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Compound Detail

CHEMBL4586133

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O=C(O)C(=O)O.c1ccc(-c2ccc(OCCCCCN3CCCCCC3)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4586133
Phase Preclinical
Structure Type MOL
InChI Key OBGUKBYLZRTUDN-UHFFFAOYSA-N
Parent Compound CHEMBL4596108
Active Moiety CHEMBL4596108
6
Targets
7
Activities
3
Assay Types
2
PK Parameters
11
Publications
0
Known Names

Molecular Properties

337.5
MW (Da)
5.78
ALogP
2
HBA
0
HBD
12.5
PSA (Ų)
0.57
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H33NO5
MW 427.54
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.80

Activity Summary

IC50 3 meas. best 8.04
Ki 3 meas. best 7.47
Kd 1 meas. best 6.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H3 receptor
CHEMBL264
 IC50 8.04 8.04 9.1 1
Histamine H3 receptor
CHEMBL264
 Ki 7.47 7.47 34.0 1
Histamine H1 receptor
CHEMBL3943
 Kd 6.14 6.14 724.4 1
Histamine H1 receptor
CHEMBL231
 Ki 5.9 5.9 1270.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.69 5.69 2030.0 1
HepG2
CHEMBL395
 IC50 4.89 4.89 12800.0 1
Histamine H4 receptor
CHEMBL3759
 Ki 4.66 4.66 21800.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 52.9 mL.min-1.kg-1 Rattus norvegicus
T1/2 0.3933 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H3 receptor IC50 = 9.08 nM 8.04 Antagonist activity at human H3R expressed in HEK293 cells assessed as reduction... 28797771
Histamine H3 receptor Ki = 34.0 nM 7.47 Displacement of [3H]-N-alpha-methylhistamine from human recombinant full length ... 28797771
Histamine H1 receptor Kd = 724.44 nM 6.14 Antagonist activity at histamine H1 receptor in guinea-pig ileum assessed as inh... 28797771
Histamine H1 receptor Ki = 1270.0 nM 5.9 Displacement of [3H]pyrilamine from human H1 receptor expressed in CHOK1 cells i... 28797771
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 2030.0 nM 5.69 Inhibition of human ERG expressed in CHO cells at holding potential of -90 mV by... 28797771
HepG2 IC50 = 12800.0 nM 4.89 Cytotoxicity against human HepG2 cells assessed as cell viability incubated for ... 28797771
Histamine H4 receptor Ki = 21800.0 nM 4.66 Displacement of [3H]histamine from human recombinant H4R expressed in CHO cells ... 28797771

Literature References

PubMed DOI Target Context # Activities
28797771 10.1016/j.bmc.2017.07.058 ADMET 13
28797771 10.1016/j.bmc.2017.07.058 Histamine H1 receptor 3
28797771 10.1016/j.bmc.2017.07.058 Histamine H3 receptor 3
28797771 10.1016/j.bmc.2017.07.058 Rattus norvegicus 2
28797771 10.1016/j.bmc.2017.07.058 HepG2 2
28797771 10.1016/j.bmc.2017.07.058 Cytochrome P450 3A4 2
28797771 10.1016/j.bmc.2017.07.058 Voltage-gated inwardly rectifying potassium channel KCNH2 1
28797771 10.1016/j.bmc.2017.07.058 Muscarinic acetylcholine receptor M3 1
28797771 10.1016/j.bmc.2017.07.058 Histamine H4 receptor 1
28797771 10.1016/j.bmc.2017.07.058 Unchecked 1
28797771 10.1016/j.bmc.2017.07.058 Cytochrome P450 2D6 1

Data from ChEMBL 36 via Core Engine