3,3-Diindolylmethane (BioDeep_00000298694)

Main id: BioDeep_00000395708

 

PANOMIX_OTCML-2023


代谢物信息卡片


3,3-Diindolylmethane

化学式: C17H14N2 (246.1156924)
中文名称: 3,3-亚甲基二吲哚
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1(CC2=CNC3=C2C=CC=C3)=CNC4=C1C=CC=C4
InChI: InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2

描述信息

C1892 - Chemopreventive Agent > C54630 - Phase II Enzymes Inducer
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents
D000970 - Antineoplastic Agents
3,3'-Diindolylmethane is a strong, pure androgen receptor (AR) antagonist.
3,3'-Diindolylmethane is a strong, pure androgen receptor (AR) antagonist.

同义名列表

5 个代谢物同义名

3,3-Diindolylmethane; DIM; Arundine; HB 236; 3,3'-Diindolylmethane



数据库引用编号

9 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

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

  • Jagadish Natesh, Priya Mondal, Dhanamjai Penta, Yahya Mukhlis, Devendra Jaganath Haware, Syed Musthapa Meeran. Protective effect of diindolylmethane-enriched dietary cabbage against doxorubicin-induced cardiotoxicity in mice. Journal of applied toxicology : JAT. 2024 06; 44(6):874-891. doi: 10.1002/jat.4588. [PMID: 38327044]
  • Paolo Tucci, Iain Brown, Guy S Bewick, Roger G Pertwee, Pietro Marini. The Plant Derived 3-3'-Diindolylmethane (DIM) Behaves as CB2 Receptor Agonist in Prostate Cancer Cellular Models. International journal of molecular sciences. 2023 Feb; 24(4):. doi: 10.3390/ijms24043620. [PMID: 36835033]
  • Yang Ye, Xue Li, Guoquan Feng, Ying Ma, Fen Ye, Haijun Shen, Kang Sun, Rongzhu Lu, Shuhan Miao. 3,3'-Diindolylmethane induces ferroptosis by BAP1-IP3R axis in BGC-823 gastric cancer cells. Anti-cancer drugs. 2022 04; 33(4):362-370. doi: 10.1097/cad.0000000000001270. [PMID: 35266886]
  • Alexander P Lakeev, Elena A Yanovskaya, Daria V Tsuran, Olga S Bryushinina, Natalia Yu Abdrashitova, Yulia G Zyuz'kova, Vladimir V Udut, Vsevolod I Kiselev, Igor N Kuznetsov. A facile and sensitive HPLC-MS/MS method for quantification of 3,3'-diindolylmethane in plasma samples. Biomedical chromatography : BMC. 2022 Mar; 36(3):e5296. doi: 10.1002/bmc.5296. [PMID: 34875720]
  • Monica L Vermillion Maier, Lisbeth K Siddens, Sandra L Uesugi, Jaewoo Choi, Scott W Leonard, Jamie M Pennington, Susan C Tilton, Jordan N Smith, Emily Ho, H H Sherry Chow, Bach D Nguyen, Siva K Kolluri, David E Williams. 3,3'-Diindolylmethane Exhibits Significant Metabolism after Oral Dosing in Humans. Drug metabolism and disposition: the biological fate of chemicals. 2021 08; 49(8):694-705. doi: 10.1124/dmd.120.000346. [PMID: 34035125]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Arun Gokul, Mogamat Fahiem Carelse, Lee-Ann Niekerk, Ashwil Klein, Ndiko Ludidi, David Mendoza-Cozatl, Marshall Keyster. Exogenous 3,3'-Diindolylmethane Improves Vanadium Stress Tolerance in Brassica napus Seedling Shoots by Modulating Antioxidant Enzyme Activities. Biomolecules. 2021 03; 11(3):. doi: 10.3390/biom11030436. [PMID: 33809550]
  • Lin-Hai Chen, Qing Zhang, Xin Xie, Fa-Jun Nan. Modulation of the G-Protein-Coupled Receptor 84 (GPR84) by Agonists and Antagonists. Journal of medicinal chemistry. 2020 12; 63(24):15399-15409. doi: 10.1021/acs.jmedchem.0c01378. [PMID: 33267584]
  • Meryem Köse, Thanigaimalai Pillaiyar, Vigneshwaran Namasivayam, Elisabetta De Filippo, Katharina Sylvester, Trond Ulven, Ivar von Kügelgen, Christa E Müller. An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights. Journal of medicinal chemistry. 2020 03; 63(5):2391-2410. doi: 10.1021/acs.jmedchem.9b01339. [PMID: 31721581]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Jin He, Tao Huang, Lin Zhao. 3,3'‑Diindolylmethane mitigates lipopolysaccharide‑induced acute kidney injury in mice by inhibiting NOX‑mediated oxidative stress and the apoptosis of renal tubular epithelial cells. Molecular medicine reports. 2019 Jun; 19(6):5115-5122. doi: 10.3892/mmr.2019.10178. [PMID: 31059037]
  • A Joseph Bloom, Pramod Upadhyaya, Evan D Kharasch. Strain-specific altered nicotine metabolism in 3,3'-diindolylmethane (DIM) exposed mice. Biopharmaceutics & drug disposition. 2019 May; 40(5-6):188-194. doi: 10.1002/bdd.2182. [PMID: 31016737]
  • Asmita Magotra, Abhishek Gour, Deepak K Sharma, Ashutosh K Dash, Gurdarshan Singh, Debaraj Mukherjee, Utpal Nandi. Pharmacokinetic evaluation of medicinally important synthetic N,N' diindolylmethane glucoside: Improved synthesis and metabolic stability. Bioorganic & medicinal chemistry letters. 2019 04; 29(8):1007-1011. doi: 10.1016/j.bmcl.2019.02.010. [PMID: 30777609]
  • Juliane Mattiazzi, Marcel Henrique Marcondes Sari, Renata Lautenchleger, Morgana Dal Prá, Elizandra Braganhol, Letícia Cruz. Incorporation of 3,3'-Diindolylmethane into Nanocapsules Improves Its Photostability, Radical Scavenging Capacity, and Cytotoxicity Against Glioma Cells. AAPS PharmSciTech. 2019 Jan; 20(2):49. doi: 10.1208/s12249-018-1240-8. [PMID: 30617655]
  • Susan Lanza-Jacoby, Guanjun Cheng. 3,3'-Diindolylmethane enhances apoptosis in docetaxel-treated breast cancer cells by generation of reactive oxygen species. Pharmaceutical biology. 2018 Dec; 56(1):407-414. doi: 10.1080/13880209.2018.1495747. [PMID: 30301388]
  • Zun-En Xia, Juan-Li Xi, Lei Shi. 3,3'-Diindolylmethane ameliorates renal fibrosis through the inhibition of renal fibroblast activation in vivo and in vitro. Renal failure. 2018 Nov; 40(1):447-454. doi: 10.1080/0886022x.2018.1490322. [PMID: 30101622]
  • Nieves Baenas, Clara Suárez-Martínez, Cristina García-Viguera, Diego A Moreno. Bioavailability and new biomarkers of cruciferous sprouts consumption. Food research international (Ottawa, Ont.). 2017 10; 100(Pt 1):497-503. doi: 10.1016/j.foodres.2017.07.049. [PMID: 28873713]
  • Subhadip Hajra, Abhishek Basu, Somnath Singha Roy, Arup Ranjan Patra, Sudin Bhattacharya. Attenuation of doxorubicin-induced cardiotoxicity and genotoxicity by an indole-based natural compound 3,3'-diindolylmethane (DIM) through activation of Nrf2/ARE signaling pathways and inhibiting apoptosis. Free radical research. 2017 Oct; 51(9-10):812-827. doi: 10.1080/10715762.2017.1381694. [PMID: 28922986]
  • 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]
  • Chandraiah Godugu, Ravi Doddapaneni, Stephen H Safe, Mandip Singh. Novel diindolylmethane derivatives based NLC formulations to improve the oral bioavailability and anticancer effects in triple negative breast cancer. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2016 Nov; 108(?):168-179. doi: 10.1016/j.ejpb.2016.08.006. [PMID: 27586082]
  • Naomi Fujioka, Benjamin W Ransom, Steven G Carmella, Pramod Upadhyaya, Bruce R Lindgren, Astia Roper-Batker, Dorothy K Hatsukami, Vincent A Fritz, Charles Rohwer, Stephen S Hecht. Harnessing the Power of Cruciferous Vegetables: Developing a Biomarker for Brassica Vegetable Consumption Using Urinary 3,3'-Diindolylmethane. Cancer prevention research (Philadelphia, Pa.). 2016 Oct; 9(10):788-793. doi: 10.1158/1940-6207.capr-16-0136. [PMID: 27538743]
  • Jason R Gee, Daniel R Saltzstein, Edward Messing, KyungMann Kim, Jill Kolesar, Wei Huang, Thomas C Havighurst, Linda Harris, Barbara W Wollmer, David Jarrard, Margaret House, Howard Parnes, Howard H Bailey. Phase Ib placebo-controlled, tissue biomarker trial of diindolylmethane (BR-DIMNG) in patients with prostate cancer who are undergoing prostatectomy. European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP). 2016 07; 25(4):312-20. doi: 10.1097/cej.0000000000000189. [PMID: 26313229]
  • Lianguo Chen, Rui Ye, Weipeng Zhang, Chenyan Hu, Bingsheng Zhou, Drew R Peterson, Doris W T Au, Paul K S Lam, Pei-Yuan Qian. Endocrine Disruption throughout the Hypothalamus-Pituitary-Gonadal-Liver (HPGL) Axis in Marine Medaka (Oryzias melastigma) Chronically Exposed to the Antifouling and Chemopreventive Agent, 3,3'-Diindolylmethane (DIM). Chemical research in toxicology. 2016 06; 29(6):1020-8. doi: 10.1021/acs.chemrestox.6b00074. [PMID: 27092574]
  • Arun Gokul, Enrico Roode, Ashwil Klein, Marshall Keyster. Exogenous 3,3'-diindolylmethane increases Brassica napus L. seedling shoot growth through modulation of superoxide and hydrogen peroxide content. Journal of plant physiology. 2016 Jun; 196-197(?):93-8. doi: 10.1016/j.jplph.2016.03.013. [PMID: 27100938]
  • Naomi Fujioka, Vincent Fritz, Pramod Upadhyaya, Fekadu Kassie, Stephen S Hecht. Research on cruciferous vegetables, indole-3-carbinol, and cancer prevention: A tribute to Lee W. Wattenberg. Molecular nutrition & food research. 2016 06; 60(6):1228-38. doi: 10.1002/mnfr.201500889. [PMID: 26840393]
  • B Prabhu, D Balakrishnan, S Sundaresan. Antiproliferative and anti-inflammatory properties of diindolylmethane and lupeol against N-butyl-N-(4-hydroxybutyl) nitrosamine induced bladder carcinogenesis in experimental rats. Human & experimental toxicology. 2016 Jun; 35(6):685-92. doi: 10.1177/0960327115597985. [PMID: 26251508]
  • Geum-A Lee, Kyung-A Hwang, Kyung-Chul Choi. Roles of Dietary Phytoestrogens on the Regulation of Epithelial-Mesenchymal Transition in Diverse Cancer Metastasis. Toxins. 2016 05; 8(6):. doi: 10.3390/toxins8060162. [PMID: 27231938]
  • Tien-Yuan Wu, Ying Huang, Chengyue Zhang, Zheng-Yuan Su, Sarandeep Boyanapalli, Tin Oo Khor, Hu Wang, Hongxia Lin, Murugesan Gounder, Leonid Kagan, Ioannis P Androulakis, Ah-Ng Tony Kong. Pharmacokinetics and pharmacodynamics of 3,3'-diindolylmethane (DIM) in regulating gene expression of phase II drug metabolizing enzymes. Journal of pharmacokinetics and pharmacodynamics. 2015 Aug; 42(4):401-8. doi: 10.1007/s10928-015-9421-5. [PMID: 26138223]
  • 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]
  • S Tomar, M Nagarkatti, P S Nagarkatti. 3,3'-Diindolylmethane attenuates LPS-mediated acute liver failure by regulating miRNAs to target IRAK4 and suppress Toll-like receptor signalling. British journal of pharmacology. 2015 Apr; 172(8):2133-47. doi: 10.1111/bph.13036. [PMID: 25521277]
  • Poornima Jayakumar, Kodukkur Vishwanath Pugalendi, Mirunalini Sankaran. Attenuation of hyperglycemia-mediated oxidative stress by indole-3-carbinol and its metabolite 3, 3'- diindolylmethane in C57BL/6J mice. Journal of physiology and biochemistry. 2014 Jun; 70(2):525-34. doi: 10.1007/s13105-014-0332-5. [PMID: 24715233]
  • Justin Moussata, Zhijun Wang, Jeffrey Wang. Development and validation of an HPLC method for the simultaneous quantification of indole-3-carbinol acetate, indole-3-carbinol, and 3,3'-diindolylmethane in mouse plasma, liver, and kidney tissues. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 May; 958(?):1-9. doi: 10.1016/j.jchromb.2014.02.026. [PMID: 24686233]
  • Naomi Fujioka, Cheryl E Ainslie-Waldman, Pramod Upadhyaya, Steven G Carmella, Vincent A Fritz, Charles Rohwer, Yunhua Fan, Diane Rauch, Chap Le, Dorothy K Hatsukami, Stephen S Hecht. Urinary 3,3'-diindolylmethane: a biomarker of glucobrassicin exposure and indole-3-carbinol uptake in humans. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2014 Feb; 23(2):282-7. doi: 10.1158/1055-9965.epi-13-0645. [PMID: 24357105]
  • Philip B Busbee, Mitzi Nagarkatti, Prakash S Nagarkatti. Natural indoles, indole-3-carbinol and 3,3'-diindolymethane, inhibit T cell activation by staphylococcal enterotoxin B through epigenetic regulation involving HDAC expression. Toxicology and applied pharmacology. 2014 Jan; 274(1):7-16. doi: 10.1016/j.taap.2013.10.022. [PMID: 24200994]
  • Jayakumar Poornima, Sankaran Mirunalini. Regulation of carbohydrate metabolism by indole-3-carbinol and its metabolite 3,3'-diindolylmethane in high-fat diet-induced C57BL/6J mice. Molecular and cellular biochemistry. 2014 Jan; 385(1-2):7-15. doi: 10.1007/s11010-013-1808-2. [PMID: 24072613]
  • Cheryl E Ainslie-Waldman, Scott W Simpkins, Pramod Upadhyaya, Steven G Carmella, Stephen S Hecht, Sabrina P Trudo. Contamination of deconjugation enzymes derived from Helix pomatia with the plant bioactive compounds 3,3'-diindolylmethane, 5-methoxypsoralen, and 8-methoxypsoralen. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Dec; 62(?):188-93. doi: 10.1016/j.fct.2013.08.055. [PMID: 23994708]
  • Somnath Kandekar, Ranjan Preet, Maneesh Kashyap, M U Renu Prasad, Purusottam Mohapatra, Dipon Das, Shakti Ranjan Satapathy, Sumit Siddharth, Vaibhav Jain, Maitrayee Choudhuri, Chanakya N Kundu, Sankar K Guchhait, Prasad V Bharatam. Structural elaboration of a natural product: identification of 3,3'-diindolylmethane aminophosphonate and urea derivatives as potent anticancer agents. ChemMedChem. 2013 Nov; 8(11):1873-84. doi: 10.1002/cmdc.201300273. [PMID: 23983049]
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  • Yangchao Luo, Thomas T Y Wang, Zi Teng, Pei Chen, Jianghao Sun, Qin Wang. Encapsulation of indole-3-carbinol and 3,3'-diindolylmethane in zein/carboxymethyl chitosan nanoparticles with controlled release property and improved stability. Food chemistry. 2013 Aug; 139(1-4):224-30. doi: 10.1016/j.foodchem.2013.01.113. [PMID: 23561099]
  • Chen Chen, Shi-Ming Chen, Bin Xu, Zhe Chen, Fei Wang, Jie Ren, Yong Xu, Yan Wang, Bo-Kui Xiao, Ze-Zhang Tao. In vivo and in vitro study on the role of 3,3'-diindolylmethane in treatment and prevention of nasopharyngeal carcinoma. Carcinogenesis. 2013 Aug; 34(8):1815-21. doi: 10.1093/carcin/bgt122. [PMID: 23568953]
  • Y-C Fang, C-T Chou, C-C Chi, K-L Lin, Y-D Li, H-H Cheng, Y-C Lu, J-S Cheng, C-C Kuo, C-R Jan. Effect of diindolylmethane on Ca(2+) homeostasis and viability in MDCK renal tubular cells. Human & experimental toxicology. 2013 Apr; 32(4):344-53. doi: 10.1177/0960327112462727. [PMID: 23613483]
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  • Jiahua Jiang, Anita Thyagarajan-Sahu, Jagadish Loganathan, Isaac Eliaz, Colin Terry, George E Sandusky, Daniel Sliva. BreastDefend™ prevents breast-to-lung cancer metastases in an orthotopic animal model of triple-negative human breast cancer. Oncology reports. 2012 Oct; 28(4):1139-45. doi: 10.3892/or.2012.1936. [PMID: 22842551]
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  • Daniel W Sepkovic, Laura Raucci, Johann Stein, Antoine D Carlisle, Karen Auborn, H Barbara Ksieski, Themba Nyirenda, H Leon Bradlow. 3,3'-Diindolylmethane increases serum interferon-γ levels in the K14-HPV16 transgenic mouse model for cervical cancer. In vivo (Athens, Greece). 2012 Mar; 26(2):207-11. doi: NULL. [PMID: 22351660]
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  • Litao Wang, Wei Wei, Yong Guo, Jian Xu, Shijun Shao. Nitro-substituted 3,3'-bis(indolyl)methane derivatives as anion receptors: electron-withdrawing effect and tunability of anion binding properties. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2011 Feb; 78(2):726-31. doi: 10.1016/j.saa.2010.12.004. [PMID: 21186137]
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