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Compound Detail

CHEMBL509895

BRUCEANTIN
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COC(=O)[C@@]12OC[C@]34[C@H]([C@@H](O)[C@@H]1O)[C@@]1(C)CC(=O)C(O)=C(C)[C@@H]1C[C@H]3OC(=O)[C@H](OC(=O)/C=C(\C)C(C)C)[C@@H]24
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL509895
Name BRUCEANTIN
Phase Preclinical
Structure Type MOL
InChI Key IRQXZTBHNKVIRL-GOTQHHPNSA-N
6
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

548.6
MW (Da)
1.15
ALogP
11
HBA
3
HBD
165.9
PSA (Ų)
0.26
QED
2
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H36O11
MW 548.59
Aromatic Rings 0
Heavy Atoms 39
NP-Likeness 3.60

Activity Summary

IC50 10 meas. best 7.91
EC50 1 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HL-60
CHEMBL383
 IC50 7.91 7.57 12.2 3
RPMI-8226
CHEMBL614882
 IC50 7.89 7.89 12.8 1
HL-60
CHEMBL383
 EC50 7.7 7.7 20.0 1
HT-29
CHEMBL384
 IC50 7.66 7.66 22.0 1
HeLa
CHEMBL399
 IC50 7.54 7.415 29.0 2
U-266
CHEMBL2366315
 IC50 7.31 7.31 49.0 1
NCI-H929
CHEMBL4296391
 IC50 6.94 6.94 115.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HL-60 IC50 = 12.2 nM 7.91 Induction of apoptosis in human HL60 cells after 24 hrs by DAPI staining 14987068
RPMI-8226 IC50 = 12.8 nM 7.89 Induction of apoptosis in human RPMI8226 cells after 24 hrs by DAPI staining 14987068
HL-60 EC50 = 20.0 nM 7.7 Induction of cell differentiation in human HL60 cells assessed as superoxide ani... 11754601
HT-29 IC50 = 22.0 nM 7.66 Antiproliferative activity against human HT-29 cells 33289552
HeLa IC50 = 29.0 nM 7.54 Antiproliferative activity against human HeLa cells 33289552
HL-60 IC50 = 40.0 nM 7.4 Antiproliferative activity against human HL60 cells assessed as inhibition of [3... 11754601
HL-60 IC50 = 40.0 nM 7.4 Cytotoxicity against human HL60 cells assessed as loss of membrane integrity aft... 11754601
U-266 IC50 = 49.0 nM 7.31 Induction of apoptosis in human U266 cells after 24 hrs by DAPI staining 14987068
HeLa IC50 = 51.0 nM 7.29 Inhibition of protein synthesis in human HeLa cells assessed as [35S]methionine ... 19199792
NCI-H929 IC50 = 115.0 nM 6.94 Induction of apoptosis in human NCI-H929 cells after 24 hrs by DAPI staining 14987068

Literature References

PubMed DOI Target Context # Activities
11754601 10.1021/np010212p HL-60 4
19026551 10.1016/j.bmc.2008.10.076 MCF7 3
14987068 10.1021/np030304+ NON-PROTEIN TARGET 3
20738103 10.1021/np100406d Mus musculus 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
14987068 10.1021/np030304+ RPMI-8226 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
14987068 10.1021/np030304+ HL-60 2
14987068 10.1021/np030304+ Daudi 1
14987068 10.1021/np030304+ U-266 1
14987068 10.1021/np030304+ K562 1
14987068 10.1021/np030304+ REH 1
14987068 10.1021/np030304+ Kasumi 1 1
15481972 10.1021/jm049934e Cytochrome P450 2D6 1
14987068 10.1021/np030304+ BV-173 1
14987068 10.1021/np030304+ U-937 1
14987068 10.1021/np030304+ NB-4 1
1710653 10.1021/np50073a012 Human immunodeficiency virus type 1 reverse transcriptase 1
11754601 10.1021/np010212p ADMET 1
11754601 10.1021/np010212p Unchecked 1

Data from ChEMBL 36 via Core Engine