(e,e)-Muconate (BioDeep_00000015796)

Main id: BioDeep_00000017800

Secondary id: BioDeep_00001870244

PANOMIX_OTCML-2023


代谢物信息卡片


1,3-Butadiene-1,4-dicarboxylic acid

化学式: C6H6O4 (142.0266076)
中文名称: 反,反-粘康酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(=CC(=O)O)C=CC(=O)O
InChI: InChI=1S/C6H6O4/c7-5(8)3-1-2-4-6(9)10/h1-4H,(H,7,8)(H,9,10)/b3-1+,4-2+

描述信息

trans-trans-Muconic acid is a urinary metabolite of benzene and has been used as a biomarker of exposure to benzene in human.

同义名列表

15 个代谢物同义名

1,3-Butadiene-1,4-dicarboxylic acid; (2E,4E)-hexa-2,4-dienedioic acid; 1,3-Butadiene-1,4-dicarboxylate; (2E,4E)-2,4-Hexadienedioic acid; (e,e)-2,4-Hexadienedioic acid; (2E,4E)-2,4-Hexadienedioate; (e,e)-2,4-Hexadienedioate; Hexa-2,4-dienedioic acid; trans-trans-muconic acid; trans,trans-Muconic Acid; cis,trans-Muconic acid; trans-trans-Muconate; Hexa-2,4-dienedioate; (e,e)-Muconic acid; (e,e)-Muconate



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Avery C Vilbert, Wayne S Kontur, Derek Gille, Daniel R Noguera, Timothy J Donohue. Engineering Novosphingobium aromaticivorans to produce cis,cis-muconic acid from biomass aromatics. Applied and environmental microbiology. 2024 Jan; 90(1):e0166023. doi: 10.1128/aem.01660-23. [PMID: 38117061]
  • Sepideh Abbaszadeh, Saeed Yousefinejad, Saeed Jafari, Esmaeel Soleimani. In-syringe ionic liquid-dispersive liquid-liquid microextraction coupled with HPLC for the determination of trans,trans-muconic acid in human urine sample. Journal of separation science. 2021 Aug; 44(16):3126-3136. doi: 10.1002/jssc.202100044. [PMID: 34114310]
  • Marcia Domínguez, Juan F Blandez, Beatriz Lozano-Torres, Cristina de la Torre, Maurizio Licchelli, Carlo Mangano, Valeria Amendola, Félix Sancenón, Ramón Martínez-Máñez. A Nanoprobe Based on Gated Mesoporous Silica Nanoparticles for The Selective and Sensitive Detection of Benzene Metabolite t,t-Muconic Acid in Urine. Chemistry (Weinheim an der Bergstrasse, Germany). 2021 Jan; 27(4):1306-1310. doi: 10.1002/chem.202004272. [PMID: 33064343]
  • Sunisa Chaiklieng, Pornnapa Suggaravetsiri, Herman Autrup. Biomatrix of health risk assessment of benzene-exposed workers at Thai gasoline stations. Journal of occupational health. 2021 Jan; 63(1):e12307. doi: 10.1002/1348-9585.12307. [PMID: 34957641]
  • Barbara Rodrigues Geraldino, Rafaella Ferreira Nascimento Nunes, Juliana Barroso Gomes, Isabela Giardini, Paula Vieira Baptista da Silva, Élida Campos, Katia Soares da Poça, Rocio Hassan, Ubirani Barros Otero, Marcia Sarpa. Analysis of Benzene Exposure in Gas Station Workers Using Trans,Trans-Muconic Acid. International journal of environmental research and public health. 2020 07; 17(15):. doi: 10.3390/ijerph17155295. [PMID: 32717818]
  • Luigi De Maria, Caterina Ledda, Antonio Caputi, Francesca Mansi, Enza Sabrina Silvana Cannone, Stefania Sponselli, Domenica Cavone, Francesco Birtolo, Emanuele Cannizzaro, Giovanni Maria Ferri, Venerando Rapisarda, Luigi Vimercati. Biological Monitoring of Exposure to Benzene in Port Workers. Frontiers in public health. 2020; 8(?):271. doi: 10.3389/fpubh.2020.00271. [PMID: 32766192]
  • Sunisa Chaiklieng, Pornnapa Suggaravetsiri, Norbert Kaminski, Herman Autrup. Factors Affecting Urinary tt-Muconic Acid Detection among Benzene Exposed Workers at Gasoline Stations. International journal of environmental research and public health. 2019 10; 16(21):. doi: 10.3390/ijerph16214209. [PMID: 31671611]
  • Cheng Zhang, Xinglu Pan, Xiaomao Wu, Fengshou Dong, Xingang Liu, Jun Xu, Xiaohu Wu, Ming Li, Yongquan Zheng. Removal of dimethachlon from soils using immobilized cells and enzymes of a novel potential degrader Providencia stuartii JD. Journal of hazardous materials. 2019 10; 378(?):120606. doi: 10.1016/j.jhazmat.2019.04.089. [PMID: 31326122]
  • Karl Forsell, Ingrid Liljelind, Göran Ljungkvist, Rolf Nordlinder, Eva Andersson, Ralph Nilsson. Benzene Exposure and Biomarkers in Alveolar Air and Urine Among Deck Crews on Tankers Transporting Gasoline. Annals of work exposures and health. 2019 10; 63(8):890-897. doi: 10.1093/annweh/wxz055. [PMID: 31382272]
  • Norma Pérez-Herrera, Lorena Díaz de León-Martínez, Rogelio Flores-Ramírez, Olivier Barbier, Manolo Ortega-Romero, Fernando May-Euán, Kelvin Saldaña-Villanueva, Javier Perera-Rios, Francisco Javier Pérez-Vázquez. Evaluation of Benzene Exposure and Early Biomarkers of Kidney Damage in Children Exposed to Solvents Due to Precarious Work in Ticul, Yucatán, México. Annals of global health. 2019 07; 85(1):. doi: 10.5334/aogh.2482. [PMID: 31276330]
  • Mohammad Mehdi Amin, Nasim Rafiei, Parinaz Poursafa, Karim Ebrahimpour, Nafiseh Mozafarian, Bahareh Shoshtari-Yeganeh, Majid Hashemi, Roya Kelishadi. Association of benzene exposure with insulin resistance, SOD, and MDA as markers of oxidative stress in children and adolescents. Environmental science and pollution research international. 2018 Dec; 25(34):34046-34052. doi: 10.1007/s11356-018-3354-7. [PMID: 30280344]
  • Mariella Carrieri, Giovanna Spatari, Giovanna Tranfo, Daniela Sapienza, Maria Luisa Scapellato, Giovanni Battista Bartolucci, Maurizio Manno. Biological monitoring of low level exposure to benzene in an oil refinery: Effect of modulating factors. Toxicology letters. 2018 Dec; 298(?):70-75. doi: 10.1016/j.toxlet.2018.08.001. [PMID: 30086327]
  • Dong-Hee Koh, Mi-Young Lee, Eun-Kyo Chung, Jae-Kil Jang, Dong-Uk Park. Comparison of personal air benzene and urine t,t-muconic acid as a benzene exposure surrogate during turnaround maintenance in petrochemical plants. Industrial health. 2018 Jul; 56(4):346-355. doi: 10.2486/indhealth.2017-0225. [PMID: 29643270]
  • Federica Rota, Anastasia Conti, Laura Campo, Chiara Favero, Laura Cantone, Valeria Motta, Elisa Polledri, Rosa Mercadante, Giorgio Dieci, Valentina Bollati, Silvia Fustinoni. Epigenetic and Transcriptional Modifications in Repetitive Elements in Petrol Station Workers Exposed to Benzene and MTBE. International journal of environmental research and public health. 2018 04; 15(4):. doi: 10.3390/ijerph15040735. [PMID: 29649143]
  • Aymerick Eudes, Roland Berthomieu, Zhangying Hao, Nanxia Zhao, Veronica Teixeira Benites, Edward E K Baidoo, Dominique Loqué. Production of muconic acid in plants. Metabolic engineering. 2018 03; 46(?):13-19. doi: 10.1016/j.ymben.2018.02.002. [PMID: 29474840]
  • Christine Brückner, Mislav Oreb, Gotthard Kunze, Eckhard Boles, Joanna Tripp. An expanded enzyme toolbox for production of cis, cis-muconic acid and other shikimate pathway derivatives in Saccharomyces cerevisiae. FEMS yeast research. 2018 03; 18(2):. doi: 10.1093/femsyr/foy017. [PMID: 29462295]
  • Abdulrahman Bahrami, Farhad Ghamari, Yadollah Yamini, Farshid Ghorbani Shahna, Ali Koolivand. Ion-pair-based hollow-fiber liquid-phase microextraction combined with high-performance liquid chromatography for the simultaneous determination of urinary benzene, toluene, and styrene metabolites. Journal of separation science. 2018 Jan; 41(2):501-508. doi: 10.1002/jssc.201700685. [PMID: 29082608]
  • K McNally, C Sams, G D Loizou, K Jones. Evidence for non-linear metabolism at low benzene exposures? A reanalysis of data. Chemico-biological interactions. 2017 Dec; 278(?):256-268. doi: 10.1016/j.cbi.2017.09.002. [PMID: 28899792]
  • Lucía G Pruneda-Alvarez, Tania Ruíz-Vera, Angeles C Ochoa-Martínez, Iván N Pérez-Maldonado. Urinary trans-trans muconic acid (exposure biomarker to benzene) and hippuric acid (exposure biomarker to toluene) concentrations in Mexican women living in high-risk scenarios of air pollution. Archives of environmental & occupational health. 2017 Nov; 72(6):351-358. doi: 10.1080/19338244.2016.1272539. [PMID: 27982738]
  • M V Rosati, A Sancini, F Tomei, C Sacco, V Traversini, A De Vita, D P De Cesare, G Giammichele, F De Marco, F Pagliara, F Massoni, L Ricci, G Tomei, S Ricci. Correlation between benzene and testosterone in workers exposed to urban pollution. La Clinica terapeutica. 2017 Nov; 168(6):e380-e387. doi: 10.7417/t.2017.2038. [PMID: 29209688]
  • Esmaeel Soleimani, Abdulrahman Bahrami, Abbas Afkhami, Farshid Ghorbani Shahna. Determination of urinary trans,trans-muconic acid using molecularly imprinted polymer in microextraction by packed sorbent followed by liquid chromatography with ultraviolet detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Sep; 1061-1062(?):65-71. doi: 10.1016/j.jchromb.2017.07.008. [PMID: 28710969]
  • Ivan N Perez-Maldonado, Angeles C Ochoa-Martinez, Sandra T Orta-Garcia, Tania Ruiz-Vera, Jose A Varela-Silva. Concentrations of Environmental Chemicals in Urine and Blood Samples of Children from San Luis Potosí, Mexico. Bulletin of environmental contamination and toxicology. 2017 Aug; 99(2):258-263. doi: 10.1007/s00128-017-2130-6. [PMID: 28646397]
  • So Young Kim, Bu-Soon Son, Hee-Jin Park, Seung Ha Oh, Jun Ho Lee, Myung-Hwan Suh, Moo Kyun Park. Impact of environmental volatile organic compounds on otitis media in children: Correlation between exposure and urinary metabolites. International journal of pediatric otorhinolaryngology. 2017 Feb; 93(?):157-162. doi: 10.1016/j.ijporl.2016.12.036. [PMID: 28109489]
  • Wesley Abplanalp, Natasha DeJarnett, Daniel W Riggs, Daniel J Conklin, James P McCracken, Sanjay Srivastava, Zhengzhi Xie, Shesh Rai, Aruni Bhatnagar, Timothy E O'Toole. Benzene exposure is associated with cardiovascular disease risk. PloS one. 2017; 12(9):e0183602. doi: 10.1371/journal.pone.0183602. [PMID: 28886060]
  • Miguel Suástegui, Zengyi Shao. Yeast factories for the production of aromatic compounds: from building blocks to plant secondary metabolites. Journal of industrial microbiology & biotechnology. 2016 11; 43(11):1611-1624. doi: 10.1007/s10295-016-1824-9. [PMID: 27581441]
  • Piero Lovreglio, Denise Doria, Maria Enrica Fracasso, Anna Barbieri, Laura Sabatini, Ignazio Drago, Francesco S Violante, Leonardo Soleo. DNA damage and repair capacity in workers exposed to low concentrations of benzene. Environmental and molecular mutagenesis. 2016 Mar; 57(2):151-8. doi: 10.1002/em.21990. [PMID: 26646167]
  • Dipanjali Majumdar, Chirasree Dutta, Subha Sen. Inhalation exposure or body burden? Better way of estimating risk--An application of PBPK model. Environmental toxicology and pharmacology. 2016 Jan; 41(?):54-61. doi: 10.1016/j.etap.2015.11.004. [PMID: 26650798]
  • Michal Kicinski, Griet Vermeir, Nicolas Van Larebeke, Elly Den Hond, Greet Schoeters, Liesbeth Bruckers, Isabelle Sioen, Esmée Bijnens, Harry A Roels, Willy Baeyens, Mineke K Viaene, Tim S Nawrot. Neurobehavioral performance in adolescents is inversely associated with traffic exposure. Environment international. 2015 Feb; 75(?):136-43. doi: 10.1016/j.envint.2014.10.028. [PMID: 25461422]
  • Elisabetta Chellini, Maria Cristina Fondelli, Maria Teresa Maurello, Gianfranco Sciarra, Maria Cristina Aprea, Giulia Carreras. [Pollutants from a plant which burns toxic waste in the Province of Arezzo (Tuscany Region, Central Italy): human biomonitoring pilot study to evaluate the possible type of environmental exposure]. Epidemiologia e prevenzione. 2015 Jan; 39(1):28-35. doi: NULL. [PMID: 25855544]
  • Piero Lovreglio, Francesca Maffei, Mariella Carrieri, Maria N D'Errico, Ignazio Drago, Patrizia Hrelia, Giovanni B Bartolucci, Leonardo Soleo. Evaluation of chromosome aberration and micronucleus frequencies in blood lymphocytes of workers exposed to low concentrations of benzene. Mutation research. Genetic toxicology and environmental mutagenesis. 2014 Aug; 770(?):55-60. doi: 10.1016/j.mrgentox.2014.04.022. [PMID: 25344164]
  • Gabriela Göethel, Natália Brucker, Angela M Moro, Mariele F Charão, Rafael Fracasso, Anelise Barth, Guilherme Bubols, Juliano Durgante, Sabrina Nascimento, Marília Baierle, Paulo H Saldiva, Solange C Garcia. Evaluation of genotoxicity in workers exposed to benzene and atmospheric pollutants. Mutation research. Genetic toxicology and environmental mutagenesis. 2014 Aug; 770(?):61-5. doi: 10.1016/j.mrgentox.2014.05.008. [PMID: 25344165]
  • Yoon-Hyeong Choi, Jin Hee Kim, Bo-Eun Lee, Yun-Chul Hong. Urinary benzene metabolite and insulin resistance in elderly adults. The Science of the total environment. 2014 Jun; 482-483(?):260-8. doi: 10.1016/j.scitotenv.2014.02.121. [PMID: 24657371]
  • Khadiga S Ibrahim, Nagat M Amer, Elsaid A El-dossuky, Ahmed M Emara, Abd El-Samei M Abd El-Fattah, Eman Mohamed Shahy. Hematological effect of benzene exposure with emphasis of muconic acid as a biomarker. Toxicology and industrial health. 2014 Jun; 30(5):467-74. doi: 10.1177/0748233712458141. [PMID: 22933555]
  • Neng-Zhong Xie, Hong Liang, Ri-Bo Huang, Ping Xu. Biotechnological production of muconic acid: current status and future prospects. Biotechnology advances. 2014 May; 32(3):615-22. doi: 10.1016/j.biotechadv.2014.04.001. [PMID: 24751381]
  • Bidisha Mukherjee, Anindita Dutta, Saswati Chowdhury, Sanghita Roychoudhury, Manas Ranjan Ray. Reduction of DNA mismatch repair protein expression in airway epithelial cells of premenopausal women chronically exposed to biomass smoke. Environmental science and pollution research international. 2014 Feb; 21(4):2826-36. doi: 10.1007/s11356-013-2218-4. [PMID: 24146321]
  • Hualiang Liu, Baoli Zhu, Junwen Shi. [Determination of urinary 8-hydroxy-2'-deoxyguanosine, trans, trans-muconic acid, and S-phenylmercapturic acid by liquid chromatography-mass spectrometry]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2014 Feb; 32(2):142-4. doi: NULL. [PMID: 24630023]
  • Sébastien Gagné. Determination of trans,trans-muconic acid in workers' urine through ultra-performance liquid chromatography coupled to tandem mass spectrometry. Biomedical chromatography : BMC. 2013 May; 27(5):664-8. doi: 10.1002/bmc.2844. [PMID: 23225372]
  • T Tunsaringkarn, S Soogarun, A Palasuwan. Occupational exposure to benzene and changes in hematological parameters and urinary trans, trans-muconic acid. The international journal of occupational and environmental medicine. 2013 Jan; 4(1):45-9. doi: NULL. [PMID: 23279797]
  • Mohana Krishna Reddy Mudiam, Abhishek Chauhan, Krishna P Singh, Shailendra K Gupta, Rajeev Jain, Ratnasekhar Ch, R C Murthy. Determination of t,t-muconic acid in urine samples using a molecular imprinted polymer combined with simultaneous ethyl chloroformate derivatization and pre-concentration by dispersive liquid-liquid microextraction. Analytical and bioanalytical chemistry. 2013 Jan; 405(1):341-9. doi: 10.1007/s00216-012-6474-9. [PMID: 23079953]
  • Carmela Protano, Roberta Andreoli, Paola Manini, Matteo Vitali. Urinary trans, trans-muconic acid and S-phenylmercapturic acid are indicative of exposure to urban benzene pollution during childhood. The Science of the total environment. 2012 Oct; 435-436(?):115-23. doi: 10.1016/j.scitotenv.2012.07.004. [PMID: 22846771]
  • Roberta Andreoli, Carmela Protano, Paola Manini, G De Palma, M Goldoni, Marta Petyx, Bruna Maria Rondinone, M Vitali, A Mutti. Association between environmental exposure to benzene and oxidative damage to nucleic acids in children. La Medicina del lavoro. 2012 Sep; 103(5):324-37. doi: NULL. [PMID: 23077793]
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  • Antonella Mansi, Roberta Bruni, Pasquale Capone, Enrico Paci, Daniela Pigini, Carla Simeoni, Rossella Gnerre, Maddalena Papacchini, Giovanna Tranfo. Low occupational exposure to benzene in a petrochemical plant: modulating effect of genetic polymorphisms and smoking habit on the urinary t,t-MA/SPMA ratio. Toxicology letters. 2012 Aug; 213(1):57-62. doi: 10.1016/j.toxlet.2011.02.001. [PMID: 21300142]
  • Mariella Carrieri, Giovanni Battista Bartolucci, Maria Luisa Scapellato, Giovanna Spatari, Daniela Sapienza, Leonardo Soleo, Piero Lovreglio, Giovanna Tranfo, Maurizio Manno, Andrea Trevisan. Influence of glutathione S-transferases polymorphisms on biological monitoring of exposure to low doses of benzene. Toxicology letters. 2012 Aug; 213(1):63-8. doi: 10.1016/j.toxlet.2011.11.031. [PMID: 22173199]
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  • Ciarrocca Manuela, Tomei Francesco, Caciari Tiziana, Capozzella Assunta, Scimitto Lara, Nardone Nadia, Andreozzi Giorgia, Scala Barbara, Fiaschetti Maria, Cetica Carlotta, Di Giorgio Valeria, Schifano Maria Pia, Tomei Gianfranco, Sancini Angela. Environmental and biological monitoring of benzene in traffic policemen, police drivers and rural outdoor male workers. Journal of environmental monitoring : JEM. 2012 May; 14(6):1542-50. doi: 10.1039/c2em30120b. [PMID: 22555192]
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  • P Lovreglio, A Barbieri, M Carrieri, L Sabatini, M E Fracasso, D Doria, I Drago, A Basso, M N D'Errico, G B Bartolucci, F S Violante, L Soleo. [Lesser validity of urinary benzene than S-phenylmercapturic acid for measuring occupational and environmental exposure to very low concentrations of benzene]. Giornale italiano di medicina del lavoro ed ergonomia. 2011 Apr; 33(2):117-24. doi: NULL. [PMID: 21796919]
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  • Tanasorn Tunsaringkarn, Jamsai Suwansaksri, Suphan Soogarun, Wattasit Siriwong, Anusorn Rungsiyothin, Kalaya Zapuang, Mark Robson. Genotoxic monitoring and benzene exposure assessment of gasoline station workers in metropolitan Bangkok: sister chromatid exchange (SCE) and urinary trans, trans-muconic acid (t,t-MA). Asian Pacific journal of cancer prevention : APJCP. 2011; 12(1):223-7. doi: NULL. [PMID: 21517262]
  • P Lovreglio, M Carrieri, A Barbieri, L Sabatini, M E Fracasso, D Doria, S Iavicoli, I Drago, M N D'errico, M Imbriani, F S Violante, G B Bartolucci, L Soleo. Applicability of urinary benzene to biological monitoring of occupational and environmental exposure to very low benzene concentrations. Giornale italiano di medicina del lavoro ed ergonomia. 2011 Jan; 33(1):41-6. doi: NULL. [PMID: 21417138]
  • Carmela Protano, Maurizio Guidotti, Paola Manini, Marta Petyx, Giuseppe La Torre, Matteo Vitali. Benzene exposure in childhood: Role of living environments and assessment of available tools. Environment international. 2010 Oct; 36(7):779-87. doi: 10.1016/j.envint.2010.06.003. [PMID: 20591482]
  • Caihong Xing, Francesco Marchetti, Guilan Li, Rosana H Weldon, Elaine Kurtovich, Suzanne Young, Thomas E Schmid, Luoping Zhang, Stephen Rappaport, Suramya Waidyanatha, Andrew J Wyrobek, Brenda Eskenazi. Benzene exposure near the U.S. permissible limit is associated with sperm aneuploidy. Environmental health perspectives. 2010 Jun; 118(6):833-9. doi: 10.1289/ehp.0901531. [PMID: 20418200]
  • Paola Manini, Giuseppe De Palma, Roberta Andreoli, Paola Mozzoni, Diana Poli, Matteo Goldoni, Marta Petyx, Pietro Apostoli, Antonio Mutti. Occupational exposure to low levels of benzene: Biomarkers of exposure and nucleic acid oxidation and their modulation by polymorphic xenobiotic metabolizing enzymes. Toxicology letters. 2010 Apr; 193(3):229-35. doi: 10.1016/j.toxlet.2010.01.013. [PMID: 20100551]
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