4-Hydroxyestradiol (BioDeep_00000009764)

Main id: BioDeep_00000637477

 

human metabolite Endogenous


代谢物信息卡片


(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,6,14-triol

化学式: C18H24O3 (288.1725354)
中文名称: 4-羟基雌二醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC2[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CCC=2C(O)=C1O
InChI: InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1

描述信息

4-Hydroxyestradiol is an oncogenic catechol estrogen produced by metabolism of Estrogen.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
A human metabolite taken as a putative food compound of mammalian origin [HMDB]

同义名列表

24 个代谢物同义名

(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,6,14-triol; (17beta)-Estra-1,3,5(10)-triene-3,4,17-triol; 3,4,17beta-Trihydroxy-1,3,5[10]-estratriene; (17Β)-estra-1,3,5(10)-triene-3,4,17-triol; 3,4,17b-Trihydroxy-1,3,5[10]-estratriene; 3,4,17Β-trihydroxy-1,3,5[10]-estratriene; estra-1,3,5(10)-triene-2,4,17beta-triol; Estra-1,3,5(10)-triene-3,4,17beta-triol; Estra-1,3,5(10)-triene-3,4,17β-triol; 4-Hydroxyestradiol-17 alpha; 4-Hydroxy-17beta-estradiol; 4-Hydroxyestradiol-17 beta; 4-Hydroxyestradiol-17beta; 4-Hydroxy-17β-estradiol; 4-Hydroxyestradiol-17β; 4-Hydroxyestradiol-17b; 3,4,17beta-Estriol; 4-hydroxyestradiol; 4-hydroxystradiol; 3,4,17Β-estriol; 3,4,17b-Estriol; 4-OH-Estradiol; ST 18:3;O3; 4OHE2



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

47 个相关的代谢反应过程信息。

Reactome(45)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

3 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

  • Saranya Sedtananun, Kornkanok Promthep. The potential of Mangifera indica Linn. and Musa acuminata extracts to attenuate 4-hydroxyestradiol (4-OHE2 )-induced DNA oxidative damage in MCF-10A cells by upregulating detoxifying and antioxidant enzymes. Journal of food biochemistry. 2021 06; 45(6):e13754. doi: 10.1111/jfbc.13754. [PMID: 33969512]
  • Wahid Ali Khan, Arshi Malik, Mohd Wajid Ali Khan. Estrogenization of insulin by catecholestrogen produced high affinity autoantibodies and altered the normal function of insulin in type 1 diabetes. Life sciences. 2020 Sep; 256(?):117910. doi: 10.1016/j.lfs.2020.117910. [PMID: 32504753]
  • Xu Mao, Jian Wang, Qian Wang, Lan Yang, Yilin Li, Hao Lin, Ying Peng, Jiang Zheng. Nitidine Chloride-Induced CYP1 Enzyme Inhibition and Alteration of Estradiol Metabolism. Drug metabolism and disposition: the biological fate of chemicals. 2019 08; 47(8):919-927. doi: 10.1124/dmd.119.086892. [PMID: 31147316]
  • Nur Ozten, Katherine Vega, Joachim Liehr, Xi Huang, Lori Horton, Ercole L Cavalieri, Eleanor G Rogan, Maarten C Bosland. Role of Estrogen in Androgen-Induced Prostate Carcinogenesis in NBL Rats. Hormones & cancer. 2019 06; 10(2-3):77-88. doi: 10.1007/s12672-019-00360-7. [PMID: 30877616]
  • Pan Wang, Bao-Ting Zhu. Unique effect of 4-hydroxyestradiol and its methylation metabolites on lipid and cholesterol profiles in ovariectomized female rats. European journal of pharmacology. 2017 Apr; 800(?):107-117. doi: 10.1016/j.ejphar.2017.02.032. [PMID: 28219710]
  • Chieh-Ming Fang, Ming-Chun Ku, Che-Kai Chang, Huei-Chen Liang, Tzu-Fan Wang, Chih-Hsing Wu, Shu-Hui Chen. Identification of Endogenous Site-specific Covalent Binding of Catechol Estrogens to Serum Proteins in Human Blood. Toxicological sciences : an official journal of the Society of Toxicology. 2015 Dec; 148(2):433-42. doi: 10.1093/toxsci/kfv190. [PMID: 26342215]
  • H Zhao, Y Jiang, Y Liu, C Yun, L Li. Endogenous estrogen metabolites as biomarkers for endometrial cancer via a novel method of liquid chromatography-mass spectrometry with hollow fiber liquid-phase microextraction. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2015 Feb; 47(2):158-64. doi: 10.1055/s-0034-1371865. [PMID: 24722971]
  • Jeyaprakash Jeyabalan, Farrukh Aqil, Lisa Soper, David J Schultz, Ramesh C Gupta. Potent Chemopreventive/Antioxidant Activity Detected in Common Spices of the Apiaceae Family. Nutrition and cancer. 2015; 67(7):1201-7. doi: 10.1080/01635581.2015.1075051. [PMID: 26381237]
  • Hui-Hui Li, Ying-Jie Zhao, Yan Li, Cai-Feng Dai, Sheikh O Jobe, Xing-Sheng Yang, Xing-Fu Li, Manish S Patankar, Ronald R Magness, Jing Zheng. Estradiol 17β and its metabolites stimulate cell proliferation and antagonize ascorbic acid-suppressed cell proliferation in human ovarian cancer cells. Reproductive sciences (Thousand Oaks, Calif.). 2014 Jan; 21(1):102-11. doi: 10.1177/1933719113492211. [PMID: 23757313]
  • Shien Zou, Qing Sang, Huan Wang, Ruizhi Feng, Qiaoli Li, Xinzhi Zhao, Qinghe Xing, Li Jin, Lin He, Lei Wang. Common genetic variation in CYP1B1 is associated with concentrations of T₄, FT₃ and FT₄ in the sera of polycystic ovary syndrome patients. Molecular biology reports. 2013 Apr; 40(4):3315-20. doi: 10.1007/s11033-012-2406-1. [PMID: 23283740]
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  • 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]
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  • 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]
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  • Jeanne Farrell, Lavoisier Ramos, Martin Tresguerres, Margarita Kamenetsky, Lonny R Levin, Jochen Buck. Somatic 'soluble' adenylyl cyclase isoforms are unaffected in Sacy tm1Lex/Sacy tm1Lex 'knockout' mice. PloS one. 2008 Sep; 3(9):e3251. doi: 10.1371/journal.pone.0003251. [PMID: 18806876]
  • Leslie A Bransfield, Alissa Rennie, Kala Visvanathan, Shelly-Ann Odwin, Thomas W Kensler, James D Yager, Marlin D Friesen, John D Groopman. Formation of two novel estrogen guanine adducts and HPLC/MS detection of 4-hydroxyestradiol-N7-guanine in human urine. Chemical research in toxicology. 2008 Aug; 21(8):1622-30. doi: 10.1021/tx800145w. [PMID: 18582124]
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  • Qingming Fang, Jagadeesan Nair, Xin Sun, Dimiter Hadjiolov, Helmut Bartsch. Etheno-DNA adduct formation in rats gavaged with linoleic acid, oleic acid and coconut oil is organ- and gender specific. Mutation research. 2007 Nov; 624(1-2):71-9. doi: 10.1016/j.mrfmmm.2007.04.002. [PMID: 17521682]
  • 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]
  • Wahid Ali Khan, Khursheed Alam, Moinuddin. Catechol-estrogen modified DNA: a better antigen for cancer autoantibody. Archives of biochemistry and biophysics. 2007 Sep; 465(1):293-300. doi: 10.1016/j.abb.2007.06.006. [PMID: 17632072]
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  • D Roy, Q D Bui, J Weisz, J G Liehr. Comparison of assays for catechol estrogen synthase activity: product isolation vs radioenzymatic catechol-O-methyltransferase-coupled procedures. Journal of steroid biochemistry. 1989 Aug; 33(2):243-9. doi: 10.1016/0022-4731(89)90300-2. [PMID: 2549304]
  • G Emons, G R Merriam, D Pfeiffer, D L Loriaux, P Ball, R Knuppen. Metabolism of exogenous 4- and 2-hydroxyestradiol in the human male. Journal of steroid biochemistry. 1987 Nov; 28(5):499-504. doi: 10.1016/0022-4731(87)90508-5. [PMID: 2824929]
  • L J Spicer, J M Hammond. Catecholestrogens stimulate progestin secretion by cultured porcine granulosa cells. Molecular and cellular endocrinology. 1987 Mar; 50(1-2):139-47. doi: 10.1016/0303-7207(87)90086-4. [PMID: 3034696]
  • G Emons, H Schuppe, M Peter, C Brack, P Ball. Modulation of LH-secretion in ovariectomized ewes by constant infusions of oestradiol and 4-hydroxyoestradiol: effects of varying infusion times and of high oestrogen doses. Acta endocrinologica. 1986 Oct; 113(2):219-25. doi: 10.1530/acta.0.1130219. [PMID: 3776435]
  • J G Liehr, W F Fang, D A Sirbasku, A Ari-Ulubelen. Carcinogenicity of catechol estrogens in Syrian hamsters. Journal of steroid biochemistry. 1986 Jan; 24(1):353-6. doi: 10.1016/0022-4731(86)90080-4. [PMID: 3009986]
  • P Ball, G Emons. Effects of short-term exposure to catecholestrogens on serum concentrations of gonadotrophins and metabolism of catecholestrogens in ovariectomized rats. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 1985 Apr; 17(4):184-8. doi: 10.1055/s-2007-1013487. [PMID: 2989139]
  • G Emons, C Brack, R Chatelain, H H Abel, S Isedor, P Ball. Effects of continuous infusions of 4-hydroxyoestradiol and oestradiol on plasma LH-levels in the ovariectomized ewe. Acta endocrinologica. 1984 Nov; 107(3):328-36. doi: 10.1530/acta.0.1070328. [PMID: 6095572]
  • S Miyabo, S Kishida, T Sugiyama, T Hashimoto, Y Fujii, M Teranishi. Effects of 2-hydroxyoestradiol and 4-hydroxyoestradiol on gonadotrophin and prolactin secretion in women. Acta endocrinologica. 1984 Jan; 105(1):1-5. doi: 10.1530/acta.0.1050001. [PMID: 6421038]
  • P Ball, G Emons, H Kayser, J Teichmann. Metabolic clearance rates of catechol estrogens in rats. Endocrinology. 1983 Nov; 113(5):1781-3. doi: 10.1210/endo-113-5-1781. [PMID: 6628326]
  • N J MacLusky, M Riskalla, L Krey, N Parvizi, F Naftolin. Anovulation in female rats induced by neonatal administration of the catechol estrogens, 2-hydroxy-estradiol and 4-hydroxy-estradiol. Neuroendocrinology. 1983 Nov; 37(5):321-7. doi: 10.1159/000123569. [PMID: 6196675]
  • G Emons, R Knuppen, P Ball. 4-Hydroxyestradiol-17 beta and 4-hydroxyestradiol-17 alpha: comparative studies on central and peripheral effects of two epimeric catecholestrogens. Endocrinology. 1981 Nov; 109(5):1799-801. doi: 10.1210/endo-109-5-1799. [PMID: 7297508]
  • S Franks, N J MacLusky, S J Naish, F Naftolin. Actions of catechol oestrogens on concentrations of serum luteinizing hormone in the adult castrated rat: various effects of 4-hydroxyoestradiol and 2-hydroxyoestradiol. The Journal of endocrinology. 1981 May; 89(2):289-95. doi: 10.1677/joe.0.0890289. [PMID: 7241016]
  • P Ball, G Emons, U Gethmann. Effect of low doses of continuously administered catecholoestrogens on peripheral and central target organs. Acta endocrinologica. 1981 Apr; 96(4):470-4. doi: 10.1530/acta.0.0960470. [PMID: 6782789]
  • S Franks, P Ball, F Naftolin, K B Ruf. Effect of catechol oestrogens on induced ovulation in the immature rat. The Journal of endocrinology. 1980 Aug; 86(2):263-8. doi: 10.1677/joe.0.0860263. [PMID: 6253586]
  • G Emons, H O Hoppen, P Ball, R Knuppen. 4-hydroxyestrone, isolation and identification in human urine. Steroids. 1980 Jul; 36(1):73-9. doi: 10.1016/0039-128x(80)90069-0. [PMID: 7414657]