Gossypol

Summary

Gossypol (CHEMBL51483) is a phase-3 clinical-stage small-molecule antispermatogenic agent; indicated across 1 condition including non-small cell lung carcinoma.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Indications: 1 condition
• Clinical trials: 2
• Chemistry: 518.6 Da · C30H30O8

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL51483
Name	Gossypol
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	3503
ChEBI	CHEBI:28584
Molecular formula	C30H30O8
Molecular weight	518.6
InChIKey	QBKSWRVVCFFDOT-UHFFFAOYSA-N

SMILES: CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O

IUPAC name: 7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde

Pharmacological roles (ChEBI): antispermatogenic agent, anti-inflammatory agent.

Other ChEBI roles (chemical / environmental): plant metabolite.

Also known as: (-)-gossypol, BL-193, Gossypol, No fertil, NSC-56817, NSC-624336, Pogosin, Tash 1, R-(-)-gossypol, (+)-gossypol, gossypol, (R)-(-)-gossypol

Parent form; salt/anhydrous children: CHEMBL1516388

Patent coverage: 5,764 distinct patent families (13,973 SureChEMBL compound mentions), from 4 matched compound structure(s). One matched structure accounts for 13,030 (93%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
	VRAC

Broader ChEMBL bioactivity targets: 63 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Microtubule-associated protein tau, Lysine-specific demethylase 4E, Ubiquitin carboxyl-terminal hydrolase 2, Nuclear receptor ROR-gamma, Survival motor neuron protein, Fructose-bisphosphate aldolase, Prelamin-A/C, ATP-dependent DNA helicase Q1, RecQ-like DNA helicase BLM, Inositol monophosphatase 1, 4’-phosphopantetheinyl transferase ffp, 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase, chloroplastic, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Galactokinase, NPC intracellular cholesterol transporter 1, Ras-related protein Rab-9A, Solute carrier organic anion transporter family member 1B1, Solute carrier organic anion transporter family member 1B3, Androgen receptor.

Bioactivity

ChEMBL activities: 128 potent at pChembl ≥ 5 of 239 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
MCL1	6.79	Ki	162	nM	CHEMBL_ACT_16782322
MCL1	6.77	IC50	170	nM	CHEMBL_ACT_12640797
BCL2	6.77	Ki	170	nM	CHEMBL_ACT_1905034
MCL1	6.75	Ki	180	nM	CHEMBL_ACT_16816373
MCL1	6.75	Ki	180	nM	CHEMBL_ACT_1773922
MCL1	6.75	Ki	180	nM	CHEMBL_ACT_19235579
MCL1	6.75	Ki	180	nM	CHEMBL_ACT_23168521
MCL1	6.75	Ki	180	nM	CHEMBL_ACT_29155675
MCL1	6.75	Ki	180	nM	CHEMBL_ACT_3526123
MCL1	6.72	Ki	190	nM	CHEMBL_ACT_12640749
MCL1	6.72	Ki	190	nM	CHEMBL_ACT_13478331
MCL1	6.72	Ki	190	nM	CHEMBL_ACT_22777100
MCL1	6.7	Ki	200	nM	CHEMBL_ACT_18069661
MCL1	6.67	Ki	213.8	nM	CHEMBL_ACT_12640765
ASPH	6.6	IC50	250	nM	CHEMBL_ACT_22416324
ASPH	6.6	IC50	250	nM	CHEMBL_ACT_22416336
P15917	6.6	Potency	251.2	nM	CHEMBL_ACT_4633423
MCL1	6.58	Ki	260	nM	CHEMBL_ACT_16560960
ASPH	6.58	IC50	260	nM	CHEMBL_ACT_22416348
BCL2	6.58	IC50	260	nM	CHEMBL_ACT_3287015
MCL1	6.55	Ki	280	nM	CHEMBL_ACT_1905039
BCL2	6.52	IC50	300	nM	CHEMBL_ACT_3287014
MCL1	6.51	Ki	310	nM	CHEMBL_ACT_15749772
BCL2L1	6.51	Ki	310	nM	CHEMBL_ACT_16654041
BCL2L1	6.51	Ki	310	nM	CHEMBL_ACT_16749051
BCL2	6.5	Ki	320	nM	CHEMBL_ACT_1771941
BCL2	6.5	Ki	320	nM	CHEMBL_ACT_19235577
BCL2	6.5	Ki	320	nM	CHEMBL_ACT_25006078
BCL2	6.5	Ki	320	nM	CHEMBL_ACT_29155651
BCL2	6.5	Ki	320	nM	CHEMBL_ACT_3526121
ALOX12	6.5	Potency	316.2	nM	CHEMBL_ACT_4533168
ASPH	6.48	IC50	330	nM	CHEMBL_ACT_22416360
MCL1	6.41	Ki	390	nM	CHEMBL_ACT_16392106
BCL2	6.38	Ki	420	nM	CHEMBL_ACT_18069636
BCL2	6.37	Ki	431	nM	CHEMBL_ACT_16560961
BCL2	6.36	Ki	440	nM	CHEMBL_ACT_16654034
BCL2	6.36	Ki	440	nM	CHEMBL_ACT_16749030
BCL2	6.35	Ki	450	nM	CHEMBL_ACT_16816386
MCL1	6.35	Ki	450	nM	CHEMBL_ACT_25033729
BAD	6.34	Ki	460	nM	CHEMBL_ACT_23168545
BCL2	6.33	Ki	467.7	nM	CHEMBL_ACT_2150734
BCL2L1	6.32	Ki	480	nM	CHEMBL_ACT_1773921
BCL2L1	6.32	Ki	480	nM	CHEMBL_ACT_19235578
BCL2L1	6.32	Ki	480	nM	CHEMBL_ACT_29155664
BCL2L1	6.32	IC50	480	nM	CHEMBL_ACT_3121861
BCL2L1	6.32	IC50	480	nM	CHEMBL_ACT_3287022
BCL2L1	6.32	Ki	480	nM	CHEMBL_ACT_3526122
AKR1B1	6.3	Ki	500	nM	CHEMBL_ACT_1181958
BCL2	6.3	IC50	500	nM	CHEMBL_ACT_1771942
BCL2L1	6.3	IC50	500	nM	CHEMBL_ACT_809170
BCL2	6.29	Ki	511	nM	CHEMBL_ACT_16782298
BCL2L1	6.27	IC50	540	nM	CHEMBL_ACT_3287021
BCL2	6.25	Ki	558	nM	CHEMBL_ACT_13478322
BCL2	6.25	Ki	560	nM	CHEMBL_ACT_16392138
POLB	6.25	Potency	562.3	nM	CHEMBL_ACT_5047952
BCL2	6.22	IC50	600	nM	CHEMBL_ACT_17999571
BCL2	6.22	IC50	600	nM	CHEMBL_ACT_24999397
BCL2	6.21	Ki	620	nM	CHEMBL_ACT_15186340
BCL2L1	6.21	Ki	610	nM	CHEMBL_ACT_23168569
BCL2L1	6.19	Ki	640	nM	CHEMBL_ACT_15749764
MCL1	6.19	Ki	640	nM	CHEMBL_ACT_16749072
BCL2L1	6.11	Ki	770	nM	CHEMBL_ACT_16392133
MCL1	6.07	IC50	856	nM	CHEMBL_ACT_16782321
ALOX12	6.05	Potency	891.3	nM	CHEMBL_ACT_4526357
BCL2L1	6	Ki	1000	nM	CHEMBL_ACT_15177076
BCL2	5.92	IC50	1191	nM	CHEMBL_ACT_16782297
LDHB	5.85	Ki	1400	nM	CHEMBL_ACT_16468238
BCL2L1	5.85	Ki	1400	nM	CHEMBL_ACT_16816380
P16125	5.85	Ki	1400	nM	CHEMBL_ACT_24744151
MCL1	5.82	IC50	1520	nM	CHEMBL_ACT_22777137
MCL1	5.82	IC50	1523	nM	CHEMBL_ACT_4734021
BCL2L1	5.77	Kd	1710	nM	CHEMBL_ACT_2254171
BID	5.76	IC50	1750	nM	CHEMBL_ACT_24723923
SLCO1B1	5.75	Ki	1780	nM	CHEMBL_ACT_13800665
LDHA	5.72	Ki	1900	nM	CHEMBL_ACT_16468211
LDHA	5.72	Ki	1900	nM	CHEMBL_ACT_18719168
LDHA	5.72	Ki	1900	nM	CHEMBL_ACT_24744150
USP2	5.7	Potency	1995	nM	CHEMBL_ACT_4699505
BCL2	5.68	IC50	2110	nM	CHEMBL_ACT_13294104
LMNA	5.65	Potency	2239	nM	CHEMBL_ACT_3650777
MCL1	5.63	Kd	2324	nM	CHEMBL_ACT_12620209
ALOX12	5.6	Potency	2512	nM	CHEMBL_ACT_4532215
ESR1	5.59	IC50	2551	nM	CHEMBL_ACT_4536752
MCL1	5.58	Kd	2650	nM	CHEMBL_ACT_12640779
MCL1	5.58	Kd	2630	nM	CHEMBL_ACT_12671265
MCL1	5.58	Kd	2650	nM	CHEMBL_ACT_12671283
MTOR	5.58	Potency	2612	nM	CHEMBL_ACT_4393077
BCL2L1	5.57	IC50	2720	nM	CHEMBL_ACT_17700127
P00346	5.55	IC50	2800	nM	CHEMBL_ACT_1914017
MPG	5.52	IC50	3000	nM	CHEMBL_ACT_15159208
BID	5.52	IC50	3030	nM	CHEMBL_ACT_24723986
RECQL	5.5	Potency	3162	nM	CHEMBL_ACT_3675845
SLCO1B1	5.49	IC50	3236	nM	CHEMBL_ACT_13800601
SLCO1B3	5.46	Ki	3470	nM	CHEMBL_ACT_13798666
KDM4E	5.45	Potency	3548	nM	CHEMBL_ACT_3702989
P51450	5.45	Potency	3548	nM	CHEMBL_ACT_4103528
SLCO1B3	5.34	IC50	4571	nM	CHEMBL_ACT_13798602
BCL2	5.32	Kd	4800	nM	CHEMBL_ACT_12640778
MCL1	5.32	IC50	4800	nM	CHEMBL_ACT_12640781
RECQL	5.3	Potency	5012	nM	CHEMBL_ACT_3684164

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 disease in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
non-small cell lung carcinoma	3	MONDO:0005233	EFO:0003060

Clinical trials

Total trials: 2.

Phase distribution

Phase	Trials
PHASE3	1
PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01977209	PHASE3	UNKNOWN	Gossypol Combined With Docetaxel and Cisplatin Scheme in Advanced Non Small-cell Lung Cancers With APE1 High Expression
NCT07337551	PHASE2	NOT_YET_RECRUITING	Gossypol Acetate + FOLFIRI + Bev in mCRC With TP53-Mutant and LRPPRC Positive

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).