Cycloheximide

Details

• Internal ID: bd6dbe88-ea34-4cb6-8414-b4c1d76f9ef8
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Hydropyridines > Tetrahydropyridines
• IUPAC Name: 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
• SMILES (Canonical): CC1CC(C(=O)C(C1)C(CC2CC(=O)NC(=O)C2)O)C
• SMILES (Isomeric): C[C@H]1C[C@@H](C(=O)[C@@H](C1)[C@@H](CC2CC(=O)NC(=O)C2)O)C
• InChI: InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1
• InChI Key: YPHMISFOHDHNIV-FSZOTQKASA-N
• Popularity: 38,524 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃NO₄
• Molecular Weight: 281.35 g/mol
• Exact Mass: 281.16270821 g/mol
• Topological Polar Surface Area (TPSA): 83.50 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 66-81-9
• ACTIDIONE
• Cicloheximide
• NARAMYCIN A
• Kaken
• Actidion
• Actidone
• Hizarocin
• Naramycin
• Neocycloheximide
• Acti-Aid
• Cycloheximid
• Actispray
• Actidione PM
• Cicloheximida
• Cicloheximidum
• Zykloheximid
• NSC-185
• Cycloheximide [USAN]
• Acti-Dione
• Actidione BR
• Actidione TGF
• Aktidion [Czech]
• C15H23NO4
• NSC 185
• U-4527
• Caswell No. 270A
• Aktidion
• Acti-dione BR
• 4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
• Cicloheximidum [INN-Latin]
• Cicloheximida [INN-Spanish]
• CCRIS 937
• CBC 500046
• NSC185
• 4-{(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione
• Cicloheximide [INN]
• DTXSID6024882
• HSDB 1552
• TCMDC-125838
• 3-((R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
• EINECS 200-636-0
• MFCD00082346
• U 4527
• Cycloheximide [BSI:ISO]
• EPA Pesticide Chemical Code 043401
• BRN 0088868
• NM-MCD 80
• AI3-15541
• CHEMBL123292
• TZA
• CHEBI:27641
• GNF-PF-5118
• 3-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
• 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide
• beta-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide
• 3-(2R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethylglutarimide
• UNII-98600C0908
• 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxo-cyclohexyl]-2-hydroxy-ethyl]piperidine-2,6-dione
• Cicloheximide (INN)
• (1S-(1alpha(S*),3alpha,5beta))-4-(2-(3,5-Dimethyl-2-oxo-cyclohexyl))-2-hydroxyethyl-2,6-piperidinedione
• 2,6-Piperidinedione, 4-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (1S-(1alpha(S*),3alpha,5beta))-
• CX
• Cycloheximide (USAN)
• FT 3422-2
• Glutarimide, 3-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-
• 2,6-Piperidinedione, 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-
• 4-((2R)-2-((1S,3S,5S)-(3,5-Dimethyl-2-oxocyclohexyl))-2-hydroxyethyl)piperidine-2,6-dione
• 4-((R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)piperidine-2,6-dione
• Cyclohemimide
• Cyclohexamide
• 5-21-13-00434 (Beilstein Handbook Reference)
• 98600C0908
• DTXCID204882
• .beta.-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide
• 4-[2-(3,5-Dimethyl-2-oxo-cyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione
• 4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-2,6-piperidinedione
• SMR000686067
• Actidione;Naramycin A;CHX
• SR-01000597484
• SR-05000001596
• CHX
• ?Actidione
• Acti-dione PM
• 3-[(R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]glutarimide
• Acti-dione TGF
• CAS-66-81-9
• NCGC00024910-01
• 2,6-Piperidinedione, 4-((2R)-2-((1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-
• 2,6-PIPERIDINEDIONE, 4-(2-(3,5-DIMETHYL-2-OXOCYCLOHEXYL)-2-HYDROXYETHYL)-, (1S-(1.ALPHA.(S*),3.ALPHA.,5.BETA.))-
• 2,6-Piperidinedione, 4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-, [1S-[1.alpha.(S*),3.alpha.,5.beta.]]-
• 4-((2R)-2-((1S,3S,5S)-3,5-DIMETHYL-2-OXOCYCLOHEXYL)-2-HYDROXYETHYL)-2,6-PIPERIDINEDIONE
• 4-((2R)-2-((1S,3S,5S)-3,5-DIMETHYL-2-OXOCYCLOHEXYL)-2-HYDROXYETHYL)PIPERIDINE-2,6-DIONE
• Prestwick_976
• Spectrum_001344
• Prestwick0_000790
• Prestwick1_000790
• Prestwick2_000790
• Prestwick3_000790
• Spectrum2_000900
• Spectrum3_001510
• Spectrum4_000914
• Spectrum5_001635
• CYCLOHEXIMIDE [MI]
• D06ZWX
• CYCLOHEXIMIDE [ISO]
• cid_6197
• CYCLOHEXIMIDE [HSDB]
• SCHEMBL26617
• BSPBio_000900
• BSPBio_003159
• KBioGR_001408
• KBioSS_001824
• ksc-8-190
• MLS001055333
• MLS002154001
• CICLOHEXIMIDE [MART.]
• DivK1c_000050
• SPECTRUM1502112
• SPBio_000720
• SPBio_002839
• 4-[2-(3,6-piperidinedione
• BPBio1_000990
• GTPL5433
• HMS500C12
• KBio1_000050
• KBio2_001824
• KBio2_004392
• KBio2_006960
• KBio3_002659
• NINDS_000050
• YPHMISFOHDHNIV-FSZOTQKASA-N
• HMS1570M22
• HMS1921L04
• HMS2092D10
• HMS2097M22
• HMS3714M22
• KUC105858N
• Pharmakon1600-01502112
• Cycloheximide, Streptomyces griseus
• Tox21_113580
• Tox21_201158
• Tox21_303652
• BDBM50080528
• CCG-39902
• Cycloheximide, >=93.0% (HPLC)
• HB2904
• NSC758187
• AKOS024282670
• Tox21_113580_1
• CS-4985
• LS-1558
• NSC-758187
• IDI1_000050
• NCGC00017363-05
• NCGC00017363-06
• NCGC00017363-07
• NCGC00017363-08
• NCGC00017363-10
• NCGC00017363-18
• NCGC00024910-02
• NCGC00024910-03
• NCGC00024910-04
• NCGC00024910-05
• NCGC00024910-06
• NCGC00169964-05
• NCGC00257430-01
• NCGC00258710-01
• 4-[(2R)-2-((1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]azaperhydro ine-2,6-dione
• AC-35130
• AS-14624
• BP-12396
• HY-12320
• NCI60_001540
• SBI-0051732.P002
• WLN: T6VMVTJ E1YQ- BL6VTJ D1 F1
• Cycloheximide 100 microg/mL in Acetonitrile
• Cycloheximide, from microbial, >=94% (TLC)
• C-9217
• C06685
• D03625
• M01527
• AB00052279_08
• Cycloheximide, PESTANAL(R), analytical standard
• Cycloheximide, Biotechnology Performance Certified
• Q412895
• Cycloheximide, Antibiotic for Culture Media Use Only
• SR-01000597484-1
• SR-01000597484-4
• SR-05000001596-1
• SR-05000001596-3
• SR-05000001596-4
• BRD-K36055864-001-05-1
• BRD-K36055864-001-07-7
• BRD-K36055864-001-09-3
• BRD-K36055864-001-16-8
• [1S-[1.alpha.(S*),3.alpha.,5.beta.]]-4-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione
• 1154-57-0
• 2, 4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-, [1S-[1.alpha.(S*),3.alpha.,5.beta.]]-
• 4-[(2R)-2-[(1S,3S,5R)-3,5-dimethyl-2-oxo-cyclohexyl]-2-hydroxy-ethyl]piperidine-2,6-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9371	93.71%
Caco-2	-	0.5983	59.83%
Blood Brain Barrier	+	0.5080	50.80%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7938	79.38%
OATP2B1 inhibitior	-	0.8485	84.85%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9604	96.04%
P-glycoprotein inhibitior	-	0.8887	88.87%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	-	0.5079	50.79%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.8308	83.08%
CYP3A4 inhibition	-	0.9133	91.33%
CYP2C9 inhibition	-	0.9098	90.98%
CYP2C19 inhibition	-	0.9382	93.82%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9529	95.29%
CYP2C8 inhibition	-	0.9353	93.53%
CYP inhibitory promiscuity	-	0.9635	96.35%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8313	83.13%
Carcinogenicity (trinary)	Non-required	0.6136	61.36%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9294	92.94%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5383	53.83%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.5927	59.27%
skin sensitisation	-	0.9370	93.70%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4619	46.19%
Acute Oral Toxicity (c)	I	0.8338	83.38%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	-	0.4932	49.32%
Aromatase binding	-	0.7712	77.12%
PPAR gamma	+	0.8611	86.11%
Honey bee toxicity	-	0.7492	74.92%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.5122	51.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	251.2 nM; 251.2 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2052028	P60842	Eukaryotic initiation factor 4A-I	87 nM	IC50	via Super-PRED
CHEMBL1902	P62942	FK506-binding protein 1A	3600 nM	IC50	PMID: 10479292
CHEMBL2535	P11166	Glucose transporter	228 nM	IC50	DOI: 10.6019/CHEMBL3433997
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	< 195 nM	AC50	via CMAUP
CHEMBL5514	P42858	Huntingtin	354.8 nM	Potency	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	63.1 nM	Potency	via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	39.8 nM	Potency	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	446.7 nM; 316.2 nM; 446.7 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	316.2 nM; 316.2 nM; 316.2 nM	Potency; Potency; Potency	via CMAUP; via Super-PRED; via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	1778.3 nM; 446.7 nM; 2818.4 nM; 891.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via Super-PRED; via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.34%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.78%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.52%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	86.65%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.32%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.11%	96.61%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.30%	89.34%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.53%	90.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.37%	100.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.47%	95.56%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.12%	85.11%
CHEMBL3045	P05771	Protein kinase C beta	80.99%	97.63%
CHEMBL255	P29275	Adenosine A2b receptor	80.32%	98.59%

Plants that contains it

• Aglaia spectabilis
• Clibadium pentaneuron
• Coespeletia thyrsiformis f. marcanoi
• Croton bonplandianus
• Croton californicus
• Culcitium canescens
• Cymbopogon nardus
• Dendrobium rotundatum
• Malva verticillata
• Nolina erumpens
• Petasites paradoxus
• Philotheca fitzgeraldii
• Piptolepis leptospermoides
• Ratibida latipalearis
• Toxicodendron succedaneum
• Weddellina squamulosa

Cross-Links

• PubChem: 6197
• NPASS: NPC253703
• ChEMBL: CHEMBL123292
• LOTUS: LTS0227054
• wikiData: Q412895