Estrogen (BioDeep_00000227695)

Main id: BioDeep_00000002242

Secondary id: BioDeep_00000398402

human metabolite


代谢物信息卡片


4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

化学式: C18H20O2 (268.1463)
中文名称: 己烯雌酚, 己烯雌酚,顺式和反式异构体混合物
谱图信息: 最多检出来源 not specific(not specific) 0%

分子结构信息

SMILES: CCC(=C(CC)C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
InChI: InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+

描述信息

A steroid hormone that stimulates or controls the development and maintenance of female sex characteristics in mammals by binding to oestrogen receptors. The oestrogens are named for their importance in the oestrous cycle. (ChEBI). Estrogen is found in date and apricot.
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CC - Estrogens, combinations with other drugs
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CB - Synthetic estrogens, plain
L - Antineoplastic and immunomodulating agents > L02 - Endocrine therapy > L02A - Hormones and related agents > L02AA - Estrogens
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D009676 - Noxae > D002273 - Carcinogens

同义名列表

33 个代谢物同义名

4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol; trans-4,4-(1,2-Diethyl-1,2-ethenediyl)bisphenol; (e)-4,4-(1,2-Diethyl-1,2-ethenediyl)bisphenol; alpha,Alpha-diethyl-(e)-4,4-stilbenediol; 4,4-Dihydroxy-alpha,beta-diethylstilbene; co Pharma brand OF diethylstilbestrol; CO-Pharma brand OF diethylstilbestrol; (e)-3,4-Bis(4-hydroxyphenyl)-3-hexene; Α,alpha-diethyl-(e)-4,4-stilbenediol; a,Alpha-diethyl-(e)-4,4-stilbenediol; Gerda brand OF diethylstilbestrol; 4,4-Dihydroxy-a,b-diethylstilbene; Diethylstilbestrol, disodium salt; 4,4-Dihydroxy-α,β-diethylstilbene; APS brand OF diethylstilbestrol; Diethylstilbestrol, (Z)-isomer; trans-Diethylstilboesterol; trans-Diethylstilbesterol; trans-Diethylstilbestrol; Diethylstilbestrolum; Diethylstilbestrol; Estrogen, stilbene; Dietilestilbestrol; Stilbene estrogen; Stilbestrol; Distilbene; Distilbène; Agostilben; Tampovagan; Estrogen; Apstil; Des; Diethylstilbestrol



数据库引用编号

17 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)

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
Cytoplasm 10 ALB, AR, CAT, DES, EGFR, ESR1, HOXA10, PGR, PRL, TP53
Peripheral membrane protein 1 ESR1
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 3 CD4, CYP19A1, EGFR
Nucleus 12 ALB, AR, DES, EGFR, ESR1, ESR2, HOXA10, NR5A1, PCNA, PGR, PRL, TP53
cytosol 8 ALB, AR, CAT, DES, ESR1, NR5A1, PGR, TP53
nuclear body 1 PCNA
centrosome 3 ALB, PCNA, TP53
nucleoplasm 9 AR, ESR1, ESR2, HOXA10, NR5A1, PCNA, PGR, PRL, TP53
RNA polymerase II transcription regulator complex 2 NR5A1, PRL
Cell membrane 5 CD4, CD8A, EGFR, ESR1, LHCGR
Cytoplasmic side 1 ESR1
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 2 CYP19A1, LHCGR
cell junction 1 EGFR
cell surface 1 EGFR
glutamatergic synapse 1 EGFR
Golgi apparatus 2 ALB, ESR1
Golgi membrane 2 EGFR, INS
lysosomal membrane 1 EGF
neuromuscular junction 1 DES
sarcolemma 1 DES
endosome 2 EGFR, LHCGR
plasma membrane 8 AR, CD4, CD8A, EGF, EGFR, ESR1, LHCGR, PGR
Membrane 7 AR, CAT, CYP19A1, EGF, EGFR, ESR1, TP53
apical plasma membrane 1 EGFR
basolateral plasma membrane 1 EGFR
extracellular exosome 5 ALB, CAT, DES, EGF, PCNA
endoplasmic reticulum 3 ALB, CYP19A1, TP53
extracellular space 7 ALB, EGF, EGFR, GNRH1, INS, LHCGR, PRL
perinuclear region of cytoplasm 1 EGFR
intercalated disc 1 DES
mitochondrion 3 CAT, ESR2, TP53
protein-containing complex 6 ALB, AR, CAT, EGFR, ESR1, TP53
intracellular membrane-bounded organelle 2 CAT, ESR2
Microsome membrane 1 CYP19A1
Single-pass type I membrane protein 3 CD4, CD8A, EGFR
Secreted 3 ALB, INS, PRL
extracellular region 7 ALB, CAT, CD8A, EGF, GNRH1, INS, PRL
mitochondrial outer membrane 1 PGR
[Isoform 2]: Secreted 1 CD8A
Mitochondrion matrix 1 TP53
mitochondrial matrix 2 CAT, TP53
anchoring junction 1 ALB
transcription regulator complex 3 ESR1, HOXA10, TP53
centriolar satellite 1 LHCGR
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
nuclear membrane 1 EGFR
external side of plasma membrane 2 CD4, CD8A
Z disc 1 DES
nucleolus 1 TP53
Early endosome 1 CD4
cell-cell junction 1 DES
Cell membrane, sarcolemma 1 DES
Membrane raft 2 CD4, EGFR
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 2 CAT, EGFR
Peroxisome 1 CAT
intracellular vesicle 1 EGFR
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 TP53
PML body 1 TP53
fascia adherens 1 DES
intermediate filament 1 DES
nuclear speck 1 AR
receptor complex 3 CD8A, EGFR, LHCGR
ciliary basal body 1 ALB
chromatin 9 AR, ESR1, ESR2, HOXA10, NR5A1, PCNA, PGR, PRL, TP53
centriole 1 ALB
spindle pole 1 ALB
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
blood microparticle 1 ALB
site of double-strand break 1 TP53
nuclear envelope 1 DES
Nucleus envelope 1 DES
endosome lumen 2 INS, PRL
euchromatin 1 ESR1
germ cell nucleus 1 TP53
replication fork 2 PCNA, TP53
intermediate filament cytoskeleton 1 DES
Cytoplasm, myofibril, sarcomere, Z line 1 DES
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
plasma membrane raft 1 CD8A
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 ALB, CD4, INS
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
male germ cell nucleus 1 PCNA
platelet alpha granule lumen 2 ALB, EGF
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
cell tip 1 DES
nuclear lamina 1 PCNA
clathrin-coated endocytic vesicle membrane 3 CD4, EGF, EGFR
[Isoform 1]: Nucleus 2 ESR1, TP53
[Isoform 1]: Cell membrane 1 CD8A
cyclin-dependent protein kinase holoenzyme complex 1 PCNA
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
T cell receptor complex 2 CD4, CD8A
cardiac myofibril 1 DES
catalase complex 1 CAT
[Isoform 4]: Mitochondrion outer membrane 1 PGR
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
ciliary transition fiber 1 ALB


文献列表

  • Shrishti Madhan, Rajib Dhar, Arikketh Devi. Plant-derived exosomes: a green approach for cancer drug delivery. Journal of materials chemistry. B. 2024 Feb; 12(9):2236-2252. doi: 10.1039/d3tb02752j. [PMID: 38351750]
  • V Alampanos, A Kabir, K G Furton, V Samanidou. Rapid exposure monitoring of six bisphenols and diethylstilbestrol in human urine using fabric phase sorptive extraction followed by high performance liquid chromatography - photodiode array analysis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Jul; 1177(?):122760. doi: 10.1016/j.jchromb.2021.122760. [PMID: 34052754]
  • Ankur Kumar Tanwar, Neha Dhiman, Amit Kumar, Vikas Jaitak. Engagement of phytoestrogens in breast cancer suppression: Structural classification and mechanistic approach. European journal of medicinal chemistry. 2021 Mar; 213(?):113037. doi: 10.1016/j.ejmech.2020.113037. [PMID: 33257172]
  • Alessio Ausili, Inés Rodríguez-González, Alejandro Torrecillas, José A Teruel, Juan C Gómez-Fernández. Diethylstilbestrol Modifies the Structure of Model Membranes and Is Localized Close to the First Carbons of the Fatty Acyl Chains. Biomolecules. 2021 02; 11(2):. doi: 10.3390/biom11020220. [PMID: 33557377]
  • Li Zhang, Qiuxia Xu, Yao Li, Hui Zhao, Xingming Shi, Fu Peng, Chenghao Yu. Ameliorative Effects of Component Chinese Medicine From Curcumae Rhizoma and Sparganii Rhizoma, a Traditional Herb Pair, on Uterine Leiomyoma in a Rat Model. Frontiers in public health. 2021; 9(?):674357. doi: 10.3389/fpubh.2021.674357. [PMID: 34123993]
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  • Xingdong Yang, Yinbiao Wang, Chunmei Song, Xiaofei Hu, Fangyu Wang, Xianyin Zeng. Hapten Synthesis and the Development of an Ultrasensitive Indirect Competitive ELISA for the Determination of Diethylstilbestrol in Food Samples. Scientific reports. 2020 02; 10(1):3270. doi: 10.1038/s41598-020-59112-1. [PMID: 32094434]
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  • Weifeng Mao, Yan Song, Haixia Sui, Pei Cao, Zhaoping Liu. Analysis of individual and combined estrogenic effects of bisphenol, nonylphenol and diethylstilbestrol in immature rats with mathematical models. Environmental health and preventive medicine. 2019 May; 24(1):32. doi: 10.1186/s12199-019-0789-5. [PMID: 31084616]
  • Po-Han Lin, Chun-Kuang Shih, Yu-Ting Yen, Wenchang Chiang, Shih-Min Hsia. Adlay (Coix lachryma-jobi L. var. ma-yuen Stapf.) Hull Extract and Active Compounds Inhibit Proliferation of Primary Human Leiomyoma Cells and Protect against Sexual Hormone-Induced Mice Smooth Muscle Hyperproliferation. Molecules (Basel, Switzerland). 2019 Apr; 24(8):. doi: 10.3390/molecules24081556. [PMID: 31010220]
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  • Tingting Wu, Tao Yan, Xue Zhang, Yixuan Feng, Dong Wei, Meng Sun, Bin Du, Qin Wei. A competitive photoelectrochemical immunosensor for the detection of diethylstilbestrol based on an Au/UiO-66(NH2)/CdS matrix and a direct Z-scheme Melem/CdTe heterojunction as labels. Biosensors & bioelectronics. 2018 Oct; 117(?):575-582. doi: 10.1016/j.bios.2018.06.050. [PMID: 30005376]
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  • Xue Dong, Guanhui Zhao, Li Liu, Xuan Li, Qin Wei, Wei Cao. Ultrasensitive competitive method-based electrochemiluminescence immunosensor for diethylstilbestrol detection based on Ru(bpy)32+ as luminophor encapsulated in metal-organic frameworks UiO-67. Biosensors & bioelectronics. 2018 Jul; 110(?):201-206. doi: 10.1016/j.bios.2018.03.066. [PMID: 29625327]
  • Zhi-Hao Liu, Qi-Liang Chen, Qiang Chen, Fang Li, Ying-Wen Li. Diethylstilbestrol arrested spermatogenesis and somatic growth in the juveniles of yellow catfish (Pelteobagrus fulvidraco), a fish with sexual dimorphic growth. Fish physiology and biochemistry. 2018 Jun; 44(3):789-803. doi: 10.1007/s10695-018-0469-1. [PMID: 29340879]
  • Ovokeroye Akpojevwe Abafe, Pumza M Gatyeni, Tlou Chokwe. Development and validation of a confirmatory method for the determination of stilbene estrogens in ostrich serum. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2018 Mar; 35(3):458-466. doi: 10.1080/19440049.2017.1411617. [PMID: 29210606]
  • Yaqin Wang, Yingwen Li, Qiliang Chen, Zhihao Liu. Diethylstilbestrol impaired oogenesis of yellow catfish juveniles through disrupting hypothalamic-pituitary-gonadal axis and germ cell development. Journal of applied toxicology : JAT. 2018 03; 38(3):308-317. doi: 10.1002/jat.3529. [PMID: 28960386]
  • Bo Zeng, Gui-Lan Chen, Eliana Garcia-Vaz, Sunil Bhandari, Nikoleta Daskoulidou, Lisa M Berglund, Hongni Jiang, Thomas Hallett, Lu-Ping Zhou, Li Huang, Zi-Hao Xu, Viji Nair, Robert G Nelson, Wenjun Ju, Matthias Kretzler, Stephen L Atkin, Maria F Gomez, Shang-Zhong Xu. ORAI channels are critical for receptor-mediated endocytosis of albumin. Nature communications. 2017 12; 8(1):1920. doi: 10.1038/s41467-017-02094-y. [PMID: 29203863]
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  • Olena Shaliutina, Anna Shaliutina-Kolešová, Ievgen Lebeda, Marek Rodina, Ievgeniia Gazo. The in vitro effect of nonylphenol, propranolol, and diethylstilbestrol on quality parameters and oxidative stress in sterlet (Acipenser ruthenus) spermatozoa. Toxicology in vitro : an international journal published in association with BIBRA. 2017 Sep; 43(?):9-15. doi: 10.1016/j.tiv.2017.05.006. [PMID: 28533019]
  • Yoshitaka Imamichi, Toshio Sekiguchi, Takeshi Kitano, Takashi Kajitani, Reiko Okada, Yoshihiko Inaoka, Kaoru Miyamoto, Junsuke Uwada, Satoru Takahashi, Takahiro Nemoto, Asuka Mano, Md Rafiqul Islam Khan, Md Tariqul Islam, Koh-Ichi Yuhki, Hitoshi Kashiwagi, Fumitaka Ushikubi, Nobuo Suzuki, Takanobu Taniguchi, Takashi Yazawa. Diethylstilbestrol administration inhibits theca cell androgen and granulosa cell estrogen production in immature rat ovary. Scientific reports. 2017 08; 7(1):8374. doi: 10.1038/s41598-017-08780-7. [PMID: 28827713]
  • Freddy O Agoreyo, B Rita Ohimai, Magdalene I Omigie. Effect of Solanum Nigrun on Uterus of Non-gravid Rats. Ethiopian journal of health sciences. 2017 May; 27(3):239-244. doi: 10.4314/ejhs.v27i3.5. [PMID: 29217922]
  • Pan Yin, Ying-Wen Li, Qi-Liang Chen, Zhi-Hao Liu. Diethylstilbestrol, flutamide and their combination impaired the spermatogenesis of male adult zebrafish through disrupting HPG axis, meiosis and apoptosis. Aquatic toxicology (Amsterdam, Netherlands). 2017 Apr; 185(?):129-137. doi: 10.1016/j.aquatox.2017.02.013. [PMID: 28213303]
  • Dai Zhang, Lifang Zhou, Yajing Lei, Zhan Zhou, Jie Zhou, Shuqing Chen. Investigation of diethylstilbestrol residue level in human urine samples by a specific monoclonal antibody. Environmental science and pollution research international. 2017 Mar; 24(8):7042-7050. doi: 10.1007/s11356-017-8405-y. [PMID: 28092005]
  • Qian-Xing Zou, Zhen Peng, Qing Zhao, Hou-Yang Chen, Yi-Min Cheng, Qing Liu, Yuan-Qiao He, Shi-Qi Weng, Hua-Feng Wang, Tao Wang, Li-Ping Zheng, Tao Luo. Diethylstilbestrol activates CatSper and disturbs progesterone actions in human spermatozoa. Human reproduction (Oxford, England). 2017 02; 32(2):290-298. doi: 10.1093/humrep/dew332. [PMID: 28031325]
  • V Plesinac-Karapandzic, S Stojanovic Rundic, R Jankovic, M Nadrljanski, Z Milovanovic, A Tomasevic, N Perisie Jeremic. Non-diethylstilbestrol exposed vaginal adenocarcinoma in young patients associated with unilateral renal agenesis: two case reports and literature review. European journal of gynaecological oncology. 2017; 38(1):157-161. doi: . [PMID: 29767889]
  • Liangliang Zhu, Ling Xiao, Wenjuan Li, Yuan Zhang, Wenwen Han, Yu Zhu, Guangbo Ge, Ling Yang. Human UDP-Glucuronosyltransferases 1A1, 1A3, 1A9, 2B4 and 2B7 are Inhibited by Diethylstilbestrol. Basic & clinical pharmacology & toxicology. 2016 Nov; 119(5):505-511. doi: 10.1111/bcpt.12618. [PMID: 27176228]
  • Giorgio Biasiotto, Isabella Zanella, Alice Masserdotti, Roberta Pedrazzani, Matteo Papa, Luigi Caimi, Diego Di Lorenzo. Municipal wastewater affects adipose deposition in male mice and increases 3T3-L1 cell differentiation. Toxicology and applied pharmacology. 2016 Apr; 297(?):32-40. doi: 10.1016/j.taap.2016.02.023. [PMID: 26944108]
  • Satoko Haeno, Naoyuki Maeda, Kousuke Yamaguchi, Michiko Sato, Aika Uto, Hiroshi Yokota. Adrenal steroidogenesis disruption caused by HDL/cholesterol suppression in diethylstilbestrol-treated adult male rat. Endocrine. 2016 Apr; 52(1):148-56. doi: 10.1007/s12020-015-0732-5. [PMID: 26349937]
  • C Yang, W Lim, H Bae, G Song. Aquaporin 3 is regulated by estrogen in the chicken oviduct and is involved in progression of epithelial cell-derived ovarian carcinomas. Domestic animal endocrinology. 2016 Apr; 55(?):97-106. doi: 10.1016/j.domaniend.2015.12.003. [PMID: 26808975]
  • Benjamin Lemaire, Akira Kubota, Conor M O'Meara, David C Lamb, Robert L Tanguay, Jared V Goldstone, John J Stegeman. Cytochrome P450 20A1 in zebrafish: Cloning, regulation and potential involvement in hyperactivity disorders. Toxicology and applied pharmacology. 2016 Apr; 296(?):73-84. doi: 10.1016/j.taap.2016.02.001. [PMID: 26853319]
  • Onat Kadioglu, Yujie Fu, Benjamin Wiench, Yuangang Zu, Thomas Efferth. Synthetic cajanin stilbene acid derivatives inhibit c-MYC in breast cancer cells. Archives of toxicology. 2016 Mar; 90(3):575-88. doi: 10.1007/s00204-015-1480-2. [PMID: 25716159]
  • Rachel G Felton, Cynthia C Steiner, Barbara S Durrant, Duane H Keisler, Matthew R Milnes, Christopher W Tubbs. Identification of California Condor Estrogen Receptors 1 and 2 and Their Activation by Endocrine Disrupting Chemicals. Endocrinology. 2015 Dec; 156(12):4448-57. doi: 10.1210/en.2015-1448. [PMID: 26372180]
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  • Bo-wen Weng, Si-chuan Hou, Hai Zhu, Luo Xu, Xiao Luan, Hai-yan Qi, Wei-min Wang, Wei Liu, Li-jiang Sun. [Expression of nNOS and ultrastructural changes in the penile tissue of rats with prolactinoma-induced erectile dysfunction]. Zhonghua nan ke xue = National journal of andrology. 2015 Oct; 21(10):871-6. doi: . [PMID: 26665672]
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  • Pei-Shan Cai, Dan Li, Jing Chen, Chao-Mei Xiong, Jin-Lan Ruan. Comparison of two thin-film microextractions for the analysis of estrogens in aqueous tea extract and environmental water samples by high performance liquid chromatography-ultraviolet detection. Food chemistry. 2015 Apr; 173(?):1158-66. doi: 10.1016/j.foodchem.2014.11.002. [PMID: 25466138]
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