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Compound Detail

CHEMBL525408

APAMIN
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CC(C)C[C@@H]1NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc3cnc[nH]3)C(N)=O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)NC(=O)[C@H](CSSC[C@H](N)C(=O)N[C@@H](CC(N)=O)C(=O)N2)NC1=O

Basic Information

ChEMBL ID CHEMBL525408
Name APAMIN
Phase Preclinical
Structure Type BOTH
InChI Key YVIIHEKJCKCXOB-STYWVVQQSA-N
5
Targets
19
Activities
3
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

2027.4
MW (Da)

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C79H131N31O24S4
MW 2027.38

Activity Summary

IC50 13 meas. best 10.96
Ki 5 meas. best 10.3
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 10.96 10.324 0.0 5
Small conductance calcium-activated potassium channel protein 1
CHEMBL2369
IC50 10.85 10.85 0.0 1
Small conductance calcium-activated potassium channel protein 1
CHEMBL3743
IC50 10.62 10.62 0.0 1
Unchecked
CHEMBL612545
Ki 10.3 10.3 0.1 1
Small conductance calcium-activated potassium channel protein 3
CHEMBL3381
IC50 10.19 9.985 0.1 4
Small conductance calcium-activated potassium channel
CHEMBL2096673
Ki 5.42 5.42 3800.0 1
Small conductance calcium-activated potassium channel
CHEMBL2096673
IC50 4.69 4.69 20400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.011 nM 10.96 Binding affinity to small conductance calcium-activated potassium channel (unkno... 23466604
Small conductance calcium-activated potassium channel protein 1 IC50 = 0.014 nM 10.85 Displacement of radiolabeled apamin from calcium-activated SK channel 18983139
Small conductance calcium-activated potassium channel protein 1 IC50 = 0.024 nM 10.62 Inhibition of rat SK Calcium channel 20875743
Unchecked IC50 = 0.024 nM 10.62 Inhibition of SKCa (unknown origin) 28849908
Unchecked IC50 = 0.03 nM 10.52 Inhibition of Kca channel 18774291
Unchecked IC50 = 0.03 nM 10.52 Binding affinity to small conductance calcium-activated potassium channel (unkno... 23582449
Unchecked Ki = 0.05 nM 10.3 Displacement of [125I]apamin from low conductance potassium channel 8496700
Small conductance calcium-activated potassium channel protein 3 IC50 = 0.064 nM 10.19 Inhibition of Kca2.3 channel expressed in HEK293 cells by electrophysiology assa... 18824351
Small conductance calcium-activated potassium channel protein 3 IC50 = 0.064 nM 10.19 Inhibition of Kca2.3 channel expressed in HEK293 cells by electrophysiology assa... 18774291
Small conductance calcium-activated potassium channel protein 3 IC50 = 0.168 nM 9.78 Inhibition of Kca2.3 channel expressed in HEK293 cells by thallium flux assay 18824351
Small conductance calcium-activated potassium channel protein 3 IC50 = 0.168 nM 9.78 Inhibition of Kca2.3 channel expressed in HEK293 cells by thallium flux assay 18774291
Unchecked IC50 = 1.0 nM 9.0 Inhibition of apamin-sensitive SKCa channel of guinea-pig hepatocytes 15225721
Small conductance calcium-activated potassium channel Ki = 3800.0 nM 5.42 Inhibition of [125I]apamin binding to calcium-activated potassium (SK) channel o... 16033276
Small conductance calcium-activated potassium channel IC50 = 20400.0 nM 4.69 Inhibition of [125I]apamin binding to calcium-activated potassium (SK) channel o... 16033276

Literature References

PubMed DOI Target Context # Activities
16033276 10.1021/jm049025p Small conductance calcium-activated potassium channel 2
18824351 10.1016/j.bmcl.2008.08.026 Small conductance calcium-activated potassium channel protein 3 2
18983139 10.1021/jm8007618 Small conductance calcium-activated potassium channel protein 1 2
8496700 10.1021/np50094a001 Unchecked 2
18774291 10.1016/j.bmcl.2008.08.023 Small conductance calcium-activated potassium channel protein 3 2
23466604 10.1016/j.ejmech.2013.01.044 Unchecked 2
28849908 10.1021/acschembio.7b00481 Unchecked 2
15225721 10.1016/j.bmcl.2004.05.031 Unchecked 1
17125273 10.1021/jm0607395 Small conductance calcium-activated potassium channel 1
18774291 10.1016/j.bmcl.2008.08.023 Unchecked 1
18588282 10.1021/jm701575k Unchecked 1
20875743 10.1016/j.bmc.2010.07.034 Small conductance calcium-activated potassium channel protein 1 1
23582449 10.1016/j.bmc.2013.03.016 Unchecked 1
23685886 10.1016/j.ejmech.2013.02.029 Small conductance calcium-activated potassium channel protein 3 1

Data from ChEMBL 36 via Core Engine