Sinapoyl malate (BioDeep_00000003583)
Secondary id: BioDeep_00000402754, BioDeep_00000403099, BioDeep_00001870148
natural product PANOMIX_OTCML-2023
代谢物信息卡片
(E)-2-((3-(4-Hydroxy-3,5-dimethoxyphenyl)acryloyl)oxy)succinic acid
化学式: C15H16O9 (340.0794286)
中文名称: 芥子酰基菜果酸酯
谱图信息:
最多检出来源 Viridiplantae(plant) 1.41%
分子结构信息
SMILES: COC1=CC(=CC(=C1O)OC)C=CC(=O)OC(CC(=O)O)C(=O)O
InChI: InChI=1S/C15H16O9/c1-22-9-5-8(6-10(23-2)14(9)19)3-4-13(18)24-11(15(20)21)7-12(16)17/h3-6,11,19H,7H2,1-2H3,(H,16,17)(H,20,21)
描述信息
Annotation level-2
Acquisition and generation of the data is financially supported in part by CREST/JST.
同义名列表
数据库引用编号
28 个数据库交叉引用编号
- ChEBI: CHEBI:190397
- ChEBI: CHEBI:139533
- KEGG: C02887
- PubChem: 14605050
- PubChem: 53779314
- PubChem: 11953815
- Metlin: METLIN64185
- CAS: 76656-81-0
- CAS: 92344-58-6
- CAS: 1204743-53-2
- CAS: 76030-88-1
- MoNA: PR309002
- MoNA: MetaboBASE1068
- MoNA: MetaboBASE1067
- MoNA: PT211790
- MoNA: PT111790
- MoNA: PS117908
- MoNA: PR101055
- MoNA: PS117907
- MoNA: PS117909
- MoNA: PS117911
- MoNA: PS117902
- MoNA: PS117901
- MoNA: PR101003
- MoNA: PS117910
- PMhub: MS000010086
- PubChem: 5818
- 3DMET: B01608
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)
6 个相关的物种来源信息
- 3702 - Arabidopsis thaliana:
- 3708 - Brassica napus: 10.1016/J.PHYTOCHEM.2005.02.031
- 3711 - Brassica rapa:
- 3711 - Brassica rapa: 10.1016/S0031-9422(97)00362-2
- 109996 - Raphanus raphanistrum: 10.1016/S0031-9422(00)83482-2
- 3726 - Raphanus sativus: 10.1016/S0031-9422(00)83482-2
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
- Weiqiang Li, Yaru Sun, Kun Li, Hongtao Tian, Jiangtao Jia, Hongyu Zhang, Yaping Wang, Hong Wang, Baodi Bi, Jinggong Guo, Lam-Son Phan Tran, Yuchen Miao. Sinapate Esters Mediate UV-B-Induced Stomatal Closure by Regulating Nitric Oxide, Hydrogen Peroxide, and Malate Accumulation in Arabidopsis thaliana.
Plant & cell physiology.
2023 Jan; 63(12):1890-1899. doi:
10.1093/pcp/pcac059. [PMID: 35475535] - Whitney L Dolan, Brian P Dilkes, Jake M Stout, Nicholas D Bonawitz, Clint Chapple. Mediator Complex Subunits MED2, MED5, MED16, and MED23 Genetically Interact in the Regulation of Phenylpropanoid Biosynthesis.
The Plant cell.
2017 12; 29(12):3269-3285. doi:
10.1105/tpc.17.00282. [PMID: 29203634] - M D Horbury, W-D Quan, A L Flourat, F Allais, V G Stavros. Elucidating nuclear motions in a plant sunscreen during photoisomerization through solvent viscosity effects.
Physical chemistry chemical physics : PCCP.
2017 Aug; 19(31):21127-21131. doi:
10.1039/c7cp04070a. [PMID: 28749499] - Karina Hettwer, Christoph Böttcher, Andrej Frolov, Juliane Mittasch, Andreas Albert, Edda von Roepenack-Lahaye, Dieter Strack, Carsten Milkowski. Dynamic metabolic changes in seeds and seedlings of Brassica napus (oilseed rape) suppressing UGT84A9 reveal plasticity and molecular regulation of the phenylpropanoid pathway.
Phytochemistry.
2016 Apr; 124(?):46-57. doi:
10.1016/j.phytochem.2016.01.014. [PMID: 26833384] - Nawaporn Onkokesung, Michael Reichelt, Arjen van Doorn, Robert C Schuurink, Marcel Dicke. Differential Costs of Two Distinct Resistance Mechanisms Induced by Different Herbivore Species in Arabidopsis.
Plant physiology.
2016 Feb; 170(2):891-906. doi:
10.1104/pp.15.01780. [PMID: 26603653] - Lewis A Baker, Michael D Horbury, Simon E Greenough, Florent Allais, Patrick S Walsh, Scott Habershon, Vasilios G Stavros. Ultrafast Photoprotecting Sunscreens in Natural Plants.
The journal of physical chemistry letters.
2016 Jan; 7(1):56-61. doi:
10.1021/acs.jpclett.5b02474. [PMID: 26654715] - Janine Colling, Jacob Pollier, Robin Vanden Bossche, Nokwanda Pearl Makunga, Laurens Pauwels, Alain Goossens. Hypersensitivity of Arabidopsis TAXIMIN1 overexpression lines to light stress is correlated with decreased sinapoyl malate abundance and countered by the antibiotic cefotaxime.
Plant signaling & behavior.
2016; 11(4):e1143998. doi:
10.1080/15592324.2016.1143998. [PMID: 26967827] - Marina Eremina, Wilfried Rozhon, Saiqi Yang, Brigitte Poppenberger. ENO2 activity is required for the development and reproductive success of plants, and is feedback-repressed by AtMBP-1.
The Plant journal : for cell and molecular biology.
2015 Mar; 81(6):895-906. doi:
10.1111/tpj.12775. [PMID: 25620024] - Jacob C Dean, Ryoji Kusaka, Patrick S Walsh, Florent Allais, Timothy S Zwier. Plant sunscreens in the UV-B: ultraviolet spectroscopy of jet-cooled sinapoyl malate, sinapic acid, and sinapate ester derivatives.
Journal of the American Chemical Society.
2014 Oct; 136(42):14780-95. doi:
10.1021/ja5059026. [PMID: 25295994] - Caspar Langenbach, Ruth Campe, Ulrich Schaffrath, Katharina Goellner, Uwe Conrath. UDP-glucosyltransferase UGT84A2/BRT1 is required for Arabidopsis nonhost resistance to the Asian soybean rust pathogen Phakopsora pachyrhizi.
The New phytologist.
2013 Apr; 198(2):536-545. doi:
10.1111/nph.12155. [PMID: 23356583] - P R Santos-Filho, S C Vitor, L Frungillo, E E Saviani, H C Oliveira, I Salgado. Nitrate reductase- and nitric oxide-dependent activation of sinapoylglucose:malate sinapoyltransferase in leaves of Arabidopsis thaliana.
Plant & cell physiology.
2012 Sep; 53(9):1607-16. doi:
10.1093/pcp/pcs104. [PMID: 22833666] - Mike Page, Nighat Sultana, Konrad Paszkiewicz, Hannah Florance, Nicholas Smirnoff. The influence of ascorbate on anthocyanin accumulation during high light acclimation in Arabidopsis thaliana: further evidence for redox control of anthocyanin synthesis.
Plant, cell & environment.
2012 Feb; 35(2):388-404. doi:
10.1111/j.1365-3040.2011.02369.x. [PMID: 21631536] - Silvia Fornalé, Xinhui Shi, Chenglin Chai, Antonio Encina, Sami Irar, Montserrat Capellades, Elisabet Fuguet, Josep-Lluís Torres, Pere Rovira, Pere Puigdomènech, Joan Rigau, Erich Grotewold, John Gray, David Caparrós-Ruiz. ZmMYB31 directly represses maize lignin genes and redirects the phenylpropanoid metabolic flux.
The Plant journal : for cell and molecular biology.
2010 Nov; 64(4):633-44. doi:
10.1111/j.1365-313x.2010.04363.x. [PMID: 21070416] - Fathi-Mohamed Sonbol, Silvia Fornalé, Montserrat Capellades, Antonio Encina, Sonia Touriño, Josep-Lluís Torres, Pere Rovira, Katia Ruel, Pere Puigdomènech, Joan Rigau, David Caparrós-Ruiz. The maize ZmMYB42 represses the phenylpropanoid pathway and affects the cell wall structure, composition and degradability in Arabidopsis thaliana.
Plant molecular biology.
2009 Jun; 70(3):283-96. doi:
10.1007/s11103-009-9473-2. [PMID: 19238561] - Dirk Meissner, Andreas Albert, Christoph Böttcher, Dieter Strack, Carsten Milkowski. The role of UDP-glucose:hydroxycinnamate glucosyltransferases in phenylpropanoid metabolism and the response to UV-B radiation in Arabidopsis thaliana.
Planta.
2008 Sep; 228(4):663-74. doi:
10.1007/s00425-008-0768-3. [PMID: 18563436] - Mohammad Mir Derikvand, Jimmy Berrio Sierra, Katia Ruel, Brigitte Pollet, Cao-Trung Do, Johanne Thévenin, Dominique Buffard, Lise Jouanin, Catherine Lapierre. Redirection of the phenylpropanoid pathway to feruloyl malate in Arabidopsis mutants deficient for cinnamoyl-CoA reductase 1.
Planta.
2008 Apr; 227(5):943-56. doi:
10.1007/s00425-007-0669-x. [PMID: 18046574] - Miyako Kusano, Atsushi Fukushima, Masanori Arita, Pär Jonsson, Thomas Moritz, Makoto Kobayashi, Naomi Hayashi, Takayuki Tohge, Kazuki Saito. Unbiased characterization of genotype-dependent metabolic regulations by metabolomic approach in Arabidopsis thaliana.
BMC systems biology.
2007 Nov; 1(?):53. doi:
10.1186/1752-0509-1-53. [PMID: 18028551] - Y-S Liang, H K Kim, A W M Lefeber, C Erkelens, Y H Choi, R Verpoorte. Identification of phenylpropanoids in methyl jasmonate treated Brassica rapa leaves using two-dimensional nuclear magnetic resonance spectroscopy.
Journal of chromatography. A.
2006 Apr; 1112(1-2):148-55. doi:
10.1016/j.chroma.2005.11.114. [PMID: 16375911] - R N Bennett, T Wenke, B Freudenberg, F A Mellon, J Ludwig-Müller. The tu8 mutation of Arabidopsis thaliana encoding a heterochromatin protein 1 homolog causes defects in the induction of secondary metabolite biosynthesis.
Plant biology (Stuttgart, Germany).
2005 Jul; 7(4):348-57. doi:
10.1055/s-2005-837634. [PMID: 16025407] - Matthew R Hemm, Max O Ruegger, Clint Chapple. The Arabidopsis ref2 mutant is defective in the gene encoding CYP83A1 and shows both phenylpropanoid and glucosinolate phenotypes.
The Plant cell.
2003 Jan; 15(1):179-94. doi:
10.1105/tpc.006544. [PMID: 12509530] - Bettina Hause, Knut Meyer, Paul V Viitanen, Clint Chapple, Dieter Strack. Immunolocalization of 1- O-sinapoylglucose:malate sinapoyltransferase in Arabidopsis thaliana.
Planta.
2002 May; 215(1):26-32. doi:
10.1007/s00425-001-0716-y. [PMID: 12012238] - Rochus Franke, Matthew R Hemm, Jeff W Denault, Max O Ruegger, John M Humphreys, Clint Chapple. Changes in secondary metabolism and deposition of an unusual lignin in the ref8 mutant of Arabidopsis.
The Plant journal : for cell and molecular biology.
2002 Apr; 30(1):47-59. doi:
10.1046/j.1365-313x.2002.01267.x. [PMID: 11967092] - Rochus Franke, John M Humphreys, Matthew R Hemm, Jeff W Denault, Max O Ruegger, Joanne C Cusumano, Clint Chapple. The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism.
The Plant journal : for cell and molecular biology.
2002 Apr; 30(1):33-45. doi:
10.1046/j.1365-313x.2002.01266.x. [PMID: 11967091] - M Ruegger, C Chapple. Mutations that reduce sinapoylmalate accumulation in Arabidopsis thaliana define loci with diverse roles in phenylpropanoid metabolism.
Genetics.
2001 Dec; 159(4):1741-9. doi:
10.1093/genetics/159.4.1741. [PMID: 11779811] - M R Hemm, K M Herrmann, C Chapple. AtMYB4: a transcription factor general in the battle against UV.
Trends in plant science.
2001 Apr; 6(4):135-6. doi:
10.1016/s1360-1385(01)01915-x. [PMID: 11286899] - J Hagemeier, B Schneider, N J Oldham, K Hahlbrock. Accumulation of soluble and wall-bound indolic metabolites in Arabidopsis thaliana leaves infected with virulent or avirulent Pseudomonas syringae pathovar tomato strains.
Proceedings of the National Academy of Sciences of the United States of America.
2001 Jan; 98(2):753-8. doi:
10.1073/pnas.98.2.753. [PMID: 11136235] - M Ruegger, K Meyer, J C Cusumano, C Chapple. Regulation of ferulate-5-hydroxylase expression in Arabidopsis in the context of sinapate ester biosynthesis.
Plant physiology.
1999 Jan; 119(1):101-10. doi:
10.1104/pp.119.1.101. [PMID: 9880351] - C C Chapple, T Vogt, B E Ellis, C R Somerville. An Arabidopsis mutant defective in the general phenylpropanoid pathway.
The Plant cell.
1992 Nov; 4(11):1413-24. doi:
10.1105/tpc.4.11.1413. [PMID: 1477555]