Compound Detail

CHEMBL51483

GOSSYPOL

🧪 Phase III

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🧪 Phase III

Cc1cc2c(C(C)C)c(O)c(O)c(C=O)c2c(O)c1-c1c(C)cc2c(C(C)C)c(O)c(O)c(C=O)c2c1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL51483
Name	GOSSYPOL
Phase	Phase III
Structure Type	MOL
InChI Key	QBKSWRVVCFFDOT-UHFFFAOYSA-N

Known Names

(-)-gossypol BL-193 Gossypol No fertil NSC-56817 NSC-624336 Pogosin Tash 1

Targets

192

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

518.6

MW (Da)

6.38

ALogP

HBA

HBD

155.5

PSA (Å²)

0.13

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Racemic

Flags

Natural Product

Extended Properties

Molecular Formula	C30H30O8
MW	518.56
Aromatic Rings	4
Heavy Atoms	38
NP-Likeness	0.77

Indications

Carcinoma, Non-Small-Cell Lung

Activity Summary

IC50 121 meas. best 7.0

Ki 57 meas. best 6.79

EC50 7 meas. best 5.85

Kd 7 meas. best 5.77

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	7.0	5.6718	100.0	17
Induced myeloid leukemia cell differentiation protein Mcl-1 CHEMBL4361	Ki	6.79	6.5467	162.0	18
Induced myeloid leukemia cell differentiation protein Mcl-1 CHEMBL4361	IC50	6.77	5.96	170.0	5
Apoptosis regulator Bcl-2 CHEMBL4860	Ki	6.77	6.3075	170.0	16
Aspartyl/asparaginyl beta-hydroxylase CHEMBL4680030	IC50	6.6	6.565	250.0	4
Apoptosis regulator Bcl-2 CHEMBL4860	IC50	6.58	6.2057	260.0	7
Bcl-2-like protein 1 CHEMBL4625	Ki	6.51	6.234	310.0	10
Unchecked CHEMBL612545	Ki	6.48	5.545	334.0	2
Bcl2-associated agonist of cell death CHEMBL3817	Ki	6.34	6.34	460.0	1
Bcl-2-like protein 1 CHEMBL4625	IC50	6.32	6.156	480.0	5
Aldo-keto reductase family 1 member B1 CHEMBL1900	Ki	6.3	6.3	500.0	1
Inosine-5'-monophosphate dehydrogenase CHEMBL4523953	IC50	6.05	6.05	900.0	1
A549 CHEMBL392	IC50	5.88	5.18	1320.0	2
L-lactate dehydrogenase B chain CHEMBL4940	Ki	5.85	5.85	1400.0	1
L-lactate dehydrogenase B chain CHEMBL5169119	Ki	5.85	5.85	1400.0	1
Unchecked CHEMBL612545	EC50	5.85	5.615	1420.0	2
Bcl-2-like protein 1 CHEMBL4625	Kd	5.77	5.77	1710.0	1
Induced myeloid leukemia cell differentiation protein Mcl-1/BH3-interacting domain death agonist CHEMBL3430886	IC50	5.76	5.76	1750.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	Ki	5.75	5.75	1780.0	1
Influenza A virus CHEMBL613740	IC50	5.73	5.575	1870.0	2
L-lactate dehydrogenase A chain CHEMBL4835	Ki	5.72	5.72	1900.0	3
MDA-MB-231 CHEMBL400	IC50	5.72	5.2683	1900.0	6
Malate dehydrogenase CHEMBL6072	IC50	5.69	5.69	2030.0	1
H5N1 subtype CHEMBL613845	IC50	5.67	5.67	2140.0	1
CT26 CHEMBL613866	IC50	5.66	5.265	2210.0	2
Induced myeloid leukemia cell differentiation protein Mcl-1 CHEMBL4361	Kd	5.63	5.5925	2324.0	4
PC-3 CHEMBL390	IC50	5.6	5.122	2500.0	5
Estrogen receptor CHEMBL206	IC50	5.59	5.59	2551.3	1
Lactate dehydrogenase CHEMBL6071	IC50	5.58	5.58	2640.0	1
Malate dehydrogenase, mitochondrial CHEMBL3444	IC50	5.55	5.55	2800.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.52	4.8127	3030.0	22
NCI-H460 CHEMBL396	EC50	5.52	5.52	3000.0	1
DNA-3-methyladenine glycosylase CHEMBL3396943	IC50	5.52	5.52	3000.0	1
Bcl-xL/BH3-interacting domain death agonist CHEMBL3883285	IC50	5.52	5.52	3030.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	5.51	5.365	3100.0	2
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	IC50	5.49	5.49	3235.9	1
PC-3 CHEMBL390	EC50	5.48	5.115	3300.0	2
HCT-116 CHEMBL394	IC50	5.48	5.07	3330.0	2
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	Ki	5.46	5.46	3470.0	1
Plasmodium falciparum CHEMBL364	IC50	5.35	4.928	4500.0	5
K562 CHEMBL385	IC50	5.34	5.1975	4550.0	4
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	5.34	5.34	4570.9	1
Apoptosis regulator Bcl-2 CHEMBL4860	Kd	5.32	5.32	4800.0	1
B16-F10 CHEMBL612656	IC50	5.26	5.005	5540.0	2
Malate dehydrogenase, cytoplasmic CHEMBL4048	IC50	5.24	5.24	5800.0	1
Androgen receptor CHEMBL1871	IC50	5.14	5.14	7160.0	1
ZR-75-1 CHEMBL614393	IC50	5.08	5.08	8400.0	1
Kinesin-like protein KIF11 CHEMBL4581	IC50	4.97	4.785	10800.0	2
HEK293 CHEMBL614818	IC50	4.96	4.96	11040.0	1
MDA-MB-435 CHEMBL614697	IC50	4.93	4.705	11780.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	15141.95	ng.hr.mL-1	Homo sapiens
AUC	3152.84	ng.hr.mL-1	Homo sapiens
AUC	3531.39	ng.hr.mL-1	Homo sapiens
CL	0.8333	mL.min-1.kg-1	Canis lupus familiaris
CL	0.8333	mL.min-1.kg-1	Canis lupus familiaris
CL	2.5	mL.min-1.kg-1	Homo sapiens
Cmax	1750.0	nM	Homo sapiens
Cmax	799.0	nM	Homo sapiens
Cmax	1270.0	nM	Homo sapiens
Ka	2.391	10'5L/mol	Homo sapiens
T1/2	133.0	hr	Homo sapiens
T1/2	4.55	hr	Homo sapiens
T1/2	3.33	hr	Homo sapiens
T1/2	1.0	hr	Homo sapiens
T1/2	1.0	hr	Canis lupus familiaris
T1/2	1.0	hr	Mus musculus
Tmax	4.6	hr	Homo sapiens
Tmax	4.6	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	100.0	nM	7.0	Inhibition of Toxoplasma gondii LDH2	34687983
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	162.0	nM	6.79	Inhibition of FAM-Bid binding to human MCL1 expressed in Escherichia coli BL21 a...	27994761
Apoptosis regulator Bcl-2	Ki	=	170.0	nM	6.77	Displacement of FAM-Bim peptide from human Bcl2 by fluorescence polarization ass...	17552510
Induced myeloid leukemia cell differentiation protein Mcl-1	IC50	=	170.0	nM	6.77	Inhibition of biotin-Bim peptide binding to Mcl1 (unknown origin) expressed in E...	23314054
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	180.0	nM	6.75	Displacement of FAM-Bid from human Mcl1 by FP assay	17034116
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	180.0	nM	6.75	Binding affinity to MCL1	20925433
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	180.0	nM	6.75	Inhibition of 5-FAM-QEDIIRNIARHLAQVGDSMDRSIPPG binding to Mcl-1 (unknown origin)...	27810438
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	180.0	nM	6.75	Inhibition of MCl-1 (unknown origin)	31129454
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	180.0	nM	6.75	Binding affinity to Mc1-1 (unknown origin) by fluorescence polarization competit...	34153472
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	190.0	nM	6.72	Displacement of FAM-Bid peptide from recombinant N-terminal His6x-tagged human M...	33218896
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	190.0	nM	6.72	Displacement of FAM-Bid BH3 peptide from recombinant Mcl-1 (unknown origin) expr...	24095762
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	190.0	nM	6.72	Inhibition of FAM-Bid peptide binding to Mcl1 (unknown origin) expressed in Esch...	23314054
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	200.0	nM	6.7	Inhibition of 6-carboxyfluorescein succinimidyl ester fluorescence tagged-Bid BH...	28343875
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	213.8	nM	6.67	Inhibition of biotin-Bim peptide binding to Mcl1 (unknown origin) expressed in E...	23314054
Aspartyl/asparaginyl beta-hydroxylase	IC50	=	250.0	nM	6.6	Inhibition of N-His6-tagged human AspH (315-755) expressed in Escherichia coli B...	33069066
Aspartyl/asparaginyl beta-hydroxylase	IC50	=	250.0	nM	6.6	Inhibition of N-His6-tagged human AspH (315-755) expressed in Escherichia coli B...	33069066
Aspartyl/asparaginyl beta-hydroxylase	IC50	=	260.0	nM	6.58	Inhibition of N-His6-tagged human AspH (315-755) expressed in Escherichia coli B...	33069066
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	260.0	nM	6.58	Displacement of FAM-Bid peptide from N-terminal 8x His-tagged MCl-1 (unknown ori...	26982372
Apoptosis regulator Bcl-2	IC50	=	260.0	nM	6.58	Displacement of FITC-labeled Bak BH3 peptide from Bcl-2 after 30 mins by fluores...	20443627
Induced myeloid leukemia cell differentiation protein Mcl-1	Ki	=	280.0	nM	6.55	Displacement of FAM-Bim peptide from human Mcl1 by fluorescence polarization ass...	17552510

Literature References

PubMed	DOI	Target Context	# Activities
19577825	10.1016/j.ejmech.2009.05.032	Staphylococcus aureus	28
27994761	10.1021/acsmedchemlett.6b00302	NON-PROTEIN TARGET	24
32916044	10.1021/acs.jmedchem.0c01177	ADMET	21
19264482	10.1016/j.bmcl.2009.02.051	Fusarium oxysporum	20
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
19447525	10.1016/j.ejmech.2009.04.025	Unchecked	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
30016095	10.1021/acs.jmedchem.8b00692	Saccharomyces cerevisiae	7
12428953	10.1021/jf0207225	Rhizoctonia solani	6
19447525	10.1016/j.ejmech.2009.04.025	HeLa	6
33069066	10.1016/j.bmc.2020.115675	Aspartyl/asparaginyl beta-hydroxylase	5
34812616	10.1021/acs.jmedchem.1c01547	Unchecked	5
23314054	10.1016/j.ejmech.2012.12.016	Induced myeloid leukemia cell differentiation protein Mcl-1	5
23538114	10.1016/j.bmcl.2013.02.101	Unchecked	5
23538114	10.1016/j.bmcl.2013.02.101	Influenza A virus	5
20684596	10.1021/jm1001698	Mus musculus	4
19577825	10.1016/j.ejmech.2009.05.032	Micrococcus luteus	4
23571415	10.1124/mol.112.084152	Solute carrier organic anion transporter family member 1B3	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
22226654	10.1016/j.bmcl.2011.12.076	Human immunodeficiency virus type 1 reverse transcriptase	4

Data from ChEMBL 36 via Core Engine