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89186-13-0 | 2-Nonenal, 4-oxo-
CAS No: 89186-13-0 Catalog No: AG004TP0 MDL No:
Product Description
Catalog Number:
AG004TP0
Chemical Name:
2-Nonenal, 4-oxo-
CAS Number:
89186-13-0
Molecular Formula:
C9H14O2
Molecular Weight:
154.2063
IUPAC Name:
4-oxonon-2-enal
InChI:
InChI=1S/C9H14O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-8H,2-4,6H2,1H3
InChI Key:
SEPPVOUBHWNCAW-UHFFFAOYSA-N
SMILES:
CCCCCC(=O)C=CC=O
Properties
Complexity:
148
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
154.099g/mol
Formal Charge:
0
Heavy Atom Count:
11
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
154.209g/mol
Monoisotopic Mass:
154.099g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
34.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
1
XLogP3:
1.6
Literature
| Title | Journal |
|---|---|
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| Effect of lipid oxidation products on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems. | Food chemistry 20121215 |
| Protein carbonylation and adipocyte mitochondrial function. | The Journal of biological chemistry 20120921 |
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| Protein carbonylation in a murine model for early alcoholic liver disease. | Chemical research in toxicology 20120521 |
| Dietary regulation of catabolic disposal of 4-hydroxynonenal analogs in rat liver. | Free radical biology & medicine 20120315 |
| Antidromic vasodilatation and the migraine mechanism. | The journal of headache and pain 20120301 |
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| Detection of N-(hexanoyl)lysine in the tropomyosin 1 protein in N-methyl-N'-nitro-N-nitrosoguanidine-induced rat gastric cancer cells. | Journal of clinical biochemistry and nutrition 20120101 |
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| Genotoxic analysis of four lipid-peroxidation products in the mouse lymphoma assay. | Mutation research 20111224 |
| Cyclooxygenase- and lipoxygenase-mediated DNA damage. | Cancer metastasis reviews 20111201 |
| Site-specific proteomic analysis of lipoxidation adducts in cardiac mitochondria reveals chemical diversity of 2-alkenal adduction. | Journal of proteomics 20111019 |
| The discovery of LOX-1, its ligands and clinical significance. | Cardiovascular drugs and therapy 20111001 |
| Activation of aldo-keto reductase family member 1B14 (AKR1B14) by bile acids: Activation mechanism and bile acid-binding site. | Biochimie 20110901 |
| 1,N2-Etheno-2'-deoxyguanosine adopts the syn conformation about the glycosyl bond when mismatched with deoxyadenosine. | Chemical research in toxicology 20110718 |
| Reversible and irreversible protein glutathionylation: biological and clinical aspects. | Expert opinion on drug metabolism & toxicology 20110701 |
| The Drosophila carbonyl reductase sniffer is an efficient 4-oxonon-2-enal (4ONE) reductase. | Chemico-biological interactions 20110530 |
| Cross-oxidation of angiotensin II by glycerophosphatidylcholine oxidation products. | Rapid communications in mass spectrometry : RCM 20110530 |
| 4-oxo-2-nonenal (4-ONE): evidence of transient receptor potential ankyrin 1-dependent and -independent nociceptive and vasoactive responses in vivo. | The Journal of pharmacology and experimental therapeutics 20110401 |
| Structure-activity analysis of diffusible lipid electrophiles associated with phospholipid peroxidation: 4-hydroxynonenal and 4-oxononenal analogues. | Chemical research in toxicology 20110321 |
| 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. | Free radical biology & medicine 20110201 |
| LC-MS/MS quantitation of mercapturic acid conjugates of lipid peroxidation products as markers of oxidative stress. | Current protocols in toxicology 20110201 |
| Trans-4-oxo-2-nonenal potently alters mitochondrial function. | Free radical biology & medicine 20110115 |
| Lipid-mediated oxidative stress and inflammation in the pathogenesis of Parkinson's disease. | Parkinson's disease 20110101 |
| TRP Channels as Sensors and Signal Integrators of Redox Status Changes. | Frontiers in pharmacology 20110101 |
| Antibodies against alpha-synuclein reduce oligomerization in living cells. | PloS one 20110101 |
| Metals, oxidative stress and neurodegenerative disorders. | Molecular and cellular biochemistry 20101201 |
| Xanthine oxidase-derived reactive oxygen species mediate 4-oxo-2-nonenal-induced hepatocyte cell death. | Toxicology and applied pharmacology 20101201 |
| Properties and tissue distribution of a novel aldo-keto reductase encoding in a rat gene (Akr1b10). | Archives of biochemistry and biophysics 20101115 |
| Mass spectrometric characterization of modifications to angiotensin II by lipid peroxidation products, 4-oxo-2(E)-nonenal and 4-hydroxy-2(E)-nonenal. | Chemical research in toxicology 20101115 |
| Caterpillar- and salivary-specific modification of plant proteins. | Journal of proteome research 20101105 |
| Identification of a lipid peroxidation product as the source of oxidation-specific epitopes recognized by anti-DNA autoantibodies. | The Journal of biological chemistry 20101029 |
| Detection of lipid peroxidation-induced DNA adducts caused by 4-oxo-2(E)-nonenal and 4-oxo-2(E)-hexenal in human autopsy tissues. | Chemical research in toxicology 20100920 |
| Comparison of the in vitro replication of the 7-(2-oxoheptyl)-1,N2-etheno-2'-deoxyguanosine and 1,N2-etheno-2'-deoxyguanosine lesions by Sulfolobus solfataricus P2 DNA polymerase IV (Dpo4). | Chemical research in toxicology 20100816 |
| Structure of the 1,N(2)-etheno-2'-deoxyguanosine lesion in the 3'-G(epsilon dG)T-5' sequence opposite a one-base deletion. | Biochemistry 20100330 |
| Quantitation of mercapturic acid conjugates of 4-hydroxy-2-nonenal and 4-oxo-2-nonenal metabolites in a smoking cessation study. | Free radical biology & medicine 20100101 |
| Reaction products of gamma-tocopherol with (E)-4-oxo-2-nonenal in acidic acetonitrile. | Bioscience, biotechnology, and biochemistry 20100101 |
| Rat aldose reductase-like protein (AKR1B14) efficiently reduces the lipid peroxidation product 4-oxo-2-nonenal. | Biological & pharmaceutical bulletin 20100101 |
| The biological and metabolic fates of endogenous DNA damage products. | Journal of nucleic acids 20100101 |
| A 4-oxo-2(E)-nonenal-derived glutathione adduct from 15-lipoxygenase-1-mediated oxidation of cytosolic and esterified arachidonic acid. | Free radical biology & medicine 20091001 |
| Effects of Lipid Peroxidation-Derived Products on the Growth of Human Colorectal Cancer Cell Line HT-29. | Journal of clinical biochemistry and nutrition 20090901 |
| Lipid aldehyde-mediated cross-linking of apolipoprotein B-100 inhibits secretion from HepG2 cells. | Biochimica et biophysica acta 20090801 |
| Mass spectrometric characterization of protein modification by the products of nonenzymatic oxidation of linoleic acid. | Chemical research in toxicology 20090801 |
| Charge-derivatized amino acids facilitate model studies on protein side-chain modifications by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | Rapid communications in mass spectrometry : RCM 20090701 |
| 5-Lipoxygenase-mediated endogenous DNA damage. | The Journal of biological chemistry 20090619 |
| Covalent cross-linking of glutathione and carnosine to proteins by 4-oxo-2-nonenal. | Chemical research in toxicology 20090601 |
| Identification of advanced reaction products originating from the initial 4-oxo-2-nonenal-cysteine Michael adducts. | Chemical research in toxicology 20090501 |
| Global analysis of protein damage by the lipid electrophile 4-hydroxy-2-nonenal. | Molecular & cellular proteomics : MCP 20090401 |
| Fenton chemistry and oxidative stress mediate the toxicity of the beta-amyloid peptide in a Drosophila model of Alzheimer's disease. | The European journal of neuroscience 20090401 |
| Role of human aldo-keto-reductase AKR1B10 in the protection against toxic aldehydes. | Chemico-biological interactions 20090316 |
| The essential role of ERK in 4-oxo-2-nonenal-mediated cytotoxicity in SH-SY5Y human neuroblastoma cells. | Journal of neurochemistry 20090301 |
| Oxidation and glycolytic cleavage of etheno and propano DNA base adducts. | Biochemistry 20090203 |
| The lipid peroxidation metabolite 4-oxo-2-nonenal cross-links alpha-synuclein causing rapid formation of stable oligomers. | Biochemical and biophysical research communications 20090123 |
| Nucleotide excision repair and recombination are engaged in repair of trans-4-hydroxy-2-nonenal adducts to DNA bases in Escherichia coli. | International journal of biological sciences 20090101 |
| Structural basis for substrate specificity in human monomeric carbonyl reductases. | PloS one 20090101 |
| Mining to find the lipid interaction networks involved in Ovarian Cancers. | Summit on translational bioinformatics 20090101 |
| Decreased expression of peroxiredoxin 6 in a mouse model of ethanol consumption. | Free radical biology & medicine 20081201 |
| A novel 4-oxo-2(E)-nonenal-derived modification to angiotensin II: oxidative decarboxylation of N-terminal aspartic acid. | Chemical research in toxicology 20081201 |
| In vitro and in silico characterization of peroxiredoxin 6 modified by 4-hydroxynonenal and 4-oxononenal. | Chemical research in toxicology 20081201 |
| The stereochemistry of trans-4-hydroxynonenal-derived exocyclic 1,N2-2'-deoxyguanosine adducts modulates formation of interstrand cross-links in the 5'-CpG-3' sequence. | Biochemistry 20081104 |
| Identification of proteins adducted by lipid peroxidation products in plasma and modifications of apolipoprotein A1 with a novel biotinylated phospholipid probe. | Journal of proteome research 20081003 |
| Use of an in vitro digestion model to study the bioaccessibility of 4-hydroxy-2-nonenal and related aldehydes present in oxidized oils rich in omega-6 acyl groups. | Journal of agricultural and food chemistry 20080924 |
| Structure of the 1,N2-ethenodeoxyguanosine adduct opposite cytosine in duplex DNA: Hoogsteen base pairing at pH 5.2. | Chemical research in toxicology 20080915 |
| Carbonyl reductase inactivation may contribute to mouse lung tumor promotion by electrophilic metabolites of butylated hydroxytoluene: protein alkylation in vivo and in vitro. | Chemical research in toxicology 20080801 |
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| Residue-specific adduction of tubulin by 4-hydroxynonenal and 4-oxononenal causes cross-linking and inhibits polymerization. | Chemical research in toxicology 20070801 |
| Serum vitamin E and oxidative protein modification in hemodialysis: a randomized clinical trial. | American journal of kidney diseases : the official journal of the National Kidney Foundation 20070801 |
| A novel 4-oxo-2(E)-nonenal-derived endogenous thiadiazabicyclo glutathione adduct formed during cellular oxidative stress. | Chemical research in toxicology 20070701 |
| Covalent adducts arising from the decomposition products of lipid hydroperoxides in the presence of cytochrome c. | Chemical research in toxicology 20070501 |
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| Carbonylation of adipose proteins in obesity and insulin resistance: identification of adipocyte fatty acid-binding protein as a cellular target of 4-hydroxynonenal. | Molecular & cellular proteomics : MCP 20070401 |
| In vitro synthesis of 1,N6-etheno-2'-deoxyadenosine and 1,N2-etheno-2'-deoxyguanosine by 2,4-dinitrophenol and 1,3-dinitropyrene in presence of a bacterial nitroreductase. | Environmental toxicology 20070401 |
| Long-lived 4-oxo-2-enal-derived apparent lysine michael adducts are actually the isomeric 4-ketoamides. | Chemical research in toxicology 20070201 |
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