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Compound Detail

CHEMBL464443

GONIOTHALAMIN
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O=C1C=CC[C@H](/C=C/c2ccccc2)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL464443
Name GONIOTHALAMIN
Phase Preclinical
Structure Type MOL
InChI Key RLGHFVLWYYVMQZ-BZYZDCJZSA-N
16
Targets
23
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

200.2
MW (Da)
2.57
ALogP
2
HBA
0
HBD
26.3
PSA (Ų)
0.69
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 C13H12O2
MW 200.24
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness 2.29

Activity Summary

IC50 23 meas. best 6.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HepG2
CHEMBL395
 IC50 6.2 5.9333 625.0 3
MDA-MB-231
CHEMBL400
 IC50 5.84 5.555 1460.0 2
P388
CHEMBL389
 IC50 5.42 5.42 3800.0 1
PC-3
CHEMBL390
 IC50 5.4 5.4 4000.0 1
MCF7
CHEMBL387
 IC50 5.35 4.72 4500.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.27 4.55 5400.0 3
Hep 3B2
CHEMBL4296437
 IC50 5.27 5.27 5400.0 1
A549
CHEMBL392
 IC50 5.24 5.24 5700.0 1
Nuclear factor NF-kappa-B complex
CHEMBL2094258
 IC50 5.16 5.16 7000.0 1
WEHI-164
CHEMBL614227
 IC50 5.07 5.07 8500.0 1
LNCaP
CHEMBL612518
 IC50 4.92 4.92 12000.0 1
DU-145
CHEMBL613508
 IC50 4.72 4.72 19000.0 1
HBL-100
CHEMBL614811
 IC50 4.68 4.68 20900.0 1
Unchecked
CHEMBL612545
 IC50 4.56 4.56 27400.0 1
HaCaT
CHEMBL614392
 IC50 4.54 4.54 28600.0 1
RAW264.7
CHEMBL612557
 IC50 4.47 4.47 34200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HepG2 IC50 = 625.0 nM 6.2 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability a... 31306909
MDA-MB-231 IC50 = 1460.0 nM 5.84 Cytotoxicity against human MDA-MB-231 cells 20381347
HepG2 IC50 = 1600.0 nM 5.8 Cytotoxicity against human HepG2 cells after 24 hrs 20392543
HepG2 IC50 = 1600.0 nM 5.8 Cytotoxicity against human HepG2 cells assessed as growth inhibition 31306909
P388 IC50 = 3800.0 nM 5.42 Cytotoxicity against mouse P388 cells 20392543
PC-3 IC50 = 4000.0 nM 5.4 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 19022676
MCF7 IC50 = 4500.0 nM 5.35 Cytotoxicity against human MCF7 cells after 24 hrs 20392543
NON-PROTEIN TARGET IC50 = 5400.0 nM 5.27 Cytotoxicity against human Hep3B cells 20392543
MDA-MB-231 IC50 = 5400.0 nM 5.27 Cytotoxicity against human MDA-MB-231 cells 20392543
Hep 3B2 IC50 = 5400.0 nM 5.27 Cytotoxicity against human Hep3B cells assessed as growth inhibition 31306909
A549 IC50 = 5700.0 nM 5.24 Antiproliferative activity against human A549 cells after 48 hrs by CellTiter-Gl... 28214230
Nuclear factor NF-kappa-B complex IC50 = 7000.0 nM 5.16 Inhibition of NF-kappaB transactivation in TNF-alpha-stimulated human K562 cells... 24775915
WEHI-164 IC50 = 8500.0 nM 5.07 Cytotoxicity against mouse WEHI164 cells 20392543
LNCaP IC50 = 12000.0 nM 4.92 Cytotoxicity against human LNCAP cells after 72 hrs by MTT assay 19022676
DU-145 IC50 = 19000.0 nM 4.72 Cytotoxicity against human DU145 cells after 72 hrs by MTT assay 19022676
HBL-100 IC50 = 20900.0 nM 4.68 Antiproliferative activity against human HBL100 cells after 48 hrs by CellTiter-... 28214230
Unchecked IC50 = 27400.0 nM 4.56 Inhibition of LPS-induced NF-kappaB activation in mouse RAW264.7 cells after 18 ... 23735825
MCF7 IC50 = 28000.0 nM 4.55 Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay 19022676
HaCaT IC50 = 28600.0 nM 4.54 Cytotoxicity against human HaCaT cells assessed as reduction in cell viability a... 25305718
RAW264.7 IC50 = 34200.0 nM 4.47 Cytotoxicity against mouse RAW264.7 cells after 18 hrs by MTT assay 23735825

Literature References

PubMed DOI Target Context # Activities
25305718 10.1016/j.ejmech.2014.09.085 PANC-1 8
25305718 10.1016/j.ejmech.2014.09.085 NON-PROTEIN TARGET 6
28214230 10.1016/j.bmc.2017.02.004 Unchecked 6
28689976 10.1016/j.bmc.2017.06.030 Exportin-1 6
20729093 10.1016/j.bmc.2010.07.053 NON-PROTEIN TARGET 5
31306909 10.1016/j.ejmech.2019.07.024 HepG2 3
20729093 10.1016/j.bmc.2010.07.053 Mus musculus 3
23735825 10.1016/j.bmc.2013.04.055 RAW264.7 2
20381347 10.1016/j.bmcl.2010.03.049 MDA-MB-231 2
28689976 10.1016/j.bmc.2017.06.030 Huh-7 2
20392543 10.1016/j.ejmech.2010.03.032 NON-PROTEIN TARGET 1
20729093 10.1016/j.bmc.2010.07.053 OVCAR-3 1
20729093 10.1016/j.bmc.2010.07.053 NCI-H460 1
20729093 10.1016/j.bmc.2010.07.053 UACC-62 1
20392543 10.1016/j.ejmech.2010.03.032 MDA-MB-231 1
31306909 10.1016/j.ejmech.2019.07.024 Hep 3B2 1
20392543 10.1016/j.ejmech.2010.03.032 P388 1
20392543 10.1016/j.ejmech.2010.03.032 HepG2 1
20381347 10.1016/j.bmcl.2010.03.049 Exportin-1 1
19022676 10.1016/j.bmc.2008.10.069 MCF7 1

Data from ChEMBL 36 via Core Engine