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Compound Detail

CHEMBL140809

BRUCEINE B
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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(C)=O)[C@@H]24
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL140809
Name BRUCEINE B
Phase Preclinical
Structure Type MOL
InChI Key YDWODLQEUPYKGJ-LZFWDZGBSA-N
10
Targets
12
Activities
2
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

480.5
MW (Da)
-0.43
ALogP
11
HBA
3
HBD
165.9
PSA (Ų)
0.35
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H28O11
MW 480.47
Aromatic Rings 0
Heavy Atoms 34
NP-Likeness 3.78

Activity Summary

IC50 8 meas. best 7.0
EC50 4 meas. best 7.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 EC50 7.62 7.62 24.0 2
HCT-116
CHEMBL394
 IC50 7.0 7.0 99.0 1
SK-OV-3
CHEMBL614925
 IC50 6.92 6.92 120.0 1
HepG2
CHEMBL395
 IC50 6.09 6.09 810.0 1
BGC-823
CHEMBL614526
 IC50 6.09 6.09 810.0 1
A549
CHEMBL392
 IC50 5.89 5.89 1300.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.72 5.72 1900.0 1
HCT-8
CHEMBL613510
 IC50 5.7 5.7 2000.0 1
Tobacco mosaic virus
CHEMBL613818
 IC50 5.46 5.46 3470.0 1
FM3A
CHEMBL614297
 EC50 5.1 5.1 8000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum EC50 = 24.0 nM 7.62 Anti-malarial activity as growth inhibition of chloroquine-resistant Plasmodium ... 9871598
Plasmodium falciparum EC50 = 24.0 nM 7.62 In vitro antimalarial activity against Plasmodium falciparum 12570385
HCT-116 IC50 = 99.0 nM 7.0 Antiproliferative activity against human HCT-116 cells incubated for 72 hrs by W... 33289552
SK-OV-3 IC50 = 120.0 nM 6.92 Cytotoxicity against human SKOV3 cells by MTT assay 22506620
HepG2 IC50 = 810.0 nM 6.09 Cytotoxicity against human HepG2 cells by MTT assay 22506620
BGC-823 IC50 = 810.0 nM 6.09 Cytotoxicity against human BGC823 cells by MTT assay 22506620
A549 IC50 = 1300.0 nM 5.89 Cytotoxicity against human A549 cells by MTT assay 22506620
NON-PROTEIN TARGET IC50 = 1900.0 nM 5.72 Antiinflammatory activity in rat polymorphonuclear leukocytes assessed as inhibi... 22506620
HCT-8 IC50 = 2000.0 nM 5.7 Cytotoxicity against human HCT8 cells by MTT assay 22506620
Tobacco mosaic virus IC50 = 3470.0 nM 5.46 In vivo antiviral activity against Tobacco mosaic virus strain U1 (TMV) infected... 20050684
FM3A EC50 = 8000.0 nM 5.1 Cytotoxicity against FM3A cells derived from a mammary tumor in mice was evaluat... 9871598

Literature References

PubMed DOI Target Context # Activities
20050684 10.1021/jf903434h Tobacco mosaic virus 8
3298551 10.1021/np50049a007 Plasmodium berghei 3
9871598 10.1016/s0960-894x(98)00045-6 FM3A 2
33289552 10.1021/acs.jmedchem.0c01449 HCT-116 1
9871598 10.1016/s0960-894x(98)00045-6 Plasmodium falciparum 1
- 10.1007/s00044-011-9767-1 Entamoeba histolytica 1
22506620 10.1021/np200920c SK-OV-3 1
22506620 10.1021/np200920c A549 1
22506620 10.1021/np200920c BGC-823 1
22506620 10.1021/np200920c HepG2 1
22506620 10.1021/np200920c HCT-8 1
22506620 10.1021/np200920c NON-PROTEIN TARGET 1
3298551 10.1021/np50049a007 Mus musculus 1
3298551 10.1021/np50049a007 Plasmodium falciparum 1
17896817 10.1021/np070236h Babesia gibsoni 1
12570385 10.1021/jm0201971 Unchecked 1
12570385 10.1021/jm0201971 FM3A 1
12570385 10.1021/jm0201971 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine