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Compound Detail

CHEMBL399680

BUFALIN
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C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL399680
Name BUFALIN
Phase Preclinical
Structure Type MOL
InChI Key QEEBRPGZBVVINN-BMPKRDENSA-N
23
Targets
39
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

386.5
MW (Da)
4.24
ALogP
4
HBA
2
HBD
70.7
PSA (Ų)
0.76
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C24H34O4
MW 386.53
Aromatic Rings 1
Heavy Atoms 28
NP-Likeness 2.78

Activity Summary

IC50 24 meas. best 8.15
EC50 11 meas. best 8.12
Kd 2 meas. best 6.33
Ki 2 meas. best 5.95

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bel-7402
CHEMBL614279
 IC50 8.15 8.15 7.0 1
Unchecked
CHEMBL612545
 IC50 8.15 6.795 7.0 4
786-0
CHEMBL613102
 EC50 8.12 8.12 7.5 1
SK-OV-3
CHEMBL614925
 EC50 8.0 8.0 10.0 1
HCT-116
CHEMBL394
 EC50 7.96 7.96 11.0 1
BXPC-3
CHEMBL614530
 EC50 7.96 7.96 11.0 1
HUVEC
CHEMBL613979
 EC50 7.92 7.92 12.0 1
NCI-H1975
CHEMBL614348
 EC50 7.89 7.89 13.0 1
U-87 MG
CHEMBL614247
 EC50 7.85 7.85 14.0 1
MES-SA/Dx5
CHEMBL613827
 EC50 7.75 7.75 18.0 1
Sodium/potassium-transporting ATPase
CHEMBL2095186
 IC50 7.66 7.66 22.0 1
MES-SA
CHEMBL614343
 EC50 7.55 7.55 28.0 1
HeLa
CHEMBL399
 IC50 7.55 6.6175 28.0 4
HepG2
CHEMBL395
 EC50 7.46 7.46 35.0 1
MCF7
CHEMBL387
 EC50 7.38 7.38 42.0 1
BGC-823
CHEMBL614526
 IC50 7.35 6.675 45.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.55 6.445 279.0 2
HepG2
CHEMBL395
 IC50 6.46 6.275 345.0 4
Cytochrome P450 3A4
CHEMBL340
 IC50 6.35 5.65 450.0 2
E3 ubiquitin-protein ligase ZFP91
CHEMBL4739701
 Kd 6.33 6.33 462.0 1
A549
CHEMBL392
 IC50 6.22 6.22 600.0 1
Cytochrome P450 3A4
CHEMBL340
 Ki 5.95 5.315 1130.0 2
Androgen receptor
CHEMBL1871
 IC50 5.72 5.72 1900.0 1
Cytochrome P450 3A5
CHEMBL3019
 IC50 5.56 5.56 2760.0 1
Unchecked
CHEMBL612545
 Kd 5.5 5.5 3150.0 1
MH60
CHEMBL614350
 IC50 4.5 4.5 31900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 7.0 nM 8.15 Inhibition of MAPK/ERK signaling pathway in human NCI-H1975 cells 38295689
Bel-7402 IC50 = 7.0 nM 8.15 Cytotoxicity against human Bel7402 cells after 72 hrs by MTT assay 15844967
786-0 EC50 = 7.5 nM 8.12 Cytotoxicity against human 786-O cells assessed as decrease in cell viability af... 30369239
SK-OV-3 EC50 = 10.0 nM 8.0 Cytotoxicity against human SKOV3 cells assessed as decrease in cell viability af... 30369239
BXPC-3 EC50 = 11.0 nM 7.96 Cytotoxicity against human BxPC3 cells assessed as decrease in cell viability af... 30369239
HCT-116 EC50 = 11.0 nM 7.96 Cytotoxicity against human HCT116 cells assessed as decrease in cell viability a... 30369239
Unchecked IC50 = 11.0 nM 7.96 Inhibition of Na(+)/K(+) ATPase in pig cerebral cortex assessed as release of in... 24050254
HUVEC EC50 = 12.0 nM 7.92 Cytotoxicity against human HUVEC cells assessed as decrease in cell viability af... 30369239
NCI-H1975 EC50 = 13.0 nM 7.89 Cytotoxicity against human NCI-H1975 cells assessed as decrease in cell viabilit... 30369239
U-87 MG EC50 = 14.0 nM 7.85 Cytotoxicity against human U87MG cells assessed as decrease in cell viability af... 30369239
MES-SA/Dx5 EC50 = 18.0 nM 7.75 Cytotoxicity against human MES-SA/Dx5 cells assessed as decrease in cell viabili... 30369239
Sodium/potassium-transporting ATPase IC50 = 22.0 nM 7.66 Inhibition of NA+/K+ ATPase (unknown origin) activity 31945667
MES-SA EC50 = 28.0 nM 7.55 Cytotoxicity against human MESSA cells assessed as decrease in cell viability af... 30369239
HeLa IC50 = 28.0 nM 7.55 Cytotoxicity against human HeLa cells after 72 hrs by MTT assay 15844967
HepG2 EC50 = 35.0 nM 7.46 Cytotoxicity against human HepG2 cells assessed as decrease in cell viability af... 30369239
MCF7 EC50 = 42.0 nM 7.38 Cytotoxicity against human MCF7 cells assessed as decrease in cell viability aft... 30369239
BGC-823 IC50 = 45.0 nM 7.35 Cytotoxicity against human BGC823 cells after 72 hrs by MTT assay 15844967
NON-PROTEIN TARGET IC50 = 279.0 nM 6.55 Cytotoxicity against human CNE1 cells assessed as growth inhibition after 48 hrs... 23799775
HeLa IC50 = 279.9 nM 6.55 Cytotoxicity activity against human HeLa cells after 48 hrs by MTT assay 30245398
HepG2 IC50 = 345.0 nM 6.46 Cytotoxicity against adriamycin-resistant human HepG2 cells assessed as growth i... 23799775

Literature References

PubMed DOI Target Context # Activities
30369239 10.1021/acs.jnatprod.8b00736 Cardiac muscle cell 29
23799775 10.1021/jm400881m H(+)/Cl(-) exchange transporter 3 18
23799775 10.1021/jm400881m Molecular identity unknown 13
35094507 10.1021/acs.jmedchem.1c01875 Cytochrome P450 3A4 8
35094507 10.1021/acs.jmedchem.1c01875 Unchecked 7
23799775 10.1021/jm400881m CNE2Z 6
30245398 10.1016/j.ejmech.2018.09.019 HeLa 6
12109909 10.1021/jm0102811 Monoclonal antibody (mAb) 4
12459012 10.1021/jm0202066 Unchecked 2
23799775 10.1021/jm400881m HepG2 2
23799775 10.1021/jm400881m NON-PROTEIN TARGET 2
28256122 10.1021/acs.jnatprod.6b01018 Unchecked 2
15620253 10.1021/np049950e MH60 2
35094507 10.1021/acs.jmedchem.1c01875 Cytochrome P450 3A5 2
35094507 10.1021/acs.jmedchem.1c01875 Cytochrome P450 3A7 2
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
15844967 10.1021/np0500023 HeLa 1
15844967 10.1021/np0500023 BGC-823 1
38295689 10.1016/j.ejmech.2023.116117 Unchecked 1
11575946 10.1021/np0101088 KB 1

Data from ChEMBL 36 via Core Engine