Alfatradiol (BioDeep_00000409850)

PANOMIX_OTCML-2023 BioNovoGene_Lab2019

代谢物信息卡片

17-alpha-Estradiol

化学式: C18H24O2 (272.17762039999997)
中文名称: α-雌二醇
谱图信息: 最多检出来源 Homo sapiens(blood) 11.29%

分子结构信息

SMILES: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)O
InChI: InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D065088 - Steroid Synthesis Inhibitors
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
D004791 - Enzyme Inhibitors > D065088 - Steroid Synthesis Inhibitors > D058891 - 5-alpha Reductase Inhibitors
C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1740 - Aromatase Inhibitor
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist
D003879 - Dermatologic Agents
CONFIDENCE standard compound; INTERNAL_ID 2817
Alpha-Estradiol is a weak estrogen and a 5α-reductase inhibitor which is used as a topical medication in the treatment of androgenic alopecia.

同义名列表

6 个代谢物同义名

α-Estradiol; Alfatradiol; 17-alpha-Estradiol; Epiestradiol; Epiestrol; Alpha-Estradiol

数据库引用编号

18 个数据库交叉引用编号

ChEBI: CHEBI:17160
KEGG: C02537
KEGGdrug: D07121
PubChem: 68570
ChEMBL: CHEMBL286452
CAS: 57-91-0
MoNA: AU281706
MoNA: AU281705
MoNA: AU281704
MoNA: AU281703
MoNA: AU281702
MoNA: AU281701
PubChem: 5544
LipidMAPS: LMST02010029
3DMET: B01587
NIKKAJI: J4.586A
medchemexpress: HY-B0141A
BioNovoGene_Lab2019: BioNovoGene_Lab2019-575

分类词条

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

Hong-Bing Zhang, Nai-Xue Sun, Hou-Cheng Liang, Xiang-Hua Xiao, Xian-Ning Liu, Ya-Ni Wang. 17-Alpha-estradiol ameliorating oxygen-induced retinopathy in a murine model. Japanese journal of ophthalmology. 2012 Jul; 56(4):407-15. doi: 10.1007/s10384-012-0136-5. [PMID: 22581453]
Guo-Chian Li, Da-Rong Wang, Wenlung Chen, Der-Lii M Tzou. Solid-state NMR analysis of steroidal conformation of 17α- and 17β-estradiol in the absence and presence of lipid environment. Steroids. 2012 Feb; 77(3):185-92. doi: 10.1016/j.steroids.2011.11.004. [PMID: 22155023]
Charles E Wood. Fetal hypothalamus-pituitary-adrenal responses to estradiol sulfate. Endocrinology. 2011 Dec; 152(12):4966-73. doi: 10.1210/en.2011-0284. [PMID: 21952234]
Li-Qun Cai, Jingjing Cai, Wendy Wu, Yuan-Shan Zhu. 17α-Estradiol and genistein inhibit high fat diet induced prostate gene expression and prostate growth in the rat. The Journal of urology. 2011 Oct; 186(4):1489-96. doi: 10.1016/j.juro.2011.05.041. [PMID: 21855913]
Anna Z Pollack, Enrique F Schisterman, Lynn R Goldman, Sunni L Mumford, Paul S Albert, Robert L Jones, Jean Wactawski-Wende. Cadmium, lead, and mercury in relation to reproductive hormones and anovulation in premenopausal women. Environmental health perspectives. 2011 Aug; 119(8):1156-61. doi: 10.1289/ehp.1003284. [PMID: 21543284]
Martin Hansen, Naja W Jacobsen, Frederik K Nielsen, Erland Björklund, Bjarne Styrishave, Bent Halling-Sørensen. Determination of steroid hormones in blood by GC-MS/MS. Analytical and bioanalytical chemistry. 2011 Jul; 400(10):3409-17. doi: 10.1007/s00216-011-5038-8. [PMID: 21533798]
René Robert, Daniel Aiham Ghazali, Frédéric Favreau, Gérard Mauco, Thierry Hauet, Jean-Michel Goujon. Gender difference and sex hormone production in rodent renal ischemia reperfusion injury and repair. Journal of inflammation (London, England). 2011 Jun; 8(?):14. doi: 10.1186/1476-9255-8-14. [PMID: 21658244]
Han Wei, Li Yan-xia, Yang Ming, Li Wei. Presence and determination of manure-borne estrogens from dairy and beef cattle feeding operations in northeast China. Bulletin of environmental contamination and toxicology. 2011 May; 86(5):465-9. doi: 10.1007/s00128-011-0247-6. [PMID: 21437787]
Zhining Wen, Zhijun Wang, Steven Wang, Ranadheer Ravula, Lun Yang, Jun Xu, Charles Wang, Zhong Zuo, Moses S S Chow, Leming Shi, Ying Huang. Discovery of molecular mechanisms of traditional Chinese medicinal formula Si-Wu-Tang using gene expression microarray and connectivity map. PloS one. 2011 Mar; 6(3):e18278. doi: 10.1371/journal.pone.0018278. [PMID: 21464939]
Eric Braekevelt, Benjamin P Y Lau, Brett Tague, Svetlana Popovic, Sheryl A Tittlemier. Effect of cooking on concentrations of β-estradiol and metabolites in model matrices and beef. Journal of agricultural and food chemistry. 2011 Feb; 59(3):915-20. doi: 10.1021/jf103064q. [PMID: 21218831]
George Kaklamanos, Georgios A Theodoridis, Themistoklis Dabalis, Ioannis Papadoyannis. Determination of anabolic steroids in bovine serum by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Jan; 879(2):225-9. doi: 10.1016/j.jchromb.2010.11.029. [PMID: 21167798]
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]
Leila Kolios, Florian Daub, Stephan Sehmisch, Karl-Heinz Frosch, Mohammed Tezval, Klaus Michael Stuermer, Wolfgang Wuttke, Ewa Klara Stuermer. Absence of positive effect of black cohosh (Cimicifuga racemosa) on fracture healing in osteopenic rodent model. Phytotherapy research : PTR. 2010 Dec; 24(12):1796-806. doi: 10.1002/ptr.3176. [PMID: 20564511]
N W Shappell, K M Hyndman, S E Bartell, H L Schoenfuss. Comparative biological effects and potency of 17α- and 17β-estradiol in fathead minnows. Aquatic toxicology (Amsterdam, Netherlands). 2010 Oct; 100(1):1-8. doi: 10.1016/j.aquatox.2010.07.005. [PMID: 20692052]
Rebecca C Stratton, Paul E Squires, Anne K Green. 17Beta-estradiol elevates cGMP and, via plasma membrane recruitment of protein kinase GIalpha, stimulates Ca2+ efflux from rat hepatocytes. The Journal of biological chemistry. 2010 Aug; 285(35):27201-27212. doi: 10.1074/jbc.m110.103630. [PMID: 20566641]
Lili Zhang, Brigitte E Blackman, Marcus D Schonemann, Tatjana Zogovic-Kapsalis, Xiaoyu Pan, Mary Tagliaferri, Heather A Harris, Isaac Cohen, Renee A Reijo Pera, Synthia H Mellon, Richard I Weiner, Dale C Leitman. Estrogen receptor beta-selective agonists stimulate calcium oscillations in human and mouse embryonic stem cell-derived neurons. PloS one. 2010 Jul; 5(7):e11791. doi: 10.1371/journal.pone.0011791. [PMID: 20668547]
Julian P Meeks, Hannah A Arnson, Timothy E Holy. Representation and transformation of sensory information in the mouse accessory olfactory system. Nature neuroscience. 2010 Jun; 13(6):723-30. doi: 10.1038/nn.2546. [PMID: 20453853]
Sarah Combalbert, Guillermina Hernandez-Raquet. Occurrence, fate, and biodegradation of estrogens in sewage and manure. Applied microbiology and biotechnology. 2010 May; 86(6):1671-92. doi: 10.1007/s00253-010-2547-x. [PMID: 20354692]
Ana R Ribeiro, Maria F Carvalho, Carlos M M Afonso, Maria E Tiritan, Paula M L Castro. Microbial degradation of 17beta -estradiol and 17alpha -ethinylestradiol followed by a validated HPLC-DAD method. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2010 May; 45(4):265-73. doi: 10.1080/03601231003704523. [PMID: 20390962]
Jennifer B Gadd, Louis A Tremblay, Grant L Northcott. Steroid estrogens, conjugated estrogens and estrogenic activity in farm dairy shed effluents. Environmental pollution (Barking, Essex : 1987). 2010 Mar; 158(3):730-6. doi: 10.1016/j.envpol.2009.10.015. [PMID: 19913339]
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: 10.1007/s11356-009-0172-y. [PMID: 19495820]
S Divari, R De Maria, F T Cannizzo, F Spada, C Mulasso, T F H Bovee, P Capra, M Leporati, B Biolatti. A RIKILT yeast estrogen bioassay (REA) for estrogen residue detection in urine of calves experimentally treated with 17beta-estradiol. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2010 Jan; 27(1):19-28. doi: 10.1080/02652030903225757. [PMID: 19763989]
Mark McDonald, Edward Malone, John McBride. Confirmation of hormones in animal serum by liquid chromatography/tandem mass spectrometry according to European Commission Decision 2002/657. Journal of AOAC International. 2010 Jan; 93(1):343-9. doi: 10.1093/jaoac/93.1.343. [PMID: 20334197]
Rebecca A Alyea, Cheryl S Watson. Nongenomic mechanisms of physiological estrogen-mediated dopamine efflux. BMC neuroscience. 2009 Jun; 10(?):59. doi: 10.1186/1471-2202-10-59. [PMID: 19531209]
L A Miranda, C A Strüssmann, G M Somoza. Effects of light and temperature conditions on the expression of GnRH and GtH genes and levels of plasma steroids in Odontesthes bonariensis females. Fish physiology and biochemistry. 2009 Mar; 35(1):101-8. doi: 10.1007/s10695-008-9232-3. [PMID: 19189237]
Yukie Hirahara, Ken-Ichi Matsuda, Wen Gao, Dina N Arvanitis, Mitsuhiro Kawata, Joan M Boggs. The localization and non-genomic function of the membrane-associated estrogen receptor in oligodendrocytes. Glia. 2009 Jan; 57(2):153-65. doi: 10.1002/glia.20742. [PMID: 18709647]
V H Ozacmak, H Sayan. The effects of 17beta estradiol, 17alpha estradiol and progesterone on oxidative stress biomarkers in ovariectomized female rat brain subjected to global cerebral ischemia. Physiological research. 2009; 58(6):909-912. doi: 10.33549/physiolres.931647. [PMID: 19093730]
Peter I Mackenzie, Anne Rogers, Joanna Treloar, Bo R Jorgensen, John O Miners, Robyn Meech. Identification of UDP glycosyltransferase 3A1 as a UDP N-acetylglucosaminyltransferase. The Journal of biological chemistry. 2008 Dec; 283(52):36205-10. doi: 10.1074/jbc.m807961200. [PMID: 18981171]
Paul A Foster, L W Lawrence Woo, Barry V L Potter, Michael J Reed, Atul Purohit. The use of steroid sulfatase inhibitors as a novel therapeutic strategy against hormone-dependent endometrial cancer. Endocrinology. 2008 Aug; 149(8):4035-42. doi: 10.1210/en.2008-0223. [PMID: 18450955]
Giovanni Ferretti, Carolina Ferranti, Teresa Crovella, Maurizio Fiori, Cinzia Civitareale, Camilla Marchiafava, Fernanda Delli Quadri, Paolo Cammarata, Luca Palleschi. Simultaneous analysis of 17alpha-estradiol and 17beta-estradiol in bovine serum by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Aug; 871(1):135-40. doi: 10.1016/j.jchromb.2008.06.049. [PMID: 18644750]
Gaud Pinel, Lauriane Rambaud, Giuseppe Cacciatore, Aldert Bergwerff, Chris Elliott, Michel Nielen, Bruno Le Bizec. Elimination kinetic of 17beta-estradiol 3-benzoate and 17beta-nandrolone laureate ester metabolites in calves' urine. The Journal of steroid biochemistry and molecular biology. 2008 May; 110(1-2):30-8. doi: 10.1016/j.jsbmb.2007.09.024. [PMID: 18356042]
Lin Zhao, Michiko Watanabe, Tetsu Yano, Junn Yanagisawa, Shunsuke Nakagawa, Hajime Oishi, Osamu Wada-Hiraike, Katsutoshi Oda, Takeo Minaguchi, Toshiharu Yasugi, Shigeaki Kato, Yuji Taketani. Analysis of the status of the novel estrogen receptor α (ERα) coactivator p72 in endometrial cancer and its cross talk with erbB-2 in the transactivation of ERα. Molecular medicine reports. 2008 May; 1(3):387-90. doi: . [PMID: 21479421]
James W Simpkins, James A Dykens. Mitochondrial mechanisms of estrogen neuroprotection. Brain research reviews. 2008 Mar; 57(2):421-30. doi: 10.1016/j.brainresrev.2007.04.007. [PMID: 17512984]
Wendy Saltzman, Kimber J Liedl, Orrie J Salper, Rebecca R Pick, David H Abbott. Post-conception reproductive competition in cooperatively breeding common marmosets. Hormones and behavior. 2008 Jan; 53(1):274-86. doi: 10.1016/j.yhbeh.2007.10.005. [PMID: 18045596]
Yaming Qiao, Zhi-Kai Zhang, Li-Qun Cai, Chen Tan, Julianne L Imperato-McGinley, Yuan-Shan Zhu. 17alpha-estradiol inhibits LAPC-4 prostatic tumor cell proliferation in cell cultures and tumor growth in xenograft animals. The Prostate. 2007 Dec; 67(16):1719-28. doi: 10.1002/pros.20656. [PMID: 17879940]
Liat Abovich Gilad, Betty Schwartz. Association of estrogen receptor beta with plasma-membrane caveola components: implication in control of vitamin D receptor. Journal of molecular endocrinology. 2007 Jun; 38(6):603-18. doi: 10.1677/jme-06-0040. [PMID: 17556531]
Meritxell Roig, Jordi Segura, Rosa Ventura. Quantitation of 17beta-nandrolone metabolites in boar and horse urine by gas chromatography-mass spectrometry. Analytica chimica acta. 2007 Mar; 586(1-2):184-95. doi: 10.1016/j.aca.2006.08.033. [PMID: 17386711]
Michel W F Nielen, Johan J P Lasaroms, Martien L Essers, Marieke B Sanders, Henri H Heskamp, Toine F H Bovee, J Hans van Rhijn, Maria J Groot. The ultimate veal calf reference experiment: hormone residue analysis data obtained by gas and liquid chromatography tandem mass spectrometry. Analytica chimica acta. 2007 Mar; 586(1-2):30-4. doi: 10.1016/j.aca.2006.07.029. [PMID: 17386693]
S Biddle, P Teale, A Robinson, J Bowman, E Houghton. Gas chromatography-mass spectrometry/mass spectrometry analysis to determine natural and post-administration levels of oestrogens in bovine serum and urine. Analytica chimica acta. 2007 Mar; 586(1-2):115-21. doi: 10.1016/j.aca.2006.10.044. [PMID: 17386702]
Takuma Furuichi, Kurunthachalam Kannan, Kazuyoshi Suzuki, Shuzo Tanaka, John P Giesy, Shigeki Masunaga. Occurrence of estrogenic compounds in and removal by a swine farm waste treatment plant. Environmental science & technology. 2006 Dec; 40(24):7896-902. doi: 10.1021/es0609598. [PMID: 17256545]
M W F Nielen, T F H Bovee, H H Heskamp, J J P Lasaroms, M B Sanders, J A Van Rhijn, M J Groot, L A P Hoogenboom. Screening for estrogen residues in calf urine: comparison of a validated yeast estrogen bioassay and gas chromatography-tandem mass spectrometry. Food additives and contaminants. 2006 Nov; 23(11):1123-31. doi: 10.1080/02652030600743797. [PMID: 17071514]
Wendy Saltzman, Brynn K Hogan, Brian M Horman, David H Abbott. Social suppression of cortisol in female marmosets: role of luteinizing hormone/chorionic gonadotropin. General and comparative endocrinology. 2006 Oct; 149(1):90-9. doi: 10.1016/j.ygcen.2006.05.007. [PMID: 16806216]
James W DuMond, Kamaleshwar P Singh, Deodutta Roy. Development of a self-proliferating Leydig cell line: a hyper-sensitive E-screening model. Oncology reports. 2006 Jul; 16(1):73-7. doi: . [PMID: 16786125]
Gregory A Brown, Drew McKenzie. Acute resistance exercise does not change the hormonal response to sublingual androstenediol intake. European journal of applied physiology. 2006 Jul; 97(4):404-12. doi: 10.1007/s00421-006-0194-9. [PMID: 16636857]
C Almeida, J M F Nogueira. Determination of steroid sex hormones in water and urine matrices by stir bar sorptive extraction and liquid chromatography with diode array detection. Journal of pharmaceutical and biomedical analysis. 2006 Jun; 41(4):1303-11. doi: 10.1016/j.jpba.2006.02.037. [PMID: 16581218]
J McMillan, S Fatehi-Sedeh, V L Sylvia, V Bingham, M Zhong, B D Boyan, Z Schwartz. Sex-specific regulation of growth plate chondrocytes by estrogen is via multiple MAP kinase signaling pathways. Biochimica et biophysica acta. 2006 Apr; 1763(4):381-92. doi: 10.1016/j.bbamcr.2006.02.010. [PMID: 16713447]
Liqin Zhao, Roberta Diaz Brinton. Select estrogens within the complex formulation of conjugated equine estrogens (Premarin) are protective against neurodegenerative insults: implications for a composition of estrogen therapy to promote neuronal function and prevent Alzheimer's disease. BMC neuroscience. 2006 Mar; 7(?):24. doi: 10.1186/1471-2202-7-24. [PMID: 16533397]
A K Sarmah, G L Northcott, F D L Leusch, L A Tremblay. A survey of endocrine disrupting chemicals (EDCs) in municipal sewage and animal waste effluents in the Waikato region of New Zealand. The Science of the total environment. 2006 Feb; 355(1-3):135-44. doi: 10.1016/j.scitotenv.2005.02.027. [PMID: 16442435]
Cleyde Vanessa Vega Helena, Maristela de Oliveira Poletini, Gilberto Luiz Sanvitto, Shinji Hayashi, Celso Rodrigues Franci, Janete Aparecida Anselmo-Franci. Changes in alpha-estradiol receptor and progesterone receptor expression in the locus coeruleus and preoptic area throughout the rat estrous cycle. The Journal of endocrinology. 2006 Feb; 188(2):155-65. doi: 10.1677/joe.1.06268. [PMID: 16461543]
Yuko Tsunoda, Yukiko Shimizu, Akira Tsunoda, Masafumi Takimoto, Masa-Aki Sakamoto, Mitsuo Kusano. Steroid sulfatase in breast carcinoma and change of serum estrogens levels after operation. Acta oncologica (Stockholm, Sweden). 2006; 45(5):584-9. doi: 10.1080/02841860600602979. [PMID: 16864173]
E A Sribnick, S K Ray, N L Banik. Estrogen prevents glutamate-induced apoptosis in C6 glioma cells by a receptor-mediated mechanism. Neuroscience. 2006; 137(1):197-209. doi: 10.1016/j.neuroscience.2005.08.074. [PMID: 16289585]
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C Dominique Toran-Allerand. Estrogen and the brain: beyond ER-alpha, ER-beta, and 17beta-estradiol. Annals of the New York Academy of Sciences. 2005 Jun; 1052(?):136-44. doi: 10.1196/annals.1347.009. [PMID: 16024756]
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Bei Ma, Weifang Rong, Philip M Dunn, Geoffery Burnstock. 17beta-estradiol attenuates alpha, beta-meATP-induced currents in rat dorsal root ganglion neurons. Life sciences. 2005 Apr; 76(22):2547-58. doi: 10.1016/j.lfs.2004.10.047. [PMID: 15769479]
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Jennifer L Temple, Eric Laing, Anushka Sunder, Susan Wray. Direct action of estradiol on gonadotropin-releasing hormone-1 neuronal activity via a transcription-dependent mechanism. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2004 Jul; 24(28):6326-33. doi: 10.1523/jneurosci.1006-04.2004. [PMID: 15254088]
Alexandra Lafaye, Christophe Junot, Béatrice Ramounet-Le Gall, Paul Fritsch, Eric Ezan, Jean-Claude Tabet. Profiling of sulfoconjugates in urine by using precursor ion and neutral loss scans in tandem mass spectrometry. Application to the investigation of heavy metal toxicity in rats. Journal of mass spectrometry : JMS. 2004 Jun; 39(6):655-64. doi: 10.1002/jms.635. [PMID: 15236304]
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Darlene C Deecher, Pamela Swiggard, Donald E Frail, Lawrence T O'Connor. Characterization of a membrane-associated estrogen receptor in a rat hypothalamic cell line (D12). Endocrine. 2003 Dec; 22(3):211-23. doi: 10.1385/endo:22:3:211. [PMID: 14709794]
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