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Compound Detail

CHEMBL104255

FLAVOKAWAIN B
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COc1cc(O)c(C(=O)/C=C/c2ccccc2)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL104255
Name FLAVOKAWAIN B
Phase Preclinical
Structure Type MOL
InChI Key QKQLSQLKXBHUSO-CMDGGOBGSA-N
15
Targets
18
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

284.3
MW (Da)
3.31
ALogP
4
HBA
1
HBD
55.8
PSA (Ų)
0.68
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C17H16O4
MW 284.31
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.60

Activity Summary

IC50 17 meas. best 5.48
EC50 1 meas. best 5.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.48 5.48 3300.0 1
RAW264.7
CHEMBL612557
 IC50 5.38 4.98 4200.0 2
Trypanosoma brucei
CHEMBL612849
 EC50 5.21 5.21 6200.0 1
HCT-116
CHEMBL394
 IC50 5.12 5.12 7500.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.11 5.11 7700.0 1
RL
CHEMBL2366175
 IC50 5.09 5.09 8200.0 1
PC-3
CHEMBL390
 IC50 5.04 5.04 9100.0 1
Caco-2
CHEMBL614058
 IC50 5.0 5.0 9900.0 1
NCI-H727
CHEMBL1075545
 IC50 4.95 4.95 11300.0 1
HaCaT
CHEMBL614392
 IC50 4.87 4.87 13600.0 1
MCF7
CHEMBL387
 IC50 4.81 4.755 15500.0 2
Huh-7
CHEMBL614039
 IC50 4.8 4.8 15900.0 1
MDA-MB-231
CHEMBL400
 IC50 4.79 4.79 16300.0 1
MIA PaCa-2
CHEMBL614725
 IC50 4.74 4.74 18200.0 1
A549
CHEMBL392
 IC50 4.71 4.71 19700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 3300.0 nM 5.48 Inhibition of cobalt chloride-induced HIF-1 activation expressed in mouse NIH3T3... 21112783
RAW264.7 IC50 = 4200.0 nM 5.38 Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells measur... 32208222
Trypanosoma brucei EC50 = 6200.0 nM 5.21 Anti-parasitic activity against Trypanosoma brucei 427 28064141
HCT-116 IC50 = 7500.0 nM 5.12 Cytotoxicity against human HCT116 cells assessed as cell viability after 48 hrs ... 28214231
NON-PROTEIN TARGET IC50 = 7700.0 nM 5.11 Antimelanogenic activity in mouse B16F10 cells assessed as inhibition of melanin... 25597012
RL IC50 = 8200.0 nM 5.09 Cytotoxicity against human RL assessed as cell viability after 48 hrs by Hoechst... 28214231
PC-3 IC50 = 9100.0 nM 5.04 Cytotoxicity against human PC3 cells assessed as cell viability after 48 hrs by ... 28214231
Caco-2 IC50 = 9900.0 nM 5.0 Cytotoxicity against human Caco2 cells assessed as cell viability after 48 hrs b... 28214231
NCI-H727 IC50 = 11300.0 nM 4.95 Cytotoxicity against human NCI-H727 cells assessed as cell viability after 48 hr... 28214231
HaCaT IC50 = 13600.0 nM 4.87 Cytotoxicity against human HaCaT cells assessed as cell viability after 48 hrs b... 28214231
MCF7 IC50 = 15500.0 nM 4.81 Cytotoxicity against human MCF7 assessed as cell viability after 48 hrs by Hoech... 28214231
Huh-7 IC50 = 15900.0 nM 4.8 Cytotoxicity against human HuH7 cells assessed as cell viability after 48 hrs by... 28214231
MDA-MB-231 IC50 = 16300.0 nM 4.79 Cytotoxicity against human MDA-MB-231 cells assessed as cell viability after 48 ... 28214231
MIA PaCa-2 IC50 = 18200.0 nM 4.74 Cytotoxicity against human MIAPaCa2 cells assessed as reduction in cell viabilit... 31673309
A549 IC50 = 19700.0 nM 4.71 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 31673309
MCF7 IC50 = 20000.0 nM 4.7 The compound was tested for antiproliferative activity against MCF-7 human breas... 11720850
RAW264.7 IC50 = 26500.0 nM 4.58 Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viabilit... 32208222

Literature References

PubMed DOI Target Context # Activities
28214231 10.1016/j.bmc.2017.01.049 HCT-116 12
28214231 10.1016/j.bmc.2017.01.049 MDA-MB-231 11
28214231 10.1016/j.bmc.2017.01.049 PC-3 11
28214231 10.1016/j.bmc.2017.01.049 Unchecked 9
28214231 10.1016/j.bmc.2017.01.049 Caco-2 7
28214231 10.1016/j.bmc.2017.01.049 Huh-7 7
28214231 10.1016/j.bmc.2017.01.049 NCI-H727 7
28214231 10.1016/j.bmc.2017.01.049 HaCaT 7
28214231 10.1016/j.bmc.2017.01.049 MCF7 5
32208222 10.1016/j.ejmech.2020.112216 RAW264.7 3
22449016 10.1021/jm2016528 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
25597012 10.1016/j.bmcl.2014.12.082 NON-PROTEIN TARGET 2
22239485 10.1021/jm2016073 MCF7 2
28214231 10.1016/j.bmc.2017.01.049 Fibroblast 2
23062825 10.1016/j.bmc.2012.09.040 Cholinesterase 1
23567958 10.1016/j.ejmech.2013.03.016 Urease subunit alpha/Urease subunit beta 1
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
21112783 10.1016/j.bmcl.2010.10.063 ADMET 1
19716299 10.1016/j.bmcl.2009.08.003 Unchecked 1
19883086 10.1021/jm901278z Unchecked 1

Data from ChEMBL 36 via Core Engine