P-Octylphenol (BioDeep_00001873728)
Main id: BioDeep_00000003638
代谢物信息卡片
4-N-Octylphenol
化学式: C14H22O (206.1671)
中文名称: 4-辛基苯酚
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCCCCC1=CC=C(C=C1)O
InChI: InChI=1S/C14H22O/c1-2-3-4-5-6-7-8-13-9-11-14(15)12-10-13/h9-12,15H,2-8H2,1H3
描述信息
A member of the class of phenols that is phenol which is substituted at the para- position by an octyl group.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
同义名列表
5 个代谢物同义名
4-N-Octylphenol; P-Octylphenol; 4-OCTYLPHENOL; 4-Octylphenol; 4-Octylphenol
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:34432
- KEGG: C14132
- PubChem: 15730
- ChEMBL: CHEMBL195437
- CAS: 1219794-55-4
- CAS: 71902-25-5
- CAS: 1806-26-4
- MetaboLights: MTBLC34432
- PubChem: 7846946
- NIKKAJI: J127.127J
- KNApSAcK: 34432
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)
0 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
- Yang Xu, Seung Hyun Park, Myung Chan Gye. Head dysgenesis and disruption of cranial neural crest stem cells behaviour by 4-octylphenol in fire-bellied toad Bombina orientalis embryos.
Environmental pollution (Barking, Essex : 1987).
2023 Oct; 338(?):122697. doi:
10.1016/j.envpol.2023.122697. [PMID: 37804908] - Guowen Zhang, Na Li, Ying Zhang, Junhui Pan, Deming Gong. Binding mechanism of 4-octylphenol with human serum albumin: Spectroscopic investigations, molecular docking and dynamics simulation.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2021 Jul; 255(?):119662. doi:
10.1016/j.saa.2021.119662. [PMID: 33780895] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Yang Xu, Ji Hyun Jang, Myung Chan Gye. 4-Octylphenol induces developmental abnormalities and interferes the differentiation of neural crest cells in Xenopus laevis embryos.
Environmental pollution (Barking, Essex : 1987).
2021 Apr; 274(?):116560. doi:
10.1016/j.envpol.2021.116560. [PMID: 33524650] - Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964. [PMID: 31515284] - Muhammad Ashfaq, Yan Li, Yuwen Wang, Dan Qin, Muhammad Saif Ur Rehman, Azhar Rashid, Chang-Ping Yu, Qian Sun. Monitoring and mass balance analysis of endocrine disrupting compounds and their transformation products in an anaerobic-anoxic-oxic wastewater treatment system in Xiamen, China.
Chemosphere.
2018 Aug; 204(?):170-177. doi:
10.1016/j.chemosphere.2018.04.028. [PMID: 29655110] - Weiyue Hu, Minjian Chen, Juan Ji, Yufeng Qin, Feng Zhang, Miaofei Xu, Wei Wu, Guizhen Du, Di Wu, Xiumei Han, Li Jin, Yankai Xia, Chuncheng Lu, Xinru Wang. Interaction between Y chromosome haplogroup O3* and 4-n-octylphenol exposure reduces the susceptibility to spermatogenic impairment in Han Chinese.
Ecotoxicology and environmental safety.
2017 Oct; 144(?):450-455. doi:
10.1016/j.ecoenv.2017.06.038. [PMID: 28667856] - Hyejin Park, Kisok Kim. Urinary Levels of 4-Nonylphenol and 4-t-Octylphenol in a Representative Sample of the Korean Adult Population.
International journal of environmental research and public health.
2017 08; 14(8):. doi:
10.3390/ijerph14080932. [PMID: 28820486] - Lisa A Hamilton, Louis A Tremblay, Grant L Northcott, Michael Boake, Richard P Lim. The impact of variations of influent loading on the efficacy of an advanced tertiary sewage treatment plant to remove endocrine disrupting chemicals.
The Science of the total environment.
2016 08; 560-561(?):101-9. doi:
10.1016/j.scitotenv.2016.04.003. [PMID: 27096490] - Pinggu Wu, Liqun Zhang, Dajin Yang, Jing Zhang, Zhengyan Hu, Liyuan Wang, Bingjie Ma. Isotope dilution gas chromatography with mass spectrometry for the analysis of 4-octyl phenol, 4-nonylphenol, and bisphenol A in vegetable oils.
Journal of separation science.
2016 Mar; 39(5):904-9. doi:
10.1002/jssc.201500887. [PMID: 26698324] - N Salgueiro-González, I Turnes-Carou, L Viñas-Diéguez, S Muniategui-Lorenzo, P López-Mahía, D Prada-Rodríguez. Occurrence of endocrine disrupting compounds in five estuaries of the northwest coast of Spain: Ecological and human health impact.
Chemosphere.
2015 Jul; 131(?):241-7. doi:
10.1016/j.chemosphere.2014.12.062. [PMID: 25648473] - Huixiao Hong, William S Branham, Hui Wen Ng, Carrie L Moland, Stacey L Dial, Hong Fang, Roger Perkins, Daniel Sheehan, Weida Tong. Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein.
Toxicological sciences : an official journal of the Society of Toxicology.
2015 Feb; 143(2):333-48. doi:
10.1093/toxsci/kfu231. [PMID: 25349334] - Minjian Chen, Rong Tang, Guangbo Fu, Bin Xu, Pengfei Zhu, Shanlei Qiao, Xiaojiao Chen, Bo Xu, Yufeng Qin, Chuncheng Lu, Bo Hang, Yankai Xia, Xinru Wang. Association of exposure to phenols and idiopathic male infertility.
Journal of hazardous materials.
2013 Apr; 250-251(?):115-21. doi:
10.1016/j.jhazmat.2013.01.061. [PMID: 23435201] - Yufeng Qin, Minjian Chen, Wei Wu, Bin Xu, Rong Tang, Xiaojiao Chen, Guizhen Du, Chuncheng Lu, John D Meeker, Zuomin Zhou, Yankai Xia, Xinru Wang. Interactions between urinary 4-tert-octylphenol levels and metabolism enzyme gene variants on idiopathic male infertility.
PloS one.
2013; 8(3):e59398. doi:
10.1371/journal.pone.0059398. [PMID: 23555028] - M T Llorente, J M Parra, S Sánchez-Fortún, A Castaño. Cytotoxicity and genotoxicity of sewage treatment plant effluents in rainbow trout cells (RTG-2).
Water research.
2012 Dec; 46(19):6351-8. doi:
10.1016/j.watres.2012.08.039. [PMID: 23022116] - Huixiao Hong, William S Branham, Stacey L Dial, Carrie L Moland, Hong Fang, Jie Shen, Roger Perkins, Daniel Sheehan, Weida Tong. Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities.
Chemical research in toxicology.
2012 Nov; 25(11):2553-66. doi:
10.1021/tx3003406. [PMID: 23013281] - Minjian Chen, Pengfei Zhu, Bin Xu, Rencheng Zhao, Shanlei Qiao, Xiaojiao Chen, Rong Tang, Di Wu, Ling Song, Shoulin Wang, Yankai Xia, Xinru Wang. Determination of nine environmental phenols in urine by ultra-high-performance liquid chromatography-tandem mass spectrometry.
Journal of analytical toxicology.
2012 Nov; 36(9):608-15. doi:
10.1093/jat/bks072. [PMID: 22989423] - Tanausú Vega-Morales, Rayco Guedes-Alonso, Zoraida Sosa-Ferrera, José Juan Santana-Rodríguez. Determination and assessment of estradiol-mimicking compounds in the dissolved and particulate phases of wastewater treatment plant samples.
Journal of AOAC International.
2012 Jul; 95(4):1195-204. doi:
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Aquatic toxicology (Amsterdam, Netherlands).
2012 Jun; 114-115(?):1-13. doi:
10.1016/j.aquatox.2012.02.005. [PMID: 22410082] - Alexandros G Asimakopoulos, Nikolaos S Thomaidis, Michael A Koupparis. Recent trends in biomonitoring of bisphenol A, 4-t-octylphenol, and 4-nonylphenol.
Toxicology letters.
2012 Apr; 210(2):141-54. doi:
10.1016/j.toxlet.2011.07.032. [PMID: 21888958] - Qian Sun, Yan Li, Pei-Hsin Chou, Po-Yi Peng, Chang-Ping Yu. Transformation of bisphenol A and alkylphenols by ammonia-oxidizing bacteria through nitration.
Environmental science & technology.
2012 Apr; 46(8):4442-8. doi:
10.1021/es204424t. [PMID: 22435736] - Philipp Hohenblum, Philipp Steinbichl, Wolfgang Raffesberg, Stefan Weiss, Wolfgang Moche, Birgit Vallant, Sigrid Scharf, Daniela Haluza, Hanns Moshammer, Michael Kundi, Brigitte Piegler, Peter Wallner, Hans-Peter Hutter. Pollution gets personal! A first population-based human biomonitoring study in Austria.
International journal of hygiene and environmental health.
2012 Feb; 215(2):176-9. doi:
10.1016/j.ijheh.2011.08.015. [PMID: 21968335] - Satyanarayanan Senthil Kumaran, Chokkalingam Kavitha, Mathan Ramesh, Tamara Grummt. Toxicity studies of nonylphenol and octylphenol: hormonal, hematological and biochemical effects in Clarias gariepinus.
Journal of applied toxicology : JAT.
2011 Nov; 31(8):752-61. doi:
10.1002/jat.1629. [PMID: 21404308] - Ting-ting Li, Liang-zhi Xu, Yong-heng Chen, Hong-mei Deng, Chun-ying Liang, Ying Liu, Xiao-fang Liu, Jing Zhang, De-ying Kang, Dong-sheng Qiu, Dai-wen Han, Rong Hu. [Effects of eight environmental endocrine disruptors on insulin resistance in patients with polycystic ovary syndrome: a preliminary investigation].
Nan fang yi ke da xue xue bao = Journal of Southern Medical University.
2011 Oct; 31(10):1753-6. doi:
NULL. [PMID: 22027783] - T Vega-Morales, Z Sosa-Ferrera, J J Santana-Rodríguez. Determination of various estradiol mimicking-compounds in sewage sludge by the combination of microwave-assisted extraction and LC-MS/MS.
Talanta.
2011 Sep; 85(4):1825-34. doi:
10.1016/j.talanta.2011.07.051. [PMID: 21872026] - Yumin Niu, Jing Zhang, Yongning Wu, Bing Shao. Simultaneous determination of bisphenol A and alkylphenol in plant oil by gel permeation chromatography and isotopic dilution liquid chromatography-tandem mass spectrometry.
Journal of chromatography. A.
2011 Aug; 1218(31):5248-53. doi:
10.1016/j.chroma.2011.06.005. [PMID: 21708384] - Malgorzata Kotula-Balak, Ewa Pochec, Anna Hejmej, Malgorzata Duda, Barbara Bilinska. Octylphenol affects morphology and steroidogenesis in mouse tumor Leydig cells.
Toxicology in vitro : an international journal published in association with BIBRA.
2011 Aug; 25(5):1018-26. doi:
10.1016/j.tiv.2011.03.021. [PMID: 21463676] - Aslı Korkmaz, Müfide Aydoğan, Dürdane Kolankaya, Nurhayat Barlas. Vitamin C coadministration augments bisphenol A, nonylphenol, and octylphenol induced oxidative damage on kidney of rats.
Environmental toxicology.
2011 Aug; 26(4):325-37. doi:
10.1002/tox.20556. [PMID: 20014407] - Xian Zhang, Yajie Gao, Qingzhao Li, Guoxin Li, Qinghai Guo, Changzhou Yan. Estrogenic compounds and estrogenicity in surface water, sediments, and organisms from Yundang Lagoon in Xiamen, China.
Archives of environmental contamination and toxicology.
2011 Jul; 61(1):93-100. doi:
10.1007/s00244-010-9588-0. [PMID: 20725718] - Zhaohan Zhang, Yujie Feng, Peng Gao, Ce Wang, Nanqi Ren. Occurrence and removal efficiencies of eight EDCs and estrogenicity in a STP.
Journal of environmental monitoring : JEM.
2011 May; 13(5):1366-73. doi:
10.1039/c0em00597e. [PMID: 21390396] - Enzhong Li, Yuping Guo, Qianji Ning, Shiqing Zhang, Dexue Li. Research for the effect of octylphenol on spermatogenesis and proteomic analysis in octylphenol-treated mice testes.
Cell biology international.
2011 Apr; 35(4):305-9. doi:
10.1042/cbi20100566. [PMID: 21108603] - S B Sainath, R Meena, C H Venkata Suneel Kumar, P Kalapana, K N Swetha, N Syamala Devi, P Sreenivasula Reddy. Embryonic exposure to octylphenol induces changes in testosterone levels and disrupts reproductive efficiency in rats at their adulthood.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Apr; 49(4):983-90. doi:
10.1016/j.fct.2011.01.004. [PMID: 21219960] - Xiao Jing, Shao Bing, Wu Xiaoyan, Sun Xiaojie, Wu Yongning. A study on bisphenol A, nonylphenol, and octylphenol in human urine amples detected by SPE-UPLC-MS.
Biomedical and environmental sciences : BES.
2011 Feb; 24(1):40-6. doi:
10.3967/0895-3988.2011.01.005. [PMID: 21440838] - Griselda Genovese, Rodrigo Da Cuña, David W Towle, María C Maggese, Fabiana Lo Nostro. Early expression of zona pellucida proteins under octylphenol exposure in Cichlasoma dimerus (Perciformes, Cichlidae).
Aquatic toxicology (Amsterdam, Netherlands).
2011 Jan; 101(1):175-85. doi:
10.1016/j.aquatox.2010.09.017. [PMID: 21035200] - Chunying Wu, Wenchao Xue, Haidong Zhou, Xia Huang, Xianghua Wen. Removal of endocrine disrupting chemicals in a large scale membrane bioreactor plant combined with anaerobic-anoxic-oxic process for municipal wastewater reclamation.
Water science and technology : a journal of the International Association on Water Pollution Research.
2011; 64(7):1511-8. doi:
10.2166/wst.2011.140. [PMID: 22179650] - Takeshi Matsui, Yuki Nomura, Mai Takano, Sofue Imai, Hideki Nakayama, Hitoshi Miyasaka, Hiroshi Okuhata, Satoshi Tanaka, Hideyuki Matsuura, Kazuo Harada, Takeshi Bamba, Kazumasa Hirata, Ko Kato. Molecular cloning and partial characterization of a peroxidase gene expressed in the roots of Portulaca oleracea cv., one potentially useful in the remediation of phenolic pollutants.
Bioscience, biotechnology, and biochemistry.
2011; 75(5):882-90. doi:
10.1271/bbb.100823. [PMID: 21597193] - Zhen Mao, Yuan-Lin Zheng, Yan-Qiu Zhang. Behavioral impairment and oxidative damage induced by chronic application of nonylphenol.
International journal of molecular sciences.
2010 Dec; 12(1):114-27. doi:
10.3390/ijms12010114. [PMID: 21339980] - T Vega-Morales, Z Sosa-Ferrera, J J Santana-Rodríguez. Determination of alkylphenol polyethoxylates, bisphenol-A, 17α-ethynylestradiol and 17β-estradiol and its metabolites in sewage samples by SPE and LC/MS/MS.
Journal of hazardous materials.
2010 Nov; 183(1-3):701-11. doi:
10.1016/j.jhazmat.2010.07.083. [PMID: 20724070] - Asli Korkmaz, Müfide Aydoğan Ahbab, Dürdane Kolankaya, Nurhayat Barlas. Influence of vitamin C on bisphenol A, nonylphenol and octylphenol induced oxidative damages in liver of male rats.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2010 Oct; 48(10):2865-71. doi:
10.1016/j.fct.2010.07.019. [PMID: 20643179] - Jaime Mendiola, Niels Jørgensen, Anna-Maria Andersson, Antonia M Calafat, Xiaoyun Ye, J Bruce Redmon, Erma Z Drobnis, Christina Wang, Amy Sparks, Sally W Thurston, Fan Liu, Shanna H Swan. Are environmental levels of bisphenol a associated with reproductive function in fertile men?.
Environmental health perspectives.
2010 Sep; 118(9):1286-91. doi:
10.1289/ehp.1002037. [PMID: 20494855] - Ase Jespersen, Tina H Rasmussen, Majken Hirche, Kristine J K Sørensen, Bodil Korsgaard. Effects of exposure to the xenoestrogen octylphenol and subsequent transfer to clean water on liver and gonad ultrastructure during early development of Zoarces viviparus embryos.
Journal of experimental zoology. Part A, Ecological genetics and physiology.
2010 Aug; 313(7):399-409. doi:
10.1002/jez.609. [PMID: 20623797] - Laura N Vandenberg, Ibrahim Chahoud, Jerrold J Heindel, Vasantha Padmanabhan, Francisco J R Paumgartten, Gilbert Schoenfelder. Urinary, circulating, and tissue biomonitoring studies indicate widespread exposure to bisphenol A.
Environmental health perspectives.
2010 Aug; 118(8):1055-70. doi:
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Drug and chemical toxicology.
2010 Apr; 33(2):193-203. doi:
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PloS one.
2010 Mar; 5(3):e9678. doi:
10.1371/journal.pone.0009678. [PMID: 20300630] - Jorge Eduardo Loyo-Rosales, Clifford Paul Rice, Alba Torrents. Fate and distribution of the octyl- and nonylphenol ethoxylates and some carboxylated transformation products in the Back River, Maryland.
Journal of environmental monitoring : JEM.
2010 Mar; 12(3):614-21. doi:
10.1039/b913229e. [PMID: 20445849] - Anastasia Arditsoglou, Dimitra Voutsa. Partitioning of endocrine disrupting compounds in inland waters and wastewaters discharged into the coastal area of Thessaloniki, Northern Greece.
Environmental science and pollution research international.
2010 Mar; 17(3):529-38. doi:
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Environmental health perspectives.
2010 Feb; 118(2):273-7. doi:
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Journal of chromatography. A.
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Wei sheng yan jiu = Journal of hygiene research.
2010 Jan; 39(1):9-12. doi:
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Aquatic toxicology (Amsterdam, Netherlands).
2009 May; 92(3):155-67. doi:
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International journal of molecular sciences.
2009 Apr; 10(4):1773-1787. doi:
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Environmental health perspectives.
2009 Apr; 117(4):645-52. doi:
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Water research.
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European journal of epidemiology.
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Chemosphere.
2008 Dec; 73(11):1716-23. doi:
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Toxicology.
2008 Jul; 249(1):35-9. doi:
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Huan jing ke xue= Huanjing kexue.
2008 Jul; 29(7):2005-11. doi:
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Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2008 Jul; 148(1):87-93. doi:
10.1016/j.cbpc.2008.03.012. [PMID: 18450520] - Raquel Céspedes, Sílvia Lacorte, Antonio Ginebreda, Damià Barceló. Occurrence and fate of alkylphenols and alkylphenol ethoxylates in sewage treatment plants and impact on receiving waters along the Ter River (Catalonia, NE Spain).
Environmental pollution (Barking, Essex : 1987).
2008 May; 153(2):384-92. doi:
10.1016/j.envpol.2007.08.026. [PMID: 18262317] - Hong Sun, Xiao-Lin Xu, Jian-Hua Qu, Xia Hong, Yu-Bang Wang, Li-Chun Xu, Xin-Ru Wang. 4-Alkylphenols and related chemicals show similar effect on the function of human and rat estrogen receptor alpha in reporter gene assay.
Chemosphere.
2008 Mar; 71(3):582-8. doi:
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Environmental pollution (Barking, Essex : 1987).
2008 Mar; 152(2):476-83. doi:
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Environmental toxicology and pharmacology.
2008 Jan; 25(1):20-6. doi:
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2007 Dec; 115 Suppl 1(?):21-7. doi:
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