4-hydroxyestrone (BioDeep_00000586371)
Main id: BioDeep_00000637483
PANOMIX_OTCML-2023
代谢物信息卡片
4-hydroxyestrone
化学式: C18H22O3 (286.1569)
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
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
A 4-hydroxy steroid that is estrone substituted by a hydroxy group at position 4.
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
2 个代谢物同义名
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:87602
- PubChem: 9971251
- Metlin: METLIN2582
- ChEMBL: CHEMBL1743300
- CAS: 3131-23-5
- MetaboLights: MTBLC87602
- RefMet: 4-Hydroxyestrone
- medchemexpress: HY-W009300
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)
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。
| 亚细胞结构定位 | 关联基因列表 |
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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] - 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] - 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] - 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] - 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] - 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] - 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] - Y Markushin, P Kapke, M Saeed, H Zhang, A Dawoud, E G Rogan, E L Cavalieri, R Jankowiak. Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies.
Chemical research in toxicology.
2005 Oct; 18(10):1520-7. doi:
10.1021/tx050013w. [PMID: 16533015] - 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] - 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] - Nikhil K Basu, Shigeki Kubota, Meselhy R Meselhy, Marco Ciotti, Bhabadeb Chowdhury, Masao Hartori, Ida S Owens. Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
The Journal of biological chemistry.
2004 Jul; 279(27):28320-9. doi:
10.1074/jbc.m401396200. [PMID: 15117964] - 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] - Brian Dean, Byron Arison, Steve Chang, Paul E Thomas, Christopher King. Identification of UGT2B9*2 and UGT2B33 isolated from female rhesus monkey liver.
Archives of biochemistry and biophysics.
2004 Jun; 426(1):55-62. doi:
10.1016/j.abb.2004.03.035. [PMID: 15130782] - Ryszard Jankowiak, Yuri Markushin, Ercole L Cavalieri, Gerald J Small. Spectroscopic characterization of the 4-hydroxy catechol estrogen quinones-derived GSH and N-acetylated Cys conjugates.
Chemical research in toxicology.
2003 Mar; 16(3):304-11. doi:
10.1021/tx020088p. [PMID: 12641430] - 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] - D W Sepkovic, H L Bradlow, M Bell. Quantitative determination of 3,3'-diindolylmethane in urine of individuals receiving indole-3-carbinol.
Nutrition and cancer.
2001; 41(1-2):57-63. doi:
10.1080/01635581.2001.9680612. [PMID: 12094629] - 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] - M D Green, E M Oturu, T R Tephly. Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates.
Drug metabolism and disposition: the biological fate of chemicals.
1994 Sep; 22(5):799-805. doi:
NULL. [PMID: 7835232] - 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] - O Y Hu, K M Chu, H S Liu, S F Chiao, W Ho, S T Ho. Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans.
Acta anaesthesiologica Scandinavica.
1993 Apr; 37(3):258-61. doi:
10.1111/j.1399-6576.1993.tb03711.x. [PMID: 8517101] - 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]
