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Compound Detail

CHEMBL120568

VANILLIC ACID
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COc1cc(C(=O)O)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL120568
Name VANILLIC ACID
Phase Preclinical
Structure Type MOL
InChI Key WKOLLVMJNQIZCI-UHFFFAOYSA-N
6
Targets
18
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

168.2
MW (Da)
1.10
ALogP
3
HBA
2
HBD
66.8
PSA (Ų)
0.69
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 C8H8O4
MW 168.15
Aromatic Rings 1
Heavy Atoms 12
NP-Likeness 0.52

Activity Summary

IC50 12 meas. best 4.63
EC50 3 meas. best 4.84
Kd 3 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 8.4 5.85 4.0 2
No relevant target
CHEMBL2362975
 EC50 4.84 4.84 14370.0 1
RAW264.7
CHEMBL612557
 IC50 4.63 4.63 23200.0 1
HT-22
CHEMBL614316
 EC50 4.56 4.56 27800.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.21 4.21 61000.0 1
Unchecked
CHEMBL612545
 IC50 4.16 4.16 69000.0 1
LoVo
CHEMBL614721
 IC50 4.04 4.04 91000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 4.0 nM 8.4 Binding affinity to quail lipocalin Q83 22889313
No relevant target EC50 = 14370.0 nM 4.84 Antioxidant activity assessed as DPPH free radical scavenging activity 28415050
RAW264.7 IC50 = 23200.0 nM 4.63 Antiinflammatory activity in mouse RAW264.7 cells assessed as decrease in LPS-in... 25666824
HT-22 EC50 = 27800.0 nM 4.56 Neuroprotective activity against glutamate-induced cell death in mouse HT-22 cel... 32991171
NON-PROTEIN TARGET IC50 = 61000.0 nM 4.21 Cytotoxicity against human OE21 cells after 72 hrs by MTT assay 21696954
Unchecked IC50 = 69000.0 nM 4.16 Inhibition of Saccharomyces sp. alpha-glucosidase 18341288
LoVo IC50 = 91000.0 nM 4.04 Cytotoxicity against human LoVo cells after 72 hrs by MTT assay 21696954
Unchecked Kd = 500000.0 nM 3.3 Binding affinity to quail lipocalin Q83 assessed as first molecule binding at 2:... 22889313

Literature References

PubMed DOI Target Context # Activities
37355024 10.1016/j.bmcl.2023.129386 Unchecked 9
- 10.1016/j.cropro.2012.09.015 Botryosphaeria dothidea 6
- 10.1016/j.cropro.2012.09.015 Lasiodiplodia theobromae 5
12762798 10.1021/np0205710 Macrophage 5
19223628 10.1128/aac.01293-08 Staphylococcus aureus 4
23145924 10.1021/jf303290g Diplodia seriata 4
21696954 10.1016/j.bmcl.2011.05.089 NON-PROTEIN TARGET 4
- 10.1016/j.cropro.2012.09.015 Neofusicoccum ribis 4
10425119 10.1021/np990033w Raji 4
10425119 10.1021/np990033w Unchecked 4
22889313 10.1021/jm301016m Unchecked 4
36095944 10.1016/j.bmc.2022.117000 B16-F10 4
3127544 10.1021/np50054a008 NON-PROTEIN TARGET 4
- 10.1016/j.cropro.2012.09.015 Diplodia seriata 3
20466556 10.1016/j.bmc.2010.04.047 NON-PROTEIN TARGET 3
27324979 10.1016/j.bmcl.2016.06.028 ADMET 2
24268551 10.1016/j.bmcl.2013.10.066 Tyrosinase 2
26079087 10.1016/j.ejmech.2015.06.010 No relevant target 2
22137340 10.1016/j.bmcl.2011.11.041 Estrogen receptor 2
28415050 10.1016/j.ejmech.2017.03.061 No relevant target 2

Data from ChEMBL 36 via Core Engine