Compound Detail

CHEMBL76602

alpha-CYANO-4-HYDROXYCINNAMIC ACID

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N#C/C(=C\c1ccc(O)cc1)C(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL76602
Name	alpha-CYANO-4-HYDROXYCINNAMIC ACID
Phase	Preclinical
Structure Type	MOL
InChI Key	AFVLVVWMAFSXCK-VMPITWQZSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

189.2

MW (Da)

1.38

ALogP

HBA

HBD

81.3

PSA (Å²)

0.54

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 13 meas. best 7.06

EC50 3 meas. best 5.01

Ki 1 meas.

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Monocarboxylate transporter 1 CHEMBL4360	IC50	7.06	5.53	87.2	2
Monocarboxylate transporter 1 CHEMBL2073709	IC50	6.55	6.55	281.0	1
G-protein coupled receptor 35 CHEMBL1293267	EC50	5.01	4.58	9800.0	2
Monocarboxylate transporter 4 CHEMBL2073663	IC50	4.97	4.665	10700.0	2
SiHa CHEMBL612542	EC50	4.97	4.97	10700.0	1
Monocarboxylate transporter 2 CHEMBL2073718	IC50	4.62	4.62	24000.0	1
G-protein coupled receptor 35 CHEMBL1293267	IC50	4.52	4.52	30400.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Monocarboxylate transporter 1	IC50	=	87.2	nM	7.06	Inhibition of MCT1 transport activity in human A549 cells using 3-BP as substrat...	36584238
Monocarboxylate transporter 1	IC50	=	281.0	nM	6.55	Inhibition of MCT1 in rat RBE4 cells assessed as reduction in [14C]lactate uptak...	34517305
G-protein coupled receptor 35	EC50	=	9800.0	nM	5.01	Agonist activity at GPR35 receptor in human HT-29 cells after 10 mins by dynamic...	24900447
SiHa	EC50	=	10700.0	nM	4.97	Cytotoxicity against human SiHa cells in lactate-containing medium after 72 hrs ...	24095010
Monocarboxylate transporter 4	IC50	=	10700.0	nM	4.97	Inhibition of MCT4-mediated [14C]-lactate uptake in human SiHa cells in lactate-...	24095010
Monocarboxylate transporter 2	IC50	=	24000.0	nM	4.62	TP_TRANSPORTER: inhibition of lactate uptake in Xenopus laevis oocytes	10417314
G-protein coupled receptor 35	IC50	=	30400.0	nM	4.52	Desensitization of GPR35 receptor in human HT-29 cells assessed as inhibition of...	24900447
Monocarboxylate transporter 4	IC50	=	43500.0	nM	4.36	Inhibition of MCT4-mediated [14C]-lactate uptake in human SiHa cells in lactate-...	24095010
G-protein coupled receptor 35	EC50	=	70700.0	nM	4.15	Agonist activity at GPR35 receptor in human U2OS cells coexpressing Gal4-VP16-TE...	24900447
Monocarboxylate transporter 1	IC50	=	100000.0	nM	4.0	Inhibition of MCT1 (unknown origin)	32388280

PubMed	DOI	Target Context	# Activities
24900447	10.1021/ml2003058	G-protein coupled receptor 35	6
33221062	10.1016/j.bmc.2020.115870	Unchecked	5
33221062	10.1016/j.bmc.2020.115870	HeLa	4
33221062	10.1016/j.bmc.2020.115870	HCT-116	3
28051863	10.1021/acs.jmedchem.6b01285	Mus musculus	3
10417314	10.1042/0264-6021:3410529	Monocarboxylate transporter 2	2
10417314	10.1042/0264-6021:3410529	Monocarboxylate transporter 1	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
24095010	10.1016/j.bmc.2013.09.010	Monocarboxylate transporter 4	2
24095010	10.1016/j.bmc.2013.09.010	SiHa	2
2552117	10.1021/jm00130a020	Epidermal growth factor receptor	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B3	1
36584238	10.1021/acs.jmedchem.2c01612	NIH3T3	1
-	10.21203/rs.3.rs-23951/v1	SARS-CoV-2	1
28051863	10.1021/acs.jmedchem.6b01285	Potassium channel subfamily K member 2	1
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B1	1
11101640	10.1111/j.1469-7793.2000.00285.x	Monocarboxylate transporter 4	1
9374487	10.1074/jbc.272.48.30096	Monocarboxylate transporter 1	1
9639576	10.1042/bj3330167	Monocarboxylate transporter 1	1

Data from ChEMBL 36 via Core Engine