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Compound Detail

CHEMBL272733

PIERICIDIN A
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C/C=C(\C)[C@H](O)[C@H](C)/C=C(C)/C=C/C/C(C)=C/Cc1nc(OC)c(OC)c(O)c1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL272733
Name PIERICIDIN A
Phase Preclinical
Structure Type MOL
InChI Key BBLGCDSLCDDALX-LKGBESRRSA-N
14
Targets
21
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

415.6
MW (Da)
5.46
ALogP
5
HBA
2
HBD
71.8
PSA (Ų)
0.39
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C25H37NO4
MW 415.57
Aromatic Rings 1
Heavy Atoms 30
NP-Likeness 1.90

Activity Summary

IC50 19 meas. best 9.37
Kd 2 meas. best 5.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
L929
CHEMBL612267
 IC50 9.37 9.37 0.4 1
NADH-ubiquinone oxidoreductase chain 1
CHEMBL4497
 IC50 8.52 8.37 3.0 2
Mitochondrial complex I; NADH oxidoreductase
CHEMBL614865
 IC50 8.3 8.3 5.0 1
HT-29
CHEMBL384
 IC50 8.19 8.15 6.4 2
Unchecked
CHEMBL612545
 IC50 7.82 7.22 15.1 3
ACHN
CHEMBL614519
 IC50 6.4 6.1 400.0 2
Peroxiredoxin-1
CHEMBL5315
 Kd 5.58 5.58 2610.0 1
Oxysterols receptor LXR-alpha
CHEMBL2808
 Kd 5.49 5.49 3240.0 1
OS-RC-2
CHEMBL2366188
 IC50 5.28 5.28 5200.0 1
786-0
CHEMBL613102
 IC50 4.52 4.52 30000.0 1
HL-60
CHEMBL383
 IC50 4.09 4.09 82100.0 1
SW480
CHEMBL612544
 IC50 4.09 4.09 82100.0 1
HeLa
CHEMBL399
 IC50 4.07 4.07 84900.0 1
U2OS
CHEMBL615023
 IC50 4.04 4.04 91500.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 36.94 nM Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
L929 IC50 = 0.43 nM 9.37 Cytotoxicity against mouse L929 fibroblasts 18054490
NADH-ubiquinone oxidoreductase chain 1 IC50 = 3.0 nM 8.52 Inhibition of Bos taurus (bovine) mitochondrial complex 1 assessed as reduction ... 12460667
Mitochondrial complex I; NADH oxidoreductase IC50 = 5.0 nM 8.3 Inhibition of NADH-ubiquinone oxidoreductase assessed as NADH oxidase activity i... 18054490
NADH-ubiquinone oxidoreductase chain 1 IC50 = 6.026 nM 8.22 Inhibition of Bos taurus (bovine) heart submitochondrial particle NDH1 assessed ... 8573592
HT-29 IC50 = 6.4 nM 8.19 Inhibition of colony formation of human HT-29 cells assessed as reduction in col... 36893622
HT-29 IC50 = 7.7 nM 8.11 Inhibition of colony formation of human HT-29 cells incubated for 7 days in abse... 36893622
Unchecked IC50 = 15.14 nM 7.82 Inhibition of Solanum tuberosum (potato) submitochondrial particle NDH1 assessed... 8573592
Unchecked IC50 = 61.0 nM 7.21 Cytotoxicity against Trichoplusia ni BTI-TN-5B1-4 cells assessed as reduction ce... 36893622
Unchecked IC50 = 234.42 nM 6.63 Inhibition of Escherichia coli GR19N NDH1 assessed as deaminoNADH-DB reductase a... 8573592
ACHN IC50 = 400.0 nM 6.4 Cytotoxicity against human ACHN cells assessed as reduction in cell viability me... 31298537
ACHN IC50 = 1600.0 nM 5.8 Cytotoxicity against human ACHN cells harboring shPRDX1 gene assessed as reducti... 31298537
Peroxiredoxin-1 Kd = 2610.0 nM 5.58 Binding affinity to full-length human PRDX1 by surface plasmon resonance analysi... 31298537
Oxysterols receptor LXR-alpha Kd = 3240.0 nM 5.49 Binding affinity to full-length human LXRalpha by surface plasmon resonance assa... 34251816
OS-RC-2 IC50 = 5200.0 nM 5.28 Cytotoxicity against human OS-RC2 cells assessed as reduction in cell viability ... 31298537
786-0 IC50 = 30000.0 nM 4.52 Cytotoxicity against human 786-O cells assessed as reduction in cell viability m... 31298537
SW480 IC50 = 82100.0 nM 4.09 Antiproliferative activity against human SW480 cells after 48 hrs by MTT assay 28406643
HL-60 IC50 = 82100.0 nM 4.09 Antiproliferative activity against human HL60 cells after 48 hrs by EZ-Cytox cel... 28406643
HeLa IC50 = 84900.0 nM 4.07 Antiproliferative activity against human HeLa cells after 48 hrs by MTT assay 28406643
U2OS IC50 = 91500.0 nM 4.04 Antiproliferative activity against human U2OS cells after 48 hrs by MTT assay 28406643

Literature References

PubMed DOI Target Context # Activities
34251816 10.1021/acs.jmedchem.1c00175 Unchecked 26
31298537 10.1021/acs.jmedchem.9b00598 ACHN 26
34251816 10.1021/acs.jmedchem.1c00175 ADMET 23
34251816 10.1021/acs.jmedchem.1c00175 Mus musculus 12
34251816 10.1021/acs.jmedchem.1c00175 HepG2 9
20409720 10.1016/j.bmc.2010.03.075 Unchecked 6
8573592 10.1016/0005-2728(95)00131-x Unchecked 4
28406643 10.1021/acs.jnatprod.6b01059 HeLa 4
31298537 10.1021/acs.jmedchem.9b00598 Peroxiredoxin-1 3
31298537 10.1021/acs.jmedchem.9b00598 ADMET 2
31298537 10.1021/acs.jmedchem.9b00598 Mus musculus 2
36893622 10.1016/j.ejmech.2023.115219 HT-29 2
28406643 10.1021/acs.jnatprod.6b01059 HL-60 1
36893622 10.1016/j.ejmech.2023.115219 HEK293 1
28362500 10.1021/acs.jnatprod.6b00235 Unchecked 1
29144750 10.1021/acs.jnatprod.7b00694 Unchecked 1
28406643 10.1021/acs.jnatprod.6b01059 U2OS 1
28406643 10.1021/acs.jnatprod.6b01059 Indoleamine 2,3-dioxygenase 1 1
28406643 10.1021/acs.jnatprod.6b01059 MDA-MB-231 1
8573592 10.1016/0005-2728(95)00131-x NADH-ubiquinone oxidoreductase chain 1 1

Data from ChEMBL 36 via Core Engine