Compound Detail

CHEMBL331627

GLIOTOXIN

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CN1C(=O)[C@]23CC4=CC=C[C@H](O)[C@H]4N2C(=O)[C@@]1(CO)SS3

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL331627
Name	GLIOTOXIN
Phase	Preclinical
Structure Type	MOL
InChI Key	FIVPIPIDMRVLAY-RBJBARPLSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

326.4

MW (Da)

-0.30

ALogP

HBA

HBD

81.1

PSA (Å²)

0.64

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C13H14N2O4S2
MW	326.40
Aromatic Rings	0
Heavy Atoms	21
NP-Likeness	3.23

Activity Summary

IC50 38 meas. best 8.52

EC50 4 meas. best 6.42

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
A549 CHEMBL392	IC50	8.52	8.52	3.0	1
Trypanosoma brucei brucei CHEMBL612851	IC50	8.0	8.0	10.0	1
P388 CHEMBL389	IC50	7.62	7.62	24.0	1
MCF7 CHEMBL387	IC50	7.1	7.1	80.0	2
HUVEC CHEMBL613979	IC50	6.91	6.91	123.0	1
CCRF-CEM CHEMBL382	IC50	6.82	6.82	150.0	1
Acetolactate synthase catalytic subunit, mitochondrial CHEMBL1075095	IC50	6.7	6.7	200.0	1
U-937 CHEMBL612794	IC50	6.7	6.49	200.0	2
HepG2 CHEMBL395	IC50	6.68	6.65	210.0	2
NCI-H460 CHEMBL396	IC50	6.68	6.65	210.0	2
SF-268 CHEMBL613977	IC50	6.62	6.62	240.0	2
Histone-lysine N-methyltransferase SUV39H1 CHEMBL1795118	IC50	6.58	6.58	260.0	1
Tetrahymena pyriformis CHEMBL612891	EC50	6.42	6.42	380.0	1
PC-3 CHEMBL390	IC50	6.41	5.605	390.0	2
HCT-116 CHEMBL394	IC50	6.39	6.15	410.0	2
Unchecked CHEMBL612545	IC50	6.3	5.095	500.0	4
Sharpin/RBCK1/RNF31 CHEMBL4296109	IC50	6.29	6.29	510.0	1
Histone-lysine N-methyltransferase EHMT2 CHEMBL6032	IC50	6.28	5.735	530.0	2
RKO CHEMBL614879	IC50	6.1	6.1	800.0	1
Protein farnesyltransferase CHEMBL2094108	IC50	5.96	5.03	1100.0	2
ADMET CHEMBL612558	EC50	5.87	5.7833	1350.0	3
HEK293 CHEMBL614818	IC50	5.8	5.8	1580.0	1
HeLa CHEMBL399	IC50	5.61	5.61	2450.0	1
Candida albicans CHEMBL366	IC50	5.51	5.51	3100.0	1
Plasmodium falciparum CHEMBL364	IC50	5.44	5.44	3600.0	1
Geranylgeranyl transferase type I CHEMBL2095164	IC50	4.77	4.77	17000.0	1
Pyruvate kinase PKM CHEMBL1075189	IC50	4.64	4.64	22640.0	1
Mycothiol S-conjugate amidase CHEMBL3703	IC50	4.3	4.3	50000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
A549	IC50	=	3.0	nM	8.52	Cytotoxicity against human A549 cells	20303767
Trypanosoma brucei brucei	IC50	=	10.0	nM	8.0	Antitrypanosomal activity against Trypanosoma brucei brucei 427-221a after 40 hr...	20303767
P388	IC50	=	24.0	nM	7.62	Cytotoxicity against mouse P388 cells after 96 hrs by MTT assay	22148349
MCF7	IC50	=	80.0	nM	7.1	Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incub...	38181652
MCF7	IC50	=	80.0	nM	7.1	Cytotoxicity against human MCF7 cells assessed as reduction in cell growth incub...	38181652
HUVEC	IC50	=	123.0	nM	6.91	Cytotoxicity against HUVEC	20303767
CCRF-CEM	IC50	=	150.0	nM	6.82	Cytotoxicity against human CEM cells after 96 hrs	16124785
Acetolactate synthase catalytic subunit, mitochondrial	IC50	=	200.0	nM	6.7	Inhibition of Saccharomyces cerevisiae acetolactate synthase	20303767
U-937	IC50	=	200.0	nM	6.7	Cytotoxicity against human U-937 cells assessed as reduction in cell viability	38181652
HepG2	IC50	=	210.0	nM	6.68	Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incu...	38181652
NCI-H460	IC50	=	210.0	nM	6.68	Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth i...	38181652
NCI-H460	IC50	=	240.0	nM	6.62	Cytotoxicity against human NCI-H460 cells assessed as reduction in cell growth i...	38181652
HepG2	IC50	=	240.0	nM	6.62	Cytotoxicity against human HepG2 cells assessed as reduction in cell growth incu...	38181652
SF-268	IC50	=	240.0	nM	6.62	Cytotoxicity against human SF-268 cells assessed as reduction in cell growth inc...	38181652
SF-268	IC50	=	240.0	nM	6.62	Cytotoxicity against human SF-268 cells assessed as reduction in cell growth inc...	38181652
Histone-lysine N-methyltransferase SUV39H1	IC50	=	260.0	nM	6.58	Inhibition of SUV39H1	22975593
Tetrahymena pyriformis	EC50	=	380.0	nM	6.42	Antiprotozoal activity against Tetrahymena pyriformis	20303767
PC-3	IC50	=	390.0	nM	6.41	Cytotoxicity against human PC-3 cells assessed as reduction in cell viability	38181652
HCT-116	IC50	=	410.0	nM	6.39	Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability...	38181652
Unchecked	IC50	=	500.0	nM	6.3	Inhibition of Trypanosoma brucei brucei recombinant cathepsin B assessed after 5...	20303767

Literature References

PubMed	DOI	Target Context	# Activities
20385871	10.1128/aac.00153-10	Cryptococcus bacillisporus	19
18212113	10.1128/aac.01393-07	Saccharomyces cerevisiae	14
20303767	10.1016/j.bmc.2010.02.034	Unchecked	7
27140429	10.1021/acs.jnatprod.5b00846	Hypoxia-inducible factor 1-alpha	6
21954885	10.1021/np200563x	DU-145	3
20303767	10.1016/j.bmc.2010.02.034	ADMET	3
20303767	10.1016/j.bmc.2010.02.034	Macrophomina phaseolina	2
38181652	10.1016/j.ejmech.2023.116081	HepG2	2
38181652	10.1016/j.ejmech.2023.116081	HCT-116	2
-	10.1016/S0960-894X(97)10052-X	Mus musculus	2
38181652	10.1016/j.ejmech.2023.116081	NCI-H460	2
38181652	10.1016/j.ejmech.2023.116081	SF-268	2
38181652	10.1016/j.ejmech.2023.116081	U-937	2
38181652	10.1016/j.ejmech.2023.116081	MCF7	2
38181652	10.1016/j.ejmech.2023.116081	PC-3	2
20303767	10.1016/j.bmc.2010.02.034	Trypanosoma brucei brucei	1
20303767	10.1016/j.bmc.2010.02.034	Jurkat	1
20303767	10.1016/j.bmc.2010.02.034	Rhodesain	1
16124785	10.1021/np050141k	Candida albicans	1
-	10.1016/S0960-894X(97)10052-X	P815	1

Data from ChEMBL 36 via Core Engine