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103560-62-9,MFCD08062226
Catalog No.:AA008RB5

103560-62-9 | 4-ONE

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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA008RB5
Chemical Name:
4-ONE
CAS Number:
103560-62-9
Molecular Formula:
C9H14O2
Molecular Weight:
154.2063
MDL Number:
MFCD08062226
SMILES:
CCCCCC(=O)/C=C\C=O
Properties
Computed Properties
 
Complexity:
148  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
2  
Rotatable Bond Count:
6  
XLogP3:
1.6  

Literature

Title: Instability of C154Y variant of aldo-keto reductase 1C3.

Journal: Chemico-biological interactions 20171001

Title: Electrophilic Modification of PKM2 by 4-Hydroxynonenal and 4-Oxononenal Results in Protein Cross-Linking and Kinase Inhibition.

Journal: Chemical research in toxicology 20170220

Title: Aldo-keto reductase 1B10 promotes development of cisplatin resistance in gastrointestinal cancer cells through down-regulating peroxisome proliferator-activated receptor-γ-dependent mechanism.

Journal: Chemico-biological interactions 20160825

Title: Angiotensin II modification by decomposition products of linoleic acid-derived lipid hydroperoxide.

Journal: Chemico-biological interactions 20150905

Title: Pathophysiological roles of aldo-keto reductases (AKR1C1 and AKR1C3) in development of cisplatin resistance in human colon cancers.

Journal: Chemico-biological interactions 20130225

Title: Modulation of activity and inhibitor sensitivity of rabbit aldose reductase-like protein (AKR1B19) by oxidized glutathione and SH-reagents.

Journal: Chemico-biological interactions 20130225

Title: Dietary regulation of catabolic disposal of 4-hydroxynonenal analogs in rat liver.

Journal: Free radical biology & medicine 20120315

Title: Fragmentation of a linoleate-derived γ-hydroperoxy-α,β-unsaturated epoxide to γ-hydroxy- and γ-oxo-alkenals involves a unique pseudo-symmetrical diepoxycarbinyl radical.

Journal: Free radical biology & medicine 20120201

Title: Genotoxic analysis of four lipid-peroxidation products in the mouse lymphoma assay.

Journal: Mutation research 20111224

Title: Reversible and irreversible protein glutathionylation: biological and clinical aspects.

Journal: Expert opinion on drug metabolism & toxicology 20110701

Title: The Drosophila carbonyl reductase sniffer is an efficient 4-oxonon-2-enal (4ONE) reductase.

Journal: Chemico-biological interactions 20110530

Title: 4-oxo-2-nonenal (4-ONE): evidence of transient receptor potential ankyrin 1-dependent and -independent nociceptive and vasoactive responses in vivo.

Journal: The Journal of pharmacology and experimental therapeutics 20110401

Title: Structure-activity analysis of diffusible lipid electrophiles associated with phospholipid peroxidation: 4-hydroxynonenal and 4-oxononenal analogues.

Journal: Chemical research in toxicology 20110321

Title: The lipid peroxidation products 4-oxo-2-nonenal and 4-hydroxy-2-nonenal promote the formation of α-synuclein oligomers with distinct biochemical, morphological, and functional properties.

Journal: Free radical biology & medicine 20110201

Title: Trans-4-oxo-2-nonenal potently alters mitochondrial function.

Journal: Free radical biology & medicine 20110115

Title: Xanthine oxidase-derived reactive oxygen species mediate 4-oxo-2-nonenal-induced hepatocyte cell death.

Journal: Toxicology and applied pharmacology 20101201

Title: Mass spectrometric characterization of modifications to angiotensin II by lipid peroxidation products, 4-oxo-2(E)-nonenal and 4-hydroxy-2(E)-nonenal.

Journal: Chemical research in toxicology 20101115

Title: Identification of a lipid peroxidation product as the source of oxidation-specific epitopes recognized by anti-DNA autoantibodies.

Journal: The Journal of biological chemistry 20101029

Title: Detection of lipid peroxidation-induced DNA adducts caused by 4-oxo-2(E)-nonenal and 4-oxo-2(E)-hexenal in human autopsy tissues.

Journal: Chemical research in toxicology 20100920

Title: Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents.

Journal: Journal of medicinal chemistry 20100722

Title: Quantitation of mercapturic acid conjugates of 4-hydroxy-2-nonenal and 4-oxo-2-nonenal metabolites in a smoking cessation study.

Journal: Free radical biology & medicine 20100101

Title: Reaction products of gamma-tocopherol with (E)-4-oxo-2-nonenal in acidic acetonitrile.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Rat aldose reductase-like protein (AKR1B14) efficiently reduces the lipid peroxidation product 4-oxo-2-nonenal.

Journal: Biological & pharmaceutical bulletin 20100101

Title: A 4-oxo-2(E)-nonenal-derived glutathione adduct from 15-lipoxygenase-1-mediated oxidation of cytosolic and esterified arachidonic acid.

Journal: Free radical biology & medicine 20091001

Title: Covalent cross-linking of glutathione and carnosine to proteins by 4-oxo-2-nonenal.

Journal: Chemical research in toxicology 20090601

Title: Identification of advanced reaction products originating from the initial 4-oxo-2-nonenal-cysteine Michael adducts.

Journal: Chemical research in toxicology 20090501

Title: Role of human aldo-keto-reductase AKR1B10 in the protection against toxic aldehydes.

Journal: Chemico-biological interactions 20090316

Title: The essential role of ERK in 4-oxo-2-nonenal-mediated cytotoxicity in SH-SY5Y human neuroblastoma cells.

Journal: Journal of neurochemistry 20090301

Title: The lipid peroxidation metabolite 4-oxo-2-nonenal cross-links alpha-synuclein causing rapid formation of stable oligomers.

Journal: Biochemical and biophysical research communications 20090123

Title: A novel 4-oxo-2(E)-nonenal-derived modification to angiotensin II: oxidative decarboxylation of N-terminal aspartic acid.

Journal: Chemical research in toxicology 20081201

Title: In vitro and in silico characterization of peroxiredoxin 6 modified by 4-hydroxynonenal and 4-oxononenal.

Journal: Chemical research in toxicology 20081201

Title: Carbonyl reductase inactivation may contribute to mouse lung tumor promotion by electrophilic metabolites of butylated hydroxytoluene: protein alkylation in vivo and in vitro.

Journal: Chemical research in toxicology 20080801

Title: Relative contributions of TRPA1 and TRPV1 channels in the activation of vagal bronchopulmonary C-fibres by the endogenous autacoid 4-oxononenal.

Journal: The Journal of physiology 20080715

Title: Mercapturic acid conjugates of 4-hydroxy-2-nonenal and 4-oxo-2-nonenal metabolites are in vivo markers of oxidative stress.

Journal: The Journal of biological chemistry 20080620

Title: Transient receptor potential A1 is a sensory receptor for multiple products of oxidative stress.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080305

Title: Protein-bound 4-hydroxy-2-nonenal: an endogenous triggering antigen of antI-DNA response.

Journal: The Journal of biological chemistry 20070831

Title: Residue-specific adduction of tubulin by 4-hydroxynonenal and 4-oxononenal causes cross-linking and inhibits polymerization.

Journal: Chemical research in toxicology 20070801

Title: A novel 4-oxo-2(E)-nonenal-derived endogenous thiadiazabicyclo glutathione adduct formed during cellular oxidative stress.

Journal: Chemical research in toxicology 20070701

Title: Long-lived 4-oxo-2-enal-derived apparent lysine michael adducts are actually the isomeric 4-ketoamides.

Journal: Chemical research in toxicology 20070201

Title: Chemical nature of stochastic generation of protein-based carbonyls: metal-catalyzed oxidation versus modification by products of lipid oxidation.

Journal: Chemical research in toxicology 20070101

Title: Mass spectrometric evidence for long-lived protein adducts of 4-oxo-2-nonenal.

Journal: Redox report : communications in free radical research 20070101

Title: Endogenous glutathione adducts.

Journal: Current drug metabolism 20061201

Title: Convenient and efficient syntheses of 4-hydroxy-2(E)-nonenal and 4-oxo-2(E)-nonenal.

Journal: Lipids 20060901

Title: Bispecific abs against modified protein and DNA with oxidized lipids.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20060418

Title: Identification of a lipid peroxidation product as a potential trigger of the p53 pathway.

Journal: The Journal of biological chemistry 20060113

Title: Inhibition of human mitochondrial aldehyde dehydrogenase by 4-hydroxynon-2-enal and 4-oxonon-2-enal.

Journal: Chemical research in toxicology 20060101

Title: Novel electrochemical approach to enhanced toxicity of 4-oxo-2-nonenal vs. 4-hydroxy-2-nonenal (role of imine): oxidative stress and therapeutic modalities.

Journal: Medical hypotheses 20060101

Title: Protein adducts generated from products of lipid oxidation: focus on HNE and one.

Journal: Drug metabolism reviews 20060101

Title: Induction of endothelial cell apoptosis by lipid hydroperoxide-derived bifunctional electrophiles.

Journal: Free radical biology & medicine 20051101

Title: Modification of heat shock protein 90 by 4-hydroxynonenal in a rat model of chronic alcoholic liver disease.

Journal: The Journal of pharmacology and experimental therapeutics 20051001

Title: 4-Oxo-2-nonenal is both more neurotoxic and more protein reactive than 4-hydroxy-2-nonenal.

Journal: Chemical research in toxicology 20050801

Title: Cysteine modification by lipid peroxidation products inhibits protein disulfide isomerase.

Journal: Chemical research in toxicology 20050801

Title: Novel lipid hydroperoxide-derived hemoglobin histidine adducts as biomarkers of oxidative stress.

Journal: Journal of mass spectrometry : JMS 20050601

Title: 4-Hydroperoxy-2-nonenal-induced formation of 1,N2-etheno-2'-deoxyguanosine adducts.

Journal: Chemical research in toxicology 20050401

Title: Nuclear glutathione S-transferase pi prevents apoptosis by reducing the oxidative stress-induced formation of exocyclic DNA products.

Journal: Free radical biology & medicine 20041201

Title: 2'-deoxycytidine in free nucleosides and double-stranded DNA as the major target of lipid peroxidation products.

Journal: Free radical biology & medicine 20040301

Title: A novel lipid hydroperoxide-derived modification to arginine.

Journal: Chemical research in toxicology 20031201

Title: Aldose reductase catalyzes reduction of the lipid peroxidation product 4-oxonon-2-enal.

Journal: Chemical research in toxicology 20031101

Title: A novel lipid hydroperoxide-derived cyclic covalent modification to histone H4.

Journal: The Journal of biological chemistry 20031024

Title: Characterization of 2'-deoxycytidine adducts derived from 4-oxo-2-nonenal, a novel lipid peroxidation product.

Journal: Chemical research in toxicology 20030701

Title: Mass spectroscopic characterization of protein modification by 4-hydroxy-2-(E)-nonenal and 4-oxo-2-(E)-nonenal.

Journal: Chemical research in toxicology 20030701

Title: Model studies on protein side chain modification by 4-oxo-2-nonenal.

Journal: Chemical research in toxicology 20030401

Title: Covalent adduction of nucleophilic amino acids by 4-hydroxynonenal and 4-oxononenal.

Journal: Chemico-biological interactions 20030201

Title: Covalent modification of amino acid nucleophiles by the lipid peroxidation products 4-hydroxy-2-nonenal and 4-oxo-2-nonenal.

Journal: Chemical research in toxicology 20021101

Title: Vitamin C-induced decomposition of lipid hydroperoxides to endogenous genotoxins.

Journal: Science (New York, N.Y.) 20010615

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Tags:103560-62-9 Molecular Formula|103560-62-9 MDL|103560-62-9 SMILES|103560-62-9 4-ONE