4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione

• ChemBase ID: 72914
• Molecular Formular: C15H23NO4
• Molecular Mass: 281.34742
• Monoisotopic Mass: 281.16270822
• SMILES: C1C(=O)NC(=O)CC1C[C@H]([C@@H]1C[C@H](C[C@@H](C1=O)C)C)O
• Canonical SMILES: C[C@H]1C[C@H](C)C(=O)[C@@H](C1)[C@@H](CC1CC(=O)NC(=O)C1)O
• 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
• InChIKey: YPHMISFOHDHNIV-FSZOTQKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
• IUPAC Traditional name: kaken
• Synonyms: 4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-2,6-piperidinedione; Acti-Aid; Acti-dione; Acti-dione BR; Acti-dione PM; Acti-dione TGF; Actidion; Cicloheximide; FT 3422-2; NSC 185; Naramycin; Naramycin Microcapsule D 80; Naramycin NM-MCU 80; TZA; U 4527; β-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide; naramycin a, hizarocin; actidione, actispray; kaken, U-4527; Cycloheximide; 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide; Actidione; Naramycin A; Cycloheximide; Neocycloheximide; Cycloheximide; Actidione; CHX; Cycloheximide solution; 3-[2-(3,5-二甲基-2-氧代环己基)-2-羟乙基]戊二酰亚胺; 奈良霉素 A; 戊二酰亚胺环己酮; 放线菌酮; 放线菌酮 溶液

Database IDs

• CAS Number: 66-81-9
• EC Number: 200-636-0
• MDL Number: MFCD00082346
• Beilstein Number: 88868
• PubChem SID: 24870128; 24892981; 162037834; 24850897; 24892732; 24845201; 24892457
• PubChem CID: 6197
• CHEBI ID: 27641
• CHEMBL: 123292
• Chemspider ID: 5962
• KEGG ID: C06685
• Unique Ingredient Identifier: 98600C0908
• Wikipedia Title: Cycloheximide

CALCULATED PROPERTIES

• Acid pKa: 11.799869
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.90476495
• LogD (pH = 7.4): 0.904748
• Log P: 0.9047651
• Molar Refractivity: 73.0893 cm^3
• Polarizability: 28.922503 Å^3
• Polar Surface Area: 83.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; ethanol: soluble, clear to hazy; Methanol
• Apperance: colourless crystals; Off-White Solid
• Melting Point: 106-110°C; 119.5–121 °C
• Flash Point: 188.6 °F; 87 °C

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: MA4375000
• European Hazard Symbols: Nature polluting (N); Highly toxic (T+); Harmful (Xn)
• UN Number: 2810; 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; 2
• Risk Statements: 22; 61-28-38-51/53-68; 61-28-51/53-68; 61-28-52/53-68; R26 R27 R28
• Safety Statements: 53-28-36/37-45-61; 53-45-61
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H315-H341-H360D-H411; H300-H341-H360D-H411; H301-H315-H319-H341-H360D-H412
• GHS Precautionary statements: P201-P264-P273-P281-P301 + P310-P308 + P313; P201-P273-P281-P301 + P310-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 2; UN 2811 6.1/PG 1
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... FKBP1A(2280), PIN1(5300)

Product Information

• Purity: ≥85% (HPLC); ≥94% (TLC); 98%
• Concentration: 0.1%; 100 mg/mL in DMSO; neat
• Grade: analytical standard; Biotechnology Performance Certified; for microbiology; PESTANAL®, analytical standard
• Salt Data: Free Base
• Packaging: pkg of 100 mg
• Suitability: cell culture tested
• Description: mixture of stereo isomers
• Impurities: endotoxin, tested
• Biological Source: from microbial; microbial
• Sterility: 0.2 μm filtered
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C15H23NO4

DETAILS

Selleck Chemicals - S2257

Related research area: Metabolic Disease

Sigma Aldrich - C4859

Biochem/physiol Actions
Cycloheximide (CHX) is an antibiotic produced by S. griseus. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.
Specificity
Tested for cell growth arrest, selection of cycloheximide resistant yeast, apoptosis induction, and facilitation of apoptosis induction by FasL.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - C7698

Biochem/physiol Actions
Cycloheximide (CHX) is an antibiotic produced by S. griseus. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - C1988

Biochem/physiol Actions
Cycloheximide (CHX) is an antibiotic produced by S. griseus that inhibits protein biosynthesis in eukaryotes. Its main biological activity is translation inhibition which results in cell growth arrest and cell death.
Cycloheximide (CHX) is an antibiotic produced by S. griseus. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.
Application
CHX is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors. It has been shown to selectively clear macrophages in atherosclerotic plaques 1 and activate cumulus-free equine oocytes 2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - C104450

Application
Inhibitor of protein synthesis.
Biochem/physiol Actions
Cycloheximide (CHX) is an antibiotic produced by S. griseus. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.

Sigma Aldrich - 46401

Biochem/physiol Actions
Cycloheximide (CHX) is an antibiotic produced by S. griseus. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - PS1002

Biochem/physiol Actions
Cycloheximide (CHX) is an antibiotic produced by S. griseus. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.

Sigma Aldrich - 01811

Biochem/physiol Actions
Cycloheximide (CHX) is an antibiotic produced by S. griseus. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.

Sigma Aldrich - 18079

General description
A selective Supplement for suppressing growth of fungi.
Physical form
Sterile filtered solution containing 0.1% cycloheximide

Toronto Research Chemicals - C988270

Cycloheximide is an antibiotic substance isolated from the beers of streptomycin-producing strains of Streptomyces griseus. Cycloheximide is used as fungicide.

REFERENCES

• ] Bitman J et al. Arch Biochem Biophys. 1966 Feb;113(2):414-20.
• Whiffen, A.J., et al.: J. Bacterial., 56, 283 (1948)
• Monsalve, E., et al.: J. Immunol., 176, 5362 (1948)
• Yang, J., et al.: J. Clin. Invest. 120, 2563 (1948)