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3,5,6-trichloro-2-pyridinol |
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CHEBI:143794 |
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A hydroxypyridine that is pyridin-2-ol substituted by chloro groups at positions 3,5 and 6. It is a metabolite of the agrochemical chlorpyrifos. |
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This entity has been manually annotated by the ChEBI Team.
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Mark Williams
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No supplier information found for this compound. |
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Molfile
XML
SDF
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more structures >>
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InChI=1S/C5H2Cl3NO/c6-2-1-3(7)5(10)9-4(2)8/h1H,(H,9,10) |
WCYYAQFQZQEUEN-UHFFFAOYSA-N |
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human urinary metabolite
Any metabolite (endogenous or exogenous) found in human urine samples.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
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View more via ChEBI Ontology
Outgoing
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3,5,6-trichloro-2-pyridinol
(CHEBI:143794)
has role
human urinary metabolite
(CHEBI:84087)
3,5,6-trichloro-2-pyridinol
(CHEBI:143794)
has role
human xenobiotic metabolite
(CHEBI:76967)
3,5,6-trichloro-2-pyridinol
(CHEBI:143794)
is a
chloropyridine
(CHEBI:39173)
3,5,6-trichloro-2-pyridinol
(CHEBI:143794)
is a
hydroxypyridine
(CHEBI:24745)
3,5,6-trichloro-2-pyridinol
(CHEBI:143794)
is tautomer of
3,5,6-trichloropyridine-2-one
(CHEBI:83490)
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Incoming
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3,5,6-trichloropyridine-2-one
(CHEBI:83490)
is tautomer of
3,5,6-trichloro-2-pyridinol
(CHEBI:143794)
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3,5,6-trichloropyridin-2-ol
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2,3,5-trichloro-6-pyridinol
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ChEBI
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2,3,5-trichloropyridine-6-ol
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ChEBI
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2-hydroxy-3,5,6-trichloropyridine
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NIST Chemistry WebBook
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3,5,6-trichloro-2-hydroxypyridine
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NIST Chemistry WebBook
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3,5,6-trichloropyridin-2-ol
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UniProt
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3,5,6-trichloropyridine-2-ol
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HMDB
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3,5,6-tris(chloranyl)pyridin-2-ol
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PDBeChem
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TCPy
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SUBMITTER
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TCpyol
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ChEBI
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6515-38-4
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CAS Registry Number
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NIST Chemistry WebBook
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6515-38-4
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CAS Registry Number
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ChemIDplus
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Wang S, Zhang C, Lv Z, Huang H, Cao X, Song Z, Shao M (2019) Degradation of 3,5,6-trichloro-2-pyridinol by a microbial consortium in dryland soil with anaerobic incubation. Biodegradation 30, 161-171 [PubMed:30929106] [show Abstract] Biodegradation of 3,5,6-trichloro-2-pyridinol (TCP) in drylands is an important biological process of detoxification. Flooding in drylands can result in the formation of anaerobic habitats. However, little is known about the microbial metabolism of TCP in dryland soil under anaerobic conditions. Here, chlorpyrifos-contaminated dryland soil was incubated to enrich the TCP-degrading microbial consortium under anaerobic conditions. Chloridion and CO2 were released with TCP degradation, and the enrichment cultures of dryland soil could metabolize 97% of TCP (100 mg/L) within 20 h. Both reductive and hydrolysis dechlorination mechanisms were involved in TCP biodegradation under anaerobic conditions. Bacterial taxonomic analysis revealed that the aerobic TCP-degrading bacteria Ochrobactrum and dechlorination bacteria Delftia were the dominant genera. Anaerobic and facultative bacteria; i.e., Bacteroides, Bacillus, and Cupriavidus had lower relative abundances, but they were significantly enriched following treatment with TCP. These results indicate that the enrichment cultures of dryland soil dominated by aerobic bacteria could dechlorinate and degrade TCP under anaerobic conditions. | Guo J, Zhang J, Wu C, Lv S, Lu D, Qi X, Jiang S, Feng C, Yu H, Liang W, Chang X, Zhang Y, Xu H, Cao Y, Wang G, Zhou Z (2019) Associations of prenatal and childhood chlorpyrifos exposure with Neurodevelopment of 3-year-old children. Environmental pollution (Barking, Essex : 1987) 251, 538-546 [PubMed:31108286] [show Abstract] Chlorpyrifos (CPF), an organophosphate insecticide, has been linked to adverse neurodevelopmental effects in animal studies. However, little is known about long-term neurotoxicity of early-life CPF exposure in humans. We aimed to evaluate the associations of both prenatal and early childhood CPF exposure with neurodevelopment of children. In this observational study based on Sheyang Mini Birth Cohort, pregnant women were recruited from an agricultural region between June 2009 and January 2010, and their children were followed up from birth to age three. Urinary 3,5,6-Trichloro-2-pyridinol (TCPy), a specific metabolite of CPF, was quantified using large-volume-injection gas chromatography-tandem mass spectrometry. Developmental quotients (DQs) of children in motor, adaptive, language, and social areas were assessed by trained pediatricians. Data from 377 mother-child pairs were used in the current study. Associations between CPF exposure and neurodevelopmental indicators were estimated using generalized linear models with adjustment for potential confounders. The median concentrations of TCPy in maternal and children's urine were 5.39 μg/L and 5.34 μg/L, respectively. No statistically significant association was found between maternal urinary TCPy concentrations and children neurodevelopment. While for postnatal exposure, we found lower motor area DQ score 0.61 [95% confidence interval (CI): -1.13, -0.09; p = 0.02] and social area DQ score 0.55 (95% CI: -1.07, -0.03; p = 0.04) per one-unit increase in the ln-transformed childhood urinary TCPy concentrations. Further stratification by sex indicated that the inverse associations were only observed in boys, but not in girls. Our findings suggest that adverse neurodevelopmental effects were associated with early childhood CPF exposure, but not prenatal exposure. Additional longitudinal studies are needed to replicate these results and to further understand the toxicological mechanisms of CPF. | Yu X, Zhu H, Yan B, Xu Y, Bañuelos G, Shutes B, Wen H, Cheng R (2019) Removal of chlorpyrifos and its hydrolytic metabolite 3,5,6-trichloro-2-pyridinol in constructed wetland mesocosms under soda saline-alkaline conditions: Effectiveness and influencing factors. Journal of hazardous materials 373, 67-74 [PubMed:30903958] [show Abstract] Chlorpyrifos (CP) is frequently detected in agricultural effluent worldwide. Both CP and its hydrolytic metabolite 3,5,6-trichloro-2-pyridinol (TCP) can cause serious environment hazards, and require removal before discharged into rivers and/or lakes. The effectiveness and main influencing factors of CP and TCP removal in mesocosm-scale subsurface flow constructed wetlands (SSFCWs) were evaluated. Results indicated that CP in SSFCWs reduced to less than detection limit in 4 d and TCP to 2 μg L-1 in 8 d. Higher influent CP concentrations lengthened the degradation process for both CP and TCP. The presence of co-existing inorganic nutrients restrained the degradation of CP during the hydraulic retention time of 2 h to 2 d. A higher pH resulting from the deterioration of soda saline-alkaline level accelerated the degradation of CP through the hydrolysis process. The SSFCWs with slag operating for another 88 d (i.e., 11 trails with HRT of 8 d for each trial) revealed a better and more stable treatment performance compared with previous studies. The results of this study demonstrated the positive feasibility of using SSFCWs with slag for the decontamination of CP-associated agricultural drainage or stormwater runoff. | Bempelou ED, Vontas JG, Liapis KS, Ziogas VN (2018) Biodegradation of chlorpyrifos and 3,5,6-trichloro-2-pyridinol by the epiphytic yeasts Rhodotorula glutinis and Rhodotorula rubra. Ecotoxicology (London, England) 27, 1368-1378 [PubMed:30343485] [show Abstract] The possible involvement of the epiphytic yeasts Rhodotorula glutinis and Rhodotorula rubra in the biodegradation of the insecticide chlorpyrifos and its metabolite 3,5,6-trichloro-2-pyridinol (TCP), in pure cultures and in plant surfaces (tomato fruits) was investigated. Higher biodegradation rates were observed as the concentration of chlorpyrifos and the inoculum of the microorganisms were increased, while the yeasts proved to be more active at 25 and 15 °C. The presence of glucose in the mineral nutrient medium, as an extra source of carbon, delayed the biodegradation by Rhodotorula glutinis, while Rhodotorula rubra proved to be more active. The detection and quantification of the parent compound and TCP was successfully achieved using a LC/MS/MS chromatographic system. The in vitro enzymatic assays applied suggested that esterases may be involved in the biodegradation of chlorpyrifos, a fact that was further enhanced after the addition of the synergists triphenyl phosphate, diethyl maleate and piperonyl butoxide in the biodegradation trials. The decrease of chlorpyrifos residues on tomato fruits confirmed the corresponding on pure cultures, resulting in the suggestion that the yeasts R. glutinis and R. rubra can possibly be used successfully for the removal or detoxification of chlorpyrifos residues on tomatoes. | Kennedy EM, Mackie JC (2018) Mechanism of the Thermal Decomposition of Chlorpyrifos and Formation of the Dioxin Analog, 2,3,7,8-Tetrachloro-1,4-dioxino-dipyridine (TCDDpy). Environmental science & technology 52, 7327-7333 [PubMed:29846064] [show Abstract] Thermal decomposition of the pesticide, chlorpyrifos (CPf) and its major degradation product, 3,5,6-trichloro-2-pyridinol (TCpyol), has been studied by quantum chemical calculation using density functional methods at the M06-2X/GTLarge//M06-2 X/6-31+G(d,p) level of theory. Chlopyrifos was found to undergo a series of unimolecular stepwise elimination reactions releasing two molecules of ethylene and finally HOPOS to form TCpyol. TCpyol underwent oxidative decomposition initiated by abstraction of its phenolic H atom by O2. Two phenoxy radicals so produced underwent combination leading to the formation of 2,3,7,8-tetrachloro-[1,4]dioxinodipyridine (TCDDpy). Via Smiles rearrangement both cis and trans TCDDpy are formed. Kinetic models have been constructed to model the decomposition of CPf into TCpyol and of the latter into cis and trans TCDDpy. Modeled results are compared with the experiments of Sakiyama et al. ( Organohalogen Compounds, 2012, 74, 1441-1444). | Zhang J, Grundström C, Brännström K, Iakovleva I, Lindberg M, Olofsson A, Andersson PL, Sauer-Eriksson AE (2018) Interspecies Variation between Fish and Human Transthyretins in Their Binding of Thyroid-Disrupting Chemicals. Environmental science & technology 52, 11865-11874 [PubMed:30226982] [show Abstract] Thyroid-disrupting chemicals (TDCs) are xenobiotics that can interfere with the endocrine system and cause adverse effects in organisms and their offspring. TDCs affect both the thyroid gland and regulatory enzymes associated with thyroid hormone homeostasis. Transthyretin (TTR) is found in the serum and cerebrospinal fluid of vertebrates, where it transports thyroid hormones. Here, we explored the interspecies variation in TDC binding to human and fish TTR (exemplified by Gilthead seabream ( Sparus aurata)). The in vitro binding experiments showed that TDCs bind with equal or weaker affinity to seabream TTR than to the human TTR, in particular, the polar TDCs (>500-fold lower affinity). Crystal structures of the seabream TTR-TDC complexes revealed that all TDCs bound at the thyroid binding sites. However, amino acid substitution of Ser117 in human TTR to Thr117 in seabream prevented polar TDCs from binding deep in the hormone binding cavity, which explains their low affinity to seabream TTR. Molecular dynamics and in silico alanine scanning simulation also suggested that the protein backbone of seabream TTR is more rigid than the human one and that Thr117 provides fewer electrostatic contributions than Ser117 to ligand binding. This provides an explanation for the weaker affinities of the ligands that rely on electrostatic interactions with Thr117. The lower affinities of TDCs to fish TTR, in particular the polar ones, could potentially lead to milder thyroid-related effects in fish. | Callahan CL, Hamad LA, Olson JR, Ismail AA, Abdel-Rasoul G, Hendy O, Rohlman DS, Bonner MR (2017) Longitudinal assessment of occupational determinants of chlorpyrifos exposure in adolescent pesticide workers in Egypt. International journal of hygiene and environmental health 220, 1356-1362 [PubMed:28939184] [show Abstract] Chlorpyrifos (CPF) is an organophosphourus insecticide applied to cotton fields by adolescents employed by the Egyptian Ministry of Agriculture. Urinary 3,5,6-trichloro-2-pyridinol (TCPy) is a biomarker of CPF exposure that has substantial variability among these applicators. In order to identify predictors of CPF exposure, we conducted a longitudinal study of 43 adolescent pesticide applicators in Egypt from April 2010 to January 2011 in Egypt. Urinary TCPy was quantified at 25 time-points, prior to, during, and following application. We used log-linear regression and a best subset selection approach to identify the exposure determinants that were most predictive of cumulative TCPy and participants' highest TCPy values (peak exposure). Applicators had cumulative urinary TCPy levels ranging from 167 to 49,8208μg/g creatinine. Total hours applying CPF (semi-partial r2=0.32), and total hours in the field applying other pesticides (semi-partial r2=0.08) were the strongest predictors of cumulative TCPy. Applicators had peak urinary TCPy levels ranging from 4 to 5715μg/g creatinine. The amount of time applying pesticides prior to blood draw was the strongest predictor of peak TCPy (semi-partial r2=0.30). We also observed evidence that wearing clean clothes to work was associated with lower longitudinal TCPy. Our results suggest there is an opportunity for targeted interventions, particularly related to hygiene or implementation of personal protective equipment usage to reduce CPF exposure among adolescent pesticide workers. |
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