Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL555017

GAMBOGIC ACID
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
CC(C)=CCC[C@]1(C)C=Cc2c(O)c3c(c(CC=C(C)C)c2O1)O[C@]12C(=C[C@@H]4C[C@H]1C(C)(C)O[C@@]2(C/C=C(/C)C(=O)O)C4=O)C3=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL555017
Name GAMBOGIC ACID
Phase Preclinical
Structure Type MOL
InChI Key GEZHEQNLKAOMCA-RRZNCOCZSA-N

Known Names

Gambogic Acid
42
Targets
86
Activities
4
Assay Types
11
PK Parameters
20
Publications
1
Known Names

Molecular Properties

628.8
MW (Da)
7.24
ALogP
7
HBA
2
HBD
119.4
PSA (Ų)
0.23
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C38H44O8
MW 628.76
Aromatic Rings 1
Heavy Atoms 46
NP-Likeness 3.63

Activity Summary

IC50 72 meas. best 6.91
EC50 7 meas. best 7.7
Ki 4 meas. best 6.72
Kd 3 meas. best 5.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 EC50 7.7 7.7 20.0 1
Apoptosis regulator Bcl-2
CHEMBL4860
 IC50 6.91 6.855 122.0 2
HL-60
CHEMBL383
 IC50 6.77 6.77 170.0 1
Bcl-2-related protein A1
CHEMBL6044
 IC50 6.75 6.34 176.0 3
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 Ki 6.72 6.51 190.0 2
HEK293
CHEMBL614818
 EC50 6.68 6.68 210.0 1
BJ
CHEMBL614358
 EC50 6.68 6.68 210.0 1
Raji
CHEMBL614628
 EC50 6.62 6.62 240.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.62 5.92 240.0 3
A549/CDDP
CHEMBL4483225
 IC50 6.54 6.54 290.0 1
HepG2
CHEMBL395
 IC50 6.54 5.8789 290.0 9
HCT-116
CHEMBL394
 IC50 6.54 6.025 290.0 2
A549/TR
CHEMBL4483226
 IC50 6.54 6.54 290.0 1
A549
CHEMBL392
 IC50 6.54 5.8133 290.0 9
U-251
CHEMBL615022
 IC50 6.54 5.8275 290.0 4
Breast carcinoma cell
CHEMBL614026
 IC50 6.38 6.38 420.0 1
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 IC50 6.33 6.33 470.0 1
Bcl-2-like protein 1
CHEMBL4625
 IC50 6.3 6.065 500.0 2
MCF7
CHEMBL387
 IC50 6.3 5.9533 500.0 3
K562
CHEMBL385
 IC50 6.21 6.21 620.0 1
Bcl-2-like protein 10
CHEMBL5988
 IC50 6.18 6.18 660.0 1
SNU-398
CHEMBL614454
 EC50 6.16 6.16 700.0 1
HeLa
CHEMBL399
 IC50 6.16 6.16 700.0 1
HCT-116
CHEMBL394
 EC50 6.16 6.16 700.0 1
T47D
CHEMBL614361
 EC50 6.16 6.16 700.0 1
Bel-7402
CHEMBL614279
 IC50 6.12 5.76 750.0 3
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
 IC50 6.1 6.1 790.0 1
SK-BR-3
CHEMBL613834
 IC50 6.05 6.05 890.0 1
SMMC-7721
CHEMBL613831
 IC50 5.95 5.725 1130.0 2
PC-3
CHEMBL390
 IC50 5.92 5.92 1190.0 1
Thioredoxin, mitochondrial
CHEMBL2189153
 Ki 5.88 5.88 1310.0 1
MDA-MB-231
CHEMBL400
 IC50 5.88 5.88 1330.0 1
SGC-7901
CHEMBL614909
 IC50 5.83 5.83 1470.0 1
HEK293
CHEMBL614818
 IC50 5.76 5.76 1720.0 1
Unchecked
CHEMBL612545
 IC50 5.7 5.7 2000.0 1
Bcl-2-like protein 2
CHEMBL4677
 IC50 5.7 5.7 2020.0 1
Serine palmitoyltransferase small subunit B
CHEMBL6067597
 IC50 5.66 5.66 2180.0 1
BGC-823
CHEMBL614526
 IC50 5.63 5.51 2350.0 3
HT-29
CHEMBL384
 IC50 5.62 5.44 2370.0 3
SK-OV-3
CHEMBL614925
 IC50 5.51 5.51 3060.0 1
Thioredoxin
CHEMBL2010624
 Ki 5.51 5.51 3110.0 1
Inhibitor of nuclear factor kappa-B kinase subunit beta
CHEMBL1991
 IC50 5.51 5.51 3070.0 1
MKN-45
CHEMBL614354
 IC50 5.37 5.37 4270.0 1
Heat shock protein HSP90
CHEMBL2095165
 Kd 5.16 5.0967 7000.0 3
Regulator of G-protein signaling 17
CHEMBL4295974
 IC50 5.0 4.96 10000.0 3
Heat shock protein HSP 90-alpha
CHEMBL3880
 IC50 4.66 4.66 21980.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2005.0 ng.hr.mL-1 Mus musculus
AUC 1072.0 ng.hr.mL-1 Mus musculus
CL 41.02 mL.min-1.kg-1 Mus musculus
Cmax 303.77 nM Mus musculus
F 13.4 % Mus musculus
MRT 4.51 hr Mus musculus
MRT 2.26 hr Mus musculus
T1/2 5.06 hr Mus musculus
T1/2 3.29 hr Mus musculus
Tmax 0.5 hr Mus musculus
Vd 19.7 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked EC50 = 20.0 nM 7.7 Suppression of staurosporine-initiated apoptosis in human T17 cells at 0.5 uM 17911251
Apoptosis regulator Bcl-2 IC50 = 122.0 nM 6.91 Inhibition of Bcl-2 (unknown origin) by fluorescence polarization assay 34034128
Apoptosis regulator Bcl-2 IC50 = 160.0 nM 6.8 Binding affinity to Bcl-2 (unknown origin) pre-incubated for 30 mins followed by... 39121336
HL-60 IC50 = 170.0 nM 6.77 Antiproliferative activity against human HL60 cells assessed as reduction in cel... 30830783
Bcl-2-related protein A1 IC50 = 176.0 nM 6.75 Inhibition of recombinant Bfl-1 (1-152) (unknown origin) by TR-FRET assay 38373466
Tyrosine-protein phosphatase non-receptor type 1 Ki = 190.0 nM 6.72 Inhibition of recombinant human PTP1B (1 to 322 residues) expressed in Escherich... 28318895
HEK293 EC50 = 210.0 nM 6.68 Cytotoxicity against HEK293 cells 25316317
BJ EC50 = 210.0 nM 6.68 Cytotoxicity against human BJ cells 25316317
Raji EC50 = 240.0 nM 6.62 Cytotoxicity against human Raji cells 25316317
NON-PROTEIN TARGET IC50 = 240.0 nM 6.62 Cytotoxicity against human QGY7701 cells after 72 hrs by MTT assay 22153338
U-251 IC50 = 290.0 nM 6.54 Antiproliferative activity against human U251 cells assessed as reduction in cel... 31546197
A549/CDDP IC50 = 290.0 nM 6.54 Antiproliferative activity against human A549/CDDP cells assessed as reduction i... 31546197
HCT-116 IC50 = 290.0 nM 6.54 Antiproliferative activity against human HCT116 cells assessed as reduction in c... 31546197
HepG2 IC50 = 290.0 nM 6.54 Antiproliferative activity against human HepG2 cells assessed as reduction in ce... 31546197
A549/TR IC50 = 290.0 nM 6.54 Antiproliferative activity against human A549/TR cells assessed as reduction in ... 31546197
A549 IC50 = 290.0 nM 6.54 Antiproliferative activity against human A549 cells assessed as reduction in cel... 31546197
Breast carcinoma cell IC50 = 420.0 nM 6.38 Cytotoxicity against patient derived inflammatory breast cancer cell spheroids a... 30831408
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 470.0 nM 6.33 Inhibition of recombinant human PTP1B (1 to 322 residues) expressed in Escherich... 28318895
Tyrosine-protein phosphatase non-receptor type 1 Ki = 499.0 nM 6.3 Inhibition of recombinant human PTP1B (1 to 322 residues) expressed in Escherich... 28318895
Bcl-2-like protein 1 IC50 = 500.0 nM 6.3 Binding affinity to Bcl-xL (unknown origin) pre-incubated for 30 mins followed b... 39121336

Literature References

PubMed DOI Target Context # Activities
26631318 10.1016/j.bmcl.2015.11.043 T98G 27
28318895 10.1016/j.bmc.2017.03.010 Tyrosine-protein phosphatase non-receptor type 1 20
21486005 10.1021/np200029q Heat shock protein HSP90 17
21191083 10.1124/dmd.110.037044 ADMET 16
23167526 10.1021/jm301593r Mus musculus 11
22663155 10.1021/np300118c Thioredoxin 8
22663155 10.1021/np300118c Thioredoxin, mitochondrial 7
21191083 10.1124/dmd.110.037044 No relevant target 6
27216998 10.1016/j.bmcl.2016.05.030 Staphylococcus aureus 6
21486005 10.1021/np200029q Unchecked 5
21191083 10.1124/dmd.110.037044 Liver microsome 5
23540934 10.1021/np400049j E3 ubiquitin-protein ligase Mdm2 5
17911251 10.1073/pnas.0706662104 High affinity nerve growth factor receptor 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
31047774 10.1016/j.bmc.2019.04.027 HCT-116 3
25958244 10.1016/j.bmcl.2015.04.031 ADMET 3
22472167 10.1016/j.ejmech.2012.02.029 Unchecked 3
23540934 10.1021/np400049j Cellular tumor antigen p53 3
17911251 10.1073/pnas.0706662104 Unchecked 3
23167526 10.1021/jm301593r NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine