau disease tumor suppressor
CHEMBL3108660
 Kd 6.95 6.78 113.0 8
von Hippel-Lindau disease tumor suppressor
CHEMBL3108660
 IC50 6.73 6.1583 185.0 6
Unchecked
CHEMBL612545
 IC50 6.69 6.122 204.0 5
von Hippel-Lindau disease tumor suppressor/Elongin-C/Elongin-B/HIF1A
CHEMBL4296117
 IC50 6.1 6.1 800.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.7 mL.min-1.g-1 Mus musculus
T1/2 0.002093 hr Homo sapiens
T1/2 3.0 hr Not specified
T1/2 0.0008278 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Von Hippel-Lindau disease tumor suppressor/Elongin B/Elongin C Kd = 107.0 nM 6.97 Binding affinity to VBC (unknown origin) at 50 uM at 20 degC by surface plasmon ... 28853884
von Hippel-Lindau disease tumor suppressor Kd = 113.0 nM 6.95 Binding affinity to N-terminal His6-tagged VHL (54 to 213 residues) (unknown ori... 34881891
von Hippel-Lindau disease tumor suppressor Kd = 120.0 nM 6.92 Surface Plasmon Resonance Assay: The surface plasmon resonance (SPR) experiments... -
Von Hippel-Lindau disease tumor suppressor/Elongin B/Elongin C Kd = 123.0 nM 6.91 Binding affinity to VBC (unknown origin) at 50 uM at 10 degC by surface plasmon ... 28853884
Von Hippel-Lindau disease tumor suppressor/Elongin B/Elongin C Kd = 150.0 nM 6.82 Displacement of FAM-labeled HIF-1alpha peptide from VBC (unknown origin) by fluo... 28853884
von Hippel-Lindau disease tumor suppressor Kd = 180.0 nM 6.75 Binding affinity to VHL (unknown origin)-NanoLuc fusion protein expressed in HEK... 38809766
von Hippel-Lindau disease tumor suppressor IC50 = 185.0 nM 6.73 Inhibition of VHL (unknown origin) by fluorescence polarization assay 32142281
von Hippel-Lindau disease tumor suppressor Kd = 185.0 nM 6.73 Binding affinity to VHL (unknown origin) by isothermal titration calorimetry 38621319
von Hippel-Lindau disease tumor suppressor Kd = 185.0 nM 6.73 Binding affinity to VHL (unknown origin) assessed as dissociation constant 37224698
von Hippel-Lindau disease tumor suppressor Kd = 185.0 nM 6.73 Binding affinity to VHL E3 ligase (unknown origin) assessed as dissociation cons... 36206538
Von Hippel-Lindau disease tumor suppressor/Elongin B/Elongin C Kd = 185.0 nM 6.73 Binding affinity to VHL (unknown origin)/elongin C (unknown origin)/elongin B (u... 28853884
von Hippel-Lindau disease tumor suppressor Kd = 185.0 nM 6.73 Binding affinity to N-terminal His6-tagged pVHL (54 to 213 amino acids) (unknown... 25166285
von Hippel-Lindau disease tumor suppressor Kd = 200.0 nM 6.7 Binding affinity to VHL (unknown origin)-NanoLuc fusion protein expressed in HEK... 38809766
Unchecked IC50 = 204.0 nM 6.69 Binding affinity to VBC (unknown origin) using FAM-DEALA-Hyp-YIPD as substrate b... 34638033
von Hippel-Lindau disease tumor suppressor IC50 = 458.0 nM 6.34 Binding affinity to VHL (unknown origin) incubated for 60 mins by FP based bindi... 30629437
Unchecked IC50 = 454.0 nM 6.34 Binding affinity to His-TEV-tagged VHL (54 to 213 residues) (unknown origin)/Elo... 30990042
von Hippel-Lindau disease tumor suppressor IC50 = 500.0 nM 6.3 Inhibition of N-terminal 6his tagged human VHL (1 to 213 residues) expressed in ... 38478885
Unchecked IC50 = 696.0 nM 6.16 Fluorescence Polarization Assay (1% in DMSO): Ability of VHL ligands to compete ... -
von Hippel-Lindau disease tumor suppressor IC50 = 696.0 nM 6.16 Fluorescence Polarization Assay (1% DMSO): Ability of VHL ligands to compete for... -
von Hippel-Lindau disease tumor suppressor/Elongin-C/Elongin-B/HIF1A IC50 = 800.0 nM 6.1 Inhibition of His-tagged VHL/elongin B/elongin C (unknown origin) interaction wi... 28692295

Literature References

PubMed DOI Target Context # Activities
28853884 10.1021/acs.jmedchem.7b00675 Von Hippel-Lindau disease tumor suppressor/Elongin B/Elongin C 11
28692295 10.1021/acs.jmedchem.7b00635 von Hippel-Lindau disease tumor suppressor/Serine/threonine-protein kinase TBK1 2
28853884 10.1021/acs.jmedchem.7b00675 No relevant target 2
28853884 10.1021/acs.jmedchem.7b00675 ADMET 2
38809766 10.1021/acs.jmedchem.3c02203 von Hippel-Lindau disease tumor suppressor 2
34638033 10.1016/j.ejmech.2021.113871 Unchecked 2
34638033 10.1016/j.ejmech.2021.113871 No relevant target 2
38478885 10.1021/acs.jmedchem.3c02123 von Hippel-Lindau disease tumor suppressor 1
25166285 10.1021/jm5011258 von Hippel-Lindau disease tumor suppressor 1
38621319 10.1016/j.bmc.2024.117718 von Hippel-Lindau disease tumor suppressor 1
37224698 10.1016/j.bmc.2023.117334 von Hippel-Lindau disease tumor suppressor 1
30629437 10.1021/acs.jmedchem.8b01631 von Hippel-Lindau disease tumor suppressor 1
36242985 10.1016/j.ejmech.2022.114821 von Hippel-Lindau disease tumor suppressor/Vascular endothelial growth factor receptor 2 1
36206538 10.1021/acs.jmedchem.2c01491 von Hippel-Lindau disease tumor suppressor 1
34638033 10.1016/j.ejmech.2021.113871 Hypoxia-inducible factor 1-alpha 1
34638033 10.1016/j.ejmech.2021.113871 HeLa 1
34881891 10.1021/acs.jmedchem.1c01496 von Hippel-Lindau disease tumor suppressor 1
32142281 10.1021/acs.jmedchem.9b01451 von Hippel-Lindau disease tumor suppressor 1
30990042 10.1021/acs.jmedchem.8b01572 Unchecked 1
28692295 10.1021/acs.jmedchem.7b00635 von Hippel-Lindau disease tumor suppressor/Elongin-C/Elongin-B/HIF1A 1

Data from ChEMBL 36 via Core Engine