cycloheximide (CHEBI:27641)

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CHEBI:27641 - cycloheximide

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ChEBI Name	cycloheximide

ChEBI ID	CHEBI:27641

Definition	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 Streptomyces griseus.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:23484, CHEBI:4015

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

3HE - Ideal conformer

Mrv1927 05272112173D

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Time for openFile(3HE - Ideal conformer

Mrv1927 05272112173D

43 44 0 0 0 0 999 V2000

3.5330 -1.3800 1.1400 C 0 0 1 0 0 0 0 0 0 0 0 0

4.4720 -0.1970 0.9030 C 0 0 1 0 0 0 0 0 0 0 0 0

4.2710 0.3360 -0.5190 C 0 0 1 0 0 0 0 0 0 0 0 0

2.8050 0.6570 -0.7100 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7870 -0.4060 -0.3600 C 0 0 1 0 0 0 0 0 0 0 0 0

2.0790 -0.9130 1.0560 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.0900 2.2790 0.8770 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.7910 1.1560 0.5310 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.7350 0.3520 0.0190 N 0 0 0 0 0 0 0 0 0 0 0 0

-4.4740 -0.8970 -0.3940 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.3700 -1.5700 -0.8570 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.0880 -1.4790 -0.2960 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.3650 0.6940 0.6770 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.0590 -0.3490 -0.4000 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.6530 -0.9130 -0.1860 C 0 0 1 0 0 0 0 0 0 0 0 0

0.3800 0.1920 -0.4130 C 0 0 1 0 0 0 0 0 0 0 0 0

0.2470 1.1860 0.6060 O 0 0 0 0 0 0 0 0 0 0 0 0

2.4560 1.7340 -1.1300 O 0 0 0 0 0 0 0 0 0 0 0 0

5.1040 1.6050 -0.7150 C 0 0 0 0 0 0 0 0 0 0 0 0

3.7850 -2.4490 0.0750 C 0 0 0 0 0 0 0 0 0 0 0 0

3.7220 -1.8010 2.1270 H 0 0 0 0 0 0 0 0 0 0 0 0

4.2510 0.5920 1.6220 H 0 0 0 0 0 0 0 0 0 0 0 0

5.5050 -0.5220 1.0270 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5770 -0.4210 -1.2410 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8610 -1.2310 -1.0690 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4150 -1.7460 1.2880 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9140 -0.1070 1.7710 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.6420 0.6870 -0.0540 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9740 -1.9890 0.6600 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9330 -2.1890 -1.1090 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6930 1.5440 0.5630 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2260 0.2480 1.6620 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1240 0.1160 -1.3840 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5640 -1.2900 0.8330 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4760 -1.7260 -0.8900 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2160 0.6480 -1.3890 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3810 0.8500 1.5030 H 0 0 0 0 0 0 0 0 0 0 0 0

4.8000 2.3550 0.0140 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1600 1.3710 -0.5770 H 0 0 0 0 0 0 0 0 0 0 0 0

4.9460 1.9910 -1.7220 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5940 -2.0300 -0.9130 H 0 0 0 0 0 0 0 0 0 0 0 0

4.8210 -2.7830 0.1330 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1200 -3.2960 0.2450 H 0 0 0 0 0 0 0 0 0 0 0 0

19 3 1 0 0 0 0

3 4 1 0 0 0 0

3 2 1 0 0 0 0

18 4 2 0 0 0 0

4 5 1 0 0 0 0

20 1 1 0 0 0 0

2 1 1 0 0 0 0

5 16 1 0 0 0 0

5 6 1 0 0 0 0

1 6 1 0 0 0 0

16 15 1 0 0 0 0

16 17 1 0 0 0 0

12 10 1 0 0 0 0

12 14 1 0 0 0 0

11 10 2 0 0 0 0

15 14 1 0 0 0 0

10 9 1 0 0 0 0

14 13 1 0 0 0 0

13 8 1 0 0 0 0

9 8 1 0 0 0 0

8 7 2 0 0 0 0

1 21 1 1 0 0 0

2 22 1 0 0 0 0

2 23 1 0 0 0 0

3 24 1 6 0 0 0

5 25 1 6 0 0 0

6 26 1 0 0 0 0

6 27 1 0 0 0 0

9 28 1 0 0 0 0

12 29 1 0 0 0 0

12 30 1 0 0 0 0

13 31 1 0 0 0 0

13 32 1 0 0 0 0

14 33 1 0 0 0 0

15 34 1 0 0 0 0

15 35 1 0 0 0 0

16 36 1 6 0 0 0

17 37 1 0 0 0 0

19 38 1 0 0 0 0

19 39 1 0 0 0 0

19 40 1 0 0 0 0

20 41 1 0 0 0 0

20 42 1 0 0 0 0

20 43 1 0 0 0 0

M END): 42 ms

reading 43 atoms

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Default Van der Waals type for model set to Babel

43 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Molfile

Wikipedia	License
4-Hydroxynonenal, or 4-hydroxy-2E-nonenal or 4-hydroxy-2-nonenal or 4-HNE or HNE, (C9H16O2), is an α,β-unsaturated hydroxyalkenal that is produced by lipid peroxidation in cells. 4-HNE is the primary α,β-unsaturated hydroxyalkenal formed in this process. It is a colorless oil. It is found throughout animal tissues, and in higher quantities during oxidative stress due to the increase in the lipid peroxidation chain reaction, due to the increase in stress events. 4-HNE has been hypothesized to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular adhesion. Early identification and characterization of 4-hydroxynonenal was reported by Esterbauer, et al., who also obtained the same compound synthetically. The topic has since been often reviewed, and one source describes the compound as "the most studied LPO (lipid peroxidation) product with pleiotropic capabilities".
Read full article at Wikipedia

Formula

C15H23NO4

Net Charge

Average Mass

281.352

Monoisotopic Mass

281.16271

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

SMILES

[H][C@]1(C[C@@H](C)C[C@H](C)C1=O)[C@H](O)CC1CC(=O)NC(=O)C1

Roles Classification
Biological Role(s):	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. protein synthesis inhibitor A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. ferroptosis inhibitor Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via heterocyclic antibiotic ) fungicide A substance used to destroy fungal pests. (via antibiotic fungicide ) antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via antibiotic antifungal agent )

Application(s):	neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders. fungicide A substance used to destroy fungal pests. (via antibiotic fungicide )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	cycloheximide (CHEBI:27641) has functional parent piperidine-2,6-dione (CHEBI:5435) cycloheximide (CHEBI:27641) has role anticoronaviral agent (CHEBI:149553) cycloheximide (CHEBI:27641) has role bacterial metabolite (CHEBI:76969) cycloheximide (CHEBI:27641) has role ferroptosis inhibitor (CHEBI:173084) cycloheximide (CHEBI:27641) has role neuroprotective agent (CHEBI:63726) cycloheximide (CHEBI:27641) has role protein synthesis inhibitor (CHEBI:48001) cycloheximide (CHEBI:27641) is a antibiotic fungicide (CHEBI:87114) cycloheximide (CHEBI:27641) is a cyclic ketone (CHEBI:3992) cycloheximide (CHEBI:27641) is a dicarboximide (CHEBI:35356) cycloheximide (CHEBI:27641) is a piperidine antibiotic (CHEBI:49318) cycloheximide (CHEBI:27641) is a piperidones (CHEBI:48589) cycloheximide (CHEBI:27641) is a secondary alcohol (CHEBI:35681)

IUPAC Name

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

INNs	Sources
cicloheximida	ChemIDplus
cicloheximide	WHO MedNet
cicloheximide	WHO MedNet
cicloheximidum	ChemIDplus

Synonyms	Sources
3-((R)-2-((1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide	ChemIDplus
Cycloheximid	ChEBI
Cycloheximide	KEGG COMPOUND
cycloheximide	UniProt
naramycin	ChemIDplus
naramycin A	ChemIDplus
Zykloheximid	ChEBI

Manual Xrefs	Databases
1680	PPDB
3HE	PDBeChem
C00047211	KNApSAcK
C06685	KEGG COMPOUND
Cycloheximide	Wikipedia
D03625	KEGG DRUG
LSM-2791	LINCS
View more database links

Registry Numbers	Types	Sources
66-81-9	CAS Registry Number	KEGG COMPOUND
66-81-9	CAS Registry Number	ChemIDplus
88868	Reaxys Registry Number	Reaxys

Citations	Types	Sources
11972861	PubMed citation	Europe PMC
16659174	PubMed citation	Europe PMC
25209664	PubMed citation	Europe PMC
26715760	PubMed citation	Europe PMC
27192630	PubMed citation	Europe PMC
27665925	PubMed citation	Europe PMC
30154175	PubMed citation	Europe PMC
30916348	PubMed citation	Europe PMC
32299921	PubMed citation	Europe PMC
33101237	PubMed citation	Europe PMC

Last Modified

27 May 2021

CHEBI:27641 - cycloheximide

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