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Compound Detail

CHEMBL394931

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CO[C@H]1/C=C\C=C(/C)C(=O)NC2=CC(=O)C(O)=C(C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@@H]1OC(N)=O)C2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL394931
Phase Preclinical
Structure Type MOL
InChI Key KKZJVQQMUCBLHR-LVBRMASUSA-N
10
Targets
10
Activities
1
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

546.6
MW (Da)
2.32
ALogP
9
HBA
4
HBD
174.5
PSA (Ų)
0.31
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H38N2O9
MW 546.62
Aromatic Rings 0
Heavy Atoms 39
NP-Likeness 2.62

Activity Summary

IC50 10 meas. best 5.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Heat shock protein HSP 90-alpha
CHEMBL3880
 IC50 5.39 5.39 4100.0 1
K562
CHEMBL385
 IC50 5.32 5.32 4800.0 1
A549
CHEMBL392
 IC50 5.11 5.11 7700.0 1
MCF7
CHEMBL387
 IC50 5.0 5.0 9900.0 1
LNCaP C4-2B
CHEMBL4296461
 IC50 4.96 4.96 11000.0 1
MDA-MB-231
CHEMBL400
 IC50 4.77 4.77 17000.0 1
MGC-803
CHEMBL3706566
 IC50 4.72 4.72 19000.0 1
NCI-H446
CHEMBL612440
 IC50 4.6 4.6 25000.0 1
CWR22R
CHEMBL612657
 IC50 4.6 4.6 25000.0 1
HL-60
CHEMBL383
 IC50 4.44 4.44 36000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Heat shock protein HSP 90-alpha IC50 = 4100.0 nM 5.39 Inhibition of HSP90alpha (unknown origin) 32273216
K562 IC50 = 4800.0 nM 5.32 Cytotoxicity against human K562 cells assessed as reduction in cell viability 32273216
A549 IC50 = 7700.0 nM 5.11 Cytotoxicity against human A549 cells assessed as reduction in cell viability 32273216
MCF7 IC50 = 9900.0 nM 5.0 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability 32273216
LNCaP C4-2B IC50 = 11000.0 nM 4.96 Cytotoxicity against human C42B cells 34225450
MDA-MB-231 IC50 = 17000.0 nM 4.77 Cytotoxicity against human MDA-MB-231 cells 34225450
MGC-803 IC50 = 19000.0 nM 4.72 Cytotoxicity against human MGC-803 cells 34225450
CWR22R IC50 = 25000.0 nM 4.6 Cytotoxicity against human 22Rv1 cells 34225450
NCI-H446 IC50 = 25000.0 nM 4.6 Cytotoxicity against human H446 cells 34225450
HL-60 IC50 = 36000.0 nM 4.44 Cytotoxicity against human HL60 cells assessed as reduction in cell viability 32273216

Literature References

PubMed DOI Target Context # Activities
37042709 10.1021/acs.jnatprod.2c01151 Staphylococcus aureus 8
32273216 10.1016/j.bmcl.2020.127168 Staphylococcus aureus 2
32273216 10.1016/j.bmcl.2020.127168 Bacillus amyloliquefaciens 2
32273216 10.1016/j.bmcl.2020.127168 Shewanella oneidensis 2
37042709 10.1021/acs.jnatprod.2c01151 Staphylococcus 1
7562911 10.1021/jm00019a010 SK-BR-3 1
34225450 10.1021/acs.jnatprod.1c00297 MGC-803 1
34225450 10.1021/acs.jnatprod.1c00297 NCI-H446 1
34225450 10.1021/acs.jnatprod.1c00297 CWR22R 1
34225450 10.1021/acs.jnatprod.1c00297 LNCaP C4-2B 1
34225450 10.1021/acs.jnatprod.1c00297 MDA-MB-231 1
32273216 10.1016/j.bmcl.2020.127168 Heat shock protein HSP 90-alpha 1
32273216 10.1016/j.bmcl.2020.127168 MCF7 1
32273216 10.1016/j.bmcl.2020.127168 A549 1
32273216 10.1016/j.bmcl.2020.127168 HL-60 1
32273216 10.1016/j.bmcl.2020.127168 K562 1
17442565 10.1016/j.bmcl.2006.12.041 Molecular identity unknown 1

Data from ChEMBL 36 via Core Engine