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Compound Detail

CHEMBL348436

CIRSIMARITIN
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COc1cc2oc(-c3ccc(O)cc3)cc(=O)c2c(O)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL348436
Name CIRSIMARITIN
Phase Preclinical
Structure Type MOL
InChI Key ZIIAJIWLQUVGHB-UHFFFAOYSA-N
7
Targets
9
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

314.3
MW (Da)
2.89
ALogP
6
HBA
2
HBD
89.1
PSA (Ų)
0.77
QED
0
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 C17H14O6
MW 314.29
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness 1.26

Activity Summary

IC50 6 meas. best 6.37
Ki 3 meas. best 5.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dipeptidyl peptidase 4
CHEMBL3813
 IC50 6.37 6.37 430.0 1
Adenosine receptor A1
CHEMBL318
 Ki 5.92 5.92 1200.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 5.85 5.85 1412.5 1
Adenosine receptor A3
CHEMBL256
 Ki 5.76 5.76 1720.0 1
Adenosine receptor A2a
CHEMBL302
 Ki 5.52 5.52 3000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.77 4.77 16900.0 1
3-oxoacyl-acyl-carrier protein reductase
CHEMBL4513
 IC50 4.16 4.16 70000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dipeptidyl peptidase 4 IC50 = 430.0 nM 6.37 Inhibition of porcine DPP4 after 30 mins by luminescence assay 29609120
Adenosine receptor A1 Ki = 1200.0 nM 5.92 Displacement of specific [3H]PIA binding from adenosine A1 receptor in rat brain... 8576921
Aldo-keto reductase family 1 member B1 IC50 = 1412.54 nM 5.85 Inhibition of rat lens aldose reductase 18585047
Adenosine receptor A3 Ki = 1720.0 nM 5.76 Displacement of [125I]AB-MECA binding to human Adenosine A3 receptor expressed i... 8576921
Adenosine receptor A2a Ki = 3000.0 nM 5.52 Affinity at Adenosine A2A receptor in rat striatal membranes by [3H]- CGS 21680 ... 8576921
Plasmodium falciparum IC50 = 16900.0 nM 4.77 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum NF54 16722653
3-oxoacyl-acyl-carrier protein reductase IC50 = 70000.0 nM 4.16 Inhibition of FabG 16722653

Literature References

PubMed DOI Target Context # Activities
28784292 10.1016/j.bmcl.2017.07.070 MDA-MB-231 9
28554870 10.1016/j.bmcl.2017.05.051 RAW264.7 8
28784292 10.1016/j.bmcl.2017.07.070 HUVEC 8
1593282 10.1021/np50081a012 Unchecked 6
26523667 10.1016/j.ejmech.2015.10.039 No relevant target 5
33378620 10.1021/acs.jnatprod.0c00832 Listeria monocytogenes 4
32182064 10.1021/acs.jnatprod.9b01024 Enterococcus faecalis 4
26523667 10.1016/j.ejmech.2015.10.039 Plasma 4
33378620 10.1021/acs.jnatprod.0c00832 Pseudomonas aeruginosa 4
28458136 10.1016/j.ejmech.2017.04.054 Acetylcholinesterase 4
33378620 10.1021/acs.jnatprod.0c00832 Escherichia coli 4
33378620 10.1021/acs.jnatprod.0c00832 Staphylococcus aureus 4
32182064 10.1021/acs.jnatprod.9b01024 Enterococcus faecium 3
28784292 10.1016/j.bmcl.2017.07.070 Unchecked 3
28458136 10.1016/j.ejmech.2017.04.054 No relevant target 3
6677714 10.1021/np50030a007 Klebsiella pneumoniae 2
6677714 10.1021/np50030a007 Proteus vulgaris 2
28784292 10.1016/j.bmcl.2017.07.070 RAC-alpha serine/threonine-protein kinase 2
28554870 10.1016/j.bmcl.2017.05.051 NF-kappa-B inhibitor alpha 2
28784292 10.1016/j.bmcl.2017.07.070 MCF7 2

Data from ChEMBL 36 via Core Engine