Compound Detail

CHEMBL123292

CYCLOHEXIMIDE

🧪 Phase II

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🧪 Phase II

C[C@@H]1C[C@@H]([C@H](O)CC2CC(=O)NC(=O)C2)C(=O)[C@@H](C)C1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL123292
Name	CYCLOHEXIMIDE
Phase	Phase II
Structure Type	MOL
InChI Key	YPHMISFOHDHNIV-FSZOTQKASA-N

Known Names

Cicloheximida Cicloheximide Cycloheximide GNF-Pf-5118 NSC-171 NSC-185 TCMDC-125838 U-4527

Targets

101

Activities

Assay Types

PK Parameters

Publications

Known Names

Mechanisms

Molecular Properties

281.4

MW (Da)

1.04

ALogP

HBA

HBD

83.5

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Year

1978

Extended Properties

Molecular Formula	C15H23NO4
MW	281.35
Aromatic Rings	0
Heavy Atoms	20
NP-Likeness	1.68

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
80S Ribosome inhibitor	INHIBITOR	80S Ribosome	✓	✓

Activity Summary

IC50 84 meas. best 7.5

EC50 9 meas. best 7.38

Ki 7 meas. best 5.47

Kd 1 meas. best 4.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Saccharomyces cerevisiae CHEMBL361	IC50	7.5	5.9589	32.0	9
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha CHEMBL2221345	IC50	7.44	7.44	36.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.38	7.1625	42.0	4
Plasmodium berghei CHEMBL612653	IC50	7.33	7.33	47.0	1
Plasmodium yoelii CHEMBL612889	IC50	7.11	7.11	78.1	1
CCRF-CEM CHEMBL382	IC50	7.1	6.9067	80.0	3
Eukaryotic initiation factor 4A-I CHEMBL2052028	IC50	7.06	6.89	87.0	4
Plasmodium falciparum CHEMBL364	IC50	7.0	6.6557	100.0	7
Plasmodium falciparum CHEMBL364	EC50	6.95	6.845	113.5	2
9L CHEMBL613105	IC50	6.7	6.7	200.0	1
Vero CHEMBL391	IC50	6.7	6.3	200.0	3
Solute carrier family 2, facilitated glucose transporter member 1 CHEMBL2535	IC50	6.64	6.64	228.0	1
Glucose transporter CHEMBL3431938	IC50	6.62	6.62	242.0	1
NIH3T3 CHEMBL614822	IC50	6.6	6.3625	250.0	8
Unchecked CHEMBL612545	IC50	6.52	6.2067	300.0	6
Hexose transporter 1 CHEMBL4697	IC50	6.51	6.51	310.0	1
Trypanosoma cruzi CHEMBL368	EC50	6.4	6.4	400.0	1
ADMET CHEMBL612558	IC50	6.34	6.01	460.0	2
Skeletonema costatum CHEMBL613052	IC50	6.3	6.3	500.0	1
MCF7 CHEMBL387	IC50	6.28	6.05	530.0	2
HeLa CHEMBL399	IC50	6.27	5.9367	532.5	3
Karenia brevis CHEMBL5465510	IC50	6.26	6.26	550.0	1
Large ribosomal subunit protein eL19A CHEMBL1741172	EC50	6.19	6.19	644.0	1
A549 CHEMBL392	IC50	6.17	6.17	670.0	1
PBMC CHEMBL613107	IC50	6.05	6.05	900.0	1
Jurkat CHEMBL397	IC50	6.03	6.03	930.0	1
Homo sapiens CHEMBL372	IC50	6.03	6.03	930.0	1
SK-MEL-28 CHEMBL614919	IC50	6.0	6.0	1000.0	1
SARS-CoV-2 CHEMBL4303835	IC50	5.94	5.94	1160.0	2
MDA-MB-231 CHEMBL400	IC50	5.92	5.92	1200.0	1
LNCaP CHEMBL612518	IC50	5.92	5.92	1200.0	1
COUP transcription factor 2 CHEMBL1961790	IC50	5.88	5.88	1315.0	1
Vaccinia virus CHEMBL613493	EC50	5.7	5.7	2000.0	1
HepG2 CHEMBL395	IC50	5.6	4.7	2500.0	3
SK-MES-1 CHEMBL614923	IC50	5.57	5.57	2700.0	1
Peptidyl-prolyl cis-trans isomerase FKBP1A CHEMBL1902	Ki	5.47	5.47	3400.0	2
PC-3 CHEMBL390	IC50	5.46	5.46	3500.0	1
AGS CHEMBL613860	IC50	5.44	5.44	3600.0	1
Peptidyl-prolyl cis-trans isomerase FKBP1A CHEMBL1902	IC50	5.44	5.44	3600.0	1
Oryctolagus cuniculus CHEMBL374	IC50	5.3	5.3	5000.0	1
Unchecked CHEMBL612545	Ki	4.99	4.99	10300.0	1
HT-29 CHEMBL384	IC50	4.89	4.89	12800.0	1
Unchecked CHEMBL612545	Kd	4.82	4.82	15000.0	1
Peptidyl-prolyl cis-trans isomerase FKBP4 CHEMBL4050	Ki	4.62	4.62	24200.0	1
PA-1 CHEMBL614949	IC50	4.39	4.39	40600.0	2
HCT-15 CHEMBL612263	IC50	4.28	4.275	52300.0	2
NCI-H522 CHEMBL614387	IC50	4.22	4.215	60100.0	2
T47D CHEMBL614361	IC50	4.19	4.19	65130.0	2
Peptidyl-prolyl cis-trans isomerase FKBP14 CHEMBL2342	Ki	4.12	4.12	76200.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	3.2	hr	Homo sapiens
T1/2	24.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Saccharomyces cerevisiae	IC50	=	32.0	nM	7.5	Antimicrobial activity against Saccharomyces cerevisiae JB503	20118940
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	IC50	=	36.0	nM	7.44	Inhibition of hypoxia-induced HIF1 activation in human HeLa cells by luciferase ...	15974627
Saccharomyces cerevisiae	IC50	=	40.0	nM	7.4	Antimicrobial activity against Saccharomyces cerevisiae after 16 hrs by serial d...	24856903
NON-PROTEIN TARGET	EC50	=	42.0	nM	7.38	Antiproliferative activity against mouse medulloblastoma cells harboring heteroz...	17417631
Plasmodium berghei	IC50	=	47.0	nM	7.33	HARVARD: Inhibition of liver stage Plasmodium berghei infection in HepG2 cells	22586124
NON-PROTEIN TARGET	EC50	=	54.0	nM	7.27	Antiproliferative activity against mouse neural precursor cells by colony format...	17417631
NON-PROTEIN TARGET	EC50	=	71.0	nM	7.15	Antiproliferative activity against mouse astrocyte cells by MTT assay	17417631
Plasmodium yoelii	IC50	=	78.1	nM	7.11	NOVARTIS: Antimalarial liver stage activity measured as reduction in Plasmodium ...	22096101
CCRF-CEM	IC50	=	80.0	nM	7.1	Cytotoxicity was determined in CEM cells, relative to RVT	15081000
Eukaryotic initiation factor 4A-I	IC50	=	87.0	nM	7.06	Inhibition of eIF4A1 in human MDA-MB-231 cells assessed as inhibition of cellula...	32470302
Saccharomyces cerevisiae	IC50	=	88.0	nM	7.06	Antimicrobial activity against Saccharomyces cerevisiae J47alpha	20118940
Plasmodium falciparum	IC50	=	100.0	nM	7.0	Inhibition of Plasmodium falciparum FCK2 growth as [3H]hypoxanthine uptake after...	17060533
Eukaryotic initiation factor 4A-I	IC50	=	101.0	nM	7.0	Inhibition of eIF4A1 in human MDA-MB-231 cells assessed as inhibition of cellula...	32470302
Plasmodium falciparum	EC50	=	113.5	nM	6.95	NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati...	18579783
CCRF-CEM	IC50	=	120.0	nM	6.92	Tested in vitro for anticancer activity against CEM cells	10072683
NON-PROTEIN TARGET	EC50	=	142.0	nM	6.85	Antiproliferative activity against mouse neural precursor cells by MTT assay	17417631
Eukaryotic initiation factor 4A-I	IC50	=	142.0	nM	6.85	Inhibition of eIF4A1 in human MDA-MB-231 cells assessed as inhibition of cellula...	32470302
Plasmodium falciparum	IC50	=	150.0	nM	6.82	Inhibition of Plasmodium falciparum FCK2 growth as [3H]hypoxanthine uptake after...	17060533
Plasmodium falciparum	EC50	=	181.7	nM	6.74	NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ...	18579783
CCRF-CEM	IC50	=	200.0	nM	6.7	Cytotoxicity against human CEM cells assessed as decrease in cell viability afte...	29778528

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	692
-	10.6019/CHEMBL3885881	Rattus norvegicus	430
18212113	10.1128/aac.01393-07	Saccharomyces cerevisiae	14
20118940	10.1038/nchembio.304	Saccharomyces cerevisiae	12
29148754	10.1021/acs.jnatprod.7b00503	Unchecked	11
19711989	10.1021/np900163f	Glycogen synthase kinase-3 beta	8
17765545	10.1016/j.bmc.2007.08.009	Candida albicans	8
17765545	10.1016/j.bmc.2007.08.009	Fusarium oxysporum	8
18725450	10.1128/aac.00245-08	Pasteurella multocida	7
20813948	10.1126/science.1193225	Plasmodium falciparum	7
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
10479292	10.1021/jm991038t	Unchecked	5
11052798	10.1021/jm000058o	Homo sapiens	5
17060533	10.1128/aac.00808-06	Plasmodium falciparum	5
17875991	10.1128/aac.00373-07	Balamuthia mandrillaris	5
20118940	10.1038/nchembio.304	Unchecked	5
20194695	10.1128/aac.01730-09	Human betaherpesvirus 5	4
17765545	10.1016/j.bmc.2007.08.009	Mucor	4
17325226	10.1128/aac.00182-07	Candida albicans	4
17417631	10.1038/nchembio873	NON-PROTEIN TARGET	4

Data from ChEMBL 36 via Core Engine