ST 19:4;O3 (BioDeep_00000637484)

 

Secondary id: BioDeep_00000001218, BioDeep_00000005781, BioDeep_00000405183

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


2-methoxy,3-hydroxy-estra-1,3,5(10)-trien-17-one

化学式: C19H24O3 (300.1725354)
中文名称: 2-甲氧基雌素酮
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.03%

分子结构信息

SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4OC)O
InChI: InChI=1S/C19H24O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10-11,14-16H,2-9H2,1H3/t14-,15-,16-,18-,19+/m0/s1

描述信息

An androstanoid that is androst-4-en-19-al substituted by oxo groups at positions 3 and 17.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
2-Methoxyestrone is a methoxylated catechol estrogen and metabolite of estrone, with a pKa of 10.81.

同义名列表

16 个代谢物同义名

19-Keto-delta(4) androstene-3,17-dione; 19-Oxo-delta(4) androstene-3,17-dione; 19-Aldehydo-4-androstene-3,17-dione; 19-Oxoandrost-4-ene-3,17-dione; 4-Androstene-3,17-dione-19-al; 3,17-dioxoandrost-4-en-19-al; 19-Aldoandrostenedione; 19-Oxoandrostenedione; 19-Oxoandrostendione; ST 19:4;O3; 4-methoxy-estra-1,3,5(10)-trien-3-ol-17-one; 4-Methoxyestrone; 2-methoxy,3-hydroxy-estra-1,3,5(10)-trien-17-one; 2-Methoxy estrone; 2-Methoxyestrone; 2-Methoxyestrone



数据库引用编号

25 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

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

  • Jean-Philippe Emond, Louis Lacombe, Patrick Caron, Véronique Turcotte, David Simonyan, Armen Aprikian, Fred Saad, Michel Carmel, Simone Chevalier, Chantal Guillemette, Eric Lévesque. Urinary oestrogen steroidome as an indicator of the risk of localised prostate cancer progression. British journal of cancer. 2021 07; 125(1):78-84. doi: 10.1038/s41416-021-01376-z. [PMID: 33828256]
  • Man Ho Choi, Ju-Yeon Moon, Sung-Hee Cho, Bong Chul Chung, Eun Jig Lee. Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma. BMC cancer. 2011 Aug; 11(?):342. doi: 10.1186/1471-2407-11-342. [PMID: 21824401]
  • Kannan Rangiah, Sumit J Shah, Anil Vachani, Eugene Ciccimaro, Ian A Blair. Liquid chromatography/mass spectrometry of pre-ionized Girard P derivatives for quantifying estrone and its metabolites in serum from postmenopausal women. Rapid communications in mass spectrometry : RCM. 2011 May; 25(9):1297-307. doi: 10.1002/rcm.4982. [PMID: 21488127]
  • Philipp Hoffmann, Michaela F Hartmann, Thomas Remer, Klaus-Peter Zimmer, Stefan A Wudy. Profiling oestrogens and testosterone in human urine by stable isotope dilution/benchtop gas chromatography-mass spectrometry. Steroids. 2010 Dec; 75(13-14):1067-74. doi: 10.1016/j.steroids.2010.06.014. [PMID: 20619283]
  • Emanuela Taioli, Annie Im, Xia Xu, Timothy D Veenstra, Gretchen Ahrendt, Seymour Garte. Comparison of estrogens and estrogen metabolites in human breast tissue and urine. Reproductive biology and endocrinology : RB&E. 2010 Aug; 8(?):93. doi: 10.1186/1477-7827-8-93. [PMID: 20678202]
  • Jadwiga Piwowarska, Stanisław Radowicki, Jan Pachecka. Simultaneous determination of eight estrogens and their metabolites in serum using liquid chromatography with electrochemical detection. Talanta. 2010 Apr; 81(1-2):275-80. doi: 10.1016/j.talanta.2009.11.069. [PMID: 20188920]
  • Daniela Matei, Jeanne Schilder, Gregory Sutton, Susan Perkins, Tim Breen, Check Quon, Carolyn Sidor. Activity of 2 methoxyestradiol (Panzem NCD) in advanced, platinum-resistant ovarian cancer and primary peritoneal carcinomatosis: a Hoosier Oncology Group trial. Gynecologic oncology. 2009 Oct; 115(1):90-96. doi: 10.1016/j.ygyno.2009.05.042. [PMID: 19577796]
  • Masatoki Katayama, Kiyoshi Takamatsu, Satoru Kaneko, Keisuke Miyaji, Hiromichi Ishikawa, Yoshifumi Matsuda. HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector. Journal of separation science. 2007 Sep; 30(14):2279-85. doi: 10.1002/jssc.200700096. [PMID: 17668912]
  • N Napoli, R Faccio, V Shrestha, S Bucchieri, G Battista Rini, R Armamento-Villareal. Estrogen metabolism modulates bone density in men. Calcified tissue international. 2007 Apr; 80(4):227-32. doi: 10.1007/s00223-007-9014-4. [PMID: 17406768]
  • Jehana James, Daryl J Murry, Anthony M Treston, Anna Maria Storniolo, George W Sledge, Carolyn Sidor, Kathy D Miller. Phase I safety, pharmacokinetic and pharmacodynamic studies of 2-methoxyestradiol alone or in combination with docetaxel in patients with locally recurrent or metastatic breast cancer. Investigational new drugs. 2007 Feb; 25(1):41-8. doi: 10.1007/s10637-006-9008-5. [PMID: 16969706]
  • T H Lippert, H Adlercreutz, M R Berger, H Seeger, A O Mueck. Urinary phytoestrogen excretion of rats bearing methylnitrosourea-induced mammary carcinoma in response to treatment with 2-methoxyestradiol. The Journal of steroid biochemistry and molecular biology. 2007 Feb; 103(2):158-62. doi: 10.1016/j.jsbmb.2006.08.005. [PMID: 17081745]
  • Nehal Lakhani, Alex Sparreboom, Jürgen Venitz, William L Dahut, William D Figg. Plasma protein binding of the investigational anticancer agent 2-methoxyestradiol. Anti-cancer drugs. 2006 Sep; 17(8):977-83. doi: 10.1097/01.cad.0000224447.08706.92. [PMID: 16940808]
  • Christopher Sweeney, Glenn Liu, Constantin Yiannoutsos, Jill Kolesar, Dorothea Horvath, Mary Jane Staab, Karen Fife, Victoria Armstrong, Anthony Treston, Carolyn Sidor, George Wilding. A phase II multicenter, randomized, double-blind, safety trial assessing the pharmacokinetics, pharmacodynamics, and efficacy of oral 2-methoxyestradiol capsules in hormone-refractory prostate cancer. Clinical cancer research : an official journal of the American Association for Cancer Research. 2005 Sep; 11(18):6625-33. doi: 10.1158/1078-0432.ccr-05-0440. [PMID: 16166441]
  • Jin Yoshida, Shinji Kumagai, Takeo Tabuchi, Hiroshi Kosaka, Susumu Akasaka, Hajime Oda. Effects of dioxin on metabolism of estrogens in waste incinerator workers. Archives of environmental & occupational health. 2005 Jul; 60(4):215-22. doi: 10.3200/aeoh.60.4.215-222. [PMID: 17214292]
  • Reina C Armamento-Villareal, Nicola Napoli, Thomas Klug, Roberto Civitelli. The oxidative metabolism of estrogen modulates response to ERT/HRT in postmenopausal women. Bone. 2004 Sep; 35(3):682-8. doi: 10.1016/j.bone.2004.05.010. [PMID: 15336604]
  • C R Ireson, S K Chander, A Purohit, S Perera, S P Newman, D Parish, M P Leese, A C Smith, B V L Potter, M J Reed. Pharmacokinetics and efficacy of 2-methoxyoestradiol and 2-methoxyoestradiol-bis-sulphamate in vivo in rodents. British journal of cancer. 2004 Feb; 90(4):932-7. doi: 10.1038/sj.bjc.6601591. [PMID: 14970876]
  • Kaori Takanashi, Yasunori Osanai, Takahiro Kyo, Itsuo Yoshizawa. Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation. Lipids. 2003 Aug; 38(8):847-54. doi: 10.1007/s11745-003-1135-4. [PMID: 14577664]
  • F W Spierto, F Gardner, S J Smith. Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults. Steroids. 2001 Jan; 66(1):59-62. doi: 10.1016/s0039-128x(00)00139-2. [PMID: 11090660]
  • H Seeger, A O Mueck, T H Lippert. Effect of estradiol metabolites on the susceptibility of low density lipoprotein to oxidation. Life sciences. 1997; 61(9):865-8. doi: 10.1016/s0024-3205(97)00588-2. [PMID: 9284079]
  • H Sekihara, Y Yazaki. 19-Oxoandrost-4-ene-3,17-dione amplifies the action of aldosterone. The Journal of steroid biochemistry and molecular biology. 1993 Jul; 46(1):69-72. doi: 10.1016/0960-0760(93)90210-n. [PMID: 8338792]
  • F D Berg, E Kuss. Urinary excretion of catecholestrogens, 2-methoxy-estrogens and 'classical estrogens' throughout the normal menstrual cycle. Archives of gynecology and obstetrics. 1991; 249(4):201-7. doi: 10.1007/bf02390388. [PMID: 1665687]
  • H Higa. [Effects of catecholestrogen and catecholestrogen 2-monomethyl ether on serum lipids and lipoproteins in rats]. Igaku kenkyu. Acta medica. 1990 Feb; 60(1):1-17. doi: . [PMID: 2288181]
  • J J Michnovicz, R J Hershcopf, N J Haley, H L Bradlow, J Fishman. Cigarette smoking alters hepatic estrogen metabolism in men: implications for atherosclerosis. Metabolism: clinical and experimental. 1989 Jun; 38(6):537-41. doi: 10.1016/0026-0495(89)90213-8. [PMID: 2725292]
  • S Kono, H Higa, H Sunagawa. Effects of catecholestrogen 2-monomethyl ether on serum cholesterol and lipoprotein levels. Asia-Oceania journal of obstetrics and gynaecology. 1988 Sep; 14(3):399-403. doi: 10.1111/j.1447-0756.1988.tb00123.x. [PMID: 3178584]
  • S Kono, M Matsumura, H Higa, H Sunagawa. [Hypocholesterolemic effect of catechol estrogen 2-monomethyl ether]. Nihon Naibunpi Gakkai zasshi. 1987 May; 63(5):712-7. doi: 10.1507/endocrine1927.63.5_712. [PMID: 3622863]
  • C Longcope, C Flood, A Femino, K I Williams. Metabolism of 2-methoxyestrone in normal men. The Journal of clinical endocrinology and metabolism. 1983 Aug; 57(2):277-82. doi: 10.1210/jcem-57-2-277. [PMID: 6863476]
  • C P Martucci. The role of 2-methoxyestrone in estrogen action. Journal of steroid biochemistry. 1983 Jul; 19(1B):635-8. doi: 10.1016/0022-4731(83)90229-7. [PMID: 6310247]
  • D Berg, H H Warnecke, E Kuss. Synthesis of immunogenic C-6 derivatives of 2-methoxyestrone and 2-methoxyestradiol-17 beta and characterization of the corresponding antisera. Hoppe-Seyler's Zeitschrift fur physiologische Chemie. 1982 Jul; 363(7):737-44. doi: 10.1515/bchm2.1982.363.2.737. [PMID: 6290363]
  • G Emons, B Klinger, O Haupt, P Ball. Radioimmunoassay for 4-hydroxyestrone 4-methyl ether in human urine. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 1982 Jul; 14(7):376-9. doi: 10.1055/s-2007-1019020. [PMID: 6288541]
  • R G Lahita, H L Bradlow, J Fishman, H G Kunkel. Abnormal estrogen and androgen metabolism in the human with systemic lupus erythematosus. American journal of kidney diseases : the official journal of the National Kidney Foundation. 1982 Jul; 2(1 Suppl 1):206-11. doi: NULL. [PMID: 7102669]
  • C Longcope, A Femino, C Flood, K I Williams. Metabolic clearance rate and conversion ratios of [3H]2-hydroxyestrone in normal men. The Journal of clinical endocrinology and metabolism. 1982 Feb; 54(2):374-80. doi: 10.1210/jcem-54-2-374. [PMID: 7054225]
  • S Kono, G R Merriam, D D Brandon, D L Loriaux, M B Lipsett. Radioimmunoassay and metabolism of the catechol estrogen 2-hydroxyestradiol. The Journal of clinical endocrinology and metabolism. 1982 Jan; 54(1):150-4. doi: 10.1210/jcem-54-1-150. [PMID: 7054211]
  • P Ball, G Reu, J Schwab, R Knuppen. Radioimmunoassay of 2-hydroxyesterone and 2-methoxyestrone in human urine. Steroids. 1979 May; 33(5):563-76. doi: 10.1016/0039-128x(79)90036-9. [PMID: 462497]
  • M L GIVNER, W S BAULD, K VAGI. A chemical method for the quantitative determination of 2-methoxyoestrone, oestrone, ring D alpha-ketolic oestrogens, oestradiol-17beta, 16-epioestriol and oestriol in human urine. The Biochemical journal. 1960 Nov; 77(?):406-15. doi: 10.1042/bj0770406. [PMID: 13705850]
  • V A FRANDSEN. The demonstration of 2-methoxyoestrone and of 2-methoxyoestradiol in human pregnancy urine. Acta endocrinologica. 1959 Aug; 31(?):603-7. doi: 10.1530/acta.0.xxxi0603. [PMID: 13824489]
  • K H LOKE, G F MARRIAN. Isolation of 2-methoxyoestrone from the urine of pregnant women. Biochimica et biophysica acta. 1958 Jan; 27(1):213-4. doi: 10.1016/0006-3002(58)90318-4. [PMID: 13510277]