Compound Detail

CHEMBL69863

PICEATANNOL

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Oc1cc(O)cc(/C=C/c2ccc(O)c(O)c2)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL69863
Name	PICEATANNOL
Phase	Preclinical
Structure Type	MOL
InChI Key	CDRPUGZCRXZLFL-OWOJBTEDSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

244.2

MW (Da)

2.68

ALogP

HBA

HBD

80.9

PSA (Å²)

0.48

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C14H12O4
MW	244.25
Aromatic Rings	2
Heavy Atoms	18
NP-Likeness	1.03

Activity Summary

IC50 50 meas. best 6.62

Ki 11 meas. best 5.93

EC50 8 meas. best 5.3

Kd 4 meas. best 5.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	6.62	5.11	240.0	12
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	6.62	6.33	240.0	3
Lactoylglutathione lyase CHEMBL2424	IC50	6.12	6.12	760.0	1
Histone deacetylase 6 CHEMBL1865	IC50	6.05	6.05	894.7	1
A disintegrin and metalloproteinase with thrombospondin motifs 5 CHEMBL2285	Ki	5.93	5.93	1180.0	1
Transthyretin CHEMBL3194	Kd	5.82	5.75	1500.0	2
Unchecked CHEMBL612545	Kd	5.8	5.32	1580.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.75	5.75	1800.0	1
J774 CHEMBL614123	IC50	5.58	5.29	2600.0	3
A disintegrin and metalloproteinase with thrombospondin motifs 4 CHEMBL2318	Ki	5.57	5.57	2680.0	1
Matrix metalloproteinase-9 CHEMBL321	Ki	5.32	5.32	4770.0	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	5.3	4.4375	5000.0	4
Tyrosine-protein kinase SYK CHEMBL2599	EC50	5.3	4.95	5000.0	2
HCT-116 CHEMBL394	IC50	5.3	5.3	5000.0	1
Transthyretin CHEMBL3194	Ki	5.27	5.27	5400.0	1
Macrophage metalloelastase CHEMBL4393	Ki	5.25	5.25	5570.0	1
Neutrophil collagenase CHEMBL4588	Ki	5.06	5.06	8710.0	1
Tyrosine-protein kinase SYK CHEMBL2599	IC50	5.0	4.8067	10000.0	3
Plasmodium falciparum CHEMBL364	IC50	5.0	4.9429	10000.0	7
72 kDa type IV collagenase CHEMBL333	Ki	4.98	4.98	10400.0	1
Myosin light chain kinase, smooth muscle CHEMBL2428	IC50	4.92	4.92	12000.0	2
Unchecked CHEMBL612545	Ki	4.82	4.82	15000.0	1
NCI-H522 CHEMBL614387	EC50	4.77	4.5633	17000.0	3
Calcium dependent protein kinase CHEMBL1075033	IC50	4.72	4.72	19000.0	1
Human immunodeficiency virus 1 CHEMBL378	EC50	4.67	4.67	21400.0	2
Mus musculus CHEMBL375	IC50	4.64	4.64	23000.0	1
Radical scavenging activity CHEMBL613712	IC50	4.55	4.55	28000.0	1
A2780 CHEMBL614004	IC50	4.39	4.39	41000.0	1
Arginase-1 CHEMBL1075060	IC50	4.33	4.235	47000.0	2
Streptococcus mutans CHEMBL612426	IC50	4.28	4.28	52000.0	1
Arginase-1 CHEMBL1075097	IC50	4.16	4.16	69000.0	1
BV-2 CHEMBL614781	IC50	4.09	4.09	80510.0	1
Hepatitis B virus CHEMBL613497	EC50	4.02	4.02	96200.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	240.0	nM	6.62	Inhibition of MAPK/ERK signaling pathway in human NCI-H1975 cells	38295689
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	240.0	nM	6.62	Inhibition of 5-LOX in human PMNL cells assessed as A23187-stimulated LTB4 produ...	31351395
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	390.0	nM	6.41	Inhibition of recombinant human 5-LOX using arachidonic acid as substrate preinc...	34479036
Lactoylglutathione lyase	IC50	=	760.0	nM	6.12	Inhibition of human N-terminal His6-tagged GLO1 expressed in baculovirus infecte...	28169168
Histone deacetylase 6	IC50	=	894.7	nM	6.05	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	1100.0	nM	5.96	Inhibition of human 5-LOX expressed in Escherichia coli BL21 using arachidonic a...	31351395
A disintegrin and metalloproteinase with thrombospondin motifs 5	Ki	=	1180.0	nM	5.93	Inhibition of ADAMTS-5 (unknown origin)	36250680
Transthyretin	Kd	=	1500.0	nM	5.82	Binding affinity to N-terminal hexa-histidine tagged TTR V30M mutant (unknown or...	37910439
Unchecked	Kd	=	1580.0	nM	5.8	Binding affinity to Streptococcus mutans GtfB	31391878
NON-PROTEIN TARGET	IC50	=	1800.0	nM	5.75	Antioxidant activity against cupric ion-induced lipid peroxidation in human LDL ...	9599270
Transthyretin	Kd	=	2100.0	nM	5.68	Binding affinity to recombinant N-terminal hexa-histidine tagged TTR V30M mutant...	37910439
J774	IC50	=	2600.0	nM	5.58	Antiinflammatory activity in mouse J774 cells assessed as reduction in LPS-induc...	29726680
A disintegrin and metalloproteinase with thrombospondin motifs 4	Ki	=	2680.0	nM	5.57	Inhibition of ADAMTS-4 (unknown origin)	36250680
Unchecked	IC50	=	3000.0	nM	5.52	Inhibition of rat liver protein kinase A	18077363
Unchecked	IC50	=	3000.0	nM	5.52	Inhibition of PKA	16441060
J774	IC50	=	4000.0	nM	5.4	Antiinflammatory activity in mouse J774 cells assessed as reduction in LPS-induc...	29726680
Unchecked	IC50	=	4500.0	nM	5.35	Anticancer activity against human AZ-AHR cells assessed as cell growth inhibitio...	32485531
Matrix metalloproteinase-9	Ki	=	4770.0	nM	5.32	Inhibition of MMP9 (unknown origin)	36250680
HCT-116	IC50	=	5000.0	nM	5.3	Anticancer activity against human HCT-116 cells assessed as cell growth inhibiti...	32485531
Tyrosine-protein kinase Lck	IC50	=	5000.0	nM	5.3	Inhibition of p56 Lck tyrosine kinase	9873567

Literature References

PubMed	DOI	Target Context	# Activities
29110988	10.1016/j.bmcl.2017.10.045	No relevant target	13
31351395	10.1016/j.ejmech.2019.07.033	H9c2	9
26453007	10.1016/j.bmcl.2015.09.064	Unchecked	8
20022753	10.1016/j.bmcl.2009.12.020	Streptococcus mutans	8
20022753	10.1016/j.bmcl.2009.12.020	Streptococcus sanguinis	8
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
37910439	10.1021/acs.jmedchem.3c01698	Transthyretin	7
6736971	10.1021/np50032a019	NON-PROTEIN TARGET	6
23145924	10.1021/jf303290g	Diplodia seriata	6
29726680	10.1021/acs.jnatprod.7b00384	J774	6
26453007	10.1016/j.bmcl.2015.09.064	Pseudomonas aeruginosa	6
28169168	10.1016/j.bmcl.2017.01.070	NCI-H522	6
33479657	10.1039/d0md00011f	Arginase-1	6
23010273	10.1016/j.bmcl.2012.08.108	Human immunodeficiency virus 1	4
16441060	10.1021/np050229y	Unchecked	4
-	10.6019/CHEMBL4808148	Histone deacetylase 6	4
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	3
28169168	10.1016/j.bmcl.2017.01.070	Lactoylglutathione lyase	3
29726680	10.1021/acs.jnatprod.7b00384	Mus musculus	3
23145924	10.1021/jf303290g	Neofusicoccum parvum	3

Data from ChEMBL 36 via Core Engine