Compound: cycloheximide
SMILES: O=C1[C@H]([C@H](O)CC2CC(=O)NC(C2)=O)C[C@@H](C)C[C@@H]1C
InChIKey: YPHMISFOHDHNIV-FSZOTQKASA-N
Synonyms: cycloheximide, 66-81-9, ACTIDIONE, Cicloheximide, NARAMYCIN A, Actidion, Hizarocin, Naramycin, Kaken, Acti-Aid, Actidone, Neocycloheximide, Cicloheximida, Actispray, Acti-Dione, Actidione PM, Cicloheximidum, NSC-185, Actidione BR, Actidione TGF, U-4527, Aktidion, NSC 185, 4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione, (-)-Cycloheximide, NM-MCD 80, CBC 500046, DTXSID6024882, U 4527, 3-((R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide, 4-{(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione, 3-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide, beta-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide, DTXCID204882, 2,6-Piperidinedione, 4-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (1S-(1alpha(S*),3alpha,5beta))-, CHEBI:27641, 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide, 98600C0908, 2,6-Piperidinedione, 4-((2R)-2-((1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, 3-[(R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]glutarimide, 4-((2R)-2-((1S,3S,5S)-3,5-DIMETHYL-2-OXOCYCLOHEXYL)-2-HYDROXYETHYL)PIPERIDINE-2,6-DIONE, RefChem:129667, 200-636-0, NSC-171, Cycloheximid, Zykloheximid, Cycloheximide [USAN], Acti-dione BR, NSC185, Cicloheximide [INN], TCMDC-125838, MFCD00082346, TZA, Cyclohexamide, 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxo-cyclohexyl]-2-hydroxy-ethyl]piperidine-2,6-dione, CHEMBL123292, GNF-PF-5118, 3-(2R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethylglutarimide, Cicloheximide (INN), (1S-(1alpha(S*),3alpha,5beta))-4-(2-(3,5-Dimethyl-2-oxo-cyclohexyl))-2-hydroxyethyl-2,6-piperidinedione, CX, Cycloheximide (USAN), 4-((R)-2-((1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)piperidine-2,6-dione, Aktidion [Czech], Cyclohemimide, Caswell No. 270A, .beta.-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide, Acti-dione PM, Acti-dione TGF, Cicloheximidum [INN-Latin], Cicloheximida [INN-Spanish], 4-[(2R)-2-((1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]azaperhydro ine-2,6-dione, SMR000686067, CCRIS 937, Actidione;Naramycin A;CHX, HSDB 1552, SR-01000597484, SR-05000001596, EINECS 200-636-0, Cycloheximide [BSI:ISO], EPA Pesticide Chemical Code 043401, BRN 0088868, Actidione;, AI3-15541, Naramycin;, Naramycin A., CAS-66-81-9, NCGC00024910-01, Acti-Aid;, CHX, Prestwick_976, UNII-98600C0908, Spectrum_001344, FT 3422-2, Prestwick0_000790, Prestwick1_000790, Prestwick2_000790, Prestwick3_000790, Spectrum2_000900, Spectrum3_001510, Spectrum4_000914, Spectrum5_001635, CYCLOHEXIMIDE [MI], CYCLOHEXIMIDE [ISO], cid_6197, 4-((2R)-2-((1S,3S,5S)-(3,5-Dimethyl-2-oxocyclohexyl))-2-hydroxyethyl)piperidine-2,6-dione, CYCLOHEXIMIDE [HSDB], SCHEMBL26617, BSPBio_000900, BSPBio_003159, KBioGR_001408, KBioSS_001824, 5-21-13-00434 (Beilstein Handbook Reference), ksc-8-190, MLS001055333, MLS002154001, CICLOHEXIMIDE [MART.], DivK1c_000050, SPECTRUM1502112, SPBio_000720, SPBio_002839, 4-[2-(3,6-piperidinedione, BPBio1_000990, GTPL5433, orb2567338, HMS500C12, KBio1_000050, KBio2_001824, KBio2_004392, KBio2_006960, KBio3_002659, NINDS_000050, GLXC-10322, HMS1570M22, HMS1921L04, HMS2092D10, HMS2097M22, HMS3714M22, KUC105858N, Pharmakon1600-01502112, Cycloheximide, Streptomyces griseus, 2,6-PIPERIDINEDIONE, 4-(2-(3,5-DIMETHYL-2-OXOCYCLOHEXYL)-2-HYDROXYETHYL)-, (1S-(1.ALPHA.(S*),3.ALPHA.,5.BETA.))-, MSK21224, Tox21_113580, Tox21_201158, Tox21_303652, BDBM50080528, CCG-39902, Cycloheximide, >=93.0% (HPLC), HB2904, NSC758187, SBB005972, AKOS024282670, Tox21_113580_1, CS-4985, EBC-436073, MSK21224-1000M, 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, AC-35130, AC172520, AS-14624, BP-12396, HY-12320, NCI60_001540, ST057527, SBI-0051732.P002, WLN: T6VMVTJ E1YQ- BL6VTJ D1 F1, Cycloheximide 100 microg/mL in Acetonitrile, NS00004971, Cycloheximide, from microbial, >=94% (TLC), C-9217, C06685, Cycloheximide Solution in Methanol, 1000_g/mL, 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, BRD-K36055864-001-19-2, BRD-K36055864-001-20-0, Cycloheximide - Antibiotic for Culture Media Use Only, 2,6-Piperidinedione, 4-[2-(3,5-dimethyl-2-oxocyclohex-1-yl)-2-hydroxy]ethyl-, [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,5S)-3,5-DIMETHYL-2-OXOCYCLOHEXYL)-2-HYDROXYETHYL)-2,6-PIPERIDINEDIONE, 4-[(2R)-2-[(1S,3S,5R)-3,5-dimethyl-2-oxo-cyclohexyl]-2-hydroxy-ethyl]piperidine-2,6-dione, 4630-75-5
Theoretical properties:
molecular_formula: C15H23NO4
molecular_weight: 281.35 g/mol
exact_mass: 281.16270821 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 3
heavy_atom_count: 20
topological_polar_surface_area: 83.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Plates from amyl acetate, water or 30% methanol
color: Plates from amyl acetate, water or 30% methanol
melting_point: 247 to 250 °F (EPA, 1998)
solubility: 10 to 50 mg/mL at 68 °F (NTP, 1992)
Descriptions:
{"pubchem": "Cycloheximide can cause developmental toxicity according to state or federal government labeling requirements.", "chebi": "A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon  bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium <em>Streptomyces griseus</em>.", "chembl": "CYCLOHEXIMIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Cycloheximide is a naturally occurring fungicide produced by the bacterium Streptomyces griseus.  Cycloheximide exerts its effects by interfering with the translocation step in protein synthesis (movement of two tRNA molecules and mRNA in relation to the ribosome), thus blocking eukaryotic translational elongation. Cycloheximide is widely used in biomedical research to inhibit protein synthesis in eukaryotic cells studied in vitro (i.e. outside of organisms).  It is inexpensive and works rapidly. Its effects are rapidly reversed by simply removing it from the culture medium.\nDue to significant toxic side effects, including DNA damage, teratogenesis, and other reproductive effects (including birth defects and toxicity to sperm), cycloheximide is generally used only in in vitro research applications, and is not suitable for human use as a therapeutic compound.  Although it has been used as a fungicide in agricultural applications, this application is now decreasing as the health risks have become better understood.\nBecause cycloheximide rapidly breaks down in a basic environment, decontamination of work surfaces and containers can be achieved by washing with a non-harmful alkali solution such as soapy water or aqueous sodium bicarbonate.\nIt is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities."}