Zaragozic acid A (BioDeep_00000614359)
代谢物信息卡片
1S-((4S-acetoxy-5R-methyl-3-methylene-6-phenylhexyl)-6-(E)-4S,6S-dimethyloct-2-enoyloxy)-4,7S-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3S,4S,5R-tricarboxylic acid
化学式: C35H46O14 (690.2887416)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCC(C)CC(C)C=CC(=O)OC1C(C2(OC(C(C1(O2)C(=O)O)(C(=O)O)O)C(=O)O)CCC(=C)C(C(C)CC3=CC=CC=C3)OC(=O)C)O
InChI: InChI=1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1
描述信息
D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents
A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase.
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
D009676 - Noxae > D000963 - Antimetabolites
D004791 - Enzyme Inhibitors
同义名列表
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:75170
- PubChem: 6438355
- Metlin: METLIN82400
- ChEMBL: CHEMBL280978
- LipidMAPS: LMPK00000001
- CAS: 142561-96-4
- CAS: 138682-84-5
- CAS: 144541-82-2
- MetaboLights: MTBLC75170
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)
0 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
- Yoshihiro Shidoji, Yuki Tabata. Unequivocal evidence for endogenous geranylgeranoic acid biosynthesized from mevalonate in mammalian cells.
Journal of lipid research.
2019 03; 60(3):579-593. doi:
10.1194/jlr.m090548. [PMID: 30622150] - Irena Pastar, Olivera Stojadinovic, Andrew P Sawaya, Rivka C Stone, Linsey E Lindley, Nkemcho Ojeh, Sasa Vukelic, Herbert H Samuels, Marjana Tomic-Canic. Skin Metabolite, Farnesyl Pyrophosphate, Regulates Epidermal Response to Inflammation, Oxidative Stress, and Migration.
Journal of cellular physiology.
2016 11; 231(11):2452-63. doi:
10.1002/jcp.25357. [PMID: 26916741] - Elizabeth A Rondini, Zofia Duniec-Dmuchowski, Daniela Cukovic, Alan A Dombkowski, Thomas A Kocarek. Differential Regulation of Gene Expression by Cholesterol Biosynthesis Inhibitors That Reduce (Pravastatin) or Enhance (Squalestatin 1) Nonsterol Isoprenoid Levels in Primary Cultured Mouse and Rat Hepatocytes.
The Journal of pharmacology and experimental therapeutics.
2016 08; 358(2):216-29. doi:
10.1124/jpet.116.233312. [PMID: 27225895] - Asmita Pant, Thomas A Kocarek. Role of Phosphatidic Acid Phosphatase Domain Containing 2 in Squalestatin 1-Mediated Activation of the Constitutive Androstane Receptor in Primary Cultured Rat Hepatocytes.
Drug metabolism and disposition: the biological fate of chemicals.
2016 Mar; 44(3):352-5. doi:
10.1124/dmd.115.068437. [PMID: 26700959] - Elizabeth A Rondini, Asmita Pant, Thomas A Kocarek. Transcriptional Regulation of Cytosolic Sulfotransferase 1C2 by Intermediates of the Cholesterol Biosynthetic Pathway in Primary Cultured Rat Hepatocytes.
The Journal of pharmacology and experimental therapeutics.
2015 Dec; 355(3):429-41. doi:
10.1124/jpet.115.226365. [PMID: 26427720] - Juan P Zúñiga-Hertz, Eduardo Rebelato, Adam Kassan, Abdelrahman M Khalifa, Sameh S Ali, Hemal H Patel, Fernando Abdulkader. Distinct pathways of cholesterol biosynthesis impact on insulin secretion.
The Journal of endocrinology.
2015 Jan; 224(1):75-84. doi:
10.1530/joe-14-0348. [PMID: 25453115] - Penny H Hamid, Jörg Hirzmann, Carlos Hermosilla, Anja Taubert. Differential inhibition of host cell cholesterol de novo biosynthesis and processing abrogates Eimeria bovis intracellular development.
Parasitology research.
2014 Nov; 113(11):4165-76. doi:
10.1007/s00436-014-4092-5. [PMID: 25199551] - Patricia Quade-Lyssy, Anna Maria Kanarek, Markus Baiersdörfer, Rolf Postina, Elzbieta Kojro. Statins stimulate the production of a soluble form of the receptor for advanced glycation end products.
Journal of lipid research.
2013 Nov; 54(11):3052-61. doi:
10.1194/jlr.m038968. [PMID: 23966666] - Ursula Fünfschilling, Wolf J Jockusch, Nandhini Sivakumar, Wiebke Möbius, Kristina Corthals, Sai Li, Susanne Quintes, Younghoon Kim, Iwan A T Schaap, Jeong-Seop Rhee, Klaus-Armin Nave, Gesine Saher. Critical time window of neuronal cholesterol synthesis during neurite outgrowth.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2012 May; 32(22):7632-45. doi:
10.1523/jneurosci.1352-11.2012. [PMID: 22649242] - Ulrika Forsman, Mats Sjöberg, Mikael Turunen, Pavel J Sindelar. 4-Nitrobenzoate inhibits coenzyme Q biosynthesis in mammalian cell cultures.
Nature chemical biology.
2010 Jul; 6(7):515-7. doi:
10.1038/nchembio.372. [PMID: 20526342] - Anna Linetti, Alessandra Fratangeli, Elena Taverna, Pamela Valnegri, Maura Francolini, Valentina Cappello, Michela Matteoli, Maria Passafaro, Patrizia Rosa. Cholesterol reduction impairs exocytosis of synaptic vesicles.
Journal of cell science.
2010 Feb; 123(Pt 4):595-605. doi:
10.1242/jcs.060681. [PMID: 20103534] - Elzbieta Kojro, Petra Füger, Claudia Prinzen, Anna Maria Kanarek, Dorothea Rat, Kristina Endres, Falk Fahrenholz, Rolf Postina. Statins and the squalene synthase inhibitor zaragozic acid stimulate the non-amyloidogenic pathway of amyloid-beta protein precursor processing by suppression of cholesterol synthesis.
Journal of Alzheimer's disease : JAD.
2010; 20(4):1215-31. doi:
10.3233/jad-2010-091621. [PMID: 20413873] - Rémi Lasserre, Xiao-Jun Guo, Fabien Conchonaud, Yannick Hamon, Omar Hawchar, Anne-Marie Bernard, Saïdi M'Homa Soudja, Pierre-François Lenne, Hervé Rigneault, Daniel Olive, Georges Bismuth, Jacques A Nunès, Bernard Payrastre, Didier Marguet, Hai-Tao He. Raft nanodomains contribute to Akt/PKB plasma membrane recruitment and activation.
Nature chemical biology.
2008 Sep; 4(9):538-47. doi:
10.1038/nchembio.103. [PMID: 18641634] - Mohini Bedi, Melissa Niesen, Dayami Lopez. Inhibition of squalene synthase upregulates PCSK9 expression in rat liver.
Archives of biochemistry and biophysics.
2008 Feb; 470(2):116-9. doi:
10.1016/j.abb.2007.11.011. [PMID: 18054775] - Rona Wilson, Clive Bate, Ronald Boshuizen, Alun Williams, James Brewer. Squalestatin alters the intracellular trafficking of a neurotoxic prion peptide.
BMC neuroscience.
2007 Nov; 8(?):99. doi:
10.1186/1471-2202-8-99. [PMID: 18034899] - Katsue Daicho, Hironori Maruyama, Asuka Suzuki, Masaru Ueno, Masahiro Uritani, Takashi Ushimaru. The ergosterol biosynthesis inhibitor zaragozic acid promotes vacuolar degradation of the tryptophan permease Tat2p in yeast.
Biochimica et biophysica acta.
2007 Jul; 1768(7):1681-90. doi:
10.1016/j.bbamem.2007.03.022. [PMID: 17531951] - Koen Brusselmans, Leen Timmermans, Tine Van de Sande, Paul P Van Veldhoven, Guimin Guan, Ishaiahu Shechter, Frank Claessens, Guido Verhoeven, Johannes V Swinnen. Squalene synthase, a determinant of Raft-associated cholesterol and modulator of cancer cell proliferation.
The Journal of biological chemistry.
2007 Jun; 282(26):18777-85. doi:
10.1074/jbc.m611763200. [PMID: 17483544] - Sonia Molina, Valérie Castet, Chantal Fournier-Wirth, Lydiane Pichard-Garcia, Rachel Avner, Dror Harats, Joseph Roitelman, Ronald Barbaras, Pierre Graber, Paola Ghersa, Moshe Smolarsky, Ada Funaro, Fabio Malavasi, Dominique Larrey, Joliette Coste, Jean-Michel Fabre, Antonio Sa-Cunha, Patrick Maurel. The low-density lipoprotein receptor plays a role in the infection of primary human hepatocytes by hepatitis C virus.
Journal of hepatology.
2007 Mar; 46(3):411-9. doi:
10.1016/j.jhep.2006.09.024. [PMID: 17156886] - J D Loike, D Y Shabtai, R Neuhut, S Malitzky, E Lu, J Husemann, I J Goldberg, S C Silverstein. Statin inhibition of Fc receptor-mediated phagocytosis by macrophages is modulated by cell activation and cholesterol.
Arteriosclerosis, thrombosis, and vascular biology.
2004 Nov; 24(11):2051-6. doi:
10.1161/01.atv.0000143858.15909.29. [PMID: 15345508] - Clive Bate, Mario Salmona, Luisa Diomede, Alun Williams. Squalestatin cures prion-infected neurons and protects against prion neurotoxicity.
The Journal of biological chemistry.
2004 Apr; 279(15):14983-90. doi:
10.1074/jbc.m313061200. [PMID: 14754889] - Laurent F Wentzinger, Thomas J Bach, Marie-Andrée Hartmann. Inhibition of squalene synthase and squalene epoxidase in tobacco cells triggers an up-regulation of 3-hydroxy-3-methylglutaryl coenzyme a reductase.
Plant physiology.
2002 Sep; 130(1):334-46. doi:
10.1104/pp.004655. [PMID: 12226513] - M A Hartmann, L Wentzinger, A Hemmerlin, T J Bach. Metabolism of farnesyl diphosphate in tobacco BY-2 cells treated with squalestatin.
Biochemical Society transactions.
2000 Dec; 28(6):794-6. doi:
. [PMID: 11171211] - T Ravid, R Doolman, R Avner, D Harats, J Roitelman. The ubiquitin-proteasome pathway mediates the regulated degradation of mammalian 3-hydroxy-3-methylglutaryl-coenzyme A reductase.
The Journal of biological chemistry.
2000 Nov; 275(46):35840-7. doi:
10.1074/jbc.m004793200. [PMID: 10964918] - S F Petras, S Lindsey, H J Harwood. HMG-CoA reductase regulation: use of structurally diverse first half-reaction squalene synthetase inhibitors to characterize the site of mevalonate-derived nonsterol regulator production in cultured IM-9 cells.
Journal of lipid research.
1999 Jan; 40(1):24-38. doi:
. [PMID: 9869647] - S Vaidya, R Bostedor, M M Kurtz, J D Bergstrom, V S Bansal. Massive production of farnesol-derived dicarboxylic acids in mice treated with the squalene synthase inhibitor zaragozic acid A.
Archives of biochemistry and biophysics.
1998 Jul; 355(1):84-92. doi:
10.1006/abbi.1998.0704. [PMID: 9647670] - R G Bostedor, J D Karkas, B H Arison, V S Bansal, S Vaidya, J I Germershausen, M M Kurtz, J D Bergstrom. Farnesol-derived dicarboxylic acids in the urine of animals treated with zaragozic acid A or with farnesol.
The Journal of biological chemistry.
1997 Apr; 272(14):9197-203. doi:
10.1074/jbc.272.14.9197. [PMID: 9083051] - M C Stankewich, S A Francis, Q U Vu, E E Schneeberger, R D Lynch. Alterations in cell cholesterol content modulate Ca(2+)-induced tight junction assembly by MDCK cells.
Lipids.
1996 Aug; 31(8):817-28. doi:
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Journal of medicinal chemistry.
1996 Mar; 39(7):1413-22. doi:
10.1021/jm950893j. [PMID: 8691471] - G C Ness, Z Zhao, D Lopez. Inhibitors of cholesterol biosynthesis increase hepatic low-density lipoprotein receptor protein degradation.
Archives of biochemistry and biophysics.
1996 Jan; 325(2):242-8. doi:
10.1006/abbi.1996.0030. [PMID: 8561503] - C Chan, D Andreotti, B Cox, B W Dymock, J L Hutson, S E Keeling, A D McCarthy, P A Procopiou, B C Ross, M Sareen, J J Scicinski, P J Sharratt, M A Snowden, N S Watson. The squalestatins: decarboxy and 4-deoxy analogues as potent squalene synthase inhibitors.
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1996 Jan; 39(1):207-16. doi:
10.1021/jm9504969. [PMID: 8568810] - K C Doerner, E C Gurley, Z R Vlahcevic, P B Hylemon. Regulation of cholesterol 7 alpha-hydroxylase expression by sterols in primary rat hepatocyte cultures.
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Annual review of microbiology.
1995; 49(?):607-39. doi:
10.1146/annurev.mi.49.100195.003135. [PMID: 8561474] - A Thelin, E Peterson, J L Hutson, A D McCarthy, J Ericsson, G Dallner. Effect of squalestatin 1 on the biosynthesis of the mevalonate pathway lipids.
Biochimica et biophysica acta.
1994 Dec; 1215(3):245-9. doi:
10.1016/0005-2760(94)90049-3. [PMID: 7811707] - P A Procopiou, E J Bailey, M J Bamford, A P Craven, B W Dymock, J G Houston, J L Hutson, B E Kirk, A D McCarthy, M Sareen. The squalestatins: novel inhibitors of squalene synthase. Enzyme inhibitory activities and in vivo evaluation of C1-modified analogues.
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1994 Sep; 37(20):3274-81. doi:
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