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Compound Detail

CHEMBL488910

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COc1ccc2c3c([nH]c2c1)[C@H](CC(C)C)N1C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)[C@@H]1C3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL488910
Phase Preclinical
Structure Type MOL
InChI Key NXNRAECHCJZNRF-JBACZVJFSA-N
17
Targets
101
Activities
2
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

469.6
MW (Da)
3.64
ALogP
5
HBA
2
HBD
100.7
PSA (Ų)
0.63
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C26H35N3O5
MW 469.58
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness 0.44

Activity Summary

IC50 84 meas. best 8.6
EC50 17 meas. best 8.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HEK293
CHEMBL614818
 IC50 8.6 7.9467 2.5 6
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 8.4 6.9058 4.0 43
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 EC50 8.27 7.4767 5.4 12
NCI-H460
CHEMBL396
 IC50 7.91 7.1767 12.3 6
Unchecked
CHEMBL612545
 IC50 7.77 6.3567 17.1 6
A549
CHEMBL392
 IC50 7.43 6.955 37.2 6
ATP-dependent translocase ABCB1
CHEMBL4302
 EC50 7.16 6.3867 70.0 3
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 6.57 5.315 271.0 2
B16-F10
CHEMBL612656
 IC50 6.12 5.515 750.0 2
HepG2
CHEMBL395
 IC50 6.0 5.035 990.0 2
Multidrug resistance-associated protein 1
CHEMBL3004
 EC50 5.75 5.73 1800.0 2
Multidrug resistance-associated protein 1
CHEMBL3004
 IC50 5.7 5.44 2000.0 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.22 5.22 6000.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.83 4.83 14710.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.76 4.76 17530.0 1
HFF-1
CHEMBL4296427
 IC50 4.25 4.25 56500.0 1
MDCK-II
CHEMBL4296466
 IC50 4.24 4.15 58260.0 2
K562/A02
CHEMBL4296448
 IC50 4.23 4.23 58740.0 1
K562
CHEMBL385
 IC50 4.15 4.15 71530.0 1
MDCK
CHEMBL614068
 IC50 4.03 4.03 93270.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 33.9 ng.hr.mL-1 Rattus norvegicus
AUC 40.2 ng.hr.mL-1 Rattus norvegicus
CL 1098.33 mL.min-1.kg-1 Rattus norvegicus
Cmax 21.4 nM Rattus norvegicus
F 3.0 % Rattus norvegicus
T1/2 0.2 hr Rattus norvegicus
Tmax 2.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HEK293 IC50 = 2.53 nM 8.6 Chemo-sensitizing activity against human HEK293 cells assessed as mitoxantrone I... 34496204
HEK293 IC50 = 2.69 nM 8.57 Chemo-sensitizing activity against human HEK293 cells assessed as SN-38 IC50 at ... 34496204
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 4.0 nM 8.4 Inhibition of human ABCG2 expressed in baculovirus infected Sf9 cell membrane as... 27280693
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 5.0 nM 8.3 TP_TRANSPORTER: efflux of Hoechst33342 in BCRP-expressing Sf9 cells 15155841
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 5.4 nM 8.27 Inhibition of BCRP (unknown origin) expressed in human HEK293/R2 cells assessed ... 31465686
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 7.1 nM 8.15 Inhibition of ABCG2 (unknown origin) 37847948
HEK293 IC50 = 8.36 nM 8.08 Chemo-sensitizing activity against ABCG2-overexpressing human HEK293/482R cells ... 34496204
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 8.7 nM 8.06 Inhibition of BCRP (unknown origin) transfected in HEK293/R2 cells assessed as r... 31465686
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 9.0 nM 8.05 Inhibition of BCRP in human MCF7/MX100 cells assessed as reversal of topotecan r... 31465686
HEK293 IC50 = 9.94 nM 8.0 Chemo-sensitizing activity against ABCG2-overexpressing human HEK293/482R cells ... 34496204
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 10.0 nM 8.0 Inhibition of human ABCG2 expressed in dog MDCK-II-BCRP cells mediated pheophorb... 35483322
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 10.0 nM 8.0 Inhibition of BCRP (unknown origin) 31465686
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 12.0 nM 7.92 Inhibition of ABCG2 (unknown origin) transfected in HEK293 cells assessed as inh... 24611893
NCI-H460 IC50 = 12.27 nM 7.91 Chemo-sensitizing activity against human NCI-H460 cells assessed as mitoxantrone... 34496204
Unchecked IC50 = 17.09 nM 7.77 Reversal of BCRP-mediated multidrug resistance in dog MDCK-II-BCRP cells assesse... 35247755
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 24.0 nM 7.62 Modulation of BCRP (unknown origin) transfected in human HEK293/R2 cells assesse... 25985195
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 24.0 nM 7.62 Inhibition of BCRP (unknown origin) transfected in human HEK293/R2 cells assesse... 31465686
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 28.0 nM 7.55 Inhibition of human ABCG2 expressed in baculovirus infected Sf9 cell membrane as... 27280693
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 29.0 nM 7.54 Inhibition of ABCG2 (unknown origin) transfected in HEK293 cells assessed as inh... 24611893
Unchecked IC50 = 31.11 nM 7.51 Reversal of BCRP-mediated multidrug resistance in MDCK-II cells assessed as pote... 33938746

Literature References

PubMed DOI Target Context # Activities
34496204 10.1021/acs.jnatprod.1c00584 A549 12
34496204 10.1021/acs.jnatprod.1c00584 NCI-H460 12
34496204 10.1021/acs.jnatprod.1c00584 HEK293 12
27280693 10.1021/acs.jmedchem.6b00035 Broad substrate specificity ATP-binding cassette transporter ABCG2 10
26642765 10.1016/j.bmcl.2015.11.077 Rattus norvegicus 8
31465686 10.1021/acs.jmedchem.9b00963 Broad substrate specificity ATP-binding cassette transporter ABCG2 8
31465686 10.1021/acs.jmedchem.9b00963 Unchecked 7
24304387 10.1021/jm401649j Broad substrate specificity ATP-binding cassette transporter ABCG2 7
32105979 10.1016/j.ejmech.2020.112133 ATP-dependent translocase ABCB1 6
27676469 10.1016/j.ejmech.2016.09.010 Broad substrate specificity ATP-binding cassette transporter ABCG2 6
27100033 10.1016/j.ejmech.2016.03.067 Broad substrate specificity ATP-binding cassette transporter ABCG2 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
35247755 10.1016/j.ejmech.2022.114231 Unchecked 4
31302589 10.1016/j.ejmech.2019.06.066 Broad substrate specificity ATP-binding cassette transporter ABCG2 4
32105979 10.1016/j.ejmech.2020.112133 Broad substrate specificity ATP-binding cassette transporter ABCG2 4
32787102 10.1021/acs.jmedchem.0c00961 Broad substrate specificity ATP-binding cassette transporter ABCG2 4
30390439 10.1016/j.ejmech.2018.10.026 Broad substrate specificity ATP-binding cassette transporter ABCG2 3
27100033 10.1016/j.ejmech.2016.03.067 ADMET 3
33938746 10.1021/acs.jmedchem.1c00246 Unchecked 3
24611893 10.1021/jm401879z Broad substrate specificity ATP-binding cassette transporter ABCG2 3

Data from ChEMBL 36 via Core Engine