Bryo 1 (BioDeep_00000176848)

   

human metabolite blood metabolite


代谢物信息卡片


25-(Acetyloxy)-1,11,21-trihydroxy-17-(1-hydroxyethyl)-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1³,⁷.1¹¹,¹⁵]nonacos-8-en-12-yl octa-2,4-dienoic acid

化学式: C47H68O17 (904.4456278)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 25%

分子结构信息

SMILES: CCCC=CC=CC(=O)OC1C(CC2CC(OC(=O)CC(O)CC3CC(OC(C)=O)C(C)(C)C(O)(CC4CC(CC(O4)C=CC(C)(C)C1(O)O2)=CC(=O)OC)O3)C(C)O)=CC(=O)OC
InChI: InChI=1S/C47H68O17/c1-10-11-12-13-14-15-39(51)62-43-31(22-41(53)58-9)21-34-25-37(28(2)48)61-42(54)24-32(50)23-35-26-38(59-29(3)49)45(6,7)46(55,63-35)27-36-19-30(20-40(52)57-8)18-33(60-36)16-17-44(4,5)47(43,56)64-34/h12-17,20,22,28,32-38,43,48,50,55-56H,10-11,18-19,21,23-27H2,1-9H3



数据库引用编号

2 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)

3 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

  • Youngki You, Joydip Das. Molecular dynamics simulation studies on binding of activator and inhibitor to Munc13-1 C1 in the presence of membrane. Journal of biomolecular structure & dynamics. 2022; 40(24):14160-14175. doi: 10.1080/07391102.2021.2001375. [PMID: 34779746]
  • Francisco A Blanco, Agnes Czikora, Noemi Kedei, Youngki You, Gary A Mitchell, Satyabrata Pany, Anamitra Ghosh, Peter M Blumberg, Joydip Das. Munc13 Is a Molecular Target of Bryostatin 1. Biochemistry. 2019 07; 58(27):3016-3030. doi: 10.1021/acs.biochem.9b00427. [PMID: 31243993]
  • Xiang Rong Tian, Hai Feng Tang, Xiao Lin Tian, Jia Jun Hu, Li Li Huang, Kirk R Gustafson. Review of bioactive secondary metabolites from marine bryozoans in the progress of new drugs discovery. Future medicinal chemistry. 2018 06; 10(12):1497-1514. doi: 10.4155/fmc-2018-0012. [PMID: 29788787]
  • Elsayed I Salim, Samar F Harras, Aisha G Abdalla, Mohmmed H Mona. Syphacia muris infection in rats attenuates colorectal carcinogenesis through oxidative stress and gene expression alterations. Implications for modulatory effects by Bryostatin-1. Acta parasitologica. 2018 Mar; 63(1):198-209. doi: 10.1515/ap-2018-0023. [PMID: 29351079]
  • Steven M Ryckbosch, Paul A Wender, Vijay S Pande. Molecular dynamics simulations reveal ligand-controlled positioning of a peripheral protein complex in membranes. Nature communications. 2017 02; 8(1):6. doi: 10.1038/s41467-016-0015-8. [PMID: 28232750]
  • Carolina Gutiérrez, Sergio Serrano-Villar, Nadia Madrid-Elena, Maria J Pérez-Elías, Maria Elena Martín, Coral Barbas, Javier Ruipérez, Eduardo Muñoz, Maria Angeles Muñoz-Fernández, Trevor Castor, Santiago Moreno. Bryostatin-1 for latent virus reactivation in HIV-infected patients on antiretroviral therapy. AIDS (London, England). 2016 06; 30(9):1385-92. doi: 10.1097/qad.0000000000001064. [PMID: 26891037]
  • Sergey Iordanskiy, Rachel Van Duyne, Gavin C Sampey, Caitlin M Woodson, Kelsi Fry, Mohammed Saifuddin, Jia Guo, Yuntao Wu, Fabio Romerio, Fatah Kashanchi. Therapeutic doses of irradiation activate viral transcription and induce apoptosis in HIV-1 infected cells. Virology. 2015 Nov; 485(?):1-15. doi: 10.1016/j.virol.2015.06.021. [PMID: 26184775]
  • Gregory M Laird, C Korin Bullen, Daniel I S Rosenbloom, Alyssa R Martin, Alison L Hill, Christine M Durand, Janet D Siliciano, Robert F Siliciano. Ex vivo analysis identifies effective HIV-1 latency-reversing drug combinations. The Journal of clinical investigation. 2015 May; 125(5):1901-12. doi: 10.1172/jci80142. [PMID: 25822022]
  • Daniel C Buehler, Matthew D Marsden, Sean Shen, Daniel B Toso, Xiaomeng Wu, Joseph A Loo, Z Hong Zhou, Valerie A Kickhoefer, Paul A Wender, Jerome A Zack, Leonard H Rome. Bioengineered vaults: self-assembling protein shell-lipophilic core nanoparticles for drug delivery. ACS nano. 2014 Aug; 8(8):7723-32. doi: 10.1021/nn5002694. [PMID: 25061969]
  • Elizabeth R Plimack, Tingting Tan, Yu-Ning Wong, Margaret M von Mehren, Lois Malizzia, Susan K Roethke, Samuel Litwin, Tianyu Li, Gary R Hudes, Naomi B Haas. A phase I study of temsirolimus and bryostatin-1 in patients with metastatic renal cell carcinoma and soft tissue sarcoma. The oncologist. 2014 Apr; 19(4):354-5. doi: 10.1634/theoncologist.2014-0020. [PMID: 24674872]
  • Thomas J Nelson, Abhik Sen, Daniel L Alkon, Miao-Kun Sun. Adduct formation in liquid chromatography-triple quadrupole mass spectrometric measurement of bryostatin 1. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jan; 944(?):55-62. doi: 10.1016/j.jchromb.2013.11.020. [PMID: 24291721]
  • Noemi Kedei, Emanuel Lubart, Nancy E Lewin, Andrea Telek, Langston Lim, Poonam Mannan, Susan H Garfield, Matthew B Kraft, Gary E Keck, Sofiya Kolusheva, Raz Jelinek, Peter M Blumberg. Some phorbol esters might partially resemble bryostatin 1 in their actions on LNCaP prostate cancer cells and U937 leukemia cells. Chembiochem : a European journal of chemical biology. 2011 May; 12(8):1242-51. doi: 10.1002/cbic.201100064. [PMID: 21542090]
  • B Douglas Smith, Richard J Jones, Eunpi Cho, Jeanne Kowalski, Judith E Karp, Steven D Gore, Milada Vala, Brooke Meade, Sharyn D Baker, Ming Zhao, Steven Piantadosi, Zhe Zhang, Gideon Blumenthal, Erica D Warlick, Robert A Brodsky, Anthony Murgo, Michelle A Rudek, William H Matsui. Differentiation therapy in poor risk myeloid malignancies: Results of a dose finding study of the combination bryostatin-1 and GM-CSF. Leukemia research. 2011 Jan; 35(1):87-94. doi: 10.1016/j.leukres.2010.06.001. [PMID: 20598742]
  • Vivian A von Burstin, Liqing Xiao, Marcelo G Kazanietz. Bryostatin 1 inhibits phorbol ester-induced apoptosis in prostate cancer cells by differentially modulating protein kinase C (PKC) delta translocation and preventing PKCdelta-mediated release of tumor necrosis factor-alpha. Molecular pharmacology. 2010 Sep; 78(3):325-32. doi: 10.1124/mol.110.064741. [PMID: 20516369]
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  • Miao-Kun Sun, Daniel L Alkon. Synergistic effects of chronic bryostatin-1 and alpha-tocopherol on spatial learning and memory in rats. European journal of pharmacology. 2008 Apr; 584(2-3):328-37. doi: 10.1016/j.ejphar.2008.02.014. [PMID: 18313045]
  • Basil F El-Rayes, Shirish Gadgeel, Anthony F Shields, Stephanie Manza, Patricia Lorusso, Philip A Philip. Phase I study of bryostatin 1 and gemcitabine. Clinical cancer research : an official journal of the American Association for Cancer Research. 2006 Dec; 12(23):7059-62. doi: 10.1158/1078-0432.ccr-06-1419. [PMID: 17145828]
  • Matthew C Tuthill, Carolyn E Oki, Patricia S Lorenzo. Differential effects of bryostatin 1 and 12-O-tetradecanoylphorbol-13-acetate on the regulation and activation of RasGRP1 in mouse epidermal keratinocytes. Molecular cancer therapeutics. 2006 Mar; 5(3):602-10. doi: 10.1158/1535-7163.mct-05-0317. [PMID: 16546974]
  • Amy C Peterson, Helena Harlin, Theodore Karrison, Nicholas J Vogelzang, James A Knost, John W Kugler, Eric Lester, Everett Vokes, Thomas F Gajewski, Walter M Stadler. A randomized phase II trial of interleukin-2 in combination with four different doses of bryostatin-1 in patients with renal cell carcinoma. Investigational new drugs. 2006 Mar; 24(2):141-9. doi: 10.1007/s10637-006-5935-4. [PMID: 16514482]
  • Trever G Bivona, Steven E Quatela, Brian O Bodemann, Ian M Ahearn, Michael J Soskis, Adam Mor, John Miura, Heidi H Wiener, Latasha Wright, Shahryar G Saba, Duke Yim, Adam Fein, Ignacio Pérez de Castro, Chi Li, Craig B Thompson, Adrienne D Cox, Mark R Philips. PKC regulates a farnesyl-electrostatic switch on K-Ras that promotes its association with Bcl-XL on mitochondria and induces apoptosis. Molecular cell. 2006 Feb; 21(4):481-93. doi: 10.1016/j.molcel.2006.01.012. [PMID: 16483930]
  • Thomas J Manning, Michael Land, Emily Rhodes, Linda Chamberlin, Jack Rudloe, Dennis Phillips, Tukiet T Lam, Jeremiah Purcell, Helen J Cooper, Mark R Emmett, Alan G Marshall. Identifying bryostatins and potential precursors from the bryozoan Bugula neritina. Natural product research. 2005 Jul; 19(5):467-91. doi: 10.1080/14786410412331280041. [PMID: 15938194]
  • Ming Zhao, Michelle A Rudek, Ping He, B Douglas Smith, Sharyn D Baker. Validation and implementation of a method for determination of bryostatin 1 in human plasma by using liquid chromatography/tandem mass spectrometry. Analytical biochemistry. 2005 Feb; 337(1):143-8. doi: 10.1016/j.ab.2004.10.030. [PMID: 15649387]
  • Caitlin Hammond, Yonghong Shi, Jenny Mena, Jelena Tomic, David Cervi, Liwei He, Amanda E Millar, Mark Debenedette, Andre C Schuh, Jeremy L Baryza, Paul A Wender, Laszlo Radvanyi, David E Spaner. Effect of serum and antioxidants on the immunogenicity of protein kinase C-activated chronic lymphocytic leukemia cells. Journal of immunotherapy (Hagerstown, Md. : 1997). 2005 Jan; 28(1):28-39. doi: 10.1097/00002371-200501000-00004. [PMID: 15614042]
  • Farr Nezhat, Scott Wadler, Franco Muggia, John Mandeli, Gary Goldberg, Jamal Rahaman, Carolyn Runowicz, Anthony J Murgo, Ginger J Gardner. Phase II trial of the combination of bryostatin-1 and cisplatin in advanced or recurrent carcinoma of the cervix: a New York Gynecologic Oncology Group study. Gynecologic oncology. 2004 Apr; 93(1):144-8. doi: 10.1016/j.ygyno.2003.12.021. [PMID: 15047228]
  • Olga V Leontieva, Jennifer D Black. Identification of two distinct pathways of protein kinase Calpha down-regulation in intestinal epithelial cells. The Journal of biological chemistry. 2004 Feb; 279(7):5788-801. doi: 10.1074/jbc.m308375200. [PMID: 14638691]
  • Ralf Schmidmaier, Mark Oellerich, Joachim Baumgart, Bertold Emmerich, Gerold Meinhardt. Treosulfan-induced apoptosis in acute myeloid leukemia cells is accompanied by translocation of protein kinase C delta and enhanced by bryostatin-1. Experimental hematology. 2004 Jan; 32(1):76-86. doi: 10.1016/j.exphem.2003.09.023. [PMID: 14725904]
  • Afshin Dowlati, Hillard M Lazarus, Paul Hartman, James W Jacobberger, Cecilia Whitacre, Stanton L Gerson, Pamela Ksenich, Brenda W Cooper, Phyllis S Frisa, Megan Gottlieb, Anthony J Murgo, Scot C Remick. Phase I and correlative study of combination bryostatin 1 and vincristine in relapsed B-cell malignancies. Clinical cancer research : an official journal of the American Association for Cancer Research. 2003 Dec; 9(16 Pt 1):5929-35. doi: . [PMID: 14676117]
  • Qiming J Wang, Tzan-Wei Fang, Dazhi Yang, Nancy E Lewin, Johan Van Lint, Victor E Marquez, Peter M Blumberg. Ligand structure-activity requirements and phospholipid dependence for the binding of phorbol esters to protein kinase D. Molecular pharmacology. 2003 Dec; 64(6):1342-8. doi: 10.1124/mol.64.6.1342. [PMID: 14645664]
  • S Madhusudan, A Protheroe, D Propper, C Han, P Corrie, H Earl, B Hancock, P Vasey, A Turner, F Balkwill, S Hoare, A L Harris. A multicentre phase II trial of bryostatin-1 in patients with advanced renal cancer. British journal of cancer. 2003 Oct; 89(8):1418-22. doi: 10.1038/sj.bjc.6601321. [PMID: 14562010]
  • Traci E Battle, David A Frank. STAT1 mediates differentiation of chronic lymphocytic leukemia cells in response to Bryostatin 1. Blood. 2003 Oct; 102(8):3016-24. doi: 10.1182/blood-2002-09-2972. [PMID: 12855573]
  • William Matsui, Carol Ann Huff, Milada Vala, James Barber, B Douglas Smith, Richard J Jones. Anti-tumour activity of interferon-alpha in multiple myeloma: role of interleukin 6 and tumor cell differentiation. British journal of haematology. 2003 Apr; 121(2):251-8. doi: 10.1046/j.1365-2141.2003.04255.x. [PMID: 12694246]
  • Jerome D Winegarden, Ann M Mauer, Thomas F Gajewski, Philip C Hoffman, Stuart Krauss, Charles M Rudin, Everett E Vokes. A phase II study of bryostatin-1 and paclitaxel in patients with advanced non-small cell lung cancer. Lung cancer (Amsterdam, Netherlands). 2003 Feb; 39(2):191-6. doi: 10.1016/s0169-5002(02)00447-6. [PMID: 12581572]
  • Tushar Varma, Si Qi Liu, Matthew West, Visith Thongboonkerd, Peter P Ruvolo, W Stratford May, Aruni Bhatnagar. Protein kinase C-dependent phosphorylation and mitochondrial translocation of aldose reductase. FEBS letters. 2003 Jan; 534(1-3):175-9. doi: 10.1016/s0014-5793(02)03834-6. [PMID: 12527382]
  • Naomi B Haas, Mitchell Smith, Nancy Lewis, Lynn Littman, Gwen Yeslow, Indira D Joshi, Anthony Murgo, Joyce Bradley, Robert Gordon, Hao Wang, Andre Rogatko, Gary R Hudes. Weekly bryostatin-1 in metastatic renal cell carcinoma: a phase II study. Clinical cancer research : an official journal of the American Association for Cancer Research. 2003 Jan; 9(1):109-14. doi: NULL. [PMID: 12538458]
  • Marco I González, Marcelo G Kazanietz, Michael B Robinson. Regulation of the neuronal glutamate transporter excitatory amino acid carrier-1 (EAAC1) by different protein kinase C subtypes. Molecular pharmacology. 2002 Oct; 62(4):901-10. doi: 10.1124/mol.62.4.901. [PMID: 12237337]
  • Yvonne Lange, Jin Ye, Theodore L Steck. Effect of protein kinase C on endoplasmic reticulum cholesterol. Biochemical and biophysical research communications. 2002 Jan; 290(1):488-93. doi: 10.1006/bbrc.2001.6156. [PMID: 11779197]
  • M Gómez-Angelats, J A Cidlowski. Protein kinase C regulates FADD recruitment and death-inducing signaling complex formation in Fas/CD95-induced apoptosis. The Journal of biological chemistry. 2001 Nov; 276(48):44944-52. doi: 10.1074/jbc.m104919200. [PMID: 11581255]
  • R G Lee, D Rosson. 12-O-tetradecanoylphorbol-13-acetate induces apoptosis in renal epithelial cells through a growth signal conflict which is prevented by activated ras. Archives of biochemistry and biophysics. 2001 Jan; 385(2):378-86. doi: 10.1006/abbi.2000.2182. [PMID: 11368020]
  • L Pagliaro, D Daliani, R Amato, S M Tu, D Jones, T Smith, C Logothetis, R Millikan. A Phase II trial of bryostatin-1 for patients with metastatic renal cell carcinoma. Cancer. 2000 Aug; 89(3):615-8. doi: 10.1002/1097-0142(20000801)89:3<615::aid-cncr17>3.0.co;2-j. [PMID: 10931461]
  • Q J Wang, D Bhattacharyya, S Garfield, K Nacro, V E Marquez, P M Blumberg. Differential localization of protein kinase C delta by phorbol esters and related compounds using a fusion protein with green fluorescent protein. The Journal of biological chemistry. 1999 Dec; 274(52):37233-9. doi: 10.1074/jbc.274.52.37233. [PMID: 10601287]
  • R Gonzalez, S Ebbinghaus, T K Henthorn, D Miller, A S Kraft. Treatment of patients with metastatic melanoma with bryostatin-1--a phase II study. Melanoma research. 1999 Dec; 9(6):599-606. doi: 10.1097/00008390-199912000-00010. [PMID: 10661772]
  • K Z Liu, C P Schultz, J B Johnston, F W Beck, A M Al-Katib, R M Mohammad, H H Mantsch. Infrared spectroscopic study of bryostatin 1-induced membrane alterations in a B-CLL cell line. Leukemia. 1999 Aug; 13(8):1273-80. doi: 10.1038/sj.leu.2401463. [PMID: 10450757]
  • S J Slater, F J Taddeo, A Mazurek, B A Stagliano, S K Milano, M B Kelly, C Ho, C D Stubbs. Inhibition of membrane lipid-independent protein kinase Calpha activity by phorbol esters, diacylglycerols, and bryostatin-1. The Journal of biological chemistry. 1998 Sep; 273(36):23160-8. doi: 10.1074/jbc.273.36.23160. [PMID: 9722545]
  • K Z Liu, C P Schultz, R M Mohammad, A M Al-Katib, J B Johnston, H H Mantsch. Similarities between the sensitivity to 2-chlorodeoxyadenosine of lymphocytes from CLL patients and bryostatin 1-treated WSU-CLL cells: an infrared spectroscopic study. Cancer letters. 1998 May; 127(1-2):185-93. doi: 10.1016/s0304-3835(98)00036-6. [PMID: 9619876]
  • P Khan, A T McGown, M J Dawson, G Jayson, J A Prendiville, G R Pettit, D Crowther. High-performance liquid chromatographic assay for the novel antitumor drug, bryostatin-1, incorporating a serum extraction technique. Journal of chromatography. B, Biomedical sciences and applications. 1998 May; 709(1):113-7. doi: 10.1016/s0378-4347(98)00007-3. [PMID: 9653932]
  • S Grant, J Roberts, E Poplin, M B Tombes, B Kyle, D Welch, M Carr, H D Bear. Phase Ib trial of bryostatin 1 in patients with refractory malignancies. Clinical cancer research : an official journal of the American Association for Cancer Research. 1998 Mar; 4(3):611-8. doi: NULL. [PMID: 9533528]
  • M F Denning, S G Guy, S M Ellerbroek, S M Norvell, A P Kowalczyk, K J Green. The expression of desmoglein isoforms in cultured human keratinocytes is regulated by calcium, serum, and protein kinase C. Experimental cell research. 1998 Feb; 239(1):50-9. doi: 10.1006/excr.1997.3890. [PMID: 9511724]
  • H W Cook, N D Ridgway, D M Byers. Involvement of phospholipase D and protein kinase C in phorbol ester and fatty acid stimulated turnover of phosphatidylcholine and phosphatidylethanolamine in neural cells. Biochimica et biophysica acta. 1998 Feb; 1390(1):103-17. doi: 10.1016/s0005-2760(97)00162-8. [PMID: 9487144]
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  • M S Matsui, I Illarda, N Wang, V A DeLeo. Protein kinase C agonist and antagonist effects in normal human epidermal keratinocytes. Experimental dermatology. 1993 Dec; 2(6):247-56. doi: 10.1111/j.1600-0625.1993.tb00041.x. [PMID: 8162345]
  • P A Philip, D Rea, P Thavasu, J Carmichael, N S Stuart, H Rockett, D C Talbot, T Ganesan, G R Pettit, F Balkwill. Phase I study of bryostatin 1: assessment of interleukin 6 and tumor necrosis factor alpha induction in vivo. The Cancer Research Campaign Phase I Committee. Journal of the National Cancer Institute. 1993 Nov; 85(22):1812-8. doi: 10.1093/jnci/85.22.1812. [PMID: 8230261]
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