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Compound Detail

CHEMBL27246

CINNAMIC ACID
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O=C(O)/C=C/c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL27246
Name CINNAMIC ACID
Phase Preclinical
Structure Type MOL
InChI Key WBYWAXJHAXSJNI-VOTSOKGWSA-N
13
Targets
39
Activities
2
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

148.2
MW (Da)
1.78
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.65
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C9H8O2
MW 148.16
Aromatic Rings 1
Heavy Atoms 11
NP-Likeness 0.40

Activity Summary

IC50 32 meas. best 6.75
Ki 7 meas. best 8.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase
CHEMBL2093865
 Ki 8.09 8.09 8.2 1
Mus musculus
CHEMBL375
 IC50 6.75 6.75 180.0 1
Tankyrase 1/2
CHEMBL3038515
 IC50 6.16 6.16 685.0 1
Mushroom tyrosinase
CHEMBL6066154
 IC50 5.54 5.54 2850.0 1
Hydroxycarboxylic acid receptor 2
CHEMBL3785
 Ki 5.31 5.31 4900.0 1
Mushroom tyrosinase
CHEMBL6066154
 Ki 5.3 5.3 5000.0 1
Leishmania amazonensis
CHEMBL612877
 IC50 4.81 4.81 15500.0 1
Unchecked
CHEMBL612545
 Ki 4.67 4.655 21500.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.61 4.455 24810.0 2
Unchecked
CHEMBL612545
 IC50 4.46 4.46 34600.0 1
Leishmania donovani
CHEMBL367
 IC50 4.42 4.42 37820.0 1
3-oxoacyl-[acyl-carrier-protein] synthase 3
CHEMBL1795135
 IC50 4.36 4.36 43400.0 1
A-375
CHEMBL613859
 IC50 4.19 4.19 64000.0 1
A549
CHEMBL392
 IC50 4.06 4.06 87000.0 1
ACHN
CHEMBL614519
 IC50 4.04 4.04 91000.0 1

Pharmacokinetic Data

Parameter Value Units Species
KA 5.41 uM Agaricus bisporus
Ka 184.84 /mM Agaricus bisporus
t1/2 - - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase Ki = 8.21 nM 8.09 Inhibition of HDAC in human Hela cells nuclear extracts by fluorimetric assay 19520580
Mus musculus IC50 = 180.0 nM 6.75 Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops fl... 21388814
Tankyrase 1/2 IC50 = 685.0 nM 6.16 Inhibition of tankyrase in human DLD1 cells assessed as reduction in Wnt activit... 25299683
Mushroom tyrosinase IC50 = 2850.0 nM 5.54 Inhibition of cresolase activity of mushroom tyrosinase using 4-[(4-Methylphenyl... 27344491
Hydroxycarboxylic acid receptor 2 Ki = 4900.0 nM 5.31 Displacement of [3H]nicotinic acid from human GPR109a receptor expressed in huma... 21167710
Mushroom tyrosinase Ki = 5000.0 nM 5.3 Inhibition of cresolase activity of mushroom tyrosinase using 4-[(4-Methylphenyl... 27344491
Leishmania amazonensis IC50 = 15500.0 nM 4.81 Antileishmanial activity against Leishmania amazonensis promastigotes 30145372
Unchecked Ki = 21500.0 nM 4.67 Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in am... 28236590
Unchecked Ki = 23000.0 nM 4.64 Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in am... 28236590
NON-PROTEIN TARGET IC50 = 24810.0 nM 4.61 Cytotoxicity against human HeLa cells assessed as decrease in cell viability aft... -
Unchecked IC50 = 34600.0 nM 4.46 Antagonist activity at Gloeobacter violaceus ligand-gated ion channel expressed ... 23682762
Leishmania donovani IC50 = 37820.0 nM 4.42 Antileishmanial activity against Leishmania donovani MHOM/ET/67/L82 amastigotes ... 30145372
3-oxoacyl-[acyl-carrier-protein] synthase 3 IC50 = 43400.0 nM 4.36 Inhibition of N-terminal His-tagged Escherichia coli FabH expressed in Escherich... 21741250
NON-PROTEIN TARGET IC50 = 50180.0 nM 4.3 Cytotoxicity against human A549 cells assessed as decrease in cell viability aft... -
A-375 IC50 = 64000.0 nM 4.19 Anticancer activity against human A375 cells after 48 hrs by MTT assay 22136907
A549 IC50 = 87000.0 nM 4.06 Anticancer activity against human A549 cells after 48 hrs by MTT assay 22136907
ACHN IC50 = 91000.0 nM 4.04 Anticancer activity against human ACHN cells after 48 hrs by MTT assay 22136907

Literature References

PubMed DOI Target Context # Activities
- 10.1039/C6MD00178E Molecular identity unknown 16
18211014 10.1021/jf0726482 Fusarium oxysporum f. sp. niveum 15
27344491 10.1016/j.ejmech.2016.06.013 Mushroom tyrosinase 12
28236590 10.1016/j.bmcl.2017.02.022 Unchecked 9
20663674 10.1016/j.bmc.2010.06.083 Tyrosine-protein kinase SYK 6
- 10.1007/s00044-012-0419-x Radical scavenging activity 6
25938986 10.1016/j.ejmech.2015.04.048 Staphylococcus aureus 4
- 10.1039/C6MD00178E NON-PROTEIN TARGET 4
31626544 10.1021/acs.jnatprod.9b00208 Unchecked 4
28236590 10.1016/j.bmcl.2017.02.022 No relevant target 3
37976709 10.1016/j.ejmech.2023.115945 No relevant target 3
10096863 10.1021/np9801559 NON-PROTEIN TARGET 3
- 10.1021/np50043a024 Abutilon theophrasti 3
27838185 10.1016/j.bmcl.2016.10.091 NON-PROTEIN TARGET 3
10888580 10.1021/jf9904160 Attelabidae 3
8704323 10.1271/bbb.60.909 Pythium 2
25938986 10.1016/j.ejmech.2015.04.048 Bacillus subtilis 2
23682762 10.1021/jm400374q Unchecked 2
19520580 10.1016/j.bmc.2009.05.042 Histone deacetylase 2
15780639 10.1016/j.bmcl.2005.01.070 Mus musculus 2

Data from ChEMBL 36 via Core Engine