Compound Detail

CHEMBL319244

CAFFEIC ACID PHENETHYL ESTER

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O=C(/C=C/c1ccc(O)c(O)c1)OCCc1ccccc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL319244
Name	CAFFEIC ACID PHENETHYL ESTER
Phase	Preclinical
Structure Type	MOL
InChI Key	SWUARLUWKZWEBQ-VQHVLOKHSA-N

Targets

123

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

284.3

MW (Da)

2.90

ALogP

HBA

HBD

66.8

PSA (Å²)

0.50

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	C17H16O4
MW	284.31
Aromatic Rings	2
Heavy Atoms	21
NP-Likeness	0.62

Activity Summary

IC50 103 meas. best 7.1

EC50 17 meas. best 6.71

Ki 3 meas. best 7.34

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aldo-keto reductase family 1 member B10 CHEMBL5983	Ki	7.34	7.34	46.0	1
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	7.1	6.755	80.0	2
Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL2903	IC50	6.89	6.89	130.0	1
RAW264.7 CHEMBL612557	EC50	6.71	6.025	193.0	2
NON-PROTEIN TARGET CHEMBL3879801	EC50	6.52	5.845	300.0	2
RAW264.7 CHEMBL612557	IC50	6.41	5.62	390.0	3
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	6.24	5.845	570.0	2
Mitogen-activated protein kinase 1 CHEMBL4040	IC50	6.16	6.16	686.0	1
Prostaglandin G/H synthase 1 CHEMBL221	IC50	6.08	5.16	833.0	2
Unchecked CHEMBL612545	EC50	6.05	6.05	890.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	6.01	6.01	970.0	1
Epidermal growth factor receptor CHEMBL203	IC50	6.0	6.0	1005.0	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL2366456	IC50	5.96	5.96	1100.0	1
Receptor tyrosine-protein kinase erbB-2 CHEMBL1824	IC50	5.88	5.88	1329.0	1
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	5.85	5.85	1414.0	1
Aldo-keto reductase family 1 member C3 CHEMBL4681	IC50	5.77	5.6	1700.0	2
PC-12 CHEMBL612556	IC50	5.7	5.7	2000.0	1
Estrogen receptor CHEMBL206	Ki	5.65	5.65	2260.0	1
Aldo-keto reductase family 1 member C4 CHEMBL4999	IC50	5.64	5.36	2300.0	2
HeLa CHEMBL399	EC50	5.63	5.63	2360.0	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	5.54	5.54	2887.0	1
BeWo CHEMBL614525	IC50	5.53	5.53	2960.0	1
A2780 CHEMBL614004	EC50	5.46	5.46	3500.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.42	5.42	3756.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.42	5.42	3787.0	1
Mus musculus CHEMBL375	IC50	5.4	4.8733	4000.0	3
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	5.38	5.38	4214.0	1
Peritoneal macrophage CHEMBL5314330	IC50	5.37	5.37	4310.0	1
SW-1736 CHEMBL614773	EC50	5.33	5.33	4700.0	1
J774.1 CHEMBL4296442	IC50	5.32	5.32	4800.0	1
Plasmodium falciparum CHEMBL364	IC50	5.3	5.1143	5011.9	7
IMR-32 CHEMBL614585	IC50	5.3	5.3	5000.0	1
Bel-7402 CHEMBL614279	IC50	5.26	5.26	5500.0	1
Unchecked CHEMBL612545	IC50	5.22	4.8333	6000.0	6
Aldo-keto reductase family 1 member C2 CHEMBL5847	IC50	5.22	4.905	6000.0	2
LNCaP CHEMBL612518	IC50	5.21	4.84	6200.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.19	4.7347	6400.0	15
BV-2 CHEMBL614781	IC50	5.19	5.19	6400.0	2
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	5.16	4.9225	7000.0	4
Estrogen receptor CHEMBL206	IC50	5.1	5.1	7912.0	1
HUVEC CHEMBL613979	EC50	5.1	5.1	8000.0	1
Amyloid-beta precursor protein CHEMBL2487	EC50	5.08	5.08	8410.0	1
Transthyretin CHEMBL3194	EC50	5.07	5.07	8600.0	1
HeLa CHEMBL399	IC50	5.06	4.74	8800.0	2
HT-1080 CHEMBL614580	EC50	5.02	5.02	9500.0	1
HL-60 CHEMBL383	IC50	5.01	5.01	9800.0	1
A549 CHEMBL392	IC50	5.01	4.552	9720.0	5
Peritoneal macrophage cell CHEMBL613703	IC50	4.96	4.96	11000.0	1
FaDu CHEMBL612250	EC50	4.92	4.92	12100.0	1
MCF7 CHEMBL387	EC50	4.92	4.92	12100.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aldo-keto reductase family 1 member B10	Ki	=	46.0	nM	7.34	Mixed-type inhibition at human recombinant N-terminus His6-tagged AKR1B10 expres...	22236472
Aldo-keto reductase family 1 member B10	IC50	=	80.0	nM	7.1	Inhibition of human recombinant N-terminus His6-tagged AKR1B10 expressed in Esch...	22236472
Polyunsaturated fatty acid lipoxygenase ALOX15	IC50	=	130.0	nM	6.89	Inhibition of thapsigargin-stimulated 15-LOX in human primary polymorphonuclear ...	28318946
RAW264.7	EC50	=	193.0	nM	6.71	Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells assess...	18667320
NON-PROTEIN TARGET	EC50	=	300.0	nM	6.52	Antiproliferative activity against mouse 26-L5 cells after 72 hrs by MTT assay	12027739
RAW264.7	IC50	=	390.0	nM	6.41	Antiinflammatory activity in LPS-induced mouse RAW264.7 cells assessed as inhibi...	37976711
Aldo-keto reductase family 1 member B10	IC50	=	390.0	nM	6.41	Inhibition of N-terminal His-tagged human AKR1B10 expressed in Escherichia coli ...	32463235
Aldo-keto reductase family 1 member B1	IC50	=	570.0	nM	6.24	Inhibition of human recombinant N-terminus His6-tagged AKR1B1 expressed in Esche...	22236472
Mitogen-activated protein kinase 1	IC50	=	686.0	nM	6.16	DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: ...	-
Prostaglandin G/H synthase 1	IC50	=	833.0	nM	6.08	DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid)	-
Unchecked	EC50	=	890.0	nM	6.05	PUBCHEM_BIOASSAY: Dose response confirmation of small molecule activators of the...	-
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	970.0	nM	6.01	Inhibition of 5-LO in human PMNL cells assessed as reduction in leukotriene form...	31260889
Epidermal growth factor receptor	IC50	=	1005.0	nM	6.0	DRUGMATRIX: Protein Tyrosine Kinase, EGF Receptor enzyme inhibition (substrate: ...	-
Voltage-dependent L-type calcium channel subunit alpha-1C	IC50	=	1100.0	nM	5.96	Inhibition of Cav1.2 calcium current measured using whole cell patch clamp in gu...	-
Receptor tyrosine-protein kinase erbB-2	IC50	=	1329.0	nM	5.88	DRUGMATRIX: Protein Tyrosine Kinase, ERBB2 (HER2) enzyme inhibition (substrate: ...	-
Aldo-keto reductase family 1 member B1	IC50	=	1414.0	nM	5.85	DRUGMATRIX: Aldose Reductase enzyme inhibition (substrate: DL-Glyceraldehyde)	-
Aldo-keto reductase family 1 member C3	IC50	=	1700.0	nM	5.77	Inhibition of human recombinant AKR1C3 expressed in Escherichia coli JM109 cells...	22506594
PC-12	IC50	=	2000.0	nM	5.7	Neuroprotection activity in rat PC12 cells assessed as reduction in H2O2-induced...	30928712
Estrogen receptor	Ki	=	2260.0	nM	5.65	DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol)	-
Aldo-keto reductase family 1 member C4	IC50	=	2300.0	nM	5.64	Inhibition of human recombinant GST-tagged AKR1C4 expressed in Escherichia coli ...	22506594

Literature References

PubMed	DOI	Target Context	# Activities
33210536	10.1021/acs.jnatprod.0c00350	Unchecked	23
21265554	10.1021/np100724f	Unchecked	15
28682072	10.1021/acs.jnatprod.7b00433	Unchecked	14
37976711	10.1016/j.ejmech.2023.115936	Mus musculus	14
18024584	10.1073/pnas.0709695104	H4	11
23876066	10.1021/np400129z	Microphthalmia-associated transcription factor	10
24080105	10.1016/j.bmc.2013.08.057	LNCaP	9
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
22831798	10.1016/j.bmc.2012.06.031	RAW264.7	7
36152388	10.1016/j.ejmech.2022.114745	Mus musculus	7
29202400	10.1016/j.ejmech.2017.11.066	Mus musculus	6
15270564	10.1021/np030529k	Macrophage	6
10560729	10.1016/s0960-894x(99)00536-3	Mus musculus	6
23870700	10.1016/j.bmc.2013.05.043	Radical scavenging activity	6
38746881	10.1021/acsmedchemlett.4c00099	MDA-MB-231	6
23876066	10.1021/np400129z	B16-F10	6
19775895	10.1016/j.bmc.2009.08.050	Peritoneal macrophage cell	5
21265554	10.1021/np100724f	NON-PROTEIN TARGET	5
15270564	10.1021/np030529k	ADMET	5
24697335	10.1021/jm500258v	NON-PROTEIN TARGET	5

Data from ChEMBL 36 via Core Engine