Soraphen A (BioDeep_00000008588)

   

natural product


代谢物信息卡片


(1S,2S,3E,5R,6S,11S,14S,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one

化学式: C29H44O8 (520.3036)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1C=CC(C(CCCCC(OC(=O)C(C2(C(C(C(C1O2)C)O)OC)O)C)C3=CC=CC=C3)OC)OC
InChI: InChI=1S/C29H44O8/c1-18-16-17-24(34-5)23(33-4)15-11-10-14-22(21-12-8-7-9-13-21)36-28(31)20(3)29(32)27(35-6)25(30)19(2)26(18)37-29/h7-9,12-13,16-20,22-27,30,32H,10-11,14-15H2,1-6H3/b17-16+/t18-,19-,20+,22-,23-,24+,25-,26+,27+,29+/m0/s1

描述信息

A macrolide and an agent highly effective against plant-pathogenic fungi. It was extensively researched for agricultural use until it was discovered to be a teratogen.

同义名列表

5 个代谢物同义名

Soraphen A; (1S,2S,3E,5R,6S,11S,14S,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one; Soraphen A1alpha; Soraphen beta; Soraphen A



数据库引用编号

18 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)

11 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 ELP3, FABP4, FASN, FOXP3, NR1H2, PPARG, PRKAA2
Endoplasmic reticulum membrane 5 CD4, ELOVL5, ELOVL6, FADS1, FADS2
Nucleus 7 ACACB, ELP3, FABP4, FOXP3, NR1H2, PPARG, PRKAA2
cytosol 10 ACACA, ACACB, ELP3, FABP4, FASN, FOXP3, NR1H2, OXSM, PPARG, PRKAA2
dendrite 2 ELOVL5, PRKAA2
nucleoplasm 4 FOXP3, NR1H2, PPARG, PRKAA2
RNA polymerase II transcription regulator complex 2 NR1H2, PPARG
Cell membrane 3 ADCY5, CD4, IFNAR1
Multi-pass membrane protein 5 ADCY5, ELOVL5, ELOVL6, FADS1, FADS2
Golgi apparatus 2 FASN, PRKAA2
Golgi membrane 1 INS
neuronal cell body 2 ELOVL5, PRKAA2
Cytoplasm, cytosol 1 ACACA
Lysosome 1 IFNAR1
endosome 1 IFNAR1
plasma membrane 5 ADCY5, CD4, FADS2, FASN, IFNAR1
Membrane 6 ADCY5, ELOVL5, FADS1, FADS2, FASN, PRKAA2
axon 1 PRKAA2
extracellular exosome 2 FABP4, FASN
endoplasmic reticulum 2 ELOVL5, ELOVL6
extracellular space 2 IL22, INS
perinuclear region of cytoplasm 1 PPARG
mitochondrion 4 ACACA, ACACB, FADS1, OXSM
protein-containing complex 1 FOXP3
intracellular membrane-bounded organelle 2 FADS1, PPARG
Single-pass type I membrane protein 2 CD4, IFNAR1
Secreted 2 IL22, INS
extracellular region 2 IL22, INS
mitochondrial outer membrane 1 ACACB
mitochondrial matrix 1 OXSM
Cell projection, cilium 1 ADCY5
external side of plasma membrane 1 CD4
actin cytoskeleton 1 ACACA
nucleolus 1 ELP3
Early endosome 1 CD4
Membrane raft 1 CD4
nuclear speck 1 PRKAA2
Late endosome 1 IFNAR1
receptor complex 1 PPARG
cilium 1 ADCY5
chromatin 3 FOXP3, NR1H2, PPARG
fibrillar center 1 ACACA
Endomembrane system 1 ADCY5
endosome lumen 1 INS
Lipid droplet 1 FABP4
[Isoform 1]: Endoplasmic reticulum membrane 1 FADS1
Cell projection, dendrite 1 ELOVL5
Melanosome 1 FASN
cytoplasmic stress granule 1 PRKAA2
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 CD4, INS
transport vesicle 1 INS
mitochondrial fatty acid beta-oxidation multienzyme complex 1 ACACB
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
[Isoform 2]: Cytoplasm 1 ELP3
clathrin-coated endocytic vesicle membrane 1 CD4
[Isoform 1]: Nucleus 1 ELP3
[Isoform 1]: Cell membrane 1 IFNAR1
nucleotide-activated protein kinase complex 1 PRKAA2
[Isoform 2]: Endoplasmic reticulum membrane 1 FADS1
elongator holoenzyme complex 1 ELP3
T cell receptor complex 1 CD4
dendritic tree 1 ELOVL5
glycogen granule 1 FASN
fatty acid elongase complex 1 ELOVL6


文献列表

  • Xiaobo Ke, Kwontae You, Matthieu Pichaud, Henry J Haiser, Daniel B Graham, Hera Vlamakis, Jeffrey A Porter, Ramnik J Xavier. Gut bacterial metabolites modulate endoplasmic reticulum stress. Genome biology. 2021 10; 22(1):292. doi: 10.1186/s13059-021-02496-8. [PMID: 34654459]
  • Felipe B Saraiva, Michele Alves-Bezerra, David Majerowicz, Lisvane Paes-Vieira, Valdir Braz, Muriel G M D Almeida, José Roberto Meyer-Fernandes, Katia C Gondim. Blood meal drives de novo lipogenesis in the fat body of Rhodnius prolixus. Insect biochemistry and molecular biology. 2021 06; 133(?):103511. doi: 10.1016/j.ibmb.2020.103511. [PMID: 33278628]
  • Angelina S Gross, Andreas Zimmermann, Tobias Pendl, Sabrina Schroeder, Hannes Schoenlechner, Oskar Knittelfelder, Laura Lamplmayr, Ana Santiso, Andreas Aufschnaiter, Daniel Waltenstorfer, Sandra Ortonobes Lara, Sarah Stryeck, Christina Kast, Christoph Ruckenstuhl, Sebastian J Hofer, Birgit Michelitsch, Martina Woelflingseder, Rolf Müller, Didac Carmona-Gutierrez, Tobias Madl, Sabrina Büttner, Kai-Uwe Fröhlich, Andrej Shevchenko, Tobias Eisenberg. Acetyl-CoA carboxylase 1-dependent lipogenesis promotes autophagy downstream of AMPK. The Journal of biological chemistry. 2019 08; 294(32):12020-12039. doi: 10.1074/jbc.ra118.007020. [PMID: 31209110]
  • Bruno Leonardo Bozaquel-Morais, Leonie Vogt, Valentina D'Angelo, Raffael Schaffrath, Roland Klassen, Mónica Montero-Lomelí. Protein Phosphatase Sit4 Affects Lipid Droplet Synthesis and Soraphen A Resistance Independent of Its Role in Regulating Elongator Dependent tRNA Modification. Biomolecules. 2018 07; 8(3):. doi: 10.3390/biom8030049. [PMID: 29997346]
  • Daniel K Glatzel, Andreas Koeberle, Helmut Pein, Konstantin Löser, Anna Stark, Nelli Keksel, Oliver Werz, Rolf Müller, Iris Bischoff, Robert Fürst. Acetyl-CoA carboxylase 1 regulates endothelial cell migration by shifting the phospholipid composition. Journal of lipid research. 2018 02; 59(2):298-311. doi: 10.1194/jlr.m080101. [PMID: 29208696]
  • Katharina Stoiber, Olga Nagło, Carla Pernpeintner, Siwei Zhang, Andreas Koeberle, Melanie Ulrich, Oliver Werz, Rolf Müller, Stefan Zahler, Theobald Lohmüller, Jochen Feldmann, Simone Braig. Targeting de novo lipogenesis as a novel approach in anti-cancer therapy. British journal of cancer. 2018 01; 118(1):43-51. doi: 10.1038/bjc.2017.374. [PMID: 29112683]
  • Bruno L Bozaquel-Morais, Juliana B Madeira, Thiago M Venâncio, Thiago Pacheco-Rosa, Claudio A Masuda, Monica Montero-Lomeli. A Chemogenomic Screen Reveals Novel Snf1p/AMPK Independent Regulators of Acetyl-CoA Carboxylase. PloS one. 2017; 12(1):e0169682. doi: 10.1371/journal.pone.0169682. [PMID: 28076367]
  • Solaiman Raha, Brenda Raud, Linda Oberdörfer, Carla N Castro, Alina Schreder, Jenny Freitag, Thomas Longerich, Matthias Lochner, Tim Sparwasser, Luciana Berod, Christian Koenecke, Immo Prinz. Disruption of de novo fatty acid synthesis via acetyl-CoA carboxylase 1 inhibition prevents acute graft-versus-host disease. European journal of immunology. 2016 09; 46(9):2233-8. doi: 10.1002/eji.201546152. [PMID: 27338930]
  • Elizabeth L Cordonier, Sarah K Jarecke, Frances E Hollinger, Janos Zempleni. Inhibition of acetyl-CoA carboxylases by soraphen A prevents lipid accumulation and adipocyte differentiation in 3T3-L1 cells. European journal of pharmacology. 2016 Jun; 780(?):202-8. doi: 10.1016/j.ejphar.2016.03.052. [PMID: 27041646]
  • George Koutsoudakis, Inés Romero-Brey, Carola Berger, Gemma Pérez-Vilaró, Paula Monteiro Perin, Florian Wolfgang Rudolf Vondran, Markus Kalesse, Kirsten Harmrolfs, Rolf Müller, Javier P Martinez, Thomas Pietschmann, Ralf Bartenschlager, Mark Brönstrup, Andreas Meyerhans, Juana Díez. Soraphen A: A broad-spectrum antiviral natural product with potent anti-hepatitis C virus activity. Journal of hepatology. 2015 Oct; 63(4):813-21. doi: 10.1016/j.jhep.2015.06.002. [PMID: 26070407]
  • Bruna Corominas-Faja, Elisabet Cuyàs, Juan Gumuzio, Joaquim Bosch-Barrera, Olatz Leis, Ángel G Martin, Javier A Menendez. Chemical inhibition of acetyl-CoA carboxylase suppresses self-renewal growth of cancer stem cells. Oncotarget. 2014 Sep; 5(18):8306-16. doi: 10.18632/oncotarget.2059. [PMID: 25246709]
  • Sasmita Tripathy, Donald B Jump. Elovl5 regulates the mTORC2-Akt-FOXO1 pathway by controlling hepatic cis-vaccenic acid synthesis in diet-induced obese mice. Journal of lipid research. 2013 Jan; 54(1):71-84. doi: 10.1194/jlr.m028787. [PMID: 23099444]
  • Nousheen Zaidi, Ines Royaux, Johannes V Swinnen, Karine Smans. ATP citrate lyase knockdown induces growth arrest and apoptosis through different cell- and environment-dependent mechanisms. Molecular cancer therapeutics. 2012 Sep; 11(9):1925-35. doi: 10.1158/1535-7163.mct-12-0095. [PMID: 22718913]
  • M Schreurs, T H van Dijk, A Gerding, R Havinga, D-J Reijngoud, F Kuipers. Soraphen, an inhibitor of the acetyl-CoA carboxylase system, improves peripheral insulin sensitivity in mice fed a high-fat diet. Diabetes, obesity & metabolism. 2009 Oct; 11(10):987-91. doi: 10.1111/j.1463-1326.2009.01078.x. [PMID: 19519866]
  • Alison M Hill, Betty L Thompson, Jonathan P Harris, Roger Segret. Investigation of the early stages in soraphen A biosynthesis. Chemical communications (Cambridge, England). 2003 Jun; ?(12):1358-9. doi: 10.1039/b303542p. [PMID: 12841240]
  • R Schneiter, C E Guerra, M Lampl, G Gogg, S D Kohlwein, H L Klein. The Saccharomyces cerevisiae hyperrecombination mutant hpr1Delta is synthetically lethal with two conditional alleles of the acetyl coenzyme A carboxylase gene and causes a defect in nuclear export of polyadenylated RNA. Molecular and cellular biology. 1999 May; 19(5):3415-22. doi: 10.1128/mcb.19.5.3415. [PMID: 10207065]
  • K Gerth, N Bedorf, H Irschik, G Höfle, H Reichenbach. The soraphens: a family of novel antifungal compounds from Sorangium cellulosum (Myxobacteria). I. Soraphen A1 alpha: fermentation, isolation, biological properties. The Journal of antibiotics. 1994 Jan; 47(1):23-31. doi: 10.7164/antibiotics.47.23. [PMID: 8119858]