Compound Detail

CHEMBL145

CAFFEIC ACID

🧪 Phase III

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Research home View demo workspace

🧪 Phase III

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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL145
Name	CAFFEIC ACID
Phase	Phase III
Structure Type	MOL
InChI Key	QAIPRVGONGVQAS-DUXPYHPUSA-N

Known Names

2-PROPENOIC ACID, 3-(3,4-DIHYDROXYPHENYL)-, (2E)- Caffeic acid Cinnamic acid, 3,4-dihydroxy- NSC-57197 NSC-623438 Trans-3,4-dihydroxycinnamic acid Trans-caffeate Trans-caffeic acid

Targets

174

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

180.2

MW (Da)

1.20

ALogP

HBA

HBD

77.8

PSA (Å²)

0.47

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C9H8O4
MW	180.16
Aromatic Rings	1
Heavy Atoms	13
NP-Likeness	1.12

Indications

Esophageal Neoplasms Purpura, Thrombocytopenic, Idiopathic

Activity Summary

IC50 136 meas. best 8.7

EC50 20 meas. best 7.32

Ki 18 meas. best 6.22

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
T47D CHEMBL614361	IC50	8.7	8.7	2.0	1
Matrix metalloproteinase-9 CHEMBL321	IC50	8.0	7.835	10.0	2
72 kDa type IV collagenase CHEMBL333	IC50	7.62	7.62	24.3	1
No relevant target CHEMBL2362975	EC50	7.32	5.38	47.8	4
Catechol O-methyltransferase CHEMBL2372	IC50	7.03	6.13	92.8	2
No relevant target CHEMBL2362975	IC50	7.0	4.8958	100.0	12
Unchecked CHEMBL612545	IC50	6.91	5.1816	124.5	25
Type-1 angiotensin II receptor CHEMBL227	IC50	6.9	6.9	124.6	1
Radical scavenging activity CHEMBL613712	IC50	6.82	5.03	150.0	12
Mus musculus CHEMBL375	IC50	6.72	6.72	190.0	2
Interstitial collagenase CHEMBL332	IC50	6.62	6.62	238.9	1
Unchecked CHEMBL612545	Ki	6.22	6.22	600.0	1
Carbonic anhydrase 2 CHEMBL205	Ki	5.79	5.79	1610.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.66	4.9738	2200.0	8
Carbonic anhydrase 1 CHEMBL261	Ki	5.62	5.62	2380.0	1
Staphylococcus epidermidis CHEMBL353	EC50	5.56	5.56	2780.0	1
Staphylococcus aureus CHEMBL352	EC50	5.56	5.56	2780.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	5.55	5.24	2800.0	3
Lysine-specific demethylase 5B CHEMBL3774295	IC50	5.54	5.54	2880.0	1
Seed linoleate 13S-lipoxygenase-1 CHEMBL4586	IC50	5.52	5.52	3000.0	1
5-lipoxygenase CHEMBL3317	IC50	5.52	5.46	3000.0	2
Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335	IC50	5.51	5.51	3060.0	1
Dipeptidyl peptidase 4 CHEMBL284	IC50	5.47	5.47	3370.0	1
Leishmania amazonensis CHEMBL612877	IC50	5.28	4.9433	5200.0	3
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	5.21	5.21	6110.0	1
Carbonic anhydrase 7 CHEMBL2326	Ki	5.19	5.19	6420.0	1
Carbonic anhydrase 5A, mitochondrial CHEMBL4789	Ki	5.19	5.19	6490.0	1
MOLM-13 CHEMBL3706572	IC50	5.19	5.19	6400.0	1
Carbonic anhydrase 6 CHEMBL3025	Ki	5.13	5.13	7330.0	1
Carbonic anhydrase 9 CHEMBL3594	Ki	5.1	5.1	7870.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	5.07	4.8167	8500.0	3
Carbonic anhydrase 14 CHEMBL3510	Ki	5.06	5.06	8710.0	2
Carbonic anhydrase 12 CHEMBL3242	Ki	5.04	5.04	9060.0	2
Carbonic anhydrase 5B, mitochondrial CHEMBL3969	Ki	5.04	5.04	9080.0	1
Radical scavenging activity CHEMBL613712	EC50	5.02	4.885	9480.0	2
U-937 CHEMBL612794	EC50	5.0	5.0	9900.0	1
Carbonic anhydrase 4 CHEMBL3729	Ki	5.0	5.0	10100.0	1
Carbonic anhydrase 3 CHEMBL2885	Ki	5.0	5.0	10000.0	1
Carbonic anhydrase 13 CHEMBL2186	Ki	4.96	4.96	10900.0	2
Histone deacetylase CHEMBL2093865	Ki	4.96	4.96	10840.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.9	4.9	12600.0	1
Amyloid-beta precursor protein CHEMBL2487	IC50	4.81	4.645	15600.0	2
Beta-secretase 1 CHEMBL4822	IC50	4.78	4.78	16670.0	1
HT-29 CHEMBL384	IC50	4.57	4.57	27160.0	1
HCT-116 CHEMBL394	IC50	4.53	4.53	29730.0	1
Leishmania donovani CHEMBL367	IC50	4.51	4.51	31100.0	1
Aldo-keto reductase family 1 member B1 CHEMBL1900	IC50	4.5	4.5	32000.0	1
SH-SY5Y CHEMBL614910	EC50	4.47	4.47	33820.0	1
Acidic alpha-glucosidase CHEMBL3513	IC50	4.46	4.46	34690.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL312	IC50	4.37	4.37	43000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
T47D	IC50	=	2.0	nM	8.7	Antiproliferative activity against human T47D cells after 5 days by MTT assay	23228470
Matrix metalloproteinase-9	IC50	=	10.0	nM	8.0	Inhibition of MMP9 in human Hep3B cells using gelatin as substrate	23375794
Matrix metalloproteinase-9	IC50	=	21.22	nM	7.67	Inhibition of human recombinant MMP9 using succinylated gelatin as substrate inc...	23375794
72 kDa type IV collagenase	IC50	=	24.26	nM	7.62	Inhibition of human recombinant MMP2 using succinylated gelatin as substrate inc...	23375794
No relevant target	EC50	=	47.8	nM	7.32	Antioxidant activity assessed as DPPH free radical scavenging activity	28415050
Catechol O-methyltransferase	IC50	=	92.82	nM	7.03	Inhibition of MB-COMT in Wistar rat brain assessed as metanephrine formation pre...	27463695
No relevant target	IC50	=	100.0	nM	7.0	Antioxidant activity assessed as inhibition of allopurinol-xanthine oxidase syst...	27162124
Unchecked	IC50	=	124.55	nM	6.91	Reversal of paclitaxel resistance in human Flp-In-293 cells expressing ABCB1 ass...	35751979
Type-1 angiotensin II receptor	IC50	=	124.6	nM	6.9	Displacement of [125-I]-[Sar1, AngII from AT1R (unknown origin) expressed in Esc...	33784102
Radical scavenging activity	IC50	=	150.0	nM	6.82	Antioxidant activity assessed as DPPH radical scavenging activity after 15 mins ...	23811091
Mus musculus	IC50	=	190.0	nM	6.72	Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops fl...	22047800
Mus musculus	IC50	=	190.0	nM	6.72	Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops fl...	21388814
Unchecked	IC50	=	198.04	nM	6.7	Reversal of vincristine resistance in human Flp-In-293 cells expressing ABCB1 as...	35751979
Interstitial collagenase	IC50	=	238.91	nM	6.62	Inhibition of human recombinant MMP1 using succinylated gelatin as substrate inc...	23375794
Unchecked	IC50	=	500.0	nM	6.3	Compound was evaluated for hydroxyl radical (OH) scavenging activity	-
Unchecked	IC50	=	596.9	nM	6.22	Reversal of doxorubicin resistance in human Flp-In-293 cells expressing ABCB1 as...	35751979
Unchecked	Ki	=	600.0	nM	6.22	Inhibition of Malassezia globosa recombinant beta-carbonic anhydrase preincubate...	28343756
Carbonic anhydrase 2	Ki	=	1610.0	nM	5.79	Inhibition of human CA2 by stopped-flow CO2 hydration assay	20185318
NON-PROTEIN TARGET	IC50	=	2200.0	nM	5.66	Antioxidant activity assessed as superoxide radical anion scavenging activity	17387019
Carbonic anhydrase 1	Ki	=	2380.0	nM	5.62	Inhibition of human CA1 by stopped-flow CO2 hydration assay	20185318

Literature References

PubMed	DOI	Target Context	# Activities
23682762	10.1021/jm400374q	Unchecked	16
29192771	10.1021/acs.jnatprod.7b00699	Unchecked	16
-	10.1007/s00044-011-9690-5	Rattus norvegicus	15
2822857	10.1021/np50051a009	Unchecked	12
28682072	10.1021/acs.jnatprod.7b00433	Unchecked	9
3430163	10.1021/np50052a004	Hepatocyte	8
28415050	10.1016/j.ejmech.2017.03.061	No relevant target	8
26410075	10.1016/j.bmcl.2015.09.003	Rattus norvegicus	7
-	10.1007/s00044-012-0419-x	Radical scavenging activity	6
18667320	10.1016/j.bmc.2008.07.006	RAW264.7	6
35751979	10.1016/j.ejmech.2022.114542	Unchecked	6
29477271	10.1016/j.bmcl.2018.02.025	Unchecked	6
22925447	10.1016/j.bmc.2012.07.043	U-937	5
26465380	10.1021/acs.jnatprod.5b00481	Unchecked	5
-	10.1039/C4MD00022F	NON-PROTEIN TARGET	5
23145924	10.1021/jf303290g	Diplodia seriata	4
32214761	10.1007/s00044-010-9309-2	Radical scavenging activity	4
21183258	10.1016/j.ejmech.2010.11.021	RAW264.7	4
10096846	10.1021/np980153o	Unchecked	4
28745898	10.1021/acs.jmedchem.7b00741	No relevant target	4

Data from ChEMBL 36 via Core Engine