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Compound Detail

CHEMBL282731

CICHORIC ACID
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O=C(/C=C/c1ccc(O)c(O)c1)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/c1ccc(O)c(O)c1)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL282731
Name CICHORIC ACID
Phase Preclinical
Structure Type MOL
InChI Key YDDGKXBLOXEEMN-IABMMNSOSA-N
7
Targets
21
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

474.4
MW (Da)
1.23
ALogP
10
HBA
6
HBD
208.1
PSA (Ų)
0.17
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H18O12
MW 474.37
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness 0.71

Activity Summary

IC50 13 meas. best 8.0
EC50 5 meas. best 6.09
Ki 2 meas. best 4.9
Kd 1 meas. best 5.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 8.0 6.2414 10.0 7
Unchecked
CHEMBL612545
 IC50 6.66 6.1533 220.0 3
Human immunodeficiency virus
CHEMBL613758
 EC50 6.09 6.09 810.0 1
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 Kd 5.52 5.52 3000.0 1
MT4
CHEMBL388
 EC50 5.28 4.95 5300.0 3
Human immunodeficiency virus 1
CHEMBL378
 EC50 4.9 4.9 12700.0 1
Tyrosine-protein phosphatase YopH
CHEMBL4404
 Ki 4.9 4.535 12500.0 2
CEM-SS
CHEMBL614548
 IC50 4.7 4.7 20100.0 1
MT4
CHEMBL388
 IC50 4.35 4.35 45000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus type 1 integrase IC50 = 10.0 nM 8.0 Inhibition of HIV1 subtype C recombinant integrase strand transfer activity prei... 30774857
Human immunodeficiency virus type 1 integrase IC50 = 34.0 nM 7.47 Inhibition of HIV-1 subtype C integrase in presence of biotinylated DNA by color... 29482943
Human immunodeficiency virus type 1 integrase IC50 = 200.0 nM 6.7 Inhibition of HIV1 integrase using U5A/U5B double-stranded DNA as substrate by E... 18243421
Unchecked IC50 = 220.0 nM 6.66 Inhibition of HIV NL4-3 recombinant histidine-tagged integrase 3'-end processing... 20977258
Unchecked IC50 = 270.0 nM 6.57 Inhibition of HIV NL4-3 recombinant histidine-tagged integrase strand transfer a... 20977258
Human immunodeficiency virus type 1 integrase IC50 = 800.0 nM 6.1 Inhibition of HIV-1 integrase by radiolabeled oligonucleotide-based assay integr... 10212126
Human immunodeficiency virus EC50 = 810.0 nM 6.09 Antiviral activity against HIV LAI infected in human MT2 cells assessed as prote... 20977258
Human immunodeficiency virus type 1 integrase IC50 = 1100.0 nM 5.96 Compound was evaluated for the inhibitory concentration against HIV-1 integrase ... 10212126
Human immunodeficiency virus type 1 integrase Kd = 3000.0 nM 5.52 Kd value against HIV-1 integrase 11063607
MT4 EC50 = 5300.0 nM 5.28 Concentration of compound required to protect 50% of MT-4 cells against retrovir... 10212126
Unchecked IC50 = 5900.0 nM 5.23 Inhibition of protease activity of Clostridium botulinum BoNT/A light chain usin... 29050781
MT4 EC50 = 12700.0 nM 4.9 Cytotoxicity gainst human MT4 cells after 3 days by MTT assay 20541944
Human immunodeficiency virus 1 EC50 = 12700.0 nM 4.9 Antiviral activity against HIV1 3B infected in human MT4 cells assessed as inhib... 18243421
Tyrosine-protein phosphatase YopH Ki = 12500.0 nM 4.9 Non-competitive mixed inhibition of Yersinia enterocolitica YopH assessed as inh... 32631548
Human immunodeficiency virus type 1 integrase IC50 = 13700.0 nM 4.86 Inhibitory activity against HIV-1 integrase 14643320
CEM-SS IC50 = 20100.0 nM 4.7 Compound was evaluated for the cytoprotection of CEM-SS cells by XTT cytoprotect... 10212126
MT4 EC50 = 21200.0 nM 4.67 Concentration of compound required to protect 50% of cells against retroviral cy... 10212126
Human immunodeficiency virus type 1 integrase IC50 = 24900.0 nM 4.6 Inhibitory activity against HIV-1 integrase 10969990
MT4 IC50 = 45000.0 nM 4.35 Concentration of compound required to reduce MT-4 cell viability by 50% 10212126
Tyrosine-protein phosphatase YopH Ki = 68300.0 nM 4.17 Non-competitive mixed inhibition of Yersinia enterocolitica YopH assessed as inh... 32631548

Literature References

PubMed DOI Target Context # Activities
29192771 10.1021/acs.jnatprod.7b00699 Unchecked 16
26593037 10.1021/acs.jnatprod.5b00668 NON-PROTEIN TARGET 7
26593037 10.1021/acs.jnatprod.5b00668 ADMET 6
32631548 10.1016/j.bmcl.2020.127350 Tyrosine-protein phosphatase YopH 4
10212126 10.1021/jm980531m MT4 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
29050781 10.1016/j.bmcl.2017.10.021 Unchecked 2
36651644 10.1021/acs.jnatprod.2c00843 Replicase polyprotein 1ab 2
30774857 10.1039/C8MD00328A Human immunodeficiency virus type 1 integrase 2
11063607 10.1021/jm000194t Human immunodeficiency virus type 1 integrase 2
26593037 10.1021/acs.jnatprod.5b00668 NF-kappa-B inhibitor alpha 2
26593037 10.1021/acs.jnatprod.5b00668 Mus musculus 2
20977258 10.1021/jm1010594 Unchecked 2
10212126 10.1021/jm980531m CEM-SS 2
10212126 10.1021/jm980531m Human immunodeficiency virus type 1 integrase 2
20977258 10.1021/jm1010594 MT2 2
18243421 10.1016/j.ejmech.2007.12.013 Human immunodeficiency virus 1 1
19427202 10.1016/j.bmcl.2009.04.083 Tyrosine-protein kinase Lck 1
18243421 10.1016/j.ejmech.2007.12.013 MT4 1
10969990 10.1016/s0960-894x(00)00355-3 Human immunodeficiency virus type 1 integrase 1

Data from ChEMBL 36 via Core Engine