Cycloheximide - Moligand™, ≥98% , CAS No.66-81-9

CAS: 66-81-9 Cat. No.: C729197 Formula: C₁₅H₂₃NO₄ Molecular Weight: 281.35 EC Number: 200-636-0

GRADE & PURITY Moligand™, ≥98%

Synonyms

NSC-185 | Actidione | Naramycin A | CHX | FT 3422-2 | NM-MCD 80 | 4-[2-(3,5-Dimethyl-2-oxo-cyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione | 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads,FedEx DG Service

Specifications

Synonyms

NSC-185 | Actidione | Naramycin A | CHX | FT 3422-2 | NM-MCD 80 | 4-[2-(3,5-Dimethyl-2-oxo-cyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione | 3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Cell permeable: yes Primary Target translocase enzyme Reversible: yes.Protein synthesis inhibitor. Antifungal antibiotic.

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads,FedEx DG Service

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Product Properties

• ALogP: 0.5

Names and Identifiers

• Pubchem Sid: 528758319
• Canonical Smiles: CC1CC(C(=O)C(C1)C(CC2CC(=O)NC(=O)C2)O)C
• IUPAC Name: 4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
• InChIKey: YPHMISFOHDHNIV-FSZOTQKASA-N
• 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
• Isomeric SMILES: C[C@H]1C[C@@H](C(=O)[C@@H](C1)[C@@H](CC2CC(=O)NC(=O)C2)O)C
• UN Number: 2811
• Packing Group: II
• Molecular Weight: 281.35
• Reaxy-Rn: 9515475
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9515475&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyridines and derivatives
      • Subclass Hydropyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyridines and derivatives
• Subclass: Hydropyridines
• Intermediate Tree Nodes: Not available
• Direct Parent: Tetrahydropyridines
• Alternative Parents: Secondary alcohols N-acylimines Lactims Cyclic ketones Propargyl-type 1,3-dipolar organic compounds Carboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Tetrahydropyridine - Ketone - Secondary alcohol - N-acylimine - Cyclic ketone - Lactim - Carboxylic acid derivative - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as tetrahydropyridines. These are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms.
• External Descriptors: Antibiotic fungicides - Cycloalkane derivatives

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

FKBP1A Tclin Peptidyl-prolyl cis-trans isomerase FKBP1A (0 Activities)

Discover Target: FKBP1A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

EIF4A1 Tchem Eukaryotic initiation factor 4A-I (4 Activities)

Discover Target: EIF4A1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

Discover Target: PDE5A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HMGCR Tclin HMG-CoA reductase (2475 Activities)

Discover Target: HMGCR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

INSR Tclin Insulin receptor (5558 Activities)

Discover Target: INSR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VDR Tclin Vitamin D receptor (26531 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FKBP1A Tclin FK506-binding protein 1A (1014 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH2 Tclin Histamine H2 receptor (5428 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOB Tclin Monoamine oxidase B (8835 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CALCR Tclin Calcitonin receptor (2215 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH1 Tclin Histamine H1 receptor (7573 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

Discover Target: PPARG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

Discover Target: AVPR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRD1 Tclin Delta opioid receptor (15096 Activities)

Discover Target: OPRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRK1 Tclin Kappa opioid receptor (16155 Activities)

Discover Target: OPRK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

Discover Target: HTR4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR2 Tclin Estrogen receptor beta (9272 Activities)

Discover Target: ESR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYSLTR1 Tclin Cysteinyl leukotriene receptor 1 (2118 Activities)

Discover Target: CYSLTR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

Discover Target: Agtr2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mc4r Melanocortin receptor 4 (1205 Activities)

Discover Target: Mc4r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ltc4s Leukotriene C4 synthase (1 Activities)

Discover Target: Ltc4s

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Sigmar1 Sigma opioid receptor (160 Activities)

Discover Target: Sigmar1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cckar Cholecystokinin A receptor (90 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Benjaminiella (5 Activities)

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Pyricularia grisea (1253 Activities)

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Pseudomonas (460 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Pseudomonas fluorescens (1630 Activities)

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Legionella pneumophila (143 Activities)

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Pasteurella multocida (1166 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Streptococcus pyogenes (16140 Activities)

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Aspergillus flavus (8875 Activities)

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Aspergillus niger (16508 Activities)

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Bacillus subtilis (32866 Activities)

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Bacillus thuringiensis (718 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Mucor (407 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Bacillus cereus (7522 Activities)

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Priestia megaterium (1154 Activities)

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Yarrowia lipolytica (267 Activities)

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Zygosaccharomyces bailii (36 Activities)

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Aspergillus fumigatus (16427 Activities)

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Trypanosoma brucei (78846 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Microbotryum violaceum (192 Activities)

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Candida albicans (78123 Activities)

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Fusarium oxysporum (3998 Activities)

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Trypanosoma cruzi (99888 Activities)

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Plasmodium berghei (192651 Activities)

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Plasmodium yoelii (6656 Activities)

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Human betaherpesvirus 5 (5122 Activities)

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Oryctolagus cuniculus (11301 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Mucor mucedo (338 Activities)

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Parastagonospora nodorum (325 Activities)

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Phoma (9 Activities)

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Aspergillus pseudoglaucus (84 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO, acetone, ethanol and methanol. Slightly soluble in water with sonication
• Sensitivity: Light sensitive
• Flash Point(°F): 230°F
• Flash Point(°C): >110°C
• Boil Point(°C): 492°C
• Melt Point(°C): 119.5-121°C
• Molecular Weight: 281.350 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 281.163 Da
• Monoisotopic Mass: 281.163 Da
• Topological Polar Surface Area: 83.500 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 404.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1