Monoisobutyl phthalic acid (BioDeep_00000018418)

   

human metabolite Endogenous blood metabolite Industrial Pollutants


代谢物信息卡片


1,2-Benzenedicarboxylic acid, mono(2-methylpropyl) ester

化学式: C12H14O4 (222.0892044)
中文名称: 邻苯二甲酸单异丁酯
谱图信息: 最多检出来源 Homo sapiens(blood) 0.45%

分子结构信息

SMILES: CC(C)COC(=O)C1=CC=CC=C1C(=O)O
InChI: InChI=1S/C12H14O4/c1-8(2)7-16-12(15)10-6-4-3-5-9(10)11(13)14/h3-6,8H,7H2,1-2H3,(H,13,14)

描述信息

Monoisobutyl phthalic acid is a phthalate metabolite that has been found in human meconium and in semen (PMID: 16970347), saliva (PMID: 15995852), and urine (PMID: 15113553). Phthalate esters are a family of multifunctional compounds widely used as plasticizers, solvents, or additives in many diverse products such as poly(vinyl chloride) (PVC) materials, pharmaceuticals and medical devices, pesticides, lubricants, and personal care products. Humans have been exposed to phthalates through the manufacture, ubiquitous use, and disposal of PVC materials and other phthalate-containing products. (PMID: 16970347).
Monoisobutyl phthalic acid is a phthalate metabolite that has been found in human meconium and in semen (PMID: 16970347), saliva (PMID: 15995852), and urine (PMID: 15113553).

同义名列表

15 个代谢物同义名

1,2-Benzenedicarboxylic acid, mono(2-methylpropyl) ester; 1,2-Benzenedicarboxylate, mono(2-methylpropyl) ester; 2-[(2-methylpropoxy)carbonyl]benzoic acid; 2-(Isobutoxycarbonyl)benzoic acid; Phthalic acid, monoisobutyl ester; Isobutyl hydrogen phthalic acid; 2-(Isobutoxycarbonyl)benzoate; Phthalate, monoisobutyl ester; mono-Iso-butyl phthalic acid; Isobutyl Hydrogen Phthalate; Monoisobutyl phthalic acid; mono-Iso-butyl phthalate; Monoisobutyl phthalate; MIBP; MiBPA



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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

  • Kelly K Ferguson, Emma M Rosen, Zaira Rosario, Zlatan Feric, Antonia M Calafat, Thomas F McElrath, Carmen Vélez Vega, José F Cordero, Akram Alshawabkeh, John D Meeker. Environmental phthalate exposure and preterm birth in the PROTECT birth cohort. Environment international. 2019 11; 132(?):105099. doi: 10.1016/j.envint.2019.105099. [PMID: 31430608]
  • Mary V Díaz Santana, Susan E Hankinson, Carol Bigelow, Susan R Sturgeon, R Thomas Zoeller, Lesley Tinker, Jo Ann E Manson, Antonia M Calafat, Jaymie R Meliker, Katherine W Reeves. Urinary concentrations of phthalate biomarkers and weight change among postmenopausal women: a prospective cohort study. Environmental health : a global access science source. 2019 03; 18(1):20. doi: 10.1186/s12940-019-0458-6. [PMID: 30866962]
  • Ronit Machtinger, Jia Zhong, Abdallah Mansur, Michal Adir, Catherine Racowsky, Russ Hauser, Kasey Brennan, Oskar Karlsson, Andrea A Baccarelli. Placental lncRNA Expression Is Associated With Prenatal Phthalate Exposure. Toxicological sciences : an official journal of the Society of Toxicology. 2018 05; 163(1):116-122. doi: 10.1093/toxsci/kfy013. [PMID: 29385630]
  • Munawar Hussain Soomro, Nour Baiz, Claire Philippat, Celine Vernet, Valerie Siroux, Cara Nichole Maesano, Shreosi Sanyal, Remy Slama, Carl-Gustaf Bornehag, Isabella Annesi-Maesano. Prenatal Exposure to Phthalates and the Development of Eczema Phenotypes in Male Children: Results from the EDEN Mother-Child Cohort Study. Environmental health perspectives. 2018 02; 126(2):027002. doi: 10.1289/ehp1829. [PMID: 29398652]
  • Jennifer J Adibi, Jessie P Buckley, Myoung Keun Lee, Paige L Williams, Allan C Just, Yaqi Zhao, Hari K Bhat, Robin M Whyatt. Maternal urinary phthalates and sex-specific placental mRNA levels in an urban birth cohort. Environmental health : a global access science source. 2017 04; 16(1):35. doi: 10.1186/s12940-017-0241-5. [PMID: 28381288]
  • Zana Percy, Yingying Xu, Heidi Sucharew, Jane C Khoury, Antonia M Calafat, Joseph M Braun, Bruce P Lanphear, Aimin Chen, Kimberly Yolton. Gestational exposure to phthalates and gender-related play behaviors in 8-year-old children: an observational study. Environmental health : a global access science source. 2016 08; 15(1):87. doi: 10.1186/s12940-016-0171-7. [PMID: 27527835]
  • Ulla Nordström Joensen, Niels Jørgensen, Michael Meldgaard, Hanne Frederiksen, Anna-Maria Andersson, Torkil Menné, Jeanne Duus Johansen, Berit Christina Carlsen, Steen Stender, Pal Bela Szecsi, Niels Erik Skakkebæk, Ewa Rajpert-De Meyts, Jacob P Thyssen. Associations of filaggrin gene loss-of-function variants with urinary phthalate metabolites and testicular function in young Danish Men. Environmental health perspectives. 2014 Apr; 122(4):345-50. doi: 10.1289/ehp.1306720. [PMID: 24380925]
  • Tamarra James-Todd, Richard Stahlhut, John D Meeker, Sheena-Gail Powell, Russ Hauser, Tianyi Huang, Janet Rich-Edwards. Urinary phthalate metabolite concentrations and diabetes among women in the National Health and Nutrition Examination Survey (NHANES) 2001-2008. Environmental health perspectives. 2012 Sep; 120(9):1307-13. doi: 10.1289/ehp.1104717. [PMID: 22796563]
  • P Monica Lind, Björn Zethelius, Lars Lind. Circulating levels of phthalate metabolites are associated with prevalent diabetes in the elderly. Diabetes care. 2012 Jul; 35(7):1519-24. doi: 10.2337/dc11-2396. [PMID: 22498808]
  • Lena Olsén, Lars Lind, P Monica Lind. Associations between circulating levels of bisphenol A and phthalate metabolites and coronary risk in the elderly. Ecotoxicology and environmental safety. 2012 Jun; 80(?):179-83. doi: 10.1016/j.ecoenv.2012.02.023. [PMID: 22421452]
  • Joe M Braun, Kristen W Smith, Paige L Williams, Antonia M Calafat, Katharine Berry, Shelley Ehrlich, Russ Hauser. Variability of urinary phthalate metabolite and bisphenol A concentrations before and during pregnancy. Environmental health perspectives. 2012 May; 120(5):739-45. doi: 10.1289/ehp.1104139. [PMID: 22262702]
  • P Monica Lind, Vendela Roos, Monika Rönn, Lars Johansson, Håkan Ahlström, Joel Kullberg, Lars Lind. Serum concentrations of phthalate metabolites are related to abdominal fat distribution two years later in elderly women. Environmental health : a global access science source. 2012 Apr; 11(?):21. doi: 10.1186/1476-069x-11-21. [PMID: 22472124]
  • Claire Philippat, Marion Mortamais, Cécile Chevrier, Claire Petit, Antonia M Calafat, Xiaoyun Ye, Manori J Silva, Christian Brambilla, Isabelle Pin, Marie-Aline Charles, Sylvaine Cordier, Rémy Slama. Exposure to phthalates and phenols during pregnancy and offspring size at birth. Environmental health perspectives. 2012 Mar; 120(3):464-70. doi: 10.1289/ehp.1103634. [PMID: 21900077]
  • Robin M Whyatt, Xinhua Liu, Virginia A Rauh, Antonia M Calafat, Allan C Just, Lori Hoepner, Diurka Diaz, James Quinn, Jennifer Adibi, Frederica P Perera, Pam Factor-Litvak. Maternal prenatal urinary phthalate metabolite concentrations and child mental, psychomotor, and behavioral development at 3 years of age. Environmental health perspectives. 2012 Feb; 120(2):290-5. doi: 10.1289/ehp.1103705. [PMID: 21893441]
  • Lena Olsén, Erik Lampa, Detlef A Birkholz, Lars Lind, P Monica Lind. Circulating levels of bisphenol A (BPA) and phthalates in an elderly population in Sweden, based on the Prospective Investigation of the Vasculature in Uppsala Seniors (PIVUS). Ecotoxicology and environmental safety. 2012 Jan; 75(1):242-8. doi: 10.1016/j.ecoenv.2011.09.004. [PMID: 21955883]
  • Thomas Göen, Lorenz Dobler, Jan Koschorreck, Johannes Müller, Gerhard Andreas Wiesmüller, Hans Drexler, Marike Kolossa-Gehring. Trends of the internal phthalate exposure of young adults in Germany--follow-up of a retrospective human biomonitoring study. International journal of hygiene and environmental health. 2011 Dec; 215(1):36-45. doi: 10.1016/j.ijheh.2011.07.011. [PMID: 21889907]
  • John D Meeker, Kelly K Ferguson. Relationship between urinary phthalate and bisphenol A concentrations and serum thyroid measures in U.S. adults and adolescents from the National Health and Nutrition Examination Survey (NHANES) 2007-2008. Environmental health perspectives. 2011 Oct; 119(10):1396-402. doi: 10.1289/ehp.1103582. [PMID: 21749963]
  • P Monica Lind, Lars Lind. Circulating levels of bisphenol A and phthalates are related to carotid atherosclerosis in the elderly. Atherosclerosis. 2011 Sep; 218(1):207-13. doi: 10.1016/j.atherosclerosis.2011.05.001. [PMID: 21621210]
  • Sheela Sathyanarayana, Joe M Braun, Kimberly Yolton, Stacey Liddy, Bruce P Lanphear. Case report: high prenatal bisphenol a exposure and infant neonatal neurobehavior. Environmental health perspectives. 2011 Aug; 119(8):1170-5. doi: 10.1289/ehp.1003064. [PMID: 21524981]
  • Kelly K Ferguson, Rita Loch-Caruso, John D Meeker. Urinary phthalate metabolites in relation to biomarkers of inflammation and oxidative stress: NHANES 1999-2006. Environmental research. 2011 Jul; 111(5):718-26. doi: 10.1016/j.envres.2011.02.002. [PMID: 21349512]
  • Lidia Casas, Mariana F Fernández, Sabrina Llop, Mònica Guxens, Ferran Ballester, Nicolás Olea, Mikel Basterrechea Irurzun, Loreto Santa Marina Rodríguez, Isolina Riaño, Adonina Tardón, Martine Vrijheid, Antonia M Calafat, Jordi Sunyer. Urinary concentrations of phthalates and phenols in a population of Spanish pregnant women and children. Environment international. 2011 Jul; 37(5):858-66. doi: 10.1016/j.envint.2011.02.012. [PMID: 21440302]
  • Michelle Romero-Franco, Raúl U Hernández-Ramírez, Antonia M Calafat, Mariano E Cebrián, Larry L Needham, Susan Teitelbaum, Mary S Wolff, Lizbeth López-Carrillo. Personal care product use and urinary levels of phthalate metabolites in Mexican women. Environment international. 2011 Jul; 37(5):867-71. doi: 10.1016/j.envint.2011.02.014. [PMID: 21429583]
  • Ruthann A Rudel, Janet M Gray, Connie L Engel, Teresa W Rawsthorne, Robin E Dodson, Janet M Ackerman, Jeanne Rizzo, Janet L Nudelman, Julia Green Brody. Food packaging and bisphenol A and bis(2-ethyhexyl) phthalate exposure: findings from a dietary intervention. Environmental health perspectives. 2011 Jul; 119(7):914-20. doi: 10.1289/ehp.1003170. [PMID: 21450549]
  • Justin A Colacino, Amr S Soliman, Antonia M Calafat, Muna S Nahar, Adrienne Van Zomeren-Dohm, Ahmed Hablas, Ibrahim A Seifeldin, Laura S Rozek, Dana C Dolinoy. Exposure to phthalates among premenstrual girls from rural and urban Gharbiah, Egypt: a pilot exposure assessment study. Environmental health : a global access science source. 2011 May; 10(?):40. doi: 10.1186/1476-069x-10-40. [PMID: 21575223]
  • Malene Boas, Hanne Frederiksen, Ulla Feldt-Rasmussen, Niels E Skakkebæk, Laszlo Hegedüs, Linda Hilsted, Anders Juul, Katharina M Main. Childhood exposure to phthalates: associations with thyroid function, insulin-like growth factor I, and growth. Environmental health perspectives. 2010 Oct; 118(10):1458-64. doi: 10.1289/ehp.0901331. [PMID: 20621847]
  • Hanne Frederiksen, Niels Jørgensen, Anna-Maria Andersson. Correlations between phthalate metabolites in urine, serum, and seminal plasma from young Danish men determined by isotope dilution liquid chromatography tandem mass spectrometry. Journal of analytical toxicology. 2010 Sep; 34(7):400-10. doi: 10.1093/jat/34.7.400. [PMID: 20822678]
  • Justin A Colacino, T Robert Harris, Arnold Schecter. Dietary intake is associated with phthalate body burden in a nationally representative sample. Environmental health perspectives. 2010 Jul; 118(7):998-1003. doi: 10.1289/ehp.0901712. [PMID: 20392686]
  • Jennifer Weuve, Russ Hauser, Antonia M Calafat, Stacey A Missmer, Lauren A Wise. Association of exposure to phthalates with endometriosis and uterine leiomyomata: findings from NHANES, 1999-2004. Environmental health perspectives. 2010 Jun; 118(6):825-32. doi: 10.1289/ehp.0901543. [PMID: 20185384]
  • S H Swan, F Liu, M Hines, R L Kruse, C Wang, J B Redmon, A Sparks, B Weiss. Prenatal phthalate exposure and reduced masculine play in boys. International journal of andrology. 2010 Apr; 33(2):259-69. doi: 10.1111/j.1365-2605.2009.01019.x. [PMID: 19919614]
  • Lizbeth López-Carrillo, Raúl U Hernández-Ramírez, Antonia M Calafat, Luisa Torres-Sánchez, Marcia Galván-Portillo, Larry L Needham, Rubén Ruiz-Ramos, Mariano E Cebrián. Exposure to phthalates and breast cancer risk in northern Mexico. Environmental health perspectives. 2010 Apr; 118(4):539-44. doi: 10.1289/ehp.0901091. [PMID: 20368132]
  • Jennifer J Adibi, Robin M Whyatt, Russ Hauser, Hari K Bhat, Barbara J Davis, Antonia M Calafat, Lori A Hoepner, Frederica P Perera, Deliang Tang, Paige L Williams. Transcriptional biomarkers of steroidogenesis and trophoblast differentiation in the placenta in relation to prenatal phthalate exposure. Environmental health perspectives. 2010 Feb; 118(2):291-6. doi: 10.1289/ehp.0900788. [PMID: 20123604]
  • John D Meeker, Howard Hu, David E Cantonwine, Hector Lamadrid-Figueroa, Antonia M Calafat, Adrienne S Ettinger, Mauricio Hernandez-Avila, Rita Loch-Caruso, Martha María Téllez-Rojo. Urinary phthalate metabolites in relation to preterm birth in Mexico city. Environmental health perspectives. 2009 Oct; 117(10):1587-92. doi: 10.1289/ehp.0800522. [PMID: 20019910]
  • Xibiao Ye, Frank H Pierik, Jürgen Angerer, Helle Margrete Meltzer, Vincent W V Jaddoe, Henning Tiemeier, Jane A Hoppin, Matthew P Longnecker. Levels of metabolites of organophosphate pesticides, phthalates, and bisphenol A in pooled urine specimens from pregnant women participating in the Norwegian Mother and Child Cohort Study (MoBa). International journal of hygiene and environmental health. 2009 Sep; 212(5):481-91. doi: 10.1016/j.ijheh.2009.03.004. [PMID: 19394271]
  • Tamar Berman, Drorit Hochner-Celnikier, Antonia M Calafat, Larry L Needham, Yona Amitai, Uri Wormser, Elihu Richter. Phthalate exposure among pregnant women in Jerusalem, Israel: results of a pilot study. Environment international. 2009 Feb; 35(2):353-7. doi: 10.1016/j.envint.2008.08.010. [PMID: 18824263]
  • Sonia Hernández-Díaz, Allen A Mitchell, Katherine E Kelley, Antonia M Calafat, Russ Hauser. Medications as a potential source of exposure to phthalates in the U.S. population. Environmental health perspectives. 2009 Feb; 117(2):185-9. doi: 10.1289/ehp.11766. [PMID: 19270786]
  • Erin P Hines, Antonia M Calafat, Manori J Silva, Pauline Mendola, Suzanne E Fenton. Concentrations of phthalate metabolites in milk, urine, saliva, and Serum of lactating North Carolina women. Environmental health perspectives. 2009 Jan; 117(1):86-92. doi: 10.1289/ehp.11610. [PMID: 19165392]
  • S Sathyanarayana, A M Calafat, F Liu, S H Swan. Maternal and infant urinary phthalate metabolite concentrations: are they related?. Environmental research. 2008 Nov; 108(3):413-8. doi: 10.1016/j.envres.2008.07.002. [PMID: 18715556]
  • Xibiao Ye, Frank H Pierik, Russ Hauser, Susan Duty, Jürgen Angerer, Melissa M Park, Alex Burdorf, Albert Hofman, Vincent W V Jaddoe, Johan P Mackenbach, Eric A P Steegers, Henning Tiemeier, Matthew P Longnecker. Urinary metabolite concentrations of organophosphorous pesticides, bisphenol A, and phthalates among pregnant women in Rotterdam, the Netherlands: the Generation R study. Environmental research. 2008 Oct; 108(2):260-7. doi: 10.1016/j.envres.2008.07.014. [PMID: 18774129]
  • Elizabeth E Hatch, Jessica W Nelson, M Mustafa Qureshi, Janice Weinberg, Lynn L Moore, Martha Singer, Thomas F Webster. Association of urinary phthalate metabolite concentrations with body mass index and waist circumference: a cross-sectional study of NHANES data, 1999-2002. Environmental health : a global access science source. 2008 Jun; 7(?):27. doi: 10.1186/1476-069x-7-27. [PMID: 18522739]
  • Jennifer J Adibi, Robin M Whyatt, Paige L Williams, Antonia M Calafat, David Camann, Robert Herrick, Heather Nelson, Hari K Bhat, Frederica P Perera, Manori J Silva, Russ Hauser. Characterization of phthalate exposure among pregnant women assessed by repeat air and urine samples. Environmental health perspectives. 2008 Apr; 116(4):467-73. doi: 10.1289/ehp.10749. [PMID: 18414628]
  • Johan Högberg, Annika Hanberg, Marika Berglund, Staffan Skerfving, Mikael Remberger, Antonia M Calafat, Agneta Falk Filipsson, Bo Jansson, Niklas Johansson, Malin Appelgren, Helen Håkansson. Phthalate diesters and their metabolites in human breast milk, blood or serum, and urine as biomarkers of exposure in vulnerable populations. Environmental health perspectives. 2008 Mar; 116(3):334-9. doi: 10.1289/ehp.10788. [PMID: 18335100]
  • Sheela Sathyanarayana, Catherine J Karr, Paula Lozano, Elizabeth Brown, Antonia M Calafat, Fan Liu, Shanna H Swan. Baby care products: possible sources of infant phthalate exposure. Pediatrics. 2008 Feb; 121(2):e260-8. doi: 10.1542/peds.2006-3766. [PMID: 18245401]
  • Richard W Stahlhut, Edwin van Wijngaarden, Timothy D Dye, Stephen Cook, Shanna H Swan. Concentrations of urinary phthalate metabolites are associated with increased waist circumference and insulin resistance in adult U.S. males. Environmental health perspectives. 2007 Jun; 115(6):876-82. doi: 10.1289/ehp.9882. [PMID: 17589594]
  • Hermann Fromme, Gabriele Bolte, Holger M Koch, Jürgen Angerer, Sigrun Boehmer, Hans Drexler, Richard Mayer, Bernhard Liebl. Occurrence and daily variation of phthalate metabolites in the urine of an adult population. International journal of hygiene and environmental health. 2007 Jan; 210(1):21-33. doi: 10.1016/j.ijheh.2006.09.005. [PMID: 17182278]
  • Jennifer Weuve, Brisa N Sánchez, Antonia M Calafat, Ted Schettler, Ronald A Green, Howard Hu, Russ Hauser. Exposure to phthalates in neonatal intensive care unit infants: urinary concentrations of monoesters and oxidative metabolites. Environmental health perspectives. 2006 Sep; 114(9):1424-31. doi: 10.1289/ehp.8926. [PMID: 16966100]
  • G Lottrup, A-M Andersson, H Leffers, G K Mortensen, J Toppari, N E Skakkebaek, K M Main. Possible impact of phthalates on infant reproductive health. International journal of andrology. 2006 Feb; 29(1):172-80; discussion 181. doi: 10.1111/j.1365-2605.2005.00642.x. [PMID: 16466537]
  • Manori J Silva, John A Reidy, Ella Samandar, Arnetra R Herbert, Larry L Needham, Antonia M Calafat. Detection of phthalate metabolites in human saliva. Archives of toxicology. 2005 Nov; 79(11):647-52. doi: 10.1007/s00204-005-0674-4. [PMID: 15995852]
  • Manori J Silva, Ella Samandar, James L Preau, John A Reidy, Larry L Needham, Antonia Calafat. Automated solid-phase extraction and quantitative analysis of 14 phthalate metabolites in human serum using isotope dilution-high-performance liquid chromatography-tandem mass spectrometry. Journal of analytical toxicology. 2005 Nov; 29(8):819-24. doi: 10.1093/jat/29.8.819. [PMID: 16374941]
  • Susan M Duty, Robin M Ackerman, Antonia M Calafat, Russ Hauser. Personal care product use predicts urinary concentrations of some phthalate monoesters. Environmental health perspectives. 2005 Nov; 113(11):1530-5. doi: 10.1289/ehp.8083. [PMID: 16263507]
  • Shanna H Swan, Katharina M Main, Fan Liu, Sara L Stewart, Robin L Kruse, Antonia M Calafat, Catherine S Mao, J Bruce Redmon, Christine L Ternand, Shannon Sullivan, J Lynn Teague. Decrease in anogenital distance among male infants with prenatal phthalate exposure. Environmental health perspectives. 2005 Aug; 113(8):1056-61. doi: 10.1289/ehp.8100. [PMID: 16079079]
  • Manori J Silva, A Ryan Slakman, John A Reidy, James L Preau, Arnetra R Herbert, Ella Samandar, Larry L Needham, Antonia M Calafat. Analysis of human urine for fifteen phthalate metabolites using automated solid-phase extraction. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Jun; 805(1):161-7. doi: 10.1016/j.jchromb.2004.02.038. [PMID: 15113553]