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Compound Detail

CHEMBL492828

ISOXANTHOHUMOL
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COc1cc(O)c(CC=C(C)C)c2c1C(=O)CC(c1ccc(O)cc1)O2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL492828
Name ISOXANTHOHUMOL
Phase Preclinical
Structure Type MOL
InChI Key YKGCBLWILMDSAV-UHFFFAOYSA-N
11
Targets
13
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

354.4
MW (Da)
4.32
ALogP
5
HBA
2
HBD
76.0
PSA (Ų)
0.80
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H22O5
MW 354.40
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 2.14

Activity Summary

IC50 12 meas. best 5.33
EC50 1 meas. best 5.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
 EC50 5.85 5.85 1400.0 1
MCF7
CHEMBL387
 IC50 5.33 4.91 4690.0 3
Ishikawa
CHEMBL614649
 IC50 4.6 4.6 24900.0 1
Beta-secretase 1
CHEMBL4822
 IC50 4.56 4.56 27700.0 1
Unchecked
CHEMBL612545
 IC50 4.51 4.51 30700.0 1
Protein kinase C theta type
CHEMBL3920
 IC50 4.5 4.5 31600.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.45 4.45 35420.0 1
Protein kinase C alpha type
CHEMBL299
 IC50 4.34 4.34 45300.0 1
3-phosphoinositide-dependent protein kinase 1
CHEMBL2534
 IC50 4.23 4.23 58700.0 1
PC-3
CHEMBL390
 IC50 4.15 4.15 71320.0 1
HT-29
CHEMBL384
 IC50 4.05 4.05 88820.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor EC50 = 1400.0 nM 5.85 Estrogenic activity at estrogen receptor alpha in human Ishikawa cells assessed ... 28812892
MCF7 IC50 = 4690.0 nM 5.33 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 33257172
MCF7 IC50 = 15300.0 nM 4.82 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 33257172
Ishikawa IC50 = 24900.0 nM 4.6 Cytotoxicity against human Ishikawa cells after 96 hrs by SRB assay 28812892
MCF7 IC50 = 26540.0 nM 4.58 Cytotoxicity against human MCF7 cells after 72 hrs by SRB assay 23434138
Beta-secretase 1 IC50 = 27700.0 nM 4.56 Inhibition of human BACE1 18565755
Unchecked IC50 = 30700.0 nM 4.51 Cytotoxicity against mouse Hepa1c1c7 cells after 48 hrs by crystal violet staini... 28812892
Protein kinase C theta type IC50 = 31600.0 nM 4.5 Inhibition of human PKC theta assessed as inhibition of [33P] incorporation into... 22537682
NON-PROTEIN TARGET IC50 = 35420.0 nM 4.45 Antioxidant activity assessed as concentration required for 50 % inhibition of m... 23434138
Protein kinase C alpha type IC50 = 45300.0 nM 4.34 Inhibition of human PKC alpha assessed as inhibition of [33P] incorporation into... 22537682
3-phosphoinositide-dependent protein kinase 1 IC50 = 58700.0 nM 4.23 Inhibition of human PDK1 assessed as inhibition of [33P] incorporation into subs... 22537682
PC-3 IC50 = 71320.0 nM 4.15 Cytotoxicity against human PC3 cells after 72 hrs by SRB assay 23434138
HT-29 IC50 = 88820.0 nM 4.05 Cytotoxicity against human HT-29 cells after 72 hrs by SRB assay 23434138

Literature References

PubMed DOI Target Context # Activities
38408389 10.1016/j.ejmech.2024.116274 Staphylococcus aureus 11
28234482 10.1021/acs.jnatprod.6b00869 Caco-2 4
33257172 10.1016/j.ejmech.2020.113037 MCF7 2
28812892 10.1021/acs.jnatprod.7b00284 Estrogen receptor 2
18565755 10.1016/j.bmc.2008.05.080 Beta-secretase 1 2
23434138 10.1016/j.bmc.2013.01.026 NON-PROTEIN TARGET 1
38408389 10.1016/j.ejmech.2024.116274 ADMET 1
38408389 10.1016/j.ejmech.2024.116274 Escherichia coli 1
33129991 10.1016/j.bmcl.2020.127639 Transient receptor potential cation channel subfamily A member 1 1
28812892 10.1021/acs.jnatprod.7b00284 Ishikawa 1
28812892 10.1021/acs.jnatprod.7b00284 NAD(P)H dehydrogenase [quinone] 1 1
28812892 10.1021/acs.jnatprod.7b00284 Unchecked 1
23434138 10.1016/j.bmc.2013.01.026 MCF7 1
23434138 10.1016/j.bmc.2013.01.026 PC-3 1
23434138 10.1016/j.bmc.2013.01.026 HT-29 1
23087590 10.1007/s00044-011-9967-8 MCF7 1
23087590 10.1007/s00044-011-9967-8 HT-29 1
23087590 10.1007/s00044-011-9967-8 CCRF-CEM 1
22537682 10.1016/j.bmc.2012.03.072 Protein kinase C theta type 1
22537682 10.1016/j.bmc.2012.03.072 Protein kinase C alpha type 1

Data from ChEMBL 36 via Core Engine