ST 18:4;O3 (BioDeep_00000637483)

 

Secondary id: BioDeep_00000001278, BioDeep_00000005782, BioDeep_00000009874, BioDeep_00000017787, BioDeep_00000026379, BioDeep_00000405247, BioDeep_00000586371, BioDeep_00001868314

PANOMIX_OTCML-2023


代谢物信息卡片


3,16alpha-dihydroxy-1,3,5(10)-estratrien-17-one

化学式: C18H22O3 (286.15688620000003)
中文名称: 4-羟雌甾酮, 16α-羟基雌酮, 2-羟基雌酮
谱图信息: 最多检出来源 Homo sapiens(blood) 0.36%

分子结构信息

SMILES: C1(=CC2=C(C=C1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)C(=O)[C@H](O)C3)CC2)O
InChI: InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1

描述信息

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
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents
D000970 - Antineoplastic Agents
4-Hydroxyestrone (4-OHE1), an estrone metabolite, has strong neuroprotective effect against oxidative neurotoxicity. 4-Hydroxyestrone increases cytoplasmic translocation of p53 resulting from SIRT1-mediated deacetylation of p53. 4-Hydroxyestrone has little estrogenic activity[1].

同义名列表

15 个代谢物同义名

16-oxo-17beta-Estradiol; 16-Ketoestradiol; ST 18:4;O3; 3,4-dihydroxy-1,3,5(10)-estratrien-17-one; 4-hydroxyestrone; 3,11beta-dihydroxy-1,3,5(10)-estratrien-17-one; 11beta-hydroxyestrone; 16b-Hydroxyestrone; 3,16alpha-dihydroxy-1,3,5(10)-estratrien-17-one; 16alpha-hydroxyestrone; 1.16a-Hydroxyestrone; 16α-Hydroxyestrone; 2,3-dihydroxy-estra-1,3,5(10)-trien-17-one; 2-hydroxyestrone; 4-OHE1



数据库引用编号

38 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)

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

  • Hongge Wang, Ming-Jie Hou, Lixi Liao, Peng Li, Tongxiang Chen, Pan Wang, Bao Ting Zhu. Strong Protection by 4-Hydroxyestrone against Erastin-Induced Ferroptotic Cell Death in Estrogen Receptor-Negative Human Breast Cancer Cells: Evidence for Protein Disulfide Isomerase as a Mechanistic Target for Protection. Biochemistry. 2024 Apr; 63(8):984-999. doi: 10.1021/acs.biochem.3c00261. [PMID: 38569593]
  • Xiaoli Zhang, Na Yang, Min Wang, JiaJia Ge, Huaijun Zhu, Jun He, Weihong Ge. Establishment and validation of a sensitive LC-MS/MS method for quantification of urinary estrogens in women with gestational diabetes mellitus. Journal of pharmaceutical and biomedical analysis. 2022 Nov; 221(?):115044. doi: 10.1016/j.jpba.2022.115044. [PMID: 36126614]
  • Xueying Ye, Tao Peng, Yuan Li, Tongwang Huang, Hui Wang, Zhong Hu. Identification of an important function of CYP123: Role in the monooxygenase activity in a novel estradiol degradation pathway in bacteria. The Journal of steroid biochemistry and molecular biology. 2022 01; 215(?):106025. doi: 10.1016/j.jsbmb.2021.106025. [PMID: 34775032]
  • 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]
  • Nhung Le, Melissa Cregger, Veronica Brown, Julio Loret de Mola, Pamela Bremer, Lyn Nguyen, Kathleen Groesch, Teresa Wilson, Paula Diaz-Sylvester, Andrea Braundmeier-Fleming. Association of microbial dynamics with urinary estrogens and estrogen metabolites in patients with endometriosis. PloS one. 2021; 16(12):e0261362. doi: 10.1371/journal.pone.0261362. [PMID: 34914785]
  • Frank Z Stanczyk. The 2-/16α-Hydroxylated Estrogen Ratio-Breast Cancer Risk Hypothesis: Insufficient Evidence for its Support. The Journal of steroid biochemistry and molecular biology. 2020 07; 201(?):105685. doi: 10.1016/j.jsbmb.2020.105685. [PMID: 32320758]
  • Shunyao Li, Juan Liu, Mark A Williams, Wanting Ling, Kai Sun, Chao Lu, Yanzheng Gao, Michael Gatheru Waigi. Metabolism of 17β-estradiol by Novosphingobium sp. ES2-1 as probed via HRMS combined with 13C3-labeling. Journal of hazardous materials. 2020 05; 389(?):121875. doi: 10.1016/j.jhazmat.2019.121875. [PMID: 31862352]
  • Karin B Michels, Nadine Binder, Frédérique Courant, Adrian A Franke, Anja Osterhues. Urinary excretion of sex steroid hormone metabolites after consumption of cow milk: a randomized crossover intervention trial. The American journal of clinical nutrition. 2019 02; 109(2):402-410. doi: 10.1093/ajcn/nqy279. [PMID: 30698629]
  • Wahid Ali Khan, Mohd Wajid Ali Khan, Subuhi Sherwani, Waseem Ahmad Siddiqui. Depression enhanced the production of autoantibodies against 16α‑hydroxyestrone-estrogen receptor adduct in breast cancer. International immunopharmacology. 2019 Jan; 66(?):251-259. doi: 10.1016/j.intimp.2018.11.018. [PMID: 30500622]
  • Vicky C Chang, Michelle Cotterchio, Beatrice A Boucher, David J A Jenkins, Lucia Mirea, Susan E McCann, Lilian U Thompson. Effect of Dietary Flaxseed Intake on Circulating Sex Hormone Levels among Postmenopausal Women: A Randomized Controlled Intervention Trial. Nutrition and cancer. 2019; 71(3):385-398. doi: 10.1080/01635581.2018.1516789. [PMID: 30375890]
  • Cynthia A Thomson, H H Sherry Chow, Betsy C Wertheim, Denise J Roe, Alison Stopeck, Gertraud Maskarinec, Maria Altbach, Pavani Chalasani, Chuan Huang, Meghan B Strom, Jean-Philippe Galons, Patricia A Thompson. A randomized, placebo-controlled trial of diindolylmethane for breast cancer biomarker modulation in patients taking tamoxifen. Breast cancer research and treatment. 2017 Aug; 165(1):97-107. doi: 10.1007/s10549-017-4292-7. [PMID: 28560655]
  • Hannah Oh, Zeina G Khodr, Mark E Sherman, Maya Palakal, Ruth M Pfeiffer, Laura Linville, Berta M Geller, Pamela M Vacek, Donald L Weaver, Rachael E Chicoine, Roni T Falk, Hisani N Horne, Daphne Papathomas, Deesha A Patel, Jackie Xiang, Xia Xu, Timothy Veenstra, Stephen M Hewitt, John A Shepherd, Louise A Brinton, Jonine D Figueroa, Gretchen L Gierach. Relation of Serum Estrogen Metabolites with Terminal Duct Lobular Unit Involution Among Women Undergoing Diagnostic Image-Guided Breast Biopsy. Hormones & cancer. 2016 12; 7(5-6):305-315. doi: 10.1007/s12672-016-0265-2. [PMID: 27138982]
  • Yang Wang, Desheng Liu, Yue Li, Lei Guo, Yinghua Cui, Xin Zhang, Enyou Li. Metabolomic analysis of serum from obese adults with hyperlipemia by UHPLC-Q-TOF MS/MS. Biomedical chromatography : BMC. 2016 Jan; 30(1):48-54. doi: 10.1002/bmc.3491. [PMID: 26043712]
  • Regina G Ziegler, Barbara J Fuhrman, Steven C Moore, Charles E Matthews. Epidemiologic studies of estrogen metabolism and breast cancer. Steroids. 2015 Jul; 99(Pt A):67-75. doi: 10.1016/j.steroids.2015.02.015. [PMID: 25725255]
  • Dina Nikitina, Marcia Llacuachaqui, Daniel Sepkovic, H Leon Bradlow, Steven A Narod, Joanne Kotsopoulos. The effect of oral 3,3'-diindolylmethane supplementation on the 2:16α-OHE ratio in BRCA1 mutation carriers. Familial cancer. 2015 Jun; 14(2):281-6. doi: 10.1007/s10689-015-9783-2. [PMID: 25613194]
  • Anushka Dikshit, Manoel Adrião Gomes Filho, Erfan Eilati, Stacey McGee, Carrie Small, Chunqi Gao, Thomas Klug, Dale Buchanan Hales. Flaxseed reduces the pro-carcinogenic micro-environment in the ovaries of normal hens by altering the PG and oestrogen pathways in a dose-dependent manner. The British journal of nutrition. 2015 May; 113(9):1384-95. doi: 10.1017/s000711451500029x. [PMID: 25850566]
  • Xiangyan Ruan, Harald Seeger, Diethelm Wallwiener, Jens Huober, Alfred O Mueck. The ratio of the estradiol metabolites 2-hydroxyestrone (2-OHE1) and 16α-hydroxyestrone (16-OHE1) may predict breast cancer risk in postmenopausal but not in premenopausal women: two case-control studies. Archives of gynecology and obstetrics. 2015 May; 291(5):1141-6. doi: 10.1007/s00404-014-3512-1. [PMID: 25318606]
  • Paulina M Merino, Daniela Martínez, German Iñiguez, Patricia Lopez, Fernando Cassorla, Francisco Perez-Bravo, Ethel Codner. Elevation of C-reactive protein during the luteal phase in healthy adolescents. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2015 Apr; 31(4):260-3. doi: 10.3109/09513590.2014.982086. [PMID: 25392126]
  • W L Gao, L S Wu, J H Zi, B Wu, Y Z Li, Y C Song, D Z Cai. Measurement of serum estrogen and estrogen metabolites in pre- and postmenopausal women with osteoarthritis using high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2015 Feb; 48(2):146-53. doi: 10.1590/1414-431x20144129. [PMID: 25410577]
  • Estela Ytelina Godínez Martínez, René Santillán Ballesteros, Ana Elena Lemus Bravo, Reyna Sámano, Maricruz Tolentino Dolores, Ana Lilia Rodríguez Ventura, Ana Rosa Juárez González. [Determination of 2-hydroxyestrone /16α-hydroxyestrone ratio in urine of Mexican women as a risk indicator for breast cancer and its relationship with other risk factors]. Nutricion hospitalaria. 2014 Oct; 31(2):835-40. doi: 10.3305/nh.2015.31.2.8172. [PMID: 25617571]
  • Alan A Arslan, Karen L Koenig, Per Lenner, Yelena Afanasyeva, Roy E Shore, Yu Chen, Eva Lundin, Paolo Toniolo, Göran Hallmans, Anne Zeleniuch-Jacquotte. Circulating estrogen metabolites and risk of breast cancer in postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2014 Jul; 23(7):1290-7. doi: 10.1158/1055-9965.epi-14-0009. [PMID: 24769889]
  • Nitin Telang, Gou Li, Daniel Sepkovic, H Leon Bradlow, George Y C Wong. Comparative efficacy of extracts from Lycium barbarum bark and fruit on estrogen receptor positive human mammary carcinoma MCF-7 cells. Nutrition and cancer. 2014; 66(2):278-84. doi: 10.1080/01635581.2014.864776. [PMID: 24377707]
  • Gertraud Maskarinec, Sreang Heak, Yukiko Morimoto, Laurie Custer, Adrian A Franke. The relation of urinary estrogen metabolites with mammographic densities in premenopausal women. Cancer epidemiology. 2012 Oct; 36(5):e310-6. doi: 10.1016/j.canep.2012.03.014. [PMID: 22537763]
  • Charles E Matthews, Renee T Fortner, Xia Xu, Susan E Hankinson, A Heather Eliassen, Regina G Ziegler. Association between physical activity and urinary estrogens and estrogen metabolites in premenopausal women. The Journal of clinical endocrinology and metabolism. 2012 Oct; 97(10):3724-33. doi: 10.1210/jc.2012-1732. [PMID: 22855335]
  • G Maskarinec, Y Morimoto, S Heak, M Isaki, A Steinbrecher, L Custer, A A Franke. Urinary estrogen metabolites in two soy trials with premenopausal women. European journal of clinical nutrition. 2012 Sep; 66(9):1044-9. doi: 10.1038/ejcn.2012.71. [PMID: 22713773]
  • L M Berstein, M P Boyarkina, D A Vasilyev, T E Poroshina, I G Kovalenko, E N Imyanitov, V F Semiglazov. Endocrine metabolic disorders in patients with breast cancer, carriers of BRCA1 gene mutations. Bulletin of experimental biology and medicine. 2012 Mar; 152(5):610-2. doi: 10.1007/s10517-012-1588-9. [PMID: 22803146]
  • Jiang Huang, Jianghao Sun, Yanhua Chen, Yongmei Song, Lijia Dong, Qinmin Zhan, Ruiping Zhang, Zeper Abliz. Analysis of multiplex endogenous estrogen metabolites in human urine using ultra-fast liquid chromatography-tandem mass spectrometry: a case study for breast cancer. Analytica chimica acta. 2012 Jan; 711(?):60-8. doi: 10.1016/j.aca.2011.10.058. [PMID: 22152797]
  • N T Telang, G Li, D W Sepkovic, H L Bradlow, G Y C Wong. Anti-proliferative effects of Chinese herb Cornus officinalis in a cell culture model for estrogen receptor-positive clinical breast cancer. Molecular medicine reports. 2012 01; 5(1):22-8. doi: 10.3892/mmr.2011.617. [PMID: 21971582]
  • Yukiko Morimoto, Shannon M Conroy, Ian S Pagano, Marissa Isaki, Adrian A Franke, Frank J Nordt, Gertraud Maskarinec. Urinary estrogen metabolites during a randomized soy trial. Nutrition and cancer. 2012; 64(2):307-14. doi: 10.1080/01635581.2012.648819. [PMID: 22293063]
  • 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]
  • Shawn Patel, Louise C Hawkley, John T Cacioppo, Christopher M Masi. Dietary fiber and serum 16α-hydroxyestrone, an estrogen metabolite associated with lower systolic blood pressure. Nutrition (Burbank, Los Angeles County, Calif.). 2011 Jul; 27(7-8):778-81. doi: 10.1016/j.nut.2010.08.017. [PMID: 21035306]
  • 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]
  • Shilpi Rajoria, Robert Suriano, Perminder Singh Parmar, Yushan Lisa Wilson, Uchechukwu Megwalu, Augustine Moscatello, H Leon Bradlow, Daniel W Sepkovic, Jan Geliebter, Stimson P Schantz, Raj K Tiwari. 3,3'-diindolylmethane modulates estrogen metabolism in patients with thyroid proliferative disease: a pilot study. Thyroid : official journal of the American Thyroid Association. 2011 Mar; 21(3):299-304. doi: 10.1089/thy.2010.0245. [PMID: 21254914]
  • Nadia Obi, Alina Vrieling, Judith Heinz, Jenny Chang-Claude. Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer?. International journal of women's health. 2011 Feb; 3(?):37-51. doi: 10.2147/ijwh.s7595. [PMID: 21339936]
  • Lulu Fu, Hong Xu. A preliminary study of the effectiveness of chinese therapeutic food on regulating female reproductive hormones. Integrative medicine insights. 2011; 6(?):7-12. doi: 10.4137/imi.s5782. [PMID: 21614163]
  • Maggie Laidlaw, Carla A Cockerline, Daniel W Sepkovic. Effects of a breast-health herbal formula supplement on estrogen metabolism in pre- and post-menopausal women not taking hormonal contraceptives or supplements: a randomized controlled trial. Breast cancer : basic and clinical research. 2010 Dec; 4(?):85-95. doi: 10.4137/bcbcr.s6505. [PMID: 21234288]
  • W Gao, C Zeng, D Cai, B Liu, Y Li, X Wen, Y Chen. Serum concentrations of selected endogenous estrogen and estrogen metabolites in pre- and post-menopausal Chinese women with osteoarthritis. Journal of endocrinological investigation. 2010 Oct; 33(9):644-9. doi: 10.1007/bf03346664. [PMID: 20339312]
  • 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]
  • R G Ziegler, J M Faupel-Badger, L Y Sue, B J Fuhrman, R T Falk, J Boyd-Morin, M K Henderson, R N Hoover, T D Veenstra, L K Keefer, X Xu. A new approach to measuring estrogen exposure and metabolism in epidemiologic studies. The Journal of steroid biochemistry and molecular biology. 2010 Aug; 121(3-5):538-45. doi: 10.1016/j.jsbmb.2010.03.068. [PMID: 20382222]
  • 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]
  • Susan R Sturgeon, Stella L Volpe, Elaine Puleo, Elizabeth R Bertone-Johnson, Joanna Heersink, Sara Sabelawski, Kristina Wahala, Carol Bigelow, Mindy S Kurzer. Effect of flaxseed consumption on urinary levels of estrogen metabolites in postmenopausal women. Nutrition and cancer. 2010; 62(2):175-80. doi: 10.1080/01635580903305342. [PMID: 20099191]
  • Jessica M Faupel-Badger, Barbara J Fuhrman, Xia Xu, Roni T Falk, Larry K Keefer, Timothy D Veenstra, Robert N Hoover, Regina G Ziegler. Comparison of liquid chromatography-tandem mass spectrometry, RIA, and ELISA methods for measurement of urinary estrogens. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2010 Jan; 19(1):292-300. doi: 10.1158/1055-9965.epi-09-0643. [PMID: 20056650]
  • Christopher M Masi, Louise C Hawkley, Xia Xu, Timothy D Veenstra, John T Cacioppo. Serum estrogen metabolites and systolic blood pressure among middle-aged and older women and men. American journal of hypertension. 2009 Nov; 22(11):1148-53. doi: 10.1038/ajh.2009.155. [PMID: 19713943]
  • Maddalena Barba, Li Yang, Holger J Schünemann, Francesca Sperati, Sara Grioni, Saverio Stranges, Kim C Westerlind, Giovanni Blandino, Michele Gallucci, Rossella Lauria, Luca Malorni, Paola Muti. Urinary estrogen metabolites and prostate cancer: a case-control study and meta-analysis. Journal of experimental & clinical cancer research : CR. 2009 Oct; 28(?):135. doi: 10.1186/1756-9966-28-135. [PMID: 19814782]
  • Martin Schmidt, Regina Hartung, Silvia Capellino, Maurizio Cutolo, Antje Pfeifer-Leeg, Rainer H Straub. Estrone/17beta-estradiol conversion to, and tumor necrosis factor inhibition by, estrogen metabolites in synovial cells of patients with rheumatoid arthritis and patients with osteoarthritis. Arthritis and rheumatism. 2009 Oct; 60(10):2913-22. doi: 10.1002/art.24859. [PMID: 19790073]
  • Annie Im, Victor G Vogel, Gretchen Ahrendt, Stacy Lloyd, Camille Ragin, Seymour Garte, Emanuela Taioli. Urinary estrogen metabolites in women at high risk for breast cancer. Carcinogenesis. 2009 Sep; 30(9):1532-5. doi: 10.1093/carcin/bgp139. [PMID: 19502596]
  • Alan A Arslan, Roy E Shore, Yelena Afanasyeva, Karen L Koenig, Paolo Toniolo, Anne Zeleniuch-Jacquotte. Circulating estrogen metabolites and risk for breast cancer in premenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2009 Aug; 18(8):2273-9. doi: 10.1158/1055-9965.epi-09-0312. [PMID: 19661086]
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  • Su-Ui Lee, Myung chull Rhee, Yong Ki Min, Seong Hwan Kim. Involvement of peroxiredoxin IV in the 16alpha-hydroxyestrone-induced proliferation of human MCF-7 breast cancer cells. Cell biology international. 2008 Apr; 32(4):401-5. doi: 10.1016/j.cellbi.2007.12.009. [PMID: 18272409]
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