4-Hydroxyestrone (BioDeep_00000026379)

Main id: BioDeep_00000637483

 

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(15R)-5,6-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one

化学式: C18H22O3 (286.15688620000003)
中文名称: 4-羟雌甾酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4O)O
InChI: InChI=1S/C18H22O3/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/h4,6,11-12,14,19,21H,2-3,5,7-9H2,1H3/t11?,12?,14?,18-/m1/s1

描述信息

4-Hydroxyestrone is metabolite originating from 17beta-estradiol, and is reported as carcinogenic and have ability to initiate cancer.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
A human metabolite taken as a putative food compound of mammalian origin [HMDB]
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

11 个代谢物同义名

(15R)-5,6-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one; 3,4-Dihydroxy-estra-1,3,5(10)-trien-17-one; 3,4-dihydroxy-1,3,5(10)-estratrien-17-one; 3,4-Dihydroxyestra-1,3,5(10)-trien-17-one; Estra-1,3,5(10)-triene-3,4-diol-17-one; 1,3,5(10)-Estratriene-3,4-diol-17-one; 4-Hydroxy catechol estrogen; 4-hydroxyestrone; SCHEMBL13123039; 4OHEs; 4-OHE1



数据库引用编号

8 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)

2 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

  • 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]
  • 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]
  • 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]
  • 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]
  • Y Markushin, N Gaikwad, H Zhang, P Kapke, E G Rogan, E L Cavalieri, B J Trock, C Pavlovich, R Jankowiak. Potential biomarker for early risk assessment of prostate cancer. The Prostate. 2006 Oct; 66(14):1565-71. doi: 10.1002/pros.20484. [PMID: 16894534]
  • V K Turan, R I Sanchez, J J Li, S A Li, K R Reuhl, P E Thomas, A H Conney, M A Gallo, F C Kauffman, S Mesia-Vela. The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone. The Journal of endocrinology. 2004 Oct; 183(1):91-9. doi: 10.1677/joe.1.05802. [PMID: 15525577]
  • Brian J Philips, Pete J Ansell, Leslie G Newton, Nobuhiro Harada, Shin-Ichiro Honda, Venkataseshu K Ganjam, George E Rottinghaus, Wade V Welshons, Dennis B Lubahn. Estrogen receptor-independent catechol estrogen binding activity: protein binding studies in wild-type, Estrogen receptor-alpha KO, and aromatase KO mice tissues. Biochemistry. 2004 Jun; 43(21):6698-708. doi: 10.1021/bi036154j. [PMID: 15157104]
  • Xia Xu, Regina G Ziegler, David J Waterhouse, Joseph E Saavedra, Larry K Keefer. Stable isotope dilution high-performance liquid chromatography-electrospray ionization mass spectrometry method for endogenous 2- and 4-hydroxyestrones in human urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2002 Nov; 780(2):315-30. doi: 10.1016/s1570-0232(02)00539-1. [PMID: 12401358]
  • X Xu, A M Duncan, B E Merz-Demlow, W R Phipps, M S Kurzer. Menstrual cycle effects on urinary estrogen metabolites. The Journal of clinical endocrinology and metabolism. 1999 Nov; 84(11):3914-8. doi: 10.1210/jcem.84.11.6134. [PMID: 10566628]
  • Z Cheng, G R Rios, C D King, B L Coffman, M D Green, B Mojarrabi, P I Mackenzie, T R Tephly. Glucuronidation of catechol estrogens by expressed human UDP-glucuronosyltransferases (UGTs) 1A1, 1A3, and 2B7. Toxicological sciences : an official journal of the Society of Toxicology. 1998 Sep; 45(1):52-7. doi: 10.1006/toxs.1998.2494. [PMID: 9848110]
  • B T Zhu, Q D Bui, J Weisz, J G Liehr. Conversion of estrone to 2- and 4-hydroxyestrone by hamster kidney and liver microsomes: implications for the mechanism of estrogen-induced carcinogenesis. Endocrinology. 1994 Nov; 135(5):1772-9. doi: 10.1210/endo.135.5.7956900. [PMID: 7956900]
  • K Saegusa, E Suzuki, T Anjo, Y Matsuki, T Nambara. Determination of catechol and guaiacol estrogens in urine by capillary gas chromatography/mass spectrometry. Biomedical chromatography : BMC. 1993 May; 7(3):172-6. doi: 10.1002/bmc.1130070315. [PMID: 8391354]
  • 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]
  • G Emons, C Mente, R Knuppen, P Ball. Radioimmunoassay for 4-hydroxyoestrone in human urine. Acta endocrinologica. 1981 Jun; 97(2):251-7. doi: 10.1530/acta.0.0970251. [PMID: 7234291]
  • K Shimada, T Tanaka, T Nambara. Studies on steroids. CLXV. Determination of isomeric catechol estrogens in pregnancy urine by high performance liquid chromatography with electrochemical detection. Journal of chromatography. 1981 Apr; 223(1):33-9. doi: NULL. [PMID: 7251774]
  • 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]