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Compound Detail

CHEMBL410316

FUMITREMORGIN
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COc1ccc2c3c([nH]c2c1)[C@H](C=C(C)C)N1C(=O)[C@@H]2CCCN2C(=O)[C@@H]1C3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL410316
Name FUMITREMORGIN
Phase Preclinical
Structure Type MOL
InChI Key DBEYVIGIPJSTOR-FHWLQOOXSA-N
8
Targets
23
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

379.5
MW (Da)
2.94
ALogP
3
HBA
1
HBD
65.6
PSA (Ų)
0.82
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H25N3O3
MW 379.46
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 0.84

Activity Summary

IC50 19 meas. best 9.09
EC50 3 meas. best 6.38
Ki 1 meas. best 5.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.09 9.09 0.8 1
Unchecked
CHEMBL612545
 IC50 8.27 8.27 5.4 1
NCI-H460
CHEMBL396
 IC50 6.83 6.78 148.0 3
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.49 6.175 321.0 10
ATP-dependent translocase ABCB1
CHEMBL4302
 EC50 6.38 6.38 412.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 EC50 6.0 5.85 1000.0 2
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 Ki 5.89 5.89 1300.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 5.74 5.74 1808.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.64 5.64 2300.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 5.02 5.02 9600.0 1
K562
CHEMBL385
 IC50 4.39 4.39 41000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 0.82 nM 9.09 Potentiation of mitoxantrone-induced cytotoxicity against HEK293 cells assessed ... 27504669
Unchecked IC50 = 5.42 nM 8.27 Inhibition of human ABCG2 R482 mutant transfected in HEK293 cells assessed as po... 27504669
NCI-H460 IC50 = 148.0 nM 6.83 Potentiation of mitoxantrone induced antiproliferative activity against human H4... 28916341
NCI-H460 IC50 = 168.0 nM 6.78 Potentiation of mitoxantrone induced antiproliferative activity against human H4... 28916341
NCI-H460 IC50 = 186.0 nM 6.73 Potentiation of mitoxantrone induced antiproliferative activity against human H4... 28916341
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 321.0 nM 6.49 Inhibition of ABCG2 in human H460/MX20 cells assessed as potentiation of mitoxan... 28916341
ATP-dependent translocase ABCB1 EC50 = 412.0 nM 6.38 Activation of ABCB1 ATPase activity (unknown origin) expressed in baculovirus in... 32105979
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 451.0 nM 6.35 Inhibition of ABCG2 in human H460/MX20 cells assessed as potentiation of mitoxan... 28916341
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 470.0 nM 6.33 Inhibition of human ABCG2 expressed in dog MDCK-II-BCRP cells mediated pheophorb... 35483322
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 612.0 nM 6.21 Inhibition of ABCG2 in human H460/MX20 cells assessed as potentiation of mitoxan... 28916341
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 731.0 nM 6.14 Inhibition of ABCG2 in human MCF7/Topo cells after 2 hrs by Hoechst 33342 microp... 24900683
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 730.0 nM 6.14 Inhibition of ABCG2 in human MCF7/Topo cells by Hoechst 33342 assay 26774038
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 731.0 nM 6.14 Inhibition of ABCG2 in human MCF7/Topo cells after 2 hrs by Hoechst 33342 staini... 30128080
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 800.0 nM 6.1 Inhibition of ABCG2 expressed in human NCI-H460 cells assessed as inhibition of ... 21275386
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 960.0 nM 6.02 Inhibition of BCRP in human MCF7/Topo cells assessed as mitoxantrone accumulatio... 27727127
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 1000.0 nM 6.0 Inhibition of BCRP (unknown origin) 31465686
Broad substrate specificity ATP-binding cassette transporter ABCG2 Ki = 1300.0 nM 5.89 TP_TRANSPORTER: inhibition of ATPase in membrane vesicle from BCRP-expressing Sf... 11437380
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 1483.0 nM 5.83 Inhibition of ABCG2 in topotecan-cultured human MCF7 cells using Hoechst 33342 a... 32105979
ATP-dependent translocase ABCB1 IC50 = 1808.0 nM 5.74 Inhibition of sulfasalazine-stimulated ABCB1 ATPase activity (unknown origin) ex... 32105979
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 2000.0 nM 5.7 Inhibition of ABCG2 (unknown origin)-mediated mitoxantrone efflux 36628850

Literature References

PubMed DOI Target Context # Activities
32105979 10.1016/j.ejmech.2020.112133 ATP-dependent translocase ABCB1 4
28916341 10.1016/j.bmcl.2017.09.009 Unchecked 3
28916341 10.1016/j.bmcl.2017.09.009 Broad substrate specificity ATP-binding cassette transporter ABCG2 3
28916341 10.1016/j.bmcl.2017.09.009 NCI-H460 3
20598550 10.1016/j.bmc.2010.06.004 Unchecked 2
15102949 10.1124/mol.65.5.1208 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
24900683 10.1021/ml4000832 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
21920748 10.1016/j.bmcl.2011.08.070 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
27504669 10.1021/acs.jnatprod.6b00597 Unchecked 2
20739103 10.1016/j.ejmech.2010.07.050 Saccharomyces cerevisiae 2
20739103 10.1016/j.ejmech.2010.07.050 Unchecked 2
20598550 10.1016/j.bmc.2010.06.004 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
27865702 10.1016/j.bmcl.2016.11.013 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
36628850 10.1016/j.ejmech.2022.115070 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
19170519 10.1021/jm8013822 ATP-dependent translocase ABCB1 2
19170519 10.1021/jm8013822 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
38377824 10.1016/j.ejmech.2024.116175 Plasmodium falciparum 1
19256529 10.1021/np800700e PC-12 1
19170519 10.1021/jm8013822 ATP-binding cassette sub-family C member 2 1
17964170 10.1016/j.bmc.2007.10.006 Broad substrate specificity ATP-binding cassette transporter ABCG2 1

Data from ChEMBL 36 via Core Engine