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Compound Detail

CHEMBL37537

PROTOCATECHUIC ACID
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O=C(O)c1ccc(O)c(O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL37537
Name PROTOCATECHUIC ACID
Phase Preclinical
Structure Type MOL
InChI Key YQUVCSBJEUQKSH-UHFFFAOYSA-N
16
Targets
37
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

154.1
MW (Da)
0.80
ALogP
3
HBA
3
HBD
77.8
PSA (Ų)
0.52
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C7H6O4
MW 154.12
Aromatic Rings 1
Heavy Atoms 11
NP-Likeness 0.74

Activity Summary

IC50 17 meas. best 6.32
Ki 14 meas. best 6.33
EC50 4 meas. best 7.24
Kd 2 meas. best 4.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
No relevant target
CHEMBL2362975
 EC50 7.24 7.24 57.4 1
Carbonic anhydrase 2
CHEMBL205
 Ki 6.33 6.33 470.0 1
Aspartyl aminopeptidase
CHEMBL1293263
 IC50 6.32 6.32 479.4 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 6.16 6.16 690.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 5.97 5.97 1080.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 5.61 5.61 2450.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.59 5.59 2560.0 1
Carbonic anhydrase
CHEMBL1795125
 Ki 5.49 5.49 3210.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.48 5.14 3310.0 2
Carbonic anhydrase 12
CHEMBL3242
 Ki 5.39 5.39 4090.0 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 5.35 5.35 4450.0 1
Carbonic anhydrase 6
CHEMBL3025
 Ki 5.33 5.33 4720.0 2
Unchecked
CHEMBL612545
 Ki 5.19 5.055 6500.0 2
Carbonic anhydrase 7
CHEMBL2326
 Ki 5.1 5.1 7870.0 1
Radical scavenging activity
CHEMBL613712
 EC50 5.05 5.05 8830.0 1
Unchecked
CHEMBL612545
 Kd 4.72 4.14 19000.0 2
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 4.59 4.59 25400.0 1
No relevant target
CHEMBL2362975
 IC50 4.58 4.51 26100.0 3
3-dehydroquinate synthase
CHEMBL3554
 Ki 4.36 4.275 44000.0 2
Unchecked
CHEMBL612545
 IC50 4.05 4.05 89000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
No relevant target EC50 = 57.4 nM 7.24 Antioxidant activity assessed as DPPH free radical scavenging activity 28415050
Carbonic anhydrase 2 Ki = 470.0 nM 6.33 Inhibition of human carbonic anhydrase 2 preincubated for 15 mins by CO2 hydrati... 21282059
Aspartyl aminopeptidase IC50 = 479.4 nM 6.32 PUBCHEM_BIOASSAY: QFRET-based biochemical high throughput dose response assay fo... -
Carbonic anhydrase 14 Ki = 690.0 nM 6.16 Inhibition of human carbonic anhydrase 14 preincubated for 15 mins by CO2 hydrat... 22668600
Carbonic anhydrase 1 Ki = 1080.0 nM 5.97 Inhibition of human carbonic anhydrase 1 preincubated for 15 mins by CO2 hydrati... 21282059
Carbonic anhydrase 4 Ki = 2450.0 nM 5.61 Inhibition of human CA4 using 4NPA as substrate for 3 mins by Lineweaver burk pl... 22687439
NON-PROTEIN TARGET EC50 = 2560.0 nM 5.59 Antioxidant activity assessed as protection against peroxyl radical-induced alka... 19361168
Carbonic anhydrase Ki = 3210.0 nM 5.49 Inhibition of Dicentrarchus labrax CA using 4-nitrophenylacetate substrate by es... 21669522
NON-PROTEIN TARGET IC50 = 3310.0 nM 5.48 Antioxidant activity assessed as superoxide anion radical scavenging activity 17907781
Carbonic anhydrase 12 Ki = 4090.0 nM 5.39 Inhibition of human carbonic anhydrase 12 preincubated for 15 mins by CO2 hydrat... 21282059
Carbonic anhydrase 9 Ki = 4450.0 nM 5.35 Inhibition of human carbonic anhydrase 9 preincubated for 15 mins by CO2 hydrati... 21282059
Carbonic anhydrase 6 Ki = 4720.0 nM 5.33 Inhibition of human CA6 using 4-nitrophenylacetate substrate by esterase assay 21669522
Carbonic anhydrase 6 Ki = 4720.0 nM 5.33 Inhibition of human CA6 using 4NPA as substrate for 3 mins by Lineweaver burk pl... 22687439
Unchecked Ki = 6500.0 nM 5.19 Inhibition of Malassezia globosa recombinant beta-carbonic anhydrase preincubate... 28343756
Carbonic anhydrase 7 Ki = 7870.0 nM 5.1 Inhibition of human carbonic anhydrase 7 preincubated for 15 mins by CO2 hydrati... 22668600
Radical scavenging activity EC50 = 8830.0 nM 5.05 Antioxidant activity assessed as DPPH radical scavenging activity by spectrophot... 24681984
Unchecked Ki = 12000.0 nM 4.92 Inhibition constant against 1A dihydroate dehydrogenase (1A DHOD) from Lactococc... 11520193
NON-PROTEIN TARGET IC50 = 15700.0 nM 4.8 ABTS radical scavenging activity 16908141
Unchecked Kd = 19000.0 nM 4.72 Dissociation constant against 1A dihydroate dehydrogenase (1A DHOD) from Lactoco... 11520193
Prostaglandin G/H synthase 2 IC50 = 25400.0 nM 4.59 Inhibition of COX-2 (unknown origin) 34479036

Literature References

PubMed DOI Target Context # Activities
21780738 10.1021/jf201611b Heterodera zeae 27
20973550 10.1021/np100281g B16 13
20973550 10.1021/np100281g Radical scavenging activity 6
32773093 10.1016/j.bmc.2020.115642 DNA polymerase beta 6
20973550 10.1021/np100281g NON-PROTEIN TARGET 6
3127544 10.1021/np50054a008 NON-PROTEIN TARGET 6
27311892 10.1016/j.bmcl.2016.04.075 Proteasome Macropain subunit MB1 5
24279769 10.1021/np4005773 NON-PROTEIN TARGET 4
30784884 10.1016/j.ejmech.2019.01.055 No relevant target 4
11325231 10.1021/np000421u NON-PROTEIN TARGET 4
11520193 10.1021/jm015535x Unchecked 3
28343756 10.1016/j.bmc.2017.03.026 Unchecked 3
25769817 10.1016/j.bmcl.2015.02.048 Unchecked 3
28415050 10.1016/j.ejmech.2017.03.061 No relevant target 3
22348826 10.1016/j.ejmech.2012.01.057 Brugia malayi 3
23769638 10.1016/j.bmcl.2013.05.030 Oxysterols receptor LXR-beta 2
17258462 10.1016/j.bmc.2006.12.038 Unchecked 2
14611153 10.1021/jf030388s Polyphenol oxidase 2
12083872 10.1021/jf020088v Saccharomyces cerevisiae 2
11412967 10.1016/s0960-894x(01)00065-8 3-dehydroquinate synthase 2

Data from ChEMBL 36 via Core Engine