Dehydroergosterol (BioDeep_00000178029)

   

human metabolite blood metabolite natural product


代谢物信息卡片


14-(5,6-dimethylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),7,9-trien-5-ol

化学式: C28H42O (394.3235482)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 80%

分子结构信息

SMILES: CC(C)C(C)C=CC(C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3=CCC12C
InChI: InChI=1S/C28H42O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,14,18-20,22,24-25,29H,11-13,15-17H2,1-6H3

描述信息

同义名列表

2 个代谢物同义名

14-(5,6-dimethylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),7,9-trien-5-ol; Dehydroergosterol



数据库引用编号

3 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

54 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

  • Ladislav Dokládal, Michal Oboril, Karel Stejskal, Zbynek Zdráhal, Nikola Ptácková, Radka Chaloupková, Jirí Damborsky, Tomás Kasparovsky, Sylvain Jeandroz, Markéta Zd'árská, Jan Lochman. Physiological and proteomic approaches to evaluate the role of sterol binding in elicitin-induced resistance. Journal of experimental botany. 2012 Mar; 63(5):2203-15. doi: 10.1093/jxb/err427. [PMID: 22223811]
  • Daniel Wüstner. Following intracellular cholesterol transport by linear and non-linear optical microscopy of intrinsically fluorescent sterols. Current pharmaceutical biotechnology. 2012 Feb; 13(2):303-18. doi: 10.2174/138920112799095301. [PMID: 21470123]
  • Yvonne Lange, Jin Ye, Theodore L Steck. Activation mobilizes the cholesterol in the late endosomes-lysosomes of Niemann Pick type C cells. PloS one. 2012; 7(1):e30051. doi: 10.1371/journal.pone.0030051. [PMID: 22276143]
  • Luis M B B Estronca, Joao C P Silva, Julio L Sampaio, Andrej Shevchenko, Paul Verkade, Alfin D N Vaz, Winchil L C Vaz, Otilia V Vieira. Molecular etiology of atherogenesis--in vitro induction of lipidosis in macrophages with a new LDL model. PloS one. 2012; 7(4):e34822. doi: 10.1371/journal.pone.0034822. [PMID: 22514671]
  • Frederick R Maxfield, Daniel Wüstner. Analysis of cholesterol trafficking with fluorescent probes. Methods in cell biology. 2012; 108(?):367-93. doi: 10.1016/b978-0-12-386487-1.00017-1. [PMID: 22325611]
  • Victor J Valdes, Alejandro Athie, Laura S Salinas, Rosa E Navarro, Luis Vaca. CUP-1 is a novel protein involved in dietary cholesterol uptake in Caenorhabditis elegans. PloS one. 2012; 7(3):e33962. doi: 10.1371/journal.pone.0033962. [PMID: 22479487]
  • Jun Tian, Xiaoquan Ban, Hong Zeng, Jingsheng He, Yuxin Chen, Youwei Wang. The mechanism of antifungal action of essential oil from dill (Anethum graveolens L.) on Aspergillus flavus. PloS one. 2012; 7(1):e30147. doi: 10.1371/journal.pone.0030147. [PMID: 22272289]
  • Alexander G Georgiev, David P Sullivan, Michael C Kersting, Jeremy S Dittman, Christopher T Beh, Anant K Menon. Osh proteins regulate membrane sterol organization but are not required for sterol movement between the ER and PM. Traffic (Copenhagen, Denmark). 2011 Oct; 12(10):1341-55. doi: 10.1111/j.1600-0854.2011.01234.x. [PMID: 21689253]
  • Aswini Gnanasekaran, Mayya Sundukova, Arn M J M van den Maagdenberg, Elsa Fabbretti, Andrea Nistri. Lipid rafts control P2X3 receptor distribution and function in trigeminal sensory neurons of a transgenic migraine mouse model. Molecular pain. 2011 Sep; 7(?):77. doi: 10.1186/1744-8069-7-77. [PMID: 21958474]
  • Leslie A McCauliff, Zhi Xu, Judith Storch. Sterol transfer between cyclodextrin and membranes: similar but not identical mechanism to NPC2-mediated cholesterol transfer. Biochemistry. 2011 Aug; 50(34):7341-7349. doi: 10.1021/bi200574f. [PMID: 21740003]
  • Brad Chazotte. Labeling membranes with fluorescent cholesterols. Cold Spring Harbor protocols. 2011 May; 2011(5):pdb.prot5624. doi: 10.1101/pdb.prot5624. [PMID: 21536756]
  • Daniel Wüstner, Lukasz Solanko, Elena Sokol, Olav Garvik, Zaiguo Li, Robert Bittman, Thomas Korte, Andreas Herrmann. Quantitative assessment of sterol traffic in living cells by dual labeling with dehydroergosterol and BODIPY-cholesterol. Chemistry and physics of lipids. 2011 Mar; 164(3):221-35. doi: 10.1016/j.chemphyslip.2011.01.004. [PMID: 21291873]
  • Peter Kohut, Daniel Wüstner, Lucia Hronska, Karl Kuchler, Ivan Hapala, Martin Valachovic. The role of ABC proteins Aus1p and Pdr11p in the uptake of external sterols in yeast: dehydroergosterol fluorescence study. Biochemical and biophysical research communications. 2011 Jan; 404(1):233-8. doi: 10.1016/j.bbrc.2010.11.099. [PMID: 21110944]
  • Daniel Wüstner, Jonathan R Brewer, Luis Bagatolli, Daniel Sage. Potential of ultraviolet wide-field imaging and multiphoton microscopy for analysis of dehydroergosterol in cellular membranes. Microscopy research and technique. 2011 Jan; 74(1):92-108. doi: 10.1002/jemt.20878. [PMID: 21181715]
  • Fernando Alvarez-Vasquez, Howard Riezman, Yusuf A Hannun, Eberhard O Voit. Mathematical modeling and validation of the ergosterol pathway in Saccharomyces cerevisiae. PloS one. 2011; 6(12):e28344. doi: 10.1371/journal.pone.0028344. [PMID: 22194828]
  • Frederick A Heberle, Jing Wu, Shih Lin Goh, Robin S Petruzielo, Gerald W Feigenson. Comparison of three ternary lipid bilayer mixtures: FRET and ESR reveal nanodomains. Biophysical journal. 2010 Nov; 99(10):3309-18. doi: 10.1016/j.bpj.2010.09.064. [PMID: 21081079]
  • Olav Garvik, Peter Benediktson, Adam Cohen Simonsen, John Hjort Ipsen, Daniel Wüstner. The fluorescent cholesterol analog dehydroergosterol induces liquid-ordered domains in model membranes. Chemistry and physics of lipids. 2009 Jun; 159(2):114-8. doi: 10.1016/j.chemphyslip.2009.03.002. [PMID: 19477318]
  • Liming Qiu, Anthony Lewis, John Como, Mark W Vaughn, Juyang Huang, Pentti Somerharju, Jorma Virtanen, Kwan Hon Cheng. Cholesterol modulates the interaction of beta-amyloid peptide with lipid bilayers. Biophysical journal. 2009 May; 96(10):4299-307. doi: 10.1016/j.bpj.2009.02.036. [PMID: 19450500]
  • Anca D Petrescu, Aude Vespa, Huan Huang, Avery L McIntosh, Friedhelm Schroeder, Ann B Kier. Fluorescent sterols monitor cell penetrating peptide Pep-1 mediated uptake and intracellular targeting of cargo protein in living cells. Biochimica et biophysica acta. 2009 Feb; 1788(2):425-41. doi: 10.1016/j.bbamem.2008.09.015. [PMID: 18992218]
  • Marie Garnier-Lhomme, Richard D Byrne, Tina M C Hobday, Stephen Gschmeissner, Rudiger Woscholski, Dominic L Poccia, Erick J Dufourc, Banafshé Larijani. Nuclear envelope remnants: fluid membranes enriched in sterols and polyphosphoinositides. PloS one. 2009; 4(1):e4255. doi: 10.1371/journal.pone.0004255. [PMID: 19165341]
  • Parkson Lee-Gau Chong, Weiwei Zhu, Berenice Venegas. On the lateral structure of model membranes containing cholesterol. Biochimica et biophysica acta. 2009 Jan; 1788(1):2-11. doi: 10.1016/j.bbamem.2008.10.010. [PMID: 19010302]
  • Avery L McIntosh, Barbara P Atshaves, Huan Huang, Adalberto M Gallegos, Ann B Kier, Friedhelm Schroeder. Fluorescence techniques using dehydroergosterol to study cholesterol trafficking. Lipids. 2008 Dec; 43(12):1185-208. doi: 10.1007/s11745-008-3194-1. [PMID: 18536950]
  • Avery L McIntosh, Barbara P Atshaves, Adalberto M Gallegos, Stephen M Storey, Joseph H Reibenspies, Ann B Kier, Edgar Meyer, Friedhelm Schroeder. Structure of dehydroergosterol monohydrate and interaction with sterol carrier protein-2. Lipids. 2008 Dec; 43(12):1165-84. doi: 10.1007/s11745-008-3267-1. [PMID: 19020914]
  • Daniel Wüstner, Nils J Faergeman. Spatiotemporal analysis of endocytosis and membrane distribution of fluorescent sterols in living cells. Histochemistry and cell biology. 2008 Nov; 130(5):891-908. doi: 10.1007/s00418-008-0488-6. [PMID: 18787836]
  • Michelle Olsher, Parkson Lee-Gau Chong. Sterol superlattice affects antioxidant potency and can be used to assess adverse effects of antioxidants. Analytical biochemistry. 2008 Nov; 382(1):1-8. doi: 10.1016/j.ab.2008.07.021. [PMID: 18694720]
  • Nicole Hartwig Petersen, Nils J Faergeman, Nils J Faegeman, Liqing Yu, Daniel Wüstner. Kinetic imaging of NPC1L1 and sterol trafficking between plasma membrane and recycling endosomes in hepatoma cells. Journal of lipid research. 2008 Sep; 49(9):2023-37. doi: 10.1194/jlr.m800145-jlr200. [PMID: 18523240]
  • Daniel Wüstner, Nils J Faergeman. Chromatic aberration correction and deconvolution for UV sensitive imaging of fluorescent sterols in cytoplasmic lipid droplets. Cytometry. Part A : the journal of the International Society for Analytical Cytology. 2008 Aug; 73(8):727-44. doi: 10.1002/cyto.a.20593. [PMID: 18561197]
  • Daniel Wüstner. Free-cholesterol loading does not trigger phase separation of the fluorescent sterol dehydroergosterol in the plasma membrane of macrophages. Chemistry and physics of lipids. 2008 Aug; 154(2):129-36. doi: 10.1016/j.chemphyslip.2008.04.009. [PMID: 18534190]
  • Giacomo Diaz, Barbara Batetta, Francesca Sanna, Sabrina Uda, Camilla Reali, Fabrizio Angius, Marta Melis, Angela Maria Falchi. Lipid droplet changes in proliferating and quiescent 3T3 fibroblasts. Histochemistry and cell biology. 2008 May; 129(5):611-21. doi: 10.1007/s00418-008-0402-2. [PMID: 18297300]
  • Chao-Sheng Cheng, Ming-Nan Chen, Yen-Ting Lai, Ting Chen, Ku-Feng Lin, Yaw-Jen Liu, Ping-Chiang Lyu. Mutagenesis study of rice nonspecific lipid transfer protein 2 reveals residues that contribute to structure and ligand binding. Proteins. 2008 Feb; 70(3):695-706. doi: 10.1002/prot.21520. [PMID: 17729272]
  • Luís M B B Estronca, Maria João Moreno, Winchil L C Vaz. Kinetics and thermodynamics of the association of dehydroergosterol with lipid bilayer membranes. Biophysical journal. 2007 Dec; 93(12):4244-53. doi: 10.1529/biophysj.107.112847. [PMID: 17766353]
  • Gerald Gimpl, Katja Gehrig-Burger. Cholesterol reporter molecules. Bioscience reports. 2007 Dec; 27(6):335-58. doi: 10.1007/s10540-007-9060-1. [PMID: 17668316]
  • Daniel Wüstner. Fluorescent sterols as tools in membrane biophysics and cell biology. Chemistry and physics of lipids. 2007 Mar; 146(1):1-25. doi: 10.1016/j.chemphyslip.2006.12.004. [PMID: 17241621]
  • Nina H Pipalia, Mingming Hao, Sushmita Mukherjee, Frederick R Maxfield. Sterol, protein and lipid trafficking in Chinese hamster ovary cells with Niemann-Pick type C1 defect. Traffic (Copenhagen, Denmark). 2007 Feb; 8(2):130-41. doi: 10.1111/j.1600-0854.2006.00513.x. [PMID: 17156101]
  • Avery L McIntosh, Barbara P Atshaves, Huan Huang, Adalberto M Gallegos, Ann B Kier, Friedhelm Schroeder, Hai Xu, Weimin Zhang, Suojin Wang, Jyh-Charn Liu. Multiphoton laser-scanning microscopy and spatial analysis of dehydroergosterol distributions on plasma membrane of living cells. Methods in molecular biology (Clifton, N.J.). 2007; 398(?):85-105. doi: 10.1007/978-1-59745-513-8_8. [PMID: 18214376]
  • Parkson Lee-Gau Chong, Michelle Olsher. Fluorometric assay for detection of sterol oxidation in liposomal membranes. Methods in molecular biology (Clifton, N.J.). 2007; 400(?):145-58. doi: 10.1007/978-1-59745-519-0_10. [PMID: 17951732]
  • Heng-Ling Liou, Sayali S Dixit, Sujuan Xu, G Stephen Tint, Ann M Stock, Peter Lobel. NPC2, the protein deficient in Niemann-Pick C2 disease, consists of multiple glycoforms that bind a variety of sterols. The Journal of biological chemistry. 2006 Dec; 281(48):36710-23. doi: 10.1074/jbc.m608743200. [PMID: 17018531]
  • Adalberto M Gallegos, Stephen M Storey, Ann B Kier, Friedhelm Schroeder, Judith M Ball. Structure and cholesterol dynamics of caveolae/raft and nonraft plasma membrane domains. Biochemistry. 2006 Oct; 45(39):12100-16. doi: 10.1021/bi0602720. [PMID: 17002310]
  • Mark P Burns, Urule Igbavboa, Lili Wang, W Gibson Wood, Karen Duff. Cholesterol distribution, not total levels, correlate with altered amyloid precursor protein processing in statin-treated mice. Neuromolecular medicine. 2006; 8(3):319-28. doi: 10.1385/nmm:8:3:319. [PMID: 16775383]
  • D Wüstner. Improved visualization and quantitative analysis of fluorescent membrane sterol in polarized hepatic cells. Journal of microscopy. 2005 Oct; 220(Pt 1):47-64. doi: 10.1111/j.1365-2818.2005.01516.x. [PMID: 16269063]
  • Manasa V Gudheti, Sum P Lee, Dganit Danino, Steven P Wrenn. Combined interaction of phospholipase C and apolipoprotein A-I with small unilamellar lecithin-cholesterol vesicles: influence of apolipoprotein A-I concentration and vesicle composition. Biochemistry. 2005 May; 44(19):7294-304. doi: 10.1021/bi047317m. [PMID: 15882068]
  • Jan Lochman, Tomas Kasparovsky, Jiri Damborsky, Hanan Osman, Antoine Marais, Radka Chaloupkova, Michel Ponchet, Jean-Pierre Blein, Vladimir Mikes. Construction of cryptogein mutants, a proteinaceous elicitor from Phytophthora, with altered abilities to induce a defense reaction in tobacco cells. Biochemistry. 2005 May; 44(17):6565-72. doi: 10.1021/bi0502285. [PMID: 15850390]
  • Daniel Wüstner, Mousumi Mondal, Ira Tabas, Frederick R Maxfield. Direct observation of rapid internalization and intracellular transport of sterol by macrophage foam cells. Traffic (Copenhagen, Denmark). 2005 May; 6(5):396-412. doi: 10.1111/j.1600-0854.2005.00285.x. [PMID: 15813750]
  • Weimin Zhang, Avery L McIntosh, Hai Xu, Di Wu, Todd Gruninger, Barbara Atshaves, J C Steve Liu, Friedhelm Schroeder. Structural analysis of sterol distributions in the plasma membrane of living cells. Biochemistry. 2005 Mar; 44(8):2864-84. doi: 10.1021/bi048172m. [PMID: 15723530]
  • Michelle Olsher, Su-In Yoon, Parkson Lee-Gau Chong. Role of sterol superlattice in free radical-induced sterol oxidation in lipid membranes. Biochemistry. 2005 Feb; 44(6):2080-7. doi: 10.1021/bi047710s. [PMID: 15697233]
  • Chao-Sheng Cheng, Dharmaraj Samuel, Yaw-Jen Liu, Je-Chyi Shyu, Szu-Ming Lai, Ku-Feng Lin, Ping-Chiang Lyu. Binding mechanism of nonspecific lipid transfer proteins and their role in plant defense. Biochemistry. 2004 Nov; 43(43):13628-36. doi: 10.1021/bi048873j. [PMID: 15504025]
  • H Raghuraman, Amitabha Chattopadhyay. Interaction of melittin with membrane cholesterol: a fluorescence approach. Biophysical journal. 2004 Oct; 87(4):2419-32. doi: 10.1529/biophysj.104.043596. [PMID: 15454440]
  • Adalberto M Gallegos, Avery L McIntosh, Barbara P Atshaves, Friedhelm Schroeder. Structure and cholesterol domain dynamics of an enriched caveolae/raft isolate. The Biochemical journal. 2004 Sep; 382(Pt 2):451-61. doi: 10.1042/bj20031562. [PMID: 15149285]
  • Mingming Hao, Sushmita Mukherjee, Yu Sun, Frederick R Maxfield. Effects of cholesterol depletion and increased lipid unsaturation on the properties of endocytic membranes. The Journal of biological chemistry. 2004 Apr; 279(14):14171-8. doi: 10.1074/jbc.m309793200. [PMID: 14734557]
  • Rodrigo F M de Almeida, Luís M S Loura, Manuel Prieto, Anthony Watts, Aleksandre Fedorov, Francisco J Barrantes. Cholesterol modulates the organization of the gammaM4 transmembrane domain of the muscle nicotinic acetylcholine receptor. Biophysical journal. 2004 Apr; 86(4):2261-72. doi: 10.1016/s0006-3495(04)74284-8. [PMID: 15041665]
  • Mei Mei Wang, Michelle Olsher, István P Sugár, Parkson Lee-Gau Chong. Cholesterol superlattice modulates the activity of cholesterol oxidase in lipid membranes. Biochemistry. 2004 Mar; 43(8):2159-66. doi: 10.1021/bi035982+. [PMID: 14979712]
  • Amanda Parker, Keith Miles, Kwan Hon Cheng, Juyang Huang. Lateral distribution of cholesterol in dioleoylphosphatidylcholine lipid bilayers: cholesterol-phospholipid interactions at high cholesterol limit. Biophysical journal. 2004 Mar; 86(3):1532-44. doi: 10.1016/s0006-3495(04)74221-6. [PMID: 14990480]
  • Daniel Wüstner, Mousumi Mondal, Amy Huang, Frederick R Maxfield. Different transport routes for high density lipoprotein and its associated free sterol in polarized hepatic cells. Journal of lipid research. 2004 Mar; 45(3):427-37. doi: 10.1194/jlr.m300440-jlr200. [PMID: 14679167]
  • Andrew J Guarino, Thomas N Tulenko, Steven P Wrenn. Cholesterol crystal nucleation from enzymatically modified low-density lipoproteins: combined effect of sphingomyelinase and cholesterol esterase. Biochemistry. 2004 Feb; 43(6):1685-93. doi: 10.1021/bi035747r. [PMID: 14769046]
  • Jiwei Wang, Megha, Erwin London. Relationship between sterol/steroid structure and participation in ordered lipid domains (lipid rafts): implications for lipid raft structure and function. Biochemistry. 2004 Feb; 43(4):1010-8. doi: 10.1021/bi035696y. [PMID: 14744146]
  • Barbara P Atshaves, Adalberto M Gallegos, Avery L McIntosh, Ann B Kier, Friedhelm Schroeder. Sterol carrier protein-2 selectively alters lipid composition and cholesterol dynamics of caveolae/lipid raft vs nonraft domains in L-cell fibroblast plasma membranes. Biochemistry. 2003 Dec; 42(49):14583-98. doi: 10.1021/bi034966+. [PMID: 14661971]
  • Holger A Scheidt, Peter Muller, Andreas Herrmann, Daniel Huster. The potential of fluorescent and spin-labeled steroid analogs to mimic natural cholesterol. The Journal of biological chemistry. 2003 Nov; 278(46):45563-9. doi: 10.1074/jbc.m303567200. [PMID: 12947110]
  • Avery L McIntosh, Adalberto M Gallegos, Barbara P Atshaves, Stephen M Storey, Deepak Kannoju, Friedhelm Schroeder. Fluorescence and multiphoton imaging resolve unique structural forms of sterol in membranes of living cells. The Journal of biological chemistry. 2003 Feb; 278(8):6384-403. doi: 10.1074/jbc.m205472200. [PMID: 12456684]
  • Karin John, Janek Kubelt, Peter Müller, Daniel Wüstner, Andreas Herrmann. Rapid transbilayer movement of the fluorescent sterol dehydroergosterol in lipid membranes. Biophysical journal. 2002 Sep; 83(3):1525-34. doi: 10.1016/s0006-3495(02)73922-2. [PMID: 12202377]
  • Daniel Wüstner, Andreas Herrmann, Mingming Hao, Frederick R Maxfield. Rapid nonvesicular transport of sterol between the plasma membrane domains of polarized hepatic cells. The Journal of biological chemistry. 2002 Aug; 277(33):30325-36. doi: 10.1074/jbc.m202626200. [PMID: 12050151]
  • Jesper E Mogensen, Reinhard Wimmer, Jørgen N Larsen, Michael D Spangfort, Daniel E Otzen. The major birch allergen, Bet v 1, shows affinity for a broad spectrum of physiological ligands. The Journal of biological chemistry. 2002 Jun; 277(26):23684-92. doi: 10.1074/jbc.m202065200. [PMID: 11953433]
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  • Mingming Hao, Sharron X Lin, Ola J Karylowski, Daniel Wüstner, Timothy E McGraw, Frederick R Maxfield. Vesicular and non-vesicular sterol transport in living cells. The endocytic recycling compartment is a major sterol storage organelle. The Journal of biological chemistry. 2002 Jan; 277(1):609-17. doi: 10.1074/jbc.m108861200. [PMID: 11682487]
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