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phenylacetic acid |
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CHEBI:30745 |
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A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:25977, CHEBI:44686, CHEBI:8085
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eMolecules:495300, ZINC000000388462 |
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Molfile
XML
SDF
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more structures >>
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Phenylacetic acid (conjugate base phenylacetate), also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogenously, it is a catabolite of phenylalanine. As a commercial chemical, because it can be used in the illicit production of phenylacetone (used in the manufacture of substituted amphetamines), it is subject to controls in countries including the United States and China. |
Read full article at Wikipedia
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InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) |
WLJVXDMOQOGPHL-UHFFFAOYSA-N |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Aspergillus niger
(NCBI:txid5061)
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of strain
var. Tieghem.
See:
Phytochemistry, 1988, 27(10), 3169-3173
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Escherichia coli
(NCBI:txid562)
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See:
PubMed
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Stachylidium
(NCBI:txid796327)
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Marine derived fungus isolated from sponge Callyspongia sp. cf. C. flammea
of strain
220
See:
PubMed
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
EC 6.4.1.1 (pyruvate carboxylase) inhibitor
An EC 6.4.1.* (carboxylase) inhibitor that interferes with the action of pyruvate carboxylase (EC 6.4.1.1).
toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
plant growth retardant
allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
auxin
Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").
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View more via ChEBI Ontology
2-PHENYLACETIC ACID
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PDBeChem
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2-Phenylethanoic acid
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HMDB
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α-toluic acid
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NIST Chemistry WebBook
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Benzeneacetic acid
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KEGG COMPOUND
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benzeneacetic acid
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NIST Chemistry WebBook
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Benzylformic acid
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KEGG COMPOUND
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Omega-Phenylacetic acid
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HMDB
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ω-phenylacetic acid
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HMDB
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PA
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ChEBI
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Phenylacetic acid
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KEGG COMPOUND
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103-82-2
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CAS Registry Number
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KEGG COMPOUND
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103-82-2
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CAS Registry Number
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NIST Chemistry WebBook
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103-82-2
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CAS Registry Number
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ChemIDplus
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1099647
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Reaxys Registry Number
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Reaxys
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68976
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Gmelin Registry Number
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Gmelin
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Ariza A, Barrionuevo E, Mayorga C, Montañez MI, Perez-Inestrosa E, Ruiz-Sánchez A, Rodríguez-Guéant RM, Fernández TD, Guéant JL, Torres MJ, Blanca M (2014) IgE to penicillins with different specificities can be identified by a multiepitope macromolecule: Bihaptenic penicillin structures and IgE specificities. Journal of immunological methods 406, 43-50 [PubMed:24631718] [show Abstract] Quantitation of specific IgE by immunoassay is a recommended in vitro test for the diagnosis of immediate hypersensitivity reactions to betalactams (BLs), particularly when skin test results are negative. IgE antibodies that recognize the common nuclear structure of all BLs or the specific side chain structure can be mainly distinguished by immunoassays. The aim of this study was to develop an immunoassay system to detect IgE antibodies with different specificities. Cellulose discs conjugated with benzylpenicillin (BP), amoxicillin (AX) or both drugs, with poly-l-lysine (PLL) as carrier molecule, were used as solid phases in the radioallergosorbent test (RAST). Direct and inhibition radioimmunoassay studies were made to verify the structures recognized by serum IgE antibodies from penicillin-allergic patients. Our results indicated that the addition of both haptens did not decrease the capacity to capture IgE when serum specific to either BP or AX was used, at least in terms of sensitivity. In addition, the inclusion of two haptens improved significantly the levels of IgE detection in patients who recognized both BP and AX. Therefore, the use of a solid phase with a carrier molecule conjugated with two determinants (AX and BP) is helpful to recognize IgE antibodies against either of these determinants and is useful for screening sera with different specificities. | Abdulmalek E, Arumugam M, Mizan HN, Abdul Rahman MB, Basri M, Salleh AB (2014) Chemoenzymatic epoxidation of alkenes and reusability study of the phenylacetic acid. TheScientificWorldJournal 2014, 756418 [PubMed:24587751] [show Abstract] Here, we focused on a simple enzymatic epoxidation of alkenes using lipase and phenylacetic acid. The immobilised Candida antarctica lipase B, Novozym 435 was used to catalyse the formation of peroxy acid instantly from hydrogen peroxide (H2O2) and phenylacetic acid. The peroxy phenylacetic acid generated was then utilised directly for in situ oxidation of alkenes. A variety of alkenes were oxidised with this system, resulting in 75-99% yield of the respective epoxides. On the other hand, the phenylacetic acid was recovered from the reaction media and reused for more epoxidation. Interestingly, the waste phenylacetic acid had the ability to be reused for epoxidation of the 1-nonene to 1-nonene oxide, giving an excellent yield of 90%. | Scholze A, Jankowski V, Henning L, Haass W, Wittstock A, Suvd-Erdene S, Zidek W, Tepel M, Jankowski J (2007) Phenylacetic acid and arterial vascular properties in patients with chronic kidney disease stage 5 on hemodialysis therapy. Nephron. Clinical practice 107, c1-6 [PubMed:17622769] [show Abstract]
BackgroundPhenylacetic acid (PAA) is a recently described uremic toxin that inhibits inducible nitric oxide synthase expression and plasma membrane calcium ATPase and may therefore also be involved in remodeling of arteries. Such vascular effects have not been evaluated yet in patients with chronic kidney disease stage 5.MethodWe prospectively measured the plasma concentrations of PAA using nuclear magnetic resonance spectroscopy in 50 patients with chronic kidney disease stage 5 (37 men, 13 women) on maintenance hemodialysis. Arterial vascular properties were quantified by the reflective index obtained from digital photoplethysmography.ResultsDuring the hemodialysis session the plasma PAA concentration was reduced from 3.38 +/- 0.24 mmol/l (mean +/- SEM; median, 2.85 mmol/l; interquartile range, 2.02-4.52 mmol/l) to 2.25 +/- 0.11 mmol/l (median, 2.06 mmol/l; interquartile range, 1.62-2.86 mmol/l; n = 50; p < 0.001). There was a significant correlation between the PAA concentration and the reflective index before the start of the hemodialysis session.ConclusionThe study demonstrates an association of PAA and arterial vascular properties in patients with chronic kidney disease stage 5. | Mangani G, Canestrari F, Berloni A, Maione M, Pagliarani S, Mangani F (2004) Gas chromatographic--mass spectrometric determination of phenylacetic acid in human blood. Annali di chimica 94, 715-719 [PubMed:15506622] [show Abstract] Phenyl acetic acid, a metabolite of 2-phenyl ethylamine, acts as a neuromodulator in the nigrostriatal dopaminergic pathway stimulating the release of dopamine. The evaluation of phenyl acetic acid concentration in the biological fluid reflects phenyl ethylamine levels thus allowing the assessment of the modulatory role of this endogenous substance. Changes in biological fluids levels of 2-phenylethylamine and/or in its metabolite have been reported in affective disorders, such as depression and schizophrenia. Recently, the occurrence of the "attention deficit hyperactivity syndrome" has been frequently reported in childhood population and involvement of dopaminergic dysfunction in this disease has been suspected. A fast, reliable and reproducible method for the determination of phenyl acetic acid in human blood, is therefore needed in order to have a screening tool for monitoring both healthy childhood population and suspected "attention deficit hyperactivity syndrome" patients. The gas chromatographic-mass spectrometric method here described makes use of a deuterated internal standard in order to overcome problems related to the lack of reproducibility often encountered when a derivatization step is performed. | Kim Y, Cho JY, Kuk JH, Moon JH, Cho JI, Kim YC, Park KH (2004) Identification and antimicrobial activity of phenylacetic acid produced by Bacillus licheniformis isolated from fermented soybean, Chungkook-Jang. Current microbiology 48, 312-317 [PubMed:15057459] [show Abstract] A bacterial strain, B65-1, which showed strong antimicrobial activity, was isolated from Chungkook-Jang, a traditional Korean fermented-soybean food with antimicrobial properties. Based on carbon utilization pattern and partial 16S rRNA sequence analysis, the B65-1 strain was identified as Bacillus licheniformis. An antibiotic compound, active against bacteria and yeast such as Staphylococcus aureus, Escherichia coli, and Candida albicans, was isolated by various chromatographic procedures from culture filtrates of B. licheniformis B65-1. The purified antibiotic was identified to be phenylacetic acid, with the molecular formula C(8)H(8)O(2) by analyses of EI-MS and NMR. The phenylacetic acid was detected in fermented soybean made with the strain B65-1 as a starter, but was not present in extracts of nonfermented soybean. Our results indicated that the phenylacetic acid produced by B. licheniformis during fermentation of soybean is one of the main compounds of antimicrobial activity of Chungkook-Jang. | Panoutsopoulos GI (2004) Metabolism of 2-phenylethylamine to phenylacetic acid, via the intermediate phenylacetaldehyde, by freshly prepared and cryopreserved guinea pig liver slices. In vivo (Athens, Greece) 18, 779-786 [PubMed:15646820] [show Abstract]
Background2-Phenylethylamine is an endogenous amine, which acts as a neuromodulator of dopaminergic responses. Exogenous 2-phenylethylamine is found in certain foodstuffs and may cause toxic side-effects in susceptible individuals.Materials and methodsThe present investigation examined the metabolism of 2-phenylethylamine to phenylacetic acid, via phenylacetaldehyde, in freshly prepared and cryopreserved liver slices. Additionally, it compared the relative contribution of aldehyde oxidase, xanthine oxidase and aldehyde dehydrogenase by using specific inhibitors for each oxidizing enzyme.ResultsIn freshly prepared and cryopreserved liver slices, phenylacetic acid was the main metabolite of 2-phenylethalamine. In freshly prepared liver slices, phenylacetic acid was completely inhibited by disulfiram (inhibitor of aldehyde dehydrogenase), whereas isovanillin (inhibitor of aldehyde oxidase) inhibited acid formation to a lesser extent and allopurinol (inhibitor of xanthine oxidase) had no effect. In cryopreserved liver slices, isovanillin inhibited phenylacetic acid by 85%, whereas disulfiram inhibited acid formation to a lesser extent and allopurinol had no effect.ConclusionIn liver slices, 2-phenylethylamine is rapidly oxidized to phenylacetic acid, via phenylacetaldehyde, by aldehyde dehydrogenase and aldehyde oxidase with no contribution from xanthine oxidase. | Zhao Z, Baldo BA, Rimmer J (2002) beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 32, 1644-1650 [PubMed:12569987] [show Abstract]
BackgroundAn appreciation of the structural heterogeneity of allergenic determinants on penicillins and cephalosporins reveals the importance of side-chain groups and their involvement in many allergies to beta-lactam drugs. Although allergenic cross-reactions between penicillins and cephalosporins are known to occur, the precise molecular bases of such recognitions and cross-sensitivities have rarely been studied and identified.ObjectivesThe unexpected finding of a high incidence of positive IgE antibody reactions with both benzylpenicillin and cephalothin prompted serological and immunochemical studies to identify the chemical basis of antibody recognition of these drugs from the two different families of beta-lactam antibiotics.MethodsAdsorption studies were employed to identify whether or not a single population of antibodies was involved in the recognition of benzylpenicillin and cephalothin. Identification of the fine structural features recognized by IgE antibodies was investigated by quantitative hapten inhibition studies employing carefully selected beta-lactam drugs, analogues and some other structurally related chemicals.ResultsAdsorption studies with penicilloic acid-solid phase clearly established that a single population of cross-reacting antibodies recognized both benzylpenicillin and cephalothin. Quantitative inhibition findings, especially with phenylacetic acid and 2-thiopheneacetic acid and with cephaloridine and cefoxitin, which have the same (2-thienyl)methyl side-chain as cephalothin, implicated the methylene group as the focus of the allergenic determinant recognized on benzylpenicillin and cephalothin. In addition to the methylene group, recognition graded into neighbouring structures including the amide group and extended weakly to the beta-lactam ring.ConclusionsResults confirmed that structural features as small as a methylene group may be allergenically important. In the present case, this group, making up only part of the different side-chains on benzylpenicillin and cephalothin, together with neighbouring structures extending toward the beta-lactam ring, accounted for the cross-reactivity seen between structures that, at first sight, appear to be not closely related. Such subtle, small, common structural features are likely to be immunologically recognized and implicated in allergic reactions to other drugs, including beta-lactam antibiotics. | Liu YQ, Jetton TL, Leahy JL (2002) beta-Cell adaptation to insulin resistance. Increased pyruvate carboxylase and malate-pyruvate shuttle activity in islets of nondiabetic Zucker fatty rats. The Journal of biological chemistry 277, 39163-39168 [PubMed:12147706] [show Abstract] The beta-cell biochemical mechanisms that account for the compensatory hyperfunction with insulin resistance (so-called beta-cell adaptation) are unknown. We investigated glucose metabolism in isolated islets from 10-12-week-old Zucker fatty (ZF) and Zucker lean (ZL) rats (results expressed per mg/islet of protein). ZF rats were obese, hyperlipidemic, and normoglycemic. They had a 3.8-fold increased beta-cell mass along with 3-10-fold increases in insulin secretion to various stimuli during pancreas perfusion despite insulin content per milligram of beta-cells being only one-third that of ZL rats. Islet glucose metabolism (utilization and oxidation) was 1.5-2-fold increased in the ZF islets despite pyruvate dehydrogenase activity being 30% lowered compared with the ZL islets. The reason was increased flux through pyruvate carboxylase (PC) and the malate-pyruvate and citrate-pyruvate shuttles based on the following observations (% ZL islets): increased V(max) of PC (160%), malate dehydrogenase (170%), and malic enzyme (275%); elevated concentrations of oxaloacetate (150%), malate (250%), citrate (140%), and pyruvate (250%); and 2-fold increased release of malate from isolated mitochondria. Inhibition of PC by 5 mm phenylacetic acid markedly lowered glucose-induced insulin secretion in ZF and ZL islets. Thus, our results suggest that PC and the pyruvate shuttles are increased in ZF islets, and this accounts for glucose mitochondrial metabolism being increased when pyruvate dehydrogenase activity is reduced. As the anaplerosis pathways are implicated in glucose-induced insulin secretion and the synthesis of glucose-derived lipid and amino acids, our results highlight the potential importance of PC and the anaplerosis pathways in the enhanced insulin secretion and beta-cell growth that characterize beta-cell adaptation to insulin resistance. | Moreno F, Blanca M, Mayorga C, Terrados S, Moya M, Pérez E, Suau R, Vega JM, García J, Miranda A (1995) Studies of the specificities of IgE antibodies found in sera from subjects with allergic reactions to penicillins. International archives of allergy and immunology 108, 74-81 [PubMed:7544181] [show Abstract] Penicillins are immunogenic when administered to humans and in some instances they can also be allergenic, inducing specific IgE antibodies. Whilst the major haptenic group, the penicilloyl, is well characterised, less is known about the relative importance of the different parts of the structure for antibody binding and how this can influence the specificity of patients response. In order to investigate this further, sera from subjects who had suffered an IgE-mediated reaction to penicillins were studied using the radioallergosorbent test (RAST) and RAST inhibition. The assays employed reagents related to the penicillins causing the reaction. Using 173 sera, positive RAST results were only found with reagents based on benzyl penicillin (BP) and amoxicillin (AX). Fifty-three positive sera were selected for further studies and categorized into three groups: (A) sera only RAST positive to AX, (B) sera only positive to BP and (C) sera positive to both penicillins. RAST inhibition studies were then carried out using monomeric penicilloyl conjugates and compounds representing parts of the penicilloyl structures of BP and AX. For all three groups, monomeric penicilloyl conjugates were the most efficient inhibitors but there were differences for the other compounds. Group A sera were also inhibited by the side chain amoxicillin, whereas group B sera were poorly inhibited by all other inhibitors. Group C sera showed two patterns of inhibition, both consistent with their more cross-reactive profile. | Mayorga C, Obispo T, Jimeno L, Blanca M, Moscoso del Prado J, Carreira J, Garcia JJ, Juarez C (1995) Epitope mapping of beta-lactam antibiotics with the use of monoclonal antibodies. Toxicology 97, 225-234 [PubMed:7716788] [show Abstract] In order to evaluate the antigenic contribution of different regions of the penicillin molecule, monoclonal antibodies were raised against amoxicillin-protein conjugates and their specificities analysed in detail. A random sample of the clones produced was analysed by a quantitative inhibition-ELISA, using, as inhibitors, monomeric conjugates of the following antibiotics to butylamine (BA), amoxicillin (AX), ampicillin (AMP), benzylpenicillin (BP) and the nuclear part of these, 6-aminopenicillanic acid (6-APA); and different parts of the following molecules: N-(p-hydroxyphenyl)-glycine (PHPG), N-phenylglycine (NPG), phenylacetic acid (PA) and thiazolidine (TIAZ). The results showed that 92% of the antibodies recognized an epitope in which the side chain was a major constituent, although with variable contributions from other regions of the molecule. There was a high degree of crossreactivity with aminopenicillins, but low or absent crossreactivity with BP. None of the antibodies recognized the thiazolidine ring or the conjugated nuclear region of the penicillins. Finally, one antibody seemed to recognize, equally, all the different structures tested. The possible relevance of these results to penicillin allergy is discussed. | Harle DG, Baldo BA (1990) Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins. International archives of allergy and applied immunology 92, 439-444 [PubMed:2083978] [show Abstract] A radioimmunoassay employing cephalothin linked to a solid phase has been developed for the detection of cephalosporin-reactive IgE antibodies. Direct binding and inhibition studies demonstrated allergenic cross-reactivity between cephalosporins and penicillins, and quantitative hapten inhibition experiments identified the 2-thiophene group, and particularly the attached methylene group, of cephalothin as an allergenic determinant. |
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