Gossypol

Representations & DB's id
ChEBI:	None
ChEMBL:	CHEMBL51483
PubChem:	3503
IUPAC:	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
Standard InChI:	InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
Standard InChI Key:	QBKSWRVVCFFDOT-UHFFFAOYSA-N
SMILES:	O=Cc1c(O)c(O)c(c2c1c(O)c(c(c2)C)c1c(C)cc2c(c1O)c(C=O)c(c(c2C(C)C)O)O)C(C)C

Molecular propeties
AlogP:	6.38
Hydrogen bonds acceptors:	8
Hydrogen bonds donors:	6
Rotatable bonds:	5
Number of rings:	4
Molecular Weight:	518.19
Topological polar surface area:	156
Number of aromatic rings:	4
Fsp3:	0.267
Number of carbons:	30

Plant sources

Part of plant	Plant name	Ref.
Plant	Gossypium herbaceum
Plant	Gossypium herbaceum

In vitro data

Activity Type	Activity Value	Target Name	UniProt ID
IC50	500 nM	Apoptosis regulator Bcl-X	Q07817
Ki	320 nM	Apoptosis regulator Bcl-2	P10415
IC50	500 nM	Apoptosis regulator Bcl-2	P10415
Ki	480 nM	Apoptosis regulator Bcl-X	Q07817
Ki	180 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Ki	170 nM	Apoptosis regulator Bcl-2	P10415
Ki	280 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Ki	10100 nM	Apoptosis regulator Bcl-2	P10415
Ki	17700 nM	Apoptosis regulator Bcl-W	Q92843
Others	60 %	Estradiol 17-beta-dehydrogenase 1	P14061
Others	64.8 %	Estradiol 17-beta-dehydrogenase 2	P37059
Potency	19952.6 nM	Ubiquitin carboxyl-terminal hydrolase 2	O75604
Potency	2238.7 nM	Prelamin-A/C	P02545
Potency	44668.4 nM	Thyroid hormone receptor beta-1	P10828
Potency	44668.4 nM	Thyroid hormone receptor beta-1	P10828
Potency	50118.7 nM	Thyroid hormone receptor beta-1	P10828
Potency	12589.3 nM	ATP-dependent DNA helicase Q1	P46063
Potency	23690.6 nM	Galactokinase	P51570
Potency	3162.3 nM	ATP-dependent DNA helicase Q1	P46063
Potency	17782.8 nM	ATP-dependent DNA helicase Q1	P46063
Potency	5011.9 nM	ATP-dependent DNA helicase Q1	P46063
Potency	5011.9 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	7943.3 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	15848.9 nM	ATP-dependent DNA helicase Q1	P46063
Potency	14125.4 nM	ATP-dependent DNA helicase Q1	P46063
Potency	3548.1 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	7943.3 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	7943.3 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	6309.6 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	7079.5 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	12589.3 nM	Huntingtin	P42858
Potency	12589.3 nM	Caspase-1	P29466
Potency	19952.6 nM	Caspase-7	P55210
Potency	58047.9 nM	Ras-related protein Rab-9A	P51151
Potency	35481.3 nM	Survival motor neuron protein	Q16637
Potency	35481.3 nM	Survival motor neuron protein	Q16637
Potency	25118.9 nM	Caspase-1	P29466
Potency	14689.2 nM	Serine/threonine-protein kinase mTOR	P42345
Potency	5623.4 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	11220.2 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	25118.9 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	14125.4 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	8912.5 nM	Tyrosyl-DNA phosphodiesterase 1	Q9NUW8
Potency	39810.7 nM	Thyroid hormone receptor beta-1	P10828
Potency	35481.3 nM	Thyroid hormone receptor beta-1	P10828
Potency	6309.6 nM	Cytochrome P450 2C19	P33261
Potency	31622.8 nM	Thyroid hormone receptor beta-1	P10828
Potency	25118.9 nM	Thyroid hormone receptor beta-1	P10828
Potency	17782.8 nM	Thyroid hormone receptor beta-1	P10828
Potency	39810.7 nM	Thyroid hormone receptor beta-1	P10828
Potency	25118.9 nM	Microtubule-associated protein tau	P10636
Potency	31622.8 nM	Microtubule-associated protein tau	P10636
Potency	19952.6 nM	Microtubule-associated protein tau	P10636
Potency	28183.8 nM	Microtubule-associated protein tau	P10636
Potency	22387.2 nM	Microtubule-associated protein tau	P10636
Potency	10000 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	11220.2 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	39810.7 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	2612.2 nM	Serine/threonine-protein kinase mTOR	P42345
Potency	10000 nM	Arachidonate 15-lipoxygenase	P16050
Potency	10000 nM	Arachidonate 15-lipoxygenase	P16050
Potency	35481.3 nM	Microtubule-associated protein tau	P10636
Potency	25118.9 nM	Microtubule-associated protein tau	P10636
Potency	10000 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	26121.6 nM	Serine/threonine-protein kinase mTOR	P42345
Potency	25118.9 nM	MAP kinase ERK2	P28482
Potency	891.3 nM	Arachidonate 12-lipoxygenase	P18054
Potency	22387.2 nM	Microtubule-associated protein tau	P10636
Potency	35481.3 nM	Microtubule-associated protein tau	P10636
Potency	35481.3 nM	Microtubule-associated protein tau	P10636
Potency	2511.9 nM	Arachidonate 12-lipoxygenase	P18054
Potency	5011.9 nM	Arachidonate 12-lipoxygenase	P18054
Potency	316.2 nM	Arachidonate 12-lipoxygenase	P18054
IC50	2551.34 nM	Estrogen receptor alpha	P03372
Potency	15848.9 nM	Caspase-1	P29466
Potency	91999.7 nM	Niemann-Pick C1 protein	O15118
Potency	1995.3 nM	Ubiquitin carboxyl-terminal hydrolase 2	O75604
Potency	28183.8 nM	MAP kinase ERK2	P28482
Potency	12589.3 nM	Caspase-7	P55210
Potency	35481.3 nM	MAP kinase ERK2	P28482
IC50	1523.1 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Potency	25118.9 nM	Ubiquitin carboxyl-terminal hydrolase 2	O75604
Potency	25118.9 nM	Caspase-1	P29466
Potency	8912.5 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	14689.2 nM	Serine/threonine-protein kinase mTOR	P42345
Potency	14125.4 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	35481.3 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	35481.3 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	12589.3 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	19952.6 nM	Cellular tumor antigen p53	P04637
Potency	5011.9 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	15848.9 nM	Cellular tumor antigen p53	P04637
Potency	19952.6 nM	Cellular tumor antigen p53	P04637
Potency	12589.3 nM	Caspase-1	P29466
Potency	10000 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	28183.8 nM	Bloom syndrome protein	P54132
Potency	8912.5 nM	Lysosomal alpha-glucosidase	P10253
Potency	17782.8 nM	Bloom syndrome protein	P54132
Potency	31622.8 nM	Bloom syndrome protein	P54132
Potency	12589.3 nM	Neuropeptide S receptor	Q6W5P4
Potency	35481.3 nM	Bloom syndrome protein	P54132
Potency	28183.8 nM	Bloom syndrome protein	P54132
Potency	31622.8 nM	Cytochrome P450 2D6	P10635
Potency	31622.8 nM	Cytochrome P450 3A4	P08684
Potency	15848.9 nM	Caspase-7	P55210
Potency	562.3 nM	DNA polymerase beta	P06746
Potency	5211.9 nM	Ubiquitin carboxyl-terminal hydrolase 2	O75604
Potency	22387.2 nM	ATP-dependent DNA helicase Q1	P46063
Potency	31622.8 nM	Cytochrome P450 3A4	P08684
Potency	31622.8 nM	Cytochrome P450 2C9	P11712
Potency	15848.9 nM	Cytochrome P450 2C9	P11712
Potency	14581 nM	Nuclear factor erythroid 2-related factor 2	Q16236
Potency	12589.3 nM	Dopamine D1 receptor	P21728
Potency	19952.6 nM	Histone acetyltransferase GCN5	Q92830
Potency	10000 nM	Histone acetyltransferase GCN5	Q92830
Potency	7943.3 nM	Histone acetyltransferase GCN5	Q92830
Potency	15003 nM	M-phase phosphoprotein 8	Q99549
Potency	29092.9 nM	ATPase family AAA domain-containing protein 5	Q96QE3
Potency	11220.2 nM	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Q96KQ7
Potency	35481.3 nM	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Q96KQ7
Potency	9466.2 nM	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Q96KQ7
Potency	10000 nM	Chromobox protein homolog 1	P83916
Potency	15848.9 nM	Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8
Potency	10000 nM	Arachidonate 15-lipoxygenase, type II	O15296
Potency	3548.1 nM	Arachidonate 15-lipoxygenase, type II	O15296
Potency	5011.9 nM	Arachidonate 15-lipoxygenase, type II	O15296
Potency	9528.3 nM	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Q13526
Potency	8196.1 nM	ATPase family AAA domain-containing protein 5	Q96QE3
Potency	22387.2 nM	Dopamine D1 receptor	P21728
Potency	11917.3 nM	Flap endonuclease 1	P39748
Potency	44668.4 nM	Nuclear factor NF-kappa-B p105 subunit	P19838
Potency	12589.3 nM	Cellular tumor antigen p53	P04637
Potency	1694.4 nM	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Q13526
Potency	27306 nM	Nuclear factor erythroid 2-related factor 2	Q16236
Potency	35481.3 nM	Glutaminase kidney isoform, mitochondrial	O94925
Potency	18356.4 nM	Geminin	O75496
Potency	15848.9 nM	Ataxin-2	Q99700
Potency	10000 nM	Ataxin-2	Q99700
Potency	1694.4 nM	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Q13526
Potency	15848.9 nM	Peroxisome proliferator-activated receptor alpha	Q07869
Kd	2324 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Ki	190 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Ki	213.8 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Kd	4800 nM	Apoptosis regulator Bcl-2	P10415
Kd	2650 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
IC50	4800 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
IC50	170 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Kd	2630.27 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Kd	2650 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
IC50	10800 nM	Kinesin-like protein 1	P52732
IC50	2110 nM	Apoptosis regulator Bcl-2	P10415
Ki	558 nM	Apoptosis regulator Bcl-2	P10415
Ki	190 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
IC50	3000 nM	DNA-3-methyladenine glycosylase	P29372
Ki	1000 nM	Apoptosis regulator Bcl-X	Q07817
Ki	620 nM	Apoptosis regulator Bcl-X	Q07817
Ki	640 nM	Apoptosis regulator Bcl-X	Q07817
Ki	310 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Ki	390 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Ki	770 nM	Apoptosis regulator Bcl-X	Q07817
Ki	560 nM	Apoptosis regulator Bcl-2	P10415
Ki	1900 nM	L-lactate dehydrogenase A chain	P00338
Ki	1400 nM	L-lactate dehydrogenase B chain	P07195
Ki	260 nM	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820
Ki	431 nM	Apoptosis regulator Bcl-2	P10415
Ki	25000 nM	p53-binding protein Mdm-2	Q00987
Others	100 %	Apoptosis regulator Bcl-2	P10415
Ki	440 nM	Apoptosis regulator Bcl-2	P10415
Others	100 %	Apoptosis regulator Bcl-X	Q07817
Ki	310 nM	Apoptosis regulator Bcl-X	Q07817

Gossypol

Representations & DB's id

Molecular propeties

Plant sources

In vitro data