fumagillin (BioDeep_00000007530)

 

Secondary id: BioDeep_00000911007

natural product PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


NCGC00163699-03_C26H34O7_2,4,6,8-Decatetraenedioic acid, mono[5-methoxy-4-[2-methyl-3-(3-methyl-2-buten-1-yl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester, (2E,4E,6E,8E)-

化学式: C26H34O7 (458.2304414)
中文名称: 夫马洁林
谱图信息: 最多检出来源 Homo sapiens(blood) 0.32%

分子结构信息

SMILES: CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)C=CC=CC=CC=CC(=O)O)OC)C
InChI: InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+

描述信息

A meroterpenoid resulting from the formal condensation of the hydroxy group of fumagillol with the carboxylic acid group of (all-E)-deca-2,4,6,8-tetraenedioic acid. Originally isolated from the fungus Aspergillus fumigatus, it is used for the control of Nosema infection in honey bees.
P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01A - Agents against amoebiasis and other protozoal diseases
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C259 - Antineoplastic Antibiotic
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
D006133 - Growth Substances > D043924 - Angiogenesis Modulating Agents
D000970 - Antineoplastic Agents > D020533 - Angiogenesis Inhibitors
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
D006133 - Growth Substances > D006131 - Growth Inhibitors
Fumagillin(NSC9168) is an antimicrobial compound first isolated in 1949 from the fungus Aspergillus fumigatu. Fumagillin can inhibits HIV‐1 infection through the inhibition of HIV-1 viral protein R (Vpr) activity.

同义名列表

8 个代谢物同义名

fumagillin; (2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid; 2,4,6,8-decatetraenedioic acid, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro(2,5)oct-6-yl ester; NCGC00163699-03_C26H34O7_2,4,6,8-Decatetraenedioic acid, mono[5-methoxy-4-[2-methyl-3-(3-methyl-2-buten-1-yl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester, (2E,4E,6E,8E)-; Fumagillinum; Amebacilin; NSC9168; Fumagillin



数据库引用编号

25 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)

20 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

  • Zahra Farhadi, Ali Asghar Sadeghi, Farahnaz Motamedi Sedeh, Mohammad Chamani. The effects of thymol, oxalic acid (Api-Bioxal) and hops extract (Nose-Go) on viability, the Nosema sp. spore load and the expression of vg and sod-1 genes in infected honey bees. Animal biotechnology. 2023 Mar; ?(?):1-10. doi: 10.1080/10495398.2023.2187409. [PMID: 36905146]
  • Ke Zhang, Jian Hu, Ziyi Zhao. Fumagillin regulates stemness and malignancies in cancer stem-like cells derived from liver cancer via targeting to MetAP-2. PloS one. 2023; 18(7):e0289024. doi: 10.1371/journal.pone.0289024. [PMID: 37506053]
  • Yanlei Sun, Bo Chen, Xinlin Li, Ying Yin, Chengshu Wang. Orchestrated Biosynthesis of the Secondary Metabolite Cocktails Enables the Producing Fungus to Combat Diverse Bacteria. mBio. 2022 10; 13(5):e0180022. doi: 10.1128/mbio.01800-22. [PMID: 36000736]
  • Luisa Ugolini, Giovanni Cilia, Eleonora Pagnotta, Lorena Malaguti, Vittorio Capano, Irene Guerra, Laura Zavatta, Sergio Albertazzi, Roberto Matteo, Luca Lazzeri, Laura Righetti, Antonio Nanetti. Glucosinolate Bioactivation by Apis mellifera Workers and Its Impact on Nosema ceranae Infection at the Colony Level. Biomolecules. 2021 11; 11(11):. doi: 10.3390/biom11111657. [PMID: 34827655]
  • Alexis Maillard, Anne Scemla, Benjamin Laffy, Nadir Mahloul, Jean-Michel Molina. Safety and efficacy of fumagillin for the treatment of intestinal microsporidiosis. A French prospective cohort study. The Journal of antimicrobial chemotherapy. 2021 01; 76(2):487-494. doi: 10.1093/jac/dkaa438. [PMID: 33128055]
  • Fenali Parekh, Katie F Daughenbaugh, Michelle L Flenniken. Chemical Stimulants and Stressors Impact the Outcome of Virus Infection and Immune Gene Expression in Honey Bees (Apis mellifera). Frontiers in immunology. 2021; 12(?):747848. doi: 10.3389/fimmu.2021.747848. [PMID: 34804032]
  • Jie An, Liping Wang, Michael L Patnode, Vanessa K Ridaura, Jonathan M Haldeman, Robert D Stevens, Olga Ilkayeva, James R Bain, Michael J Muehlbauer, Erin L Glynn, Steven Thomas, Deborah Muoio, Scott A Summers, James E Vath, Thomas E Hughes, Jeffrey I Gordon, Christopher B Newgard. Physiological mechanisms of sustained fumagillin-induced weight loss. JCI insight. 2018 03; 3(5):. doi: 10.1172/jci.insight.99453. [PMID: 29515039]
  • Joise Hander Mares, Karina Peres Gramacho, Everton Cruz Santos, André da Silva Santiago, Juliano Oliveira Santana, Aurizângela Oliveira de Sousa, Fátima Cerqueira Alvim, Carlos Priminho Pirovani. Proteomic analysis during of spore germination of Moniliophthora perniciosa, the causal agent of witches' broom disease in cacao. BMC microbiology. 2017 Aug; 17(1):176. doi: 10.1186/s12866-017-1085-4. [PMID: 28818052]
  • Michael Morgen, Christian Jöst, Mona Malz, Robert Janowski, Dierk Niessing, Christian D Klein, Nikolas Gunkel, Aubry K Miller. Spiroepoxytriazoles Are Fumagillin-like Irreversible Inhibitors of MetAP2 with Potent Cellular Activity. ACS chemical biology. 2016 Apr; 11(4):1001-11. doi: 10.1021/acschembio.5b00755. [PMID: 26686773]
  • Alex J Guseman, Kaliah Miller, Grace Kunkle, Galen P Dively, Jeffrey S Pettis, Jay D Evans, Dennis vanEngelsdorp, David J Hawthorne. Multi-Drug Resistance Transporters and a Mechanism-Based Strategy for Assessing Risks of Pesticide Combinations to Honey Bees. PloS one. 2016; 11(2):e0148242. doi: 10.1371/journal.pone.0148242. [PMID: 26840460]
  • Ruiying Zhang, Dipanjan Pan, Xin Cai, Xiaoxia Yang, Angana Senpan, John S Allen, Gregory M Lanza, Lihong V Wang. alphaVbeta3-targeted copper nanoparticles incorporating an Sn 2 lipase-labile fumagillin prodrug for photoacoustic neovascular imaging and treatment. Theranostics. 2015; 5(2):124-33. doi: 10.7150/thno.10014. [PMID: 25553103]
  • G Desoubeaux, Z Maakaroun-Vermesse, C Lier, E Bailly, F Morio, F Labarthe, L Bernard, J Chandenier. Successful treatment with fumagillin of the first pediatric case of digestive microsporidiosis in a liver-kidney transplant. Transplant infectious disease : an official journal of the Transplantation Society. 2013 Dec; 15(6):E250-9. doi: 10.1111/tid.12158. [PMID: 24298986]
  • Cristina Botías, Raquel Martín-Hernández, Aránzazu Meana, Mariano Higes. Screening alternative therapies to control Nosemosis type C in honey bee (Apis mellifera iberiensis) colonies. Research in veterinary science. 2013 Dec; 95(3):1041-5. doi: 10.1016/j.rvsc.2013.09.012. [PMID: 24148868]
  • Astrid Godron, Isabelle Accoceberry, Axelle Couret, Brigitte Llanas, Jérôme Harambat. Intestinal microsporidiosis due to Enterocytozoon bieneusi in a pediatric kidney transplant recipient successfully treated with fumagillin. Transplantation. 2013 Oct; 96(8):e66-7. doi: 10.1097/tp.0b013e3182a902e7. [PMID: 24132119]
  • A Audemard, M L Le Bellec, L Carluer, S Dargère, R Verdon, C Castrale, T Lobbedez, B Hurault de Ligny. Fumagillin-induced aseptic meningoencephalitis in a kidney transplant recipient with microsporidiosis. Transplant infectious disease : an official journal of the Transplantation Society. 2012 Dec; 14(6):E147-9. doi: 10.1111/tid.12010. [PMID: 23025483]
  • Hui-Fang Zhou, Huimin Yan, Angana Senpan, Samuel A Wickline, Dipanjan Pan, Gregory M Lanza, Christine T N Pham. Suppression of inflammation in a mouse model of rheumatoid arthritis using targeted lipase-labile fumagillin prodrug nanoparticles. Biomaterials. 2012 Nov; 33(33):8632-40. doi: 10.1016/j.biomaterials.2012.08.005. [PMID: 22922023]
  • Fred R Musser, Kathy S Knighten, Sarah R Self. Impact of Nosema (Microsporidia) infection and fumagillin treatment on Lygus lineolaris (Hemiptera: Miridae). Journal of invertebrate pathology. 2012 Oct; 111(2):101-5. doi: 10.1016/j.jip.2012.07.001. [PMID: 22820067]
  • L Champion, A Durrbach, P Lang, M Delahousse, C Chauvet, C Sarfati, D Glotz, J-M Molina. Fumagillin for treatment of intestinal microsporidiosis in renal transplant recipients. American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons. 2010 Aug; 10(8):1925-30. doi: 10.1111/j.1600-6143.2010.03166.x. [PMID: 20636462]
  • Xiaochuan Feng, Venudhar K Reddy, Harriet Mayanja-Kizza, Louis M Weiss, Laurence J Marton, Saul Tzipori. Therapeutic evaluation of polyamine analogue drug candidates against Enterocytozoon bieneusi in a SCID mouse model. Antimicrobial agents and chemotherapy. 2009 Jun; 53(6):2417-23. doi: 10.1128/aac.01113-08. [PMID: 19289524]
  • F Lanternier, D Boutboul, J Menotti, M O Chandesris, C Sarfati, M F Mamzer Bruneel, Y Calmus, F Mechaï, J P Viard, M Lecuit, M E Bougnoux, O Lortholary. Microsporidiosis in solid organ transplant recipients: two Enterocytozoon bieneusi cases and review. Transplant infectious disease : an official journal of the Transplantation Society. 2009 Feb; 11(1):83-8. doi: 10.1111/j.1399-3062.2008.00347.x. [PMID: 18803616]
  • J Dupuy, A Lespine, J F Sutra, M Alvinerie. Fumagillin, a new P-glycoprotein-interfering agent able to modulate moxidectin efflux in rat hepatocytes. Journal of veterinary pharmacology and therapeutics. 2006 Dec; 29(6):489-94. doi: 10.1111/j.1365-2885.2006.00780.x. [PMID: 17083452]
  • Nadia Arzouk, Hugues Michelon, Renaud Snanoudj, Anne-Marie Taburet, Antoine Durrbach, Valérie Furlan. Interaction between tacrolimus and fumagillin in two kidney transplant recipients. Transplantation. 2006 Jan; 81(1):136-7. doi: 10.1097/01.tp.0000189947.55624.74. [PMID: 16421493]
  • E Karagouni, F Athanassopoulou, A Lytra, C Komis, E Dotsika. Antiparasitic and immunomodulatory effect of innovative treatments against Myxobolus sp. infection in Diplodus puntazzo. Veterinary parasitology. 2005 Dec; 134(3-4):215-28. doi: 10.1016/j.vetpar.2005.07.020. [PMID: 16169152]
  • Ho Sup Lee, Won Kyu Choi, Hoe Joo Son, Sung Sook Lee, Joon Kyum Kim, Soon Kil Ahn, Chung Il Hong, Hye-Ki Min, Myungsoo Kim, Seung-Woon Myung. Absorption, distribution, metabolism, and excretion of CKD-732, a novel antiangiogenic fumagillin derivative, in rats, mice, and dogs. Archives of pharmacal research. 2004 Feb; 27(2):265-72. doi: 10.1007/bf02980116. [PMID: 15029870]
  • Jean Menotti, Bruno Cassinat, Raphaël Porcher, Claudine Sarfati, Francis Derouin, Jean-Michel Molina. Development of a real-time polymerase-chain-reaction assay for quantitative detection of Enterocytozoon bieneusi DNA in stool specimens from immunocompromised patients with intestinal microsporidiosis. The Journal of infectious diseases. 2003 May; 187(9):1469-74. doi: 10.1086/374620. [PMID: 12717629]
  • Jean-Michel Molina, Muriel Tourneur, Claudine Sarfati, Sylvie Chevret, Amaury de Gouvello, Jean-Gérard Gobert, Suna Balkan, Francis Derouin. Fumagillin treatment of intestinal microsporidiosis. The New England journal of medicine. 2002 Jun; 346(25):1963-9. doi: 10.1056/nejmoa012924. [PMID: 12075057]
  • Manisha Kar, P G L Lalitkumar, Latika Dhawan, Jayasree Sengupta, D Ghosh. Effect of vaginally administered fumagillin on immunohistochemical distribution of leukemia inhibitory factor, interleukin 6, transforming growth factor beta and vascular endothelial growth factor in implantation stage endometrium of the rhesus monkey. Indian journal of physiology and pharmacology. 2002 Jan; 46(1):25-35. doi: . [PMID: 12024954]
  • D Ghosh, P G Lalitkumar, V Wong, L Dhawan, J F Rosario, A G Hendrickx, B L Lasley, J W Overstreet, J Sengupta. Effect of vaginally administered fumagillin on the morphology of implantation stage endometrium in the rhesus monkey. Contraception. 2001 Feb; 63(2):95-102. doi: 10.1016/s0010-7824(01)00177-9. [PMID: 11292474]
  • J M Molina, J Goguel, C Sarfati, J F Michiels, I Desportes-Livage, S Balkan, C Chastang, L Cotte, C Maslo, A Struxiano, F Derouin, J M Decazes. Trial of oral fumagillin for the treatment of intestinal microsporidiosis in patients with HIV infection. ANRS 054 Study Group. Agence Nationale de Recherche sur le SIDA. AIDS (London, England). 2000 Jul; 14(10):1341-8. doi: 10.1097/00002030-200007070-00006. [PMID: 10930148]
  • W van't Hof, M D Resh. Targeting proteins to plasma membrane and membrane microdomains by N-terminal myristoylation and palmitoylation. Methods in enzymology. 2000; 327(?):317-30. doi: 10.1016/s0076-6879(00)27287-x. [PMID: 11044994]
  • E S Didier, J A Maddry, C D Kwong, L C Green, K F Snowden, J A Shadduck. Screening of compounds for antimicrosporidial activity in vitro. Folia parasitologica. 1998; 45(2):129-39. doi: . [PMID: 9684323]
  • G J Leitch, M Scanlon, A Shaw, G S Visvesvara, S Wallace. Use of a fluorescent probe to assess the activities of candidate agents against intracellular forms of Encephalitozoon microsporidia. Antimicrobial agents and chemotherapy. 1997 Feb; 41(2):337-44. doi: 10.1128/aac.41.2.337. [PMID: 9021189]
  • H Stepień, M Grochal, K W Zieliński, S Mucha, J Kunert-Radek, A Kulig, A Stawowy, H Pisarek. Inhibitory effects of fumagillin and its analogue TNP-470 on the function, morphology and angiogenesis of an oestrogen-induced prolactinoma in Fischer 344 rats. The Journal of endocrinology. 1996 Jul; 150(1):99-106. doi: 10.1677/joe.0.1500099. [PMID: 8708569]
  • C Y Lowder, J T McMahon, D M Meisler, E M Dodds, L H Calabrese, E S Didier, A Cali. Microsporidial keratoconjunctivitis caused by Septata intestinalis in a patient with acquired immunodeficiency syndrome. American journal of ophthalmology. 1996 Jun; 121(6):715-7. doi: 10.1016/s0002-9394(14)70642-7. [PMID: 8644819]
  • E S Didier, L B Rogers, A D Brush, S Wong, V Traina-Dorge, D Bertucci. Diagnosis of disseminated microsporidian Encephalitozoon hellem infection by PCR-Southern analysis and successful treatment with albendazole and fumagillin. Journal of clinical microbiology. 1996 Apr; 34(4):947-52. doi: 10.1128/jcm.34.4.947-952.1996. [PMID: 8815114]
  • F F Franssen, J T Lumeij, F van Knapen. Susceptibility of Encephalitozoon cuniculi to several drugs in vitro. Antimicrobial agents and chemotherapy. 1995 Jun; 39(6):1265-8. doi: 10.1128/aac.39.6.1265. [PMID: 7574513]
  • K Molnár. Recent achievements in the chemotherapy of myxosporean infections of fish. Acta veterinaria Hungarica. 1993; 41(1-2):51-8. doi: NULL. [PMID: 8116501]
  • G Füllner, W Müller. [The therapy of swimbladder inflammation (renicola sphaerosporosis) of carp]. Angewandte Parasitologie. 1992 May; 33(2):79-90. doi: NULL. [PMID: 1610018]
  • D J Laurén, A Wishkovsky, J M Groff, R P Hedrick, D E Hinton. Toxicity and pharmacokinetics of the antibiotic fumagillin in yearling rainbow trout (Salmo gairdneri). Toxicology and applied pharmacology. 1989 May; 98(3):444-53. doi: 10.1016/0041-008x(89)90173-7. [PMID: 2718173]
  • J A Shadduck. Effect of fumagillin on in vitro multiplication of Encephalitozoon cuniculi. The Journal of protozoology. 1980 May; 27(2):202-8. doi: 10.1111/j.1550-7408.1980.tb04681.x. [PMID: 6772772]