4-Vinylcyclohexene dioxide (BioDeep_00000012748)
Secondary id: BioDeep_00001867952
human metabolite blood metabolite
代谢物信息卡片
化学式: C8H12O2 (140.0837252)
中文名称: 3-环氧乙烷基7-氧杂二环[4.1.0]庚烷, 二氧化乙烯基环己烯
谱图信息:
最多检出来源 Homo sapiens(blood) 73.74%
分子结构信息
SMILES: C1CC2C(O2)CC1C3CO3
InChI: InChI=1S/C8H12O2/c1-2-6-7(10-6)3-5(1)8-4-9-8/h5-8H,1-4H2
描述信息
D009676 - Noxae > D002273 - Carcinogens
同义名列表
19 个代谢物同义名
3-(1,2-Epoxyethyl)-7-oxabicyclo(4.1.0)heptane; 4-(1,2-Epoxyethyl)-7-oxabicyclo(4.1.0)heptane; 3-(oxiran-2-yl)-7-oxabicyclo[4.1.0]heptane; 4-(Epoxyethyl)-7-oxabicyclo(4.1.0)heptane; 3-(Epoxyethyl)-7-oxabicyclo(4.1.0)heptane; 3-(2-Oxiranyl)-7-oxabicyclo[4.1.0]heptane; 3-Oxiranyl-7-oxabicyclo(4.1.0)heptane; 1-Ethyleneoxy-3,4-epoxycyclohexane; 1-Epoxyethyl-3,4-epoxycyclohexane; 4-Vinyl-1,2-cyclohexene diepoxide; 1-Vinyl-3-cyclohexene dioxide; 4-Vinyl-1-cyclohexene dioxide; 4-Vinylcyclohexene diepoxide; Vinyl cyclohexene diepoxide; Vinyl cyclohexane diepoxide; 4-Vinylcyclohexene dioxide; Vinylcyclohexene diepoxide; Vinyl cyclohexene dioxide; UNII:596C064IG4
数据库引用编号
12 个数据库交叉引用编号
- ChEBI: CHEBI:59001
- KEGG: C19311
- PubChem: 7833
- HMDB: HMDB0246593
- Metlin: METLIN73022
- ChEMBL: CHEMBL1734307
- Wikipedia: Vinylcyclohexene dioxide
- chemspider: 7545
- CAS: 25086-25-3
- CAS: 106-87-6
- PMhub: MS000027077
- PubChem: 124489983
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。
文献列表
- Ang Li, Fei Li, Wei Song, Zi-Li Lei, Chang-Yin Zhou, Xue Zhang, Qing-Yuan Sun, Qin Zhang, Teng Zhang. Maternal exposure to 4-vinylcyclohexene diepoxide during pregnancy leads to disorder of gut microbiota and bile acid metabolism in offspring.
Ecotoxicology and environmental safety.
2024 Jan; 269(?):115811. doi:
10.1016/j.ecoenv.2023.115811
. [PMID: 38086265] - Ke Sui, Ali Yasrebi, Candace R Longoria, Avery T MacDonell, Zehra H Jaffri, Savannah A Martinez, Samuel E Fisher, Natasha Malonza, Katie Jung, Kevin M Tveter, Kimberly R Wiersielis, Mehmet Uzumcu, Sue A Shapses, Sara C Campbell, Troy A Roepke, Diana E Roopchand. Coconut Oil Saturated Fatty Acids Improved Energy Homeostasis but not Blood Pressure or Cognition in VCD-Treated Female Mice.
Endocrinology.
2023 01; 164(3):. doi:
10.1210/endocr/bqad001
. [PMID: 36626144] - Hyun Joo Lee, Min Jung Park, Bo Sun Joo, Jong Kil Joo, Yeon Hee Kim, Sun Woo Yang, Chang-Woon Kim, Ki Hyung Kim. Effects of coenzyme Q10 on ovarian surface epithelium-derived ovarian stem cells and ovarian function in a 4-vinylcyclohexene diepoxide-induced murine model of ovarian failure.
Reproductive biology and endocrinology : RB&E.
2021 Apr; 19(1):59. doi:
10.1186/s12958-021-00736-x
. [PMID: 33888135] - Xianzhi Su, Xiaomei Wang, Yifei Liu, Wenjuan Kong, Fei Yan, Fuguo Han, Qingfei Liu, Yun Shi. Effect of Jiajian Guishen Formula on the senescence-associated heterochromatic foci in mouse ovaria after induction of premature ovarian aging by the endocrine-disrupting agent 4-vinylcyclohexene diepoxide.
Journal of ethnopharmacology.
2021 Apr; 269(?):113720. doi:
10.1016/j.jep.2020.113720
. [PMID: 33358858] - Feyyaz Özel, Müge Kiray, Aslı Göker, Selma Aydemir, Serap Cilaker Mıcılı. Protective effect of alpha lipoic acid on 4-vinylcyclohexene diepoxide induced primary ovarian failure in female rats.
Taiwanese journal of obstetrics & gynecology.
2020 Mar; 59(2):293-300. doi:
10.1016/j.tjog.2020.01.020
. [PMID: 32127153] - Astrid C Ovalles, Natalina H Contoreggi, Jose Marques-Lopes, Tracey A Van Kempen, Costantino Iadecola, Elizabeth M Waters, Michael J Glass, Teresa A Milner. Plasma Membrane Affiliated AMPA GluA1 in Estrogen Receptor β-containing Paraventricular Hypothalamic Neurons Increases Following Hypertension in a Mouse Model of Post-menopause.
Neuroscience.
2019 12; 423(?):192-205. doi:
10.1016/j.neuroscience.2019.09.026
. [PMID: 31682817] - Li Xie, Sining Wu, Dongdong Cao, Meifang Li, Jian Liu, Guangning Nie, Yang Li, Hongyan Yang. Huyang yangkun formula protects against 4-Vinylcyclohexene diepoxide-induced premature ovarian insufficiency in rats via the Hippo-JAK2/STAT3 signaling pathway.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2019 Aug; 116(?):109008. doi:
10.1016/j.biopha.2019.109008
. [PMID: 31152926] - Flaviano Lorenzon, Bruna B Simas, Tamires Gregorio, Janete A Anselmo-Franci, Cilene Lino de Oliveira, Domitila A Huber, Fernanda B Lima. Ovarian failure induced by 4-vinylcyclohexene diepoxide worsens the autonomic cardiovascular response to chronic unpredictable stress in rats.
Life sciences.
2019 Jun; 226(?):130-139. doi:
10.1016/j.lfs.2019.04.007
. [PMID: 30965055] - Deokho Kim, Quan Feng Liu, Ha Jin Jeong, Seung-Hee Han, Dong-Il Kim, Songhee Jeon. A Modified Formulation of Sutaehwan Ameliorates Menopausal Anxiety, Depression and Heart Hypertrophy in the VCD-Induced Menopausal Mouse Model.
Biological & pharmaceutical bulletin.
2019; 42(9):1471-1481. doi:
10.1248/bpb.b19-00056
. [PMID: 31474708] - Ruither O G Carolino, Paulo T Barros, Bruna Kalil, Janete Anselmo-Franci. Endocrine profile of the VCD-induced perimenopausal model rat.
PloS one.
2019; 14(12):e0226874. doi:
10.1371/journal.pone.0226874
. [PMID: 31887176] - Dinh Nam Tran, Eui-Man Jung, Yeong-Min Yoo, Changhwan Ahn, Hee Young Kang, Kyung-Chul Choi, Sang-Hwan Hyun, Vu Hoang Dang, Thi Ngoc Pham, Eui-Bae Jeung. Depletion of follicles accelerated by combined exposure to phthalates and 4-vinylcyclohexene diepoxide, leading to premature ovarian failure in rats.
Reproductive toxicology (Elmsford, N.Y.).
2018 09; 80(?):60-67. doi:
10.1016/j.reprotox.2018.06.071
. [PMID: 29969652] - Sun-Ji Park, Jung-Hak Kim, Dong Gil Lee, Jin-Man Kim, Dong-Seok Lee. Peroxiredoxin 2 deficiency accelerates age-related ovarian failure through the reactive oxygen species-mediated JNK pathway in mice.
Free radical biology & medicine.
2018 08; 123(?):96-106. doi:
10.1016/j.freeradbiomed.2018.05.059
. [PMID: 29778464] - Abul Kalam, Sushama Talegaonkar, Divya Vohora. Effects of raloxifene against letrozole-induced bone loss in chemically-induced model of menopause in mice.
Molecular and cellular endocrinology.
2017 01; 440(?):34-43. doi:
10.1016/j.mce.2016.11.005
. [PMID: 27832985] - Jose Marques-Lopes, Ephrath Tesfaye, Sigal Israilov, Tracey A Van Kempen, Gang Wang, Michael J Glass, Virginia M Pickel, Costantino Iadecola, Elizabeth M Waters, Teresa A Milner. Redistribution of NMDA Receptors in Estrogen-Receptor-β-Containing Paraventricular Hypothalamic Neurons following Slow-Pressor Angiotensin II Hypertension in Female Mice with Accelerated Ovarian Failure.
Neuroendocrinology.
2017; 104(3):239-256. doi:
10.1159/000446073
. [PMID: 27078860] - Francielle Garghetti Battiston, Cristiane Dos Santos, Amanda Marreiro Barbosa, Sibele Sehnem, Ellen Cristina Rivas Leonel, Sebastião Roberto Taboga, Janete A Anselmo-Franci, Fernanda Barbosa Lima, Alex Rafacho. Glucose homeostasis in rats treated with 4-vinylcyclohexene diepoxide is not worsened by dexamethasone treatment.
The Journal of steroid biochemistry and molecular biology.
2017 01; 165(Pt B):170-181. doi:
10.1016/j.jsbmb.2016.06.001
. [PMID: 27264932] - Eun-Young Nam, Sun Ah Kim, Heejung Kim, Su-Hyun Kim, Jae-Hyun Han, Ju-Hee Lee, Dong-Il Kim. Akt activation by Evodiae Fructus extract protects ovary against 4-vinylcyclohexene diepoxide-induced ovotoxicity.
Journal of ethnopharmacology.
2016 Dec; 194(?):733-739. doi:
10.1016/j.jep.2016.10.048
. [PMID: 27769945] - Xiaoxue Xing, Lina Su, Patrick Fordjour Asare, Lingyan Wang, Lan Li, Erwei Liu, Bing Yu, Yan Zhu, Xiumei Gao, Guanwei Fan. Danzhi Qing'e (DZQE) activates AMPK pathway and regulates lipid metabolism in a rat model of perimenopausal hyperlipidaemia.
Experimental physiology.
2016 11; 101(11):1406-1417. doi:
10.1113/ep085786
. [PMID: 27456335] - Ting Zhang, Dawei Yan, Yang Yang, Aicui Ma, Lei Li, Zhonghui Wang, Qi Pan, Zuyue Sun. The comparison of animal models for premature ovarian failure established by several different source of inducers.
Regulatory toxicology and pharmacology : RTP.
2016 Nov; 81(?):223-232. doi:
10.1016/j.yrtph.2016.09.002
. [PMID: 27612992] - Amos Olalekan Abolaji, Pere-Ebi Toloyai, Titilope Deborah Odeleye, Susan Akinduro, Joao Batista Teixeira Rocha, Ebenezer Olatunde Farombi. Hepatic and renal toxicological evaluations of an industrial ovotoxic chemical, 4-vinylcyclohexene diepoxide, in both sexes of Wistar rats.
Environmental toxicology and pharmacology.
2016 Jul; 45(?):28-40. doi:
10.1016/j.etap.2016.05.010
. [PMID: 27258136] - H L Brooks, D P Pollow, P B Hoyer. The VCD Mouse Model of Menopause and Perimenopause for the Study of Sex Differences in Cardiovascular Disease and the Metabolic Syndrome.
Physiology (Bethesda, Md.).
2016 07; 31(4):250-7. doi:
10.1152/physiol.00057.2014
. [PMID: 27252160] - Dennis P Pollow, Melissa J Romero-Aleshire, Jessica N Sanchez, John P Konhilas, Heddwen L Brooks. ANG II-induced hypertension in the VCD mouse model of menopause is prevented by estrogen replacement during perimenopause.
American journal of physiology. Regulatory, integrative and comparative physiology.
2015 Dec; 309(12):R1546-52. doi:
10.1152/ajpregu.00170.2015
. [PMID: 26491098] - Wei Liu, Ling-Yan Wang, Xiao-Xue Xing, Guan-Wei Fan. Conditions and possible mechanisms of VCD-induced ovarian failure.
Alternatives to laboratory animals : ATLA.
2015 Dec; 43(6):385-92. doi:
10.1177/026119291504300606
. [PMID: 26753941] - Kristen A Roosa, Devin A Zysling, Ned J Place. An assessment of anti-Müllerian hormone in predicting mating outcomes in female hamsters that have undergone natural and chemically-accelerated reproductive aging.
General and comparative endocrinology.
2015 Apr; 214(?):56-61. doi:
10.1016/j.ygcen.2015.03.007
. [PMID: 25801548] - Lei Zhu, Ji Li, Nannan Xing, Dongwei Han, Haixue Kuang, Pengling Ge. American ginseng regulates gene expression to protect against premature ovarian failure in rats.
BioMed research international.
2015; 2015(?):767124. doi:
10.1155/2015/767124
. [PMID: 25705687] - Pengling Ge, Nannan Xing, Yanhai Ren, Lei Zhu, Dongwei Han, Haixue Kuang, Ji Li. Preventive effect of American ginseng against premature ovarian failure in a rat model.
Drug development research.
2014 Dec; 75(8):521-8. doi:
10.1002/ddr.21234
. [PMID: 25424468] - F M C V Reis, N Pestana-Oliveira, C M Leite, F B Lima, M L Brandão, F G Graeff, C M Del-Ben, J A Anselmo-Franci. Hormonal changes and increased anxiety-like behavior in a perimenopause-animal model induced by 4-vinylcyclohexene diepoxide (VCD) in female rats.
Psychoneuroendocrinology.
2014 Nov; 49(?):130-40. doi:
10.1016/j.psyneuen.2014.06.019
. [PMID: 25080405] - Jennifer B Frye, Ashley L Lukefahr, Laura E Wright, Sam L Marion, Patricia B Hoyer, Janet L Funk. Modeling perimenopause in Sprague-Dawley rats by chemical manipulation of the transition to ovarian failure.
Comparative medicine.
2012 Jun; 62(3):193-202. doi:
NULL
. [PMID: 22776052] - A L Lukefahr, J B Frye, L E Wright, S L Marion, P B Hoyer, J L Funk. Decreased bone mineral density in rats rendered follicle-deplete by an ovotoxic chemical correlates with changes in follicle-stimulating hormone and inhibin A.
Calcified tissue international.
2012 Mar; 90(3):239-49. doi:
10.1007/s00223-011-9565-2
. [PMID: 22249524] - Virginia M Miller, Jay R Kaplan, Nicholas J Schork, Pamela Ouyang, Sarah L Berga, Nanette K Wenger, Leslee J Shaw, R Clinton Webb, Monica Mallampalli, Meir Steiner, Doris A Taylor, C Noel Bairey Merz, Jane F Reckelhoff. Strategies and methods to study sex differences in cardiovascular structure and function: a guide for basic scientists.
Biology of sex differences.
2011 Dec; 2(?):14. doi:
10.1186/2042-6410-2-14
. [PMID: 22152231] - Sarah M Greising, Ryan S Carey, Jennifer E Blackford, Laurin E Dalton, Allison M Kosir, Dawn A Lowe. Estradiol treatment, physical activity, and muscle function in ovarian-senescent mice.
Experimental gerontology.
2011 Aug; 46(8):685-93. doi:
10.1016/j.exger.2011.04.006
. [PMID: 21570459] - Maggie K Diamond-Stanic, Melissa J Romero-Aleshire, Patricia B Hoyer, Kevin Greer, James B Hoying, Heddwen L Brooks. Midkine, a heparin-binding protein, is increased in the diabetic mouse kidney postmenopause.
American journal of physiology. Renal physiology.
2011 Jan; 300(1):F139-46. doi:
10.1152/ajprenal.00249.2010
. [PMID: 21048029] - Alexander P Sobinoff, Victoria Pye, Brett Nixon, Shaun D Roman, Eileen A McLaughlin. Adding insult to injury: effects of xenobiotic-induced preantral ovotoxicity on ovarian development and oocyte fusibility.
Toxicological sciences : an official journal of the Society of Toxicology.
2010 Dec; 118(2):653-66. doi:
10.1093/toxsci/kfq272
. [PMID: 20829426] - Susan E Appt, Thomas B Clarkson, Patricia B Hoyer, Nancy D Kock, Amanda K Goode, M Christina May, Joseph T Persyn, Neal K Vail, Kelly F Ethun, Haiying Chen, Nivedita Sen, Jay R Kaplan. Experimental induction of reduced ovarian reserve in a nonhuman primate model (Macaca fascicularis).
Comparative medicine.
2010 Oct; 60(5):380-8. doi:
NULL
. [PMID: 21262124] - Sukhdeep K Sahambi, Jenny A Visser, Axel P N Themmen, Loretta P Mayer, Patrick J Devine. Correlation of serum anti-Müllerian hormone with accelerated follicle loss following 4-vinylcyclohexene diepoxide-induced follicle loss in mice.
Reproductive toxicology (Elmsford, N.Y.).
2008 Oct; 26(2):116-22. doi:
10.1016/j.reprotox.2008.07.005
. [PMID: 18706995] - Maggie Keck, Melissa J Romero-Aleshire, Qi Cai, Patricia B Hoyer, Heddwen L Brooks. Hormonal status affects the progression of STZ-induced diabetes and diabetic renal damage in the VCD mouse model of menopause.
American journal of physiology. Renal physiology.
2007 Jul; 293(1):F193-9. doi:
10.1152/ajprenal.00022.2007
. [PMID: 17389681] - Jessica C Lohff, Patricia J Christian, Samuel L Marion, Patricia B Hoyer. Effect of duration of dosing on onset of ovarian failure in a chemical-induced mouse model of perimenopause.
Menopause (New York, N.Y.).
2006 May; 13(3):482-8. doi:
10.1097/01.gme.0000191883.59799.2e
. [PMID: 16735946] - Jessica C Lohff, Patricia J Christian, Samuel L Marion, Anthony Arrandale, Patricia B Hoyer. Characterization of cyclicity and hormonal profile with impending ovarian failure in a novel chemical-induced mouse model of perimenopause.
Comparative medicine.
2005 Dec; 55(6):523-7. doi:
NULL
. [PMID: 16422148] - Loretta P Mayer, Patrick J Devine, Cheryl A Dyer, Patricia B Hoyer. The follicle-deplete mouse ovary produces androgen.
Biology of reproduction.
2004 Jul; 71(1):130-8. doi:
10.1095/biolreprod.103.016113
. [PMID: 14998904] - Trish Berger, Catherine M Horner. In vivo exposure of female rats to toxicants may affect oocyte quality.
Reproductive toxicology (Elmsford, N.Y.).
2003 May; 17(3):273-81. doi:
10.1016/s0890-6238(03)00009-1
. [PMID: 12759095] - Loretta P Mayer, Nicole A Pearsall, Patricia J Christian, Patrick J Devine, Claire M Payne, Margaret K McCuskey, Samuel L Marion, I Glenn Sipes, Patricia B Hoyer. Long-term effects of ovarian follicular depletion in rats by 4-vinylcyclohexene diepoxide.
Reproductive toxicology (Elmsford, N.Y.).
2002 Nov; 16(6):775-81. doi:
10.1016/s0890-6238(02)00048-5
. [PMID: 12401505] - S Dhillon, R Von Burg. Vinylcyclohexene dioxide.
Journal of applied toxicology : JAT.
1996 Sep; 16(5):465-8. doi:
10.1002/jat.2550160503
. [PMID: 8889800] - B J Smith, D E Carter, I G Sipes. Comparison of the disposition and in vitro metabolism of 4-vinylcyclohexene in the female mouse and rat.
Toxicology and applied pharmacology.
1990 Sep; 105(3):364-71. doi:
10.1016/0041-008x(90)90140-p
. [PMID: 2237911] - R S Chhabra, M R Elwell, A Peters. Toxicity of 4-vinyl-1-cyclohexene diepoxide after 13 weeks of dermal or oral exposure in rats and mice.
Fundamental and applied toxicology : official journal of the Society of Toxicology.
1990 May; 14(4):745-51. doi:
10.1016/0272-0590(90)90299-y
. [PMID: 2361574] - R Patterson, K E Harris, W Stopford, G Van der Heiden, L C Grammer, W Bunn. Irritant symptoms and immunologic responses to multiple chemicals: importance of clinical and immunologic correlations.
International archives of allergy and applied immunology.
1988; 85(4):467-71. doi:
10.1159/000234553
. [PMID: 3356477]