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Compound Detail

CHEMBL305881

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O=C(OCCN1CCOCC1)C1(c2ccccc2)CCCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL305881
Phase Preclinical
Structure Type MOL
InChI Key RQHKZUBCUZVZEF-UHFFFAOYSA-N
6
Targets
15
Activities
2
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

317.4
MW (Da)
2.76
ALogP
4
HBA
0
HBD
38.8
PSA (Ų)
0.78
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H27NO3
MW 317.43
Aromatic Rings 1
Heavy Atoms 23
NP-Likeness -0.94

Activity Summary

IC50 8 meas. best 7.36
Ki 7 meas. best 8.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 8.66 7.7533 2.2 3
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 IC50 7.36 7.36 44.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 Ki 7.36 7.36 44.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.3 5.0167 5011.9 6
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 5.27 5.27 5340.0 2
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 4.49 4.49 32100.0 1
Lysosomal Pro-X carboxypeptidase
CHEMBL2335
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sigma non-opioid intracellular receptor 1 Ki = 2.2 nM 8.66 Binding affinity to SIGMAR1 (unknown origin) 36490325
Sigma non-opioid intracellular receptor 1 IC50 = 44.0 nM 7.36 Inhibition of [3H]NANM binding to sigma receptor obtained from tissue homogenate... 9484497
Sigma non-opioid intracellular receptor 1 Ki = 44.0 nM 7.36 Tested for its binding affinity towards sigma-1 site in rat brain, using [3H]-(+... 8057277
Sigma non-opioid intracellular receptor 1 Ki = 46.5 nM 7.33 Binding affinity against Sigma receptor type 1 was determined by the displacemen... 12801223
Sigma non-opioid intracellular receptor 1 Ki = 53.2 nM 7.27 Binding affinity to human sigma 1 receptor 36202063
Plasmodium falciparum IC50 = 5011.87 nM 5.3 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Sodium-dependent dopamine transporter Ki = 5340.0 nM 5.27 Binding affinity against dopamine transporter was determined by the displacement... 12801223
Sodium-dependent dopamine transporter Ki = 5370.32 nM 5.27 Binding affinity to dopamine transporter (DAT) using [3H]WIN-35428 as a radiolig... 11063611
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Sigma intracellular receptor 2 Ki = 32100.0 nM 4.49 Binding affinity to human sigma 2 receptor 36202063
Lysosomal Pro-X carboxypeptidase IC50 = 100000.0 nM 4.0 Inhibition of binding to PCP receptor obtained from tissue homogenate preparatio... 9484497

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
12801223 10.1021/jm030008u Sodium-dependent dopamine transporter 1
12801223 10.1021/jm030008u Sigma non-opioid intracellular receptor 1 1
12801223 10.1021/jm030008u Unchecked 1
9484497 10.1021/jm970059p Lysosomal Pro-X carboxypeptidase 1
9484497 10.1021/jm970059p Sigma non-opioid intracellular receptor 1 1
8057277 10.1021/jm00041a006 Sigma non-opioid intracellular receptor 1 1
11063611 10.1021/jm990472s Sodium-dependent dopamine transporter 1
17417631 10.1038/nchembio873 Unchecked 1
23582449 10.1016/j.bmc.2013.03.016 Sigma non-opioid intracellular receptor 1 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
36202063 10.1016/j.bmc.2022.117032 Sigma non-opioid intracellular receptor 1 1
36202063 10.1016/j.bmc.2022.117032 Sigma intracellular receptor 2 1
36490325 10.1021/acs.jmedchem.2c00799 Sigma non-opioid intracellular receptor 1 1

Data from ChEMBL 36 via Core Engine