Compound Detail

CHEMBL249447

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O=C(/C=C/c1ccc(O)c(O)c1)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](OC(=O)/C=C/c2ccc(O)c(O)c2)[C@H]1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL249447
Phase	Preclinical
Structure Type	MOL
InChI Key	KRZBCHWVBQOTNZ-PSEXTPKNSA-N

Known Names

3,5-Dicaffeoylquinicacid

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

516.5

MW (Da)

1.03

ALogP

HBA

HBD

211.3

PSA (Å²)

0.16

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	C25H24O12
MW	516.46
Aromatic Rings	2
Heavy Atoms	37
NP-Likeness	1.35

Activity Summary

IC50 20 meas. best 7.06

EC50 1 meas. best 4.04

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	7.06	7.06	88.0	1
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	6.89	6.89	130.0	1
Aldo-keto reductase family 1 member B1 CHEMBL2622	IC50	6.52	6.52	300.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	6.19	6.04	640.0	2
Unchecked CHEMBL612545	IC50	5.72	4.8067	1900.0	3
Bifunctional epoxide hydrolase 2 CHEMBL2409	IC50	5.55	5.55	2800.0	1
Influenza A virus H3N2 CHEMBL2366902	IC50	5.31	5.31	4900.0	1
Molecular identity unknown CHEMBL612546	IC50	5.26	5.26	5530.0	1
No relevant target CHEMBL2362975	IC50	5.18	5.18	6600.0	1
Amyloid-beta precursor protein CHEMBL2487	IC50	4.79	4.79	16400.0	1
Radical scavenging activity CHEMBL613712	IC50	4.49	4.49	32400.0	1
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	4.42	4.42	37900.0	1
Glucose-6-phosphate 1-dehydrogenase CHEMBL5347	IC50	4.42	4.42	37660.0	1
Hepatitis B virus CHEMBL613497	EC50	4.04	4.04	90500.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aldo-keto reductase family 1 member B1	IC50	=	88.0	nM	7.06	Inhibition of human recombinant N-terminus His6-tagged AKR1B1 expressed in Esche...	22236472
Aldo-keto reductase family 1 member B10	IC50	=	130.0	nM	6.89	Inhibition of human recombinant N-terminus His6-tagged AKR1B10 expressed in Esch...	22236472
Aldo-keto reductase family 1 member B1	IC50	=	300.0	nM	6.52	Inhibition of Sprague-Dawley rat lens aldose reductase	22264115
Human immunodeficiency virus type 1 integrase	IC50	=	640.0	nM	6.19	Inhibition of HIV1 integrase catalyzed reactions	18674899
Human immunodeficiency virus type 1 integrase	IC50	=	1300.0	nM	5.89	Inhibitory activity against Human Immunodeficiency Virus Type 1 integrase (HIV-1...	9986720
Unchecked	IC50	=	1900.0	nM	5.72	Inhibition of HIV1 integrase activity assessed as suppression of viral replicati...	27676157
Bifunctional epoxide hydrolase 2	IC50	=	2800.0	nM	5.55	Inhibition of sEH (unknown origin) using PHOME as substrate after 40 mins by flu...	28279529
Influenza A virus H3N2	IC50	=	4900.0	nM	5.31	Antiviral activity against Influenza virus A/Hanfang/359/95 (H3N2)	24279769
Molecular identity unknown	IC50	=	5530.0	nM	5.26	Inhibition of recombinant HIV-1 integrase using 32-P labeled dBY-1 as substrate ...	32731188
No relevant target	IC50	=	6600.0	nM	5.18	Inhibition of advanced glycation end-products formation after 14 days by spectro...	22264115
Amyloid-beta precursor protein	IC50	=	16400.0	nM	4.79	Inhibition of human amyloid beta (1 to 42) aggregation after 24 hrs by thioflavi...	22921742
Unchecked	IC50	=	23600.0	nM	4.63	Inhibition of collagenase type 5	15921434
Radical scavenging activity	IC50	=	32400.0	nM	4.49	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins ...	23356964
Tyrosine-protein phosphatase non-receptor type 1	IC50	=	37900.0	nM	4.42	Inhibition of PTP1B (unknown origin)	29525218
Glucose-6-phosphate 1-dehydrogenase	IC50	=	37660.0	nM	4.42	Inhibition of G6PD (unknown origin) assessed as reduction in 6-phospho-D-glucono...	33689874
Unchecked	IC50	=	85900.0	nM	4.07	Inhibition of A23187-induced LTB4 formation in human polymorphonuclear leukocyte...	2822857
Hepatitis B virus	EC50	=	90500.0	nM	4.04	Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as re...	36709647

Literature References

PubMed	DOI	Target Context	# Activities
21469692	10.1021/np100934u	Mus musculus	11
2822857	10.1021/np50051a009	Unchecked	10
22096083	10.1124/dmd.111.041665	ADMET	9
7623043	10.1021/np50119a001	Monocyte	8
36848642	10.1021/acs.jnatprod.2c00788	Aedes aegypti	6
30030001	10.1016/j.bmc.2018.07.014	Unchecked	4
21469692	10.1021/np100934u	RAW264.7	4
24279769	10.1021/np4005773	NON-PROTEIN TARGET	4
28279529	10.1016/j.bmcl.2017.02.013	Bifunctional epoxide hydrolase 2	4
36709647	10.1016/j.ejmech.2023.115128	Hepatitis B virus	3
28520428	10.1021/acs.jnatprod.6b00703	Bacillus cereus	2
28520428	10.1021/acs.jnatprod.6b00703	Plasma	2
26996372	10.1016/j.bmcl.2016.03.010	Histone deacetylase	2
30030001	10.1016/j.bmc.2018.07.014	B16-F1	2
22921742	10.1016/j.bmc.2012.08.001	Amyloid-beta precursor protein	2
18029179	10.1016/j.bmcl.2007.10.046	Hepatitis B virus	2
29525218	10.1016/j.bmcl.2018.02.052	Tyrosine-protein phosphatase non-receptor type 1	2
16643034	10.1021/np050447r	NON-PROTEIN TARGET	2
10096846	10.1021/np980153o	Unchecked	2
11430019	10.1021/np0003995	Human immunodeficiency virus type 1 integrase	1

Data from ChEMBL 36 via Core Engine