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Compound Detail

CHEMBL4588786

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CC(=O)OC[C@@]1(C)[C@@H]2CC[C@]3(C)[C@H](CC=C4[C@@H]5CC(C)(C)CC[C@]5(C(=O)OCCCCO[N+](=O)[O-])CC[C@]43C)[C@@]2(C)CC[C@@H]1OC(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4588786
Phase Preclinical
Structure Type MOL
InChI Key HBSYDVIQZRPYNU-ISMKCZDJSA-N
7
Targets
9
Activities
1
Assay Types
0
PK Parameters
7
Publications
0
Known Names

Molecular Properties

673.9
MW (Da)
7.79
ALogP
9
HBA
0
HBD
131.3
PSA (Ų)
0.06
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C38H59NO9
MW 673.89
Aromatic Rings 0
Heavy Atoms 48
NP-Likeness 2.44

Activity Summary

IC50 9 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 8.0 7.61 10.0 2
A549
CHEMBL392
 IC50 5.34 5.34 4600.0 1
Unchecked
CHEMBL612545
 IC50 5.32 5.32 4800.0 1
MCF7
CHEMBL387
 IC50 5.3 5.3 5000.0 1
KB
CHEMBL398
 IC50 5.29 5.29 5100.0 1
MDA-MB-231
CHEMBL400
 IC50 5.28 5.28 5200.0 1
NCI-H1975
CHEMBL614348
 IC50 5.12 5.105 7600.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 10.0 nM 8.0 Inhibition of C-terminal His-tagged/ N-terminal GST-tagged recombinant human EGF... 31718182
Epidermal growth factor receptor IC50 = 60.0 nM 7.22 Inhibition of C-terminal His-tagged/ N-terminal GST-tagged recombinant human EGF... 31718182
A549 IC50 = 4600.0 nM 5.34 Antiproliferative activity against human A549 cells harbouring wild type EGFR in... 31718182
Unchecked IC50 = 4800.0 nM 5.32 Antiproliferative activity against human KB-VIN10 cells incubated for 72 hrs by ... 31718182
MCF7 IC50 = 5000.0 nM 5.3 Antiproliferative activity against human MCF7 cells incubated for 72 hrs by SRB ... 31718182
KB IC50 = 5100.0 nM 5.29 Antiproliferative activity against human KB cells incubated for 72 hrs by SRB as... 31718182
MDA-MB-231 IC50 = 5200.0 nM 5.28 Antiproliferative activity against human MDA-MB-231 cells incubated for 72 hrs b... 31718182
NCI-H1975 IC50 = 7600.0 nM 5.12 Antiproliferative activity against human NCI-H1975 cells harbouring EGFR L858R/T... 31718182
NCI-H1975 IC50 = 8100.0 nM 5.09 Antiproliferative activity against human NCI-H1975 cells incubated for 72 hrs by... 31718182

Literature References

PubMed DOI Target Context # Activities
31718182 10.1021/acs.jnatprod.9b00659 NCI-H1975 4
31718182 10.1021/acs.jnatprod.9b00659 Epidermal growth factor receptor 3
31718182 10.1021/acs.jnatprod.9b00659 A549 1
31718182 10.1021/acs.jnatprod.9b00659 MDA-MB-231 1
31718182 10.1021/acs.jnatprod.9b00659 KB 1
31718182 10.1021/acs.jnatprod.9b00659 Unchecked 1
31718182 10.1021/acs.jnatprod.9b00659 MCF7 1

Data from ChEMBL 36 via Core Engine