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Compound Detail

CHEMBL223256

NYMPHAEOL A
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CC(C)=CCC/C(C)=C/Cc1c(O)cc2c(c1O)C(=O)C[C@@H](c1ccc(O)c(O)c1)O2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL223256
Name NYMPHAEOL A
Phase Preclinical
Structure Type MOL
InChI Key XCYSQFHYFNWYFP-CEMXSPGASA-N
15
Targets
21
Activities
3
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

424.5
MW (Da)
5.45
ALogP
6
HBA
4
HBD
107.2
PSA (Ų)
0.36
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C25H28O6
MW 424.49
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness 2.31

Activity Summary

IC50 14 meas. best 7.3
Ki 4 meas. best 5.92
EC50 3 meas. best 5.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 7.3 7.3 50.0 1
Butyrylcholinesterase
CHEMBL5077
 Ki 5.92 5.92 1200.0 1
Butyrylcholinesterase
CHEMBL5077
 IC50 5.85 5.85 1400.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 5.75 5.75 1800.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.64 5.01 2300.0 2
U-266
CHEMBL2366315
 EC50 5.62 5.62 2400.0 1
CCRF-CEM
CHEMBL382
 EC50 5.5 5.5 3200.0 1
A549
CHEMBL392
 IC50 5.4 5.4 4000.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 5.38 5.38 4200.0 1
Unchecked
CHEMBL612545
 Ki 5.29 5.29 5100.0 1
BJ
CHEMBL614358
 EC50 5.23 5.23 5900.0 1
Acetylcholinesterase
CHEMBL220
 IC50 5.14 5.14 7200.0 1
Acetylcholinesterase
CHEMBL220
 Ki 5.08 5.08 8400.0 1
Unchecked
CHEMBL612545
 IC50 4.98 4.98 10400.0 1
A2780cisR
CHEMBL614023
 IC50 4.98 4.98 10500.0 1
Radical scavenging activity
CHEMBL613712
 IC50 4.85 4.85 14000.0 1
ADMET
CHEMBL612558
 IC50 4.84 4.84 14300.0 1
Neutrophil elastase
CHEMBL248
 Ki 4.8 4.8 15700.0 1
Neutrophil elastase
CHEMBL248
 IC50 4.64 4.64 22800.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 5.486 10'3L/M Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 50.0 nM 7.3 Inhibition of human recombinant 5-LOX assessed as reduction in leukotriene B4 pr... 28322565
Butyrylcholinesterase Ki = 1200.0 nM 5.92 Mixed type inhibition of equine BChE using butyrylthiocholine iodide as substrat... 22445674
Butyrylcholinesterase IC50 = 1400.0 nM 5.85 Inhibition of equine BChE assessed as butyrylthiocholine iodide hydrolysis after... 22445674
Prostaglandin G/H synthase 1 IC50 = 1800.0 nM 5.75 Inhibition of ram seminal vesicle COX1 assessed as reduction in PGE2 formation p... 28322565
NON-PROTEIN TARGET IC50 = 2300.0 nM 5.64 Antioxidant activity assessed as hypochlorous acid scavenging activity by fluore... 23947936
U-266 EC50 = 2400.0 nM 5.62 Cytotoxicity against human U266 cells assessed as viable cells after 72 hrs by c... 20192247
CCRF-CEM EC50 = 3200.0 nM 5.5 Cytotoxicity against human CEM cells assessed as viable cells after 72 hrs by ca... 20192247
A549 IC50 = 4000.0 nM 5.4 Growth inhibition of human A549 cells 28814374
Prostaglandin G/H synthase 2 IC50 = 4200.0 nM 5.38 Inhibition of human recombinant COX2 assessed as reduction in PGE2 formation pre... 28322565
Unchecked Ki = 5100.0 nM 5.29 Mixed-type of inhibition of SARS coronavirus papain-like protease (1541 to 1855 ... 23623680
BJ EC50 = 5900.0 nM 5.23 Cytotoxicity against human BJ cells assessed as viable cells after 72 hrs by cal... 20192247
Acetylcholinesterase IC50 = 7200.0 nM 5.14 Inhibition of human erythrocyte AChE assessed as acetylthiocholine iodide hydrol... 22445674
Acetylcholinesterase Ki = 8400.0 nM 5.08 Mixed type inhibition of human erythrocyte AChE using acetylthiocholine iodide a... 22445674
A2780cisR IC50 = 10500.0 nM 4.98 Antiproliferative activity against drug-sensitive human A2780 cells 17326683
Unchecked IC50 = 10400.0 nM 4.98 Inhibition of SARS coronavirus papain-like protease (1541 to 1855 amino acids) e... 23623680
Radical scavenging activity IC50 = 14000.0 nM 4.85 Antioxidant activity assessed as DPPH radical scavenging activity by TLC autogra... 15974621
ADMET IC50 = 14300.0 nM 4.84 Cytotoxicity against rat WB344 cells after 24 hrs 17625893
Neutrophil elastase Ki = 15700.0 nM 4.8 Noncompetitive inhibition of human neutrophil elastase using varying levels of M... 28968119
Neutrophil elastase IC50 = 22800.0 nM 4.64 Inhibition of human neutrophil elastase using MeOSuc-AAPV-pNA as substrate measu... 28968119
NON-PROTEIN TARGET IC50 = 41200.0 nM 4.38 Antioxidant activity assessed as NADH/phenazine methosulfate generated superoxid... 23947936

Literature References

PubMed DOI Target Context # Activities
28322565 10.1021/acs.jnatprod.6b01011 THP-1 10
22445674 10.1016/j.bmc.2012.02.044 Acetylcholinesterase 7
17625893 10.1021/np070063w ADMET 4
23947936 10.1021/np400242e J774.A1 4
25735399 10.1021/acs.jnatprod.5b00005 NON-PROTEIN TARGET 4
23947936 10.1021/np400242e NON-PROTEIN TARGET 3
28322565 10.1021/acs.jnatprod.6b01011 Polyunsaturated fatty acid 5-lipoxygenase 3
23623680 10.1016/j.bmc.2013.03.027 Unchecked 3
22445674 10.1016/j.bmc.2012.02.044 Butyrylcholinesterase 2
28322565 10.1021/acs.jnatprod.6b01011 Prostaglandin G/H synthase 2 2
25735399 10.1021/acs.jnatprod.5b00005 THP-1 2
28968119 10.1021/acs.jnatprod.7b00325 Neutrophil elastase 2
18293924 10.1021/np070446u Staphylococcus epidermidis 1
17326683 10.1021/np060484y A2780cisR 1
15974621 10.1021/np0500272 NON-PROTEIN TARGET 1
18293924 10.1021/np070446u Pseudomonas aeruginosa 1
18293924 10.1021/np070446u Staphylococcus aureus 1
18293924 10.1021/np070446u Listeria monocytogenes 1
28814374 10.1016/j.ejmech.2017.07.043 A549 1
18293924 10.1021/np070446u Bacillus cereus 1

Data from ChEMBL 36 via Core Engine