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Compound Detail

CHEMBL29660

CHICORIC 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 CHEMBL29660
Name CHICORIC ACID
Phase Preclinical
Structure Type MOL
InChI Key YDDGKXBLOXEEMN-QFZCZCNSSA-N
6
Targets
21
Activities
3
Assay Types
0
PK Parameters
15
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

EC50 9 meas. best 5.77
IC50 7 meas. best 7.16
Ki 5 meas. best 6.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 7.16 6.485 70.0 4
Botulinum neurotoxin type A
CHEMBL5192
 Ki 6.16 5.678 700.0 5
MT4
CHEMBL388
 EC50 5.77 5.42 1700.0 2
Unchecked
CHEMBL612545
 IC50 5.38 5.38 4200.0 1
CEM-SS
CHEMBL614548
 EC50 5.01 4.5583 9800.0 6
Human immunodeficiency virus 1
CHEMBL378
 EC50 4.96 4.96 10900.0 1
CEM-SS
CHEMBL614548
 IC50 4.45 4.45 35500.0 1
MT4
CHEMBL388
 IC50 4.4 4.4 39700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus type 1 integrase IC50 = 70.0 nM 7.16 Inhibitory activity against Human Immunodeficiency Virus Type 1 integrase (HIV-1... 9986720
Human immunodeficiency virus type 1 integrase IC50 = 300.0 nM 6.52 Inhibition of HIV1 integrase using U5A/U5B double-stranded DNA as substrate by E... 18243421
Human immunodeficiency virus type 1 integrase IC50 = 500.0 nM 6.3 Inhibition of HIV-1 integrase by radiolabeled oligonucleotide-based assay integr... 10212126
Botulinum neurotoxin type A Ki = 700.0 nM 6.16 Inhibition of Clostridium botulinum BoNT/A light chain using SNAP-25 as substrat... 27543389
Human immunodeficiency virus type 1 integrase IC50 = 1100.0 nM 5.96 Compound was evaluated for the inhibitory concentration against HIV-1 integrase ... 10212126
Botulinum neurotoxin type A Ki = 1400.0 nM 5.85 Competitive inhibition of Clostridium botulinum full length BoNT/A light chain (... 23565325
Botulinum neurotoxin type A Ki = 1600.0 nM 5.8 Uncompetitive inhibition of Clostridium botulinum truncated BoNT/A light chain (... 23565325
MT4 EC50 = 1700.0 nM 5.77 Concentration of compound required to protect 50% of MT-4 cells against retrovir... 10212126
Botulinum neurotoxin type A Ki = 3900.0 nM 5.41 Uncompetitive inhibition of Clostridium botulinum full length BoNT/A light chain... 23565325
Unchecked IC50 = 4200.0 nM 5.38 Inhibition of HIV1 integrase activity assessed as suppression of viral replicati... 27676157
Botulinum neurotoxin type A Ki = 6700.0 nM 5.17 Competitive inhibition of Clostridium botulinum truncated BoNT/A light chain (1-... 23565325
MT4 EC50 = 8600.0 nM 5.07 Concentration of compound required to protect 50% of MT-4 cells against retrovir... 10212126
CEM-SS EC50 = 9800.0 nM 5.01 Concentration of compound required to protect 50% of CEM-SS cells against retrov... 10212126
Human immunodeficiency virus 1 EC50 = 10900.0 nM 4.96 Antiviral activity against HIV1 3B infected in human MT4 cells assessed as inhib... 18243421
CEM-SS EC50 = 16700.0 nM 4.78 Compound was evaluated for the cytoprotection of CEM-SS cells by XTT cytoprotect... 10212126
CEM-SS EC50 = 27000.0 nM 4.57 Concentration of compound required to protect 50% of CEM-SS cells against retrov... 10212126
CEM-SS EC50 = 32000.0 nM 4.5 Concentration of compound required to protect 50% of CEM-SS cells against retrov... 10212126
CEM-SS IC50 = 35500.0 nM 4.45 Compound was evaluated for the cytoprotection of CEM-SS cells by XTT cytoprotect... 10212126
CEM-SS EC50 = 39200.0 nM 4.41 Concentration of compound required to protect 50% of CEM-SS cells against retrov... 10212126
MT4 IC50 = 39700.0 nM 4.4 Concentration of compound required to reduce MT-4 cell viability by 50% 10212126

Literature References

PubMed DOI Target Context # Activities
10212126 10.1021/jm980531m CEM-SS 25
10212126 10.1021/jm980531m NON-PROTEIN TARGET 8
23565325 10.1021/ml300428s Botulinum neurotoxin type A 4
10212126 10.1021/jm980531m MT4 3
10212126 10.1021/jm980531m Human immunodeficiency virus type 1 integrase 2
9986720 10.1021/jm9804735 Human immunodeficiency virus type 1 integrase 2
10212126 10.1021/jm980531m ADMET 1
9986720 10.1021/jm9804735 MT2 1
9986720 10.1021/jm9804735 Human immunodeficiency virus 1 1
10785435 10.1021/np990492x P388 1
18243421 10.1016/j.ejmech.2007.12.013 Human immunodeficiency virus type 1 integrase 1
18243421 10.1016/j.ejmech.2007.12.013 Human immunodeficiency virus 1 1
18243421 10.1016/j.ejmech.2007.12.013 MT4 1
27676157 10.1021/acs.jmedchem.6b00461 Unchecked 1
27543389 10.1016/j.bmc.2016.07.031 Botulinum neurotoxin type A 1

Data from ChEMBL 36 via Core Engine