16α-Hydroxyestrone (BioDeep_00001868314)

Main id: BioDeep_00000637483

 

natural product


代谢物信息卡片


16alpha-hydroxyestrone

化学式: C18H22O3 (286.1569)
中文名称: 16α-羟基雌酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC12CCC3C(C1CC(C2=O)O)CCC4=C3C=CC(=C4)O
InChI: InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,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
The 16alpha-hydroxy derivative of estrone; a minor estrogen metabolite.

同义名列表

3 个代谢物同义名

16alpha-hydroxyestrone; 16α-Hydroxyestrone; 16alpha-Hydroxyestrone



数据库引用编号

14 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)

13 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 7 ALB, CCND1, CYP1A1, ESR1, HPGDS, NOX4, PGR
Peripheral membrane protein 3 CYP1A1, CYP1B1, ESR1
Endoplasmic reticulum membrane 5 CYP19A1, CYP1A1, CYP1A2, CYP1B1, NOX4
Nucleus 6 ALB, CCND1, ESR1, IGFBP3, NOX4, PGR
cytosol 6 ALB, CCND1, COMT, ESR1, HPGDS, PGR
dendrite 2 BMPR2, COMT
centrosome 2 ALB, CCND1
nucleoplasm 5 BMPR2, CCND1, ESR1, HPGDS, PGR
Cell membrane 6 BMPR2, COMT, ESR1, NOX1, NOX4, TNF
Cytoplasmic side 1 ESR1
Multi-pass membrane protein 4 CYP19A1, DUOX1, NOX1, NOX4
Synapse 1 COMT
cell surface 4 BMPR2, DUOX1, TNF, TNR
glutamatergic synapse 1 TNR
Golgi apparatus 2 ALB, ESR1
Golgi membrane 1 INS
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 2 BMPR2, TNF
plasma membrane 8 BMPR2, COMT, DUOX1, ESR1, NOX1, NOX4, PGR, TNF
Membrane 7 COMT, CYP19A1, CYP1B1, DUOX1, ESR1, NOX1, NOX4
apical plasma membrane 2 BMPR2, DUOX1
axon 2 BMPR2, COMT
caveola 1 BMPR2
extracellular exosome 3 ALB, COMT, SHBG
endoplasmic reticulum 4 ALB, CYP19A1, DUOX1, NOX4
extracellular space 6 ALB, BMPR2, IGFBP3, INS, TNF, TNR
perinuclear region of cytoplasm 1 NOX4
Schaffer collateral - CA1 synapse 1 TNR
adherens junction 1 BMPR2
bicellular tight junction 1 CCND1
mitochondrion 3 CYP1A1, CYP1B1, NOX4
protein-containing complex 2 ALB, ESR1
intracellular membrane-bounded organelle 5 COMT, CYP1A1, CYP1A2, CYP1B1, HPGDS
Microsome membrane 4 CYP19A1, CYP1A1, CYP1A2, CYP1B1
postsynaptic density 1 BMPR2
Secreted 4 ALB, IGFBP3, INS, SHBG
extracellular region 6 ALB, IGFBP3, INS, SHBG, TNF, TNR
mitochondrial outer membrane 1 PGR
Extracellular side 1 COMT
anchoring junction 2 ALB, NOX1
transcription regulator complex 1 ESR1
Nucleus membrane 1 CCND1
nuclear membrane 1 CCND1
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 TNR
nucleolus 1 NOX4
Early endosome 1 NOX1
clathrin-coated pit 1 BMPR2
recycling endosome 1 TNF
Single-pass type II membrane protein 2 COMT, TNF
Apical cell membrane 1 DUOX1
Cytoplasm, perinuclear region 1 NOX4
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 2 TNF, TNR
Cell junction, focal adhesion 1 NOX4
focal adhesion 1 NOX4
collagen-containing extracellular matrix 1 TNR
receptor complex 1 BMPR2
ciliary basal body 1 ALB
chromatin 2 ESR1, PGR
cell leading edge 1 DUOX1
cell projection 1 NOX1
phagocytic cup 1 TNF
centriole 1 ALB
[Isoform 5]: Cytoplasm 1 NOX4
Nucleus, nucleolus 1 NOX4
spindle pole 1 ALB
blood microparticle 1 ALB
endosome lumen 1 INS
euchromatin 1 ESR1
basal plasma membrane 1 BMPR2
[Isoform 3]: Cytoplasm 1 NOX4
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 ALB, IGFBP3, INS
transcription repressor complex 1 CCND1
platelet alpha granule lumen 1 ALB
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
perineuronal net 1 TNR
perinuclear endoplasmic reticulum 1 NOX4
[Isoform 1]: Nucleus 1 ESR1
[Isoform 4]: Nucleus 1 NOX4
cyclin-dependent protein kinase holoenzyme complex 1 CCND1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
NADPH oxidase complex 3 DUOX1, NOX1, NOX4
insulin-like growth factor binding protein complex 1 IGFBP3
insulin-like growth factor ternary complex 1 IGFBP3
Cell projection, invadopodium membrane 1 NOX1
[Isoform 4]: Mitochondrion outer membrane 1 PGR
[Isoform 6]: Cytoplasm 1 NOX4
cyclin D1-CDK4 complex 1 CCND1
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
tenascin complex 1 TNR
cyclin D1-CDK6 complex 1 CCND1
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • 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]
  • 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]
  • 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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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  • MaryFran Sowers, Daniel McConnell, Mary L Jannausch, John F Randolph, Robert Brook, Ellen B Gold, Sybil Crawford, Bill Lasley. Oestrogen metabolites in relation to isoprostanes as a measure of oxidative stress. Clinical endocrinology. 2008 May; 68(5):806-13. doi: 10.1111/j.1365-2265.2007.03108.x. [PMID: 17980014]
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