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Compound Detail

CHEMBL19980

BREFELDIN A
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C[C@H]1CCC/C=C/[C@@H]2C[C@H](O)C[C@H]2[C@H](O)/C=C/C(=O)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL19980
Name BREFELDIN A
Phase Preclinical
Structure Type MOL
InChI Key KQNZDYYTLMIZCT-KQPMLPITSA-N
23
Targets
45
Activities
4
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

280.4
MW (Da)
1.96
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.53
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H24O4
MW 280.36
Aromatic Rings 0
Heavy Atoms 20
NP-Likeness 2.66

Activity Summary

IC50 37 meas. best 7.7
EC50 5 meas. best 5.3
Ki 2 meas. best 4.82
Kd 1 meas. best 5.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SARS-CoV-2
CHEMBL4303835
 IC50 7.7 7.7 20.0 2
Bel-7402
CHEMBL614279
 IC50 7.62 7.1833 24.0 3
HL-60
CHEMBL383
 IC50 7.6 7.6 25.0 1
A-375
CHEMBL613859
 IC50 7.41 7.41 39.0 1
HeLa
CHEMBL399
 IC50 7.36 7.26 44.0 2
MDA-MB-231
CHEMBL400
 IC50 7.27 7.27 54.0 1
dengue virus type 2
CHEMBL613966
 IC50 7.26 7.26 54.6 1
A549
CHEMBL392
 IC50 7.25 7.25 56.0 1
PC-3
CHEMBL390
 IC50 7.17 7.17 68.0 2
HepG2
CHEMBL395
 IC50 7.1 6.8075 80.0 4
PANC-1
CHEMBL614139
 IC50 7.1 7.1 80.0 1
L02
CHEMBL4296457
 IC50 7.03 7.015 94.0 2
Nuclear receptor subfamily 0 group B member 1
CHEMBL1795094
 IC50 6.87 6.87 134.3 1
ECa-109 cell line
CHEMBL614668
 IC50 6.85 6.85 140.0 1
HT-29
CHEMBL384
 IC50 6.8 6.8 160.0 1
DU-145
CHEMBL613508
 IC50 6.8 6.8 160.0 1
Unchecked
CHEMBL612545
 IC50 6.38 5.62 420.0 3
Bel7402/5-FU
CHEMBL4483230
 IC50 6.09 6.09 820.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.7 5.6714 1995.3 7
Major prion protein
CHEMBL4869
 IC50 5.46 5.46 3505.0 1
Unchecked
CHEMBL612545
 EC50 5.3 5.3 5000.0 1
Unchecked
CHEMBL612545
 Kd 5.07 5.07 8600.0 1
Unchecked
CHEMBL612545
 Ki 4.82 4.82 15000.0 2
dengue virus type 1
CHEMBL613360
 EC50 4.26 4.26 54600.0 1
dengue virus type 4
CHEMBL613728
 EC50 4.26 4.26 54600.0 1
dengue virus type 3
CHEMBL612717
 EC50 4.26 4.26 54600.0 1
dengue virus type 2
CHEMBL613966
 EC50 4.26 4.26 54600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4126.64 ng.hr.mL-1 Mus musculus
AUC 4837.38 ng.hr.mL-1 Mus musculus
CL 173.38 mL.min-1.kg-1 Mus musculus
CL 1577.31 ml/kg Mus musculus
Cmax 25485.09 nM Mus musculus
Cmax 47046.65 nM Mus musculus
F 18.96 % Mus musculus
T1/2 24.0 hr Rattus norvegicus
T1/2 2.12 hr Mus musculus
T1/2 9.05 hr Mus musculus
Vd 31.87 L.kg-1 Mus musculus
Vd 20.6 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SARS-CoV-2 IC50 = 20.0 nM 7.7 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
SARS-CoV-2 IC50 = 20.0 nM 7.7 Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity o... -
Bel-7402 IC50 = 24.0 nM 7.62 Antiproliferative activity against human Bel7402 cells after 72 hrs by MTT assay 29524728
HL-60 IC50 = 25.0 nM 7.6 Antiproliferative activity against human HL60 cells after 72 hrs by MTT assay 29524728
A-375 IC50 = 39.0 nM 7.41 Antiproliferative activity against human A-375 cells assessed as reduction in ce... 37329677
HeLa IC50 = 44.0 nM 7.36 Antiproliferative activity against human HeLa cells assessed as reduction in cel... 37329677
MDA-MB-231 IC50 = 54.0 nM 7.27 Antiproliferative activity against human MDA-MB-231 cells assessed as reduction ... 37329677
dengue virus type 2 IC50 = 54.6 nM 7.26 Antiviral activity against DENV2 00st-22A infected in Vero cells assessed as red... 34438338
A549 IC50 = 56.0 nM 7.25 Antiproliferative activity against human A549 cells assessed as reduction in cel... 37329677
PC-3 IC50 = 68.0 nM 7.17 Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay 28494251
PC-3 IC50 = 68.0 nM 7.17 Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay 29524728
Bel-7402 IC50 = 70.0 nM 7.16 Antiproliferative activity against human Bel-7402 cells by MTT assay 36089748
HeLa IC50 = 70.0 nM 7.16 Antiproliferative activity against human HeLa cells measured after 72 hrs by MTT... 35849940
PANC-1 IC50 = 80.0 nM 7.1 Antiproliferative activity against human PANC-1 cells measured after 72 hrs by M... 35849940
HepG2 IC50 = 80.0 nM 7.1 Antiproliferative activity against human HepG2 cells by MTT assay 36089748
L02 IC50 = 94.0 nM 7.03 Antiproliferative activity against human L02 cells assessed as reduction in cell... 37329677
L02 IC50 = 100.0 nM 7.0 Cytotoxicity against human L02 cells measured after 72 hrs by MTT assay 35849940
HepG2 IC50 = 120.0 nM 6.92 Antiproliferative activity against human HepG2 cells assessed as reduction in ce... 37329677
Nuclear receptor subfamily 0 group B member 1 IC50 = 134.26 nM 6.87 PubChem BioAssay. Luminescence-based cell-based high throughput dose response as... -
ECa-109 cell line IC50 = 140.0 nM 6.85 Antiproliferative activity against human Eca-109 cells measured after 72 hrs by ... 35849940

Literature References

PubMed DOI Target Context # Activities
19182783 10.1038/nchembio.144 Unchecked 20
36089748 10.1021/acs.jmedchem.2c00532 ADMET 17
28462831 10.1016/j.bmcl.2017.04.047 PC-3 11
36089748 10.1021/acs.jmedchem.2c00532 No relevant target 8
- 10.1016/S0960-894X(00)80319-4 Unchecked 7
23805957 10.1021/jm400615g Unchecked 7
18809934 10.1128/aac.00740-08 Candida dubliniensis 7
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
17325226 10.1128/aac.00182-07 Candida albicans 4
18809934 10.1128/aac.00740-08 Candida albicans 4
28462831 10.1016/j.bmcl.2017.04.047 RWPE-1 3
17563369 10.1073/pnas.0700773104 Unchecked 3
17125221 10.1021/np060178k ADMET 2
28462831 10.1016/j.bmcl.2017.04.047 Mitogen-activated protein kinase 3 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
28462831 10.1016/j.bmcl.2017.04.047 RAC-alpha serine/threonine-protein kinase 2
28462831 10.1016/j.bmcl.2017.04.047 LNCaP 2
23805957 10.1021/jm400615g Coxsackievirus B3 2
17125221 10.1021/np060178k NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine