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Compound Detail

CHEMBL494083

XANTHOANGELOL
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CC(C)=CCC/C(C)=C/Cc1c(O)ccc(C(=O)/C=C/c2ccc(O)cc2)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL494083
Name XANTHOANGELOL
Phase Preclinical
Structure Type MOL
InChI Key LRSMBOSQWGHYCW-MDGZPELGSA-N
12
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

392.5
MW (Da)
5.93
ALogP
4
HBA
3
HBD
77.8
PSA (Ų)
0.30
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C25H28O4
MW 392.50
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 1.65

Activity Summary

IC50 12 meas. best 6.01
EC50 5 meas. best 5.99

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.01 5.4925 980.0 4
Streptokinase A
CHEMBL1293228
 EC50 5.99 5.99 1019.0 1
Streptococcus sp. 'group A'
CHEMBL612389
 EC50 5.98 5.98 1048.0 1
Streptococcus
CHEMBL612313
 EC50 5.77 5.77 1681.0 1
K562
CHEMBL385
 IC50 5.4 5.4 3980.0 1
Chikungunya virus
CHEMBL4296563
 EC50 5.15 5.15 7100.0 1
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 4.88 4.88 13200.0 1
HepG2
CHEMBL395
 IC50 4.86 4.86 13700.0 1
HEK293
CHEMBL614818
 IC50 4.67 4.67 21500.0 1
MRC5
CHEMBL614181
 IC50 4.66 4.63 21700.0 2
THP-1
CHEMBL614245
 IC50 4.63 4.615 23600.0 2
Protein RecA
CHEMBL1741171
 EC50 4.05 4.05 88400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 980.0 nM 6.01 Inhibition of melanin synthesis in NHEM after 24 hrs by liquid scintillation 19102656
Streptokinase A EC50 = 1019.0 nM 5.99 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Unchecked IC50 = 1030.0 nM 5.99 Inhibition of TNF-alpha-induced NF-kappaB activation in human HeLa cells by SEAP... 18841906
Streptococcus sp. 'group A' EC50 = 1048.0 nM 5.98 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptococcus EC50 = 1681.0 nM 5.77 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Unchecked IC50 = 1830.0 nM 5.74 Inhibition of LPS-induced NF-kappaB activation in mouse RAW264.7 cells by SEAP r... 18841906
K562 IC50 = 3980.0 nM 5.4 Antitumor activity against human K562 cells incubated for 48 hrs by MTT assay 25590864
Chikungunya virus EC50 = 7100.0 nM 5.15 Antiviral activity against CHIKV infected in hamster BHK-21 cells assessed as in... 36940609
Amine oxidase [flavin-containing] B IC50 = 13200.0 nM 4.88 Inhibition of human MAO-B using kynuramine as substrate incubated for 20 mins by... 32920430
HepG2 IC50 = 13700.0 nM 4.86 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i... 31648878
HEK293 IC50 = 21500.0 nM 4.67 Cytotoxicity against human HEK293 cells assessed as reduction in cell viability ... 31648878
MRC5 IC50 = 21700.0 nM 4.66 Cytotoxicity against human MRC5 cells assessed as reduction in cell viability in... 31648878
THP-1 IC50 = 23600.0 nM 4.63 Cytotoxicity against human THP1 cells assessed as reduction in cell viability in... 31648878
MRC5 IC50 = 25000.0 nM 4.6 Cytotoxicity against human MRC5 cells after 48 hrs by resazurin dye-based fluore... 28075580
THP-1 IC50 = 25000.0 nM 4.6 Cytotoxicity against human THP1 cells after 48 hrs by resazurin dye-based fluore... 28075580
Unchecked IC50 = 58800.0 nM 4.23 Cytotoxicity against human CLS54 cells assessed as reduction in cell viability i... 31648878
Protein RecA EC50 = 88400.0 nM 4.05 PUBCHEM_BIOASSAY: Fluorescence Cell-Free Homogeneous Dose Retest to Identify Inh... -

Literature References

PubMed DOI Target Context # Activities
31648878 10.1016/j.bmc.2019.115151 Bacillus subtilis 43
31648878 10.1016/j.bmc.2019.115151 Staphylococcus aureus 12
31648878 10.1016/j.bmc.2019.115151 Unchecked 7
16441065 10.1021/np058080d Unchecked 6
31648878 10.1016/j.bmc.2019.115151 Enterococcus faecalis 4
25590864 10.1016/j.ejmech.2015.01.007 K562 3
28075580 10.1021/acs.jnatprod.6b00809 Staphylococcus aureus 2
31648878 10.1016/j.bmc.2019.115151 Acinetobacter baumannii 2
31648878 10.1016/j.bmc.2019.115151 THP-1 2
31648878 10.1016/j.bmc.2019.115151 MRC5 2
28075580 10.1021/acs.jnatprod.6b00809 Enterococcus faecium 2
28075580 10.1021/acs.jnatprod.6b00809 Enterococcus faecalis 2
18841906 10.1021/np800383q Unchecked 2
31648878 10.1016/j.bmc.2019.115151 HEK293 2
25891102 10.1016/j.bmcl.2015.04.003 Tyrosine-protein phosphatase non-receptor type 1 2
36940609 10.1016/j.bmc.2023.117239 Chikungunya virus 2
31648878 10.1016/j.bmc.2019.115151 HepG2 2
36940609 10.1016/j.bmc.2023.117239 ADMET 1
25638569 10.1016/j.ejmech.2015.01.051 Solute carrier family 2, facilitated glucose transporter member 4 1
19102656 10.1021/np800535g Unchecked 1

Data from ChEMBL 36 via Core Engine