12-oxo-PDA (BioDeep_00000004066)

 

Secondary id: BioDeep_00000016641, BioDeep_00000911286, BioDeep_00001028829, BioDeep_00001869048

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


8-[(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl]octanoic acid

化学式: C18H28O3 (292.2038338)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 0.05%

分子结构信息

SMILES: C1=C[C@@H]([C@@H](C1=O)C/C=C\CC)CCCCCCCC(=O)O
InChI: InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-/t15-,16-/m0/s1

描述信息

12-oxo-pda, also known as (15z)-12-oxophyto-10,15-dienoate or 12-oxo-10,15(Z)-phytodienoic acid, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, 12-oxo-pda is considered to be an octadecanoid lipid molecule. 12-oxo-pda is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 12-oxo-pda can be found in corn, which makes 12-oxo-pda a potential biomarker for the consumption of this food product.
D006133 - Growth Substances > D010937 - Plant Growth Regulators

同义名列表

24 个代谢物同义名

8-[(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl]octanoic acid; 8-(2-(cis-2-Pentenyl)-3-oxo-cis-4-cyclopentenyl)octanoic acid; 8-(2-(cis-2-Pentenyl)-3-oxo-cis-4-cyclopentenyl)octanoate; 4-oxo-5-(2Z-pentenyl)-2-cyclopentene-1-octanoic acid; 4-oxo-5-(2-Pentenyl)-2-cyclopentene-1-octanoic acid; 4-oxo-5-(2-Pentenyl)-2-cyclopentene-1-octanoate; 12-oxo-cis-10, cis-15-Phytodienoic acid; (15Z)-12-oxophyto-10,15-Dienoic acid; 12-Oxo-cis-10,15-phytodienoic acid; 12-oxo-10,15(Z)-Phytodienoic acid; (15Z)-12-Oxophyto-10,15-dienoate; (9S,13S)-12-Oxophytodienoic acid; 2-Cyclopentene-1-octanoic acid; 12-oxo-10,15(Z)-Phytodienoate; 12-oxo-phytodienoic acid; 12-oxo Phytodienoic Acid; 12-Oxophytodienoic acid; 9(S),13(S)-12-oxo-PDA; 12-Oxophytodienoate; 12-oxo-PDA; 12-oxo PDA; OPDA acid; 12-OPDA; OPDA



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

225 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(225)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

9 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

  • Longying Wu, Ruolin Wang, Mingyu Li, Zhiye Du, Yufan Jin, Yang Shi, Wenjun Jiang, Ji Chen, Yuan Jiao, Binhua Hu, Jin Huang. Functional analysis of a rice 12-oxo-phytodienoic acid reductase gene (OsOPR1) involved in Cd stress tolerance. Molecular biology reports. 2024 Jan; 51(1):198. doi: 10.1007/s11033-023-09159-w. [PMID: 38270739]
  • Liang Wang, Yanxia Zhu, Jianping Jiang, Guiyu Tan, Qing Ma, Hongsheng Zhang. Dynamic changes in the levels of metabolites and endogenous hormones during the germination of Zanthoxylum nitidum (Roxb.) DC. Seeds. Plant signaling & behavior. 2023 Dec; 18(1):2251750. doi: 10.1080/15592324.2023.2251750. [PMID: 37639213]
  • Yan-Yu Zhang, Yun-Da Yao, Fang Chen, Xin Guo, Jun-Li Kang, Yu-Feng Huang, Fan He, Yan Dong, Ying Xie, Peng Wu, Hua Zhou. (9S,13R)-12-oxo-phytodienoic acid attenuates inflammation by inhibiting mPGES-1 and modulating macrophage polarization via NF-κB and Nrf2/HO-1 pathways. Pharmacological research. 2022 08; 182(?):106310. doi: 10.1016/j.phrs.2022.106310. [PMID: 35714824]
  • Feiyan Huang, Farhat Abbas, Dylan O'Neill Rothenberg, Muhammad Imran, Sajid Fiaz, Naveed Ur Rehman, Sikandar Amanullah, Afifa Younas, Yan Ding, Xianjie Cai, Xiaolong Chen, Lei Yu, Xianwen Ye, Lin Jiang, Yanguo Ke, Yuansheng He. Molecular cloning, characterization and expression analysis of two 12-oxophytodienoate reductases (NtOPR1 and NtOPR2) from Nicotiana tabacum. Molecular biology reports. 2022 Jun; 49(6):5379-5387. doi: 10.1007/s11033-022-07114-9. [PMID: 35149935]
  • Yusuke Ito, Kento Sasaki, Tsuyoshi Ogihara, Naoki Kitaoka, Kosaku Takahahi, Hideyuki Matsuura. Verification of the versatility of the in vitro enzymatic reaction giving (+)-cis-12-Oxo-phytodienoic acid. Bioorganic & medicinal chemistry letters. 2021 10; 49(?):128284. doi: 10.1016/j.bmcl.2021.128284. [PMID: 34311085]
  • Daniel Maynard, Kamel Chibani, Sonja Schmidtpott, Thorsten Seidel, Jens Spross, Andrea Viehhauser, Karl-Josef Dietz. Biochemical Characterization of 13-Lipoxygenases of Arabidopsis thaliana. International journal of molecular sciences. 2021 Sep; 22(19):. doi: 10.3390/ijms221910237. [PMID: 34638573]
  • Xin Zhao, Nannan Li, Qin Song, Xiaohong Li, Hongjun Meng, Keming Luo. OPDAT1, a plastid envelope protein involved in 12-oxo-phytodienoic acid export for jasmonic acid biosynthesis in Populus. Tree physiology. 2021 09; 41(9):1714-1728. doi: 10.1093/treephys/tpab037. [PMID: 33835169]
  • Kadis Mujiono, Tilisa Tohi, Islam S Sobhy, Yuko Hojo, Tomonori Shinya, Ivan Galis. Herbivore-induced and constitutive volatiles are controlled by different oxylipin-dependent mechanisms in rice. Plant, cell & environment. 2021 08; 44(8):2687-2699. doi: 10.1111/pce.14126. [PMID: 34114241]
  • Daniel Maynard, Andrea Viehhauser, Madita Knieper, Anna Dreyer, Ghamdan Manea, Wilena Telman, Falk Butter, Kamel Chibani, Renate Scheibe, Karl-Josef Dietz. The In Vitro Interaction of 12-Oxophytodienoic Acid and Related Conjugated Carbonyl Compounds with Thiol Antioxidants. Biomolecules. 2021 03; 11(3):. doi: 10.3390/biom11030457. [PMID: 33803875]
  • Antonio López-Orenes, Juan M Alba, Merijn R Kant, Antonio A Calderón, María A Ferrer. OPDA and ABA accumulation in Pb-stressed Zygophyllum fabago can be primed by salicylic acid and coincides with organ-specific differences in accumulation of phenolics. Plant physiology and biochemistry : PPB. 2020 Sep; 154(?):612-621. doi: 10.1016/j.plaphy.2020.06.028. [PMID: 32912492]
  • Ken-Der Wang, Zachary Gorman, Pei-Cheng Huang, Charles M Kenerley, Michael V Kolomiets. Trichoderma virens colonization of maize roots triggers rapid accumulation of 12-oxophytodienoate and two ᵧ-ketols in leaves as priming agents of induced systemic resistance. Plant signaling & behavior. 2020 09; 15(9):1792187. doi: 10.1080/15592324.2020.1792187. [PMID: 32657209]
  • Wenshan Liu, Izailda Barbosa Dos Santos, Anna Moye, Sang-Wook Park. CYP20-3 deglutathionylates 2-CysPRX A and suppresses peroxide detoxification during heat stress. Life science alliance. 2020 09; 3(9):. doi: 10.26508/lsa.202000775. [PMID: 32732254]
  • Daniel Maynard, Vijay Kumar, Jens Sproï, Karl-Josef Dietz. 12-Oxophytodienoic Acid Reductase 3 (OPR3) Functions as NADPH-Dependent α,β-Ketoalkene Reductase in Detoxification and Monodehydroascorbate Reductase in Redox Homeostasis. Plant & cell physiology. 2020 Mar; 61(3):584-595. doi: 10.1093/pcp/pcz226. [PMID: 31834385]
  • Weifeng Luo, Setsuko Komatsu, Tatsuya Abe, Hideyuki Matsuura, Kosaku Takahashi. Comparative Proteomic Analysis of Wild-Type Physcomitrella Patens and an OPDA-Deficient Physcomitrella Patens Mutant with Disrupted PpAOS1 and PpAOS2 Genes after Wounding. International journal of molecular sciences. 2020 Feb; 21(4):. doi: 10.3390/ijms21041417. [PMID: 32093080]
  • Hidenori Matsui, Hidekazu Iwakawa, Gang-Su Hyon, Izumi Yotsui, Shinpei Katou, Isabel Monte, Ryuichi Nishihama, Rainer Franzen, Roberto Solano, Hirofumi Nakagami. Isolation of Natural Fungal Pathogens from Marchantia polymorpha Reveals Antagonism between Salicylic Acid and Jasmonate during Liverwort-Fungus Interactions. Plant & cell physiology. 2020 Feb; 61(2):265-275. doi: 10.1093/pcp/pcz187. [PMID: 31560390]
  • Ken-Der Wang, Eli J Borrego, Charles M Kenerley, Michael V Kolomiets. Oxylipins Other Than Jasmonic Acid Are Xylem-Resident Signals Regulating Systemic Resistance Induced by Trichoderma virens in Maize. The Plant cell. 2020 01; 32(1):166-185. doi: 10.1105/tpc.19.00487. [PMID: 31690653]
  • Damián Balfagón, Soham Sengupta, Aurelio Gómez-Cadenas, Felix B Fritschi, Rajeev K Azad, Ron Mittler, Sara I Zandalinas. Jasmonic Acid Is Required for Plant Acclimation to a Combination of High Light and Heat Stress. Plant physiology. 2019 12; 181(4):1668-1682. doi: 10.1104/pp.19.00956. [PMID: 31594842]
  • María Peñuelas, Isabel Monte, Fabian Schweizer, Armelle Vallat, Philippe Reymond, Gloria García-Casado, Jose M Franco-Zorrilla, Roberto Solano. Jasmonate-Related MYC Transcription Factors Are Functionally Conserved in Marchantia polymorpha. The Plant cell. 2019 10; 31(10):2491-2509. doi: 10.1105/tpc.18.00974. [PMID: 31391256]
  • Li Guan, Niels Denkert, Ahmed Eisa, Martin Lehmann, Inga Sjuts, Arne Weiberg, Jürgen Soll, Michael Meinecke, Serena Schwenkert. JASSY, a chloroplast outer membrane protein required for jasmonate biosynthesis. Proceedings of the National Academy of Sciences of the United States of America. 2019 05; 116(21):10568-10575. doi: 10.1073/pnas.1900482116. [PMID: 31068459]
  • Natalia Kłeczek, Barbara Michalak, Janusz Malarz, Anna Karolina Kiss, Anna Stojakowska. Carpesium divaricatum Sieb. & Zucc. Revisited: Newly Identified Constituents from Aerial Parts of the Plant and Their Possible Contribution to the Biological Activity of the Plant. Molecules (Basel, Switzerland). 2019 Apr; 24(8):. doi: 10.3390/molecules24081614. [PMID: 31022860]
  • Suresh Varsani, Sajjan Grover, Shaoqun Zhou, Kyle G Koch, Pei-Cheng Huang, Michael V Kolomiets, W Paul Williams, Tiffany Heng-Moss, Gautam Sarath, Dawn S Luthe, Georg Jander, Joe Louis. 12-Oxo-Phytodienoic Acid Acts as a Regulator of Maize Defense against Corn Leaf Aphid. Plant physiology. 2019 04; 179(4):1402-1415. doi: 10.1104/pp.18.01472. [PMID: 30643012]
  • Rocío Escobar-Bravo, Jasmijn Ruijgrok, Hye Kyong Kim, Katharina Grosser, Nicole M Van Dam, Peter G L Klinkhamer, Kirsten A Leiss. Light Intensity-Mediated Induction of Trichome-Associated Allelochemicals Increases Resistance Against Thrips in Tomato. Plant & cell physiology. 2018 Dec; 59(12):2462-2475. doi: 10.1093/pcp/pcy166. [PMID: 30124946]
  • Daniel Maynard, Harald Gröger, Thomas Dierks, Karl-Josef Dietz. The function of the oxylipin 12-oxophytodienoic acid in cell signaling, stress acclimation, and development. Journal of experimental botany. 2018 11; 69(22):5341-5354. doi: 10.1093/jxb/ery316. [PMID: 30169821]
  • Claus Wasternack, Miroslav Strnad. Jasmonates: News on Occurrence, Biosynthesis, Metabolism and Action of an Ancient Group of Signaling Compounds. International journal of molecular sciences. 2018 Aug; 19(9):. doi: 10.3390/ijms19092539. [PMID: 30150593]
  • Carlos De Ollas, Vicent Arbona, Aurelio Gómez-Cadenas, Ian C Dodd. Attenuated accumulation of jasmonates modifies stomatal responses to water deficit. Journal of experimental botany. 2018 04; 69(8):2103-2116. doi: 10.1093/jxb/ery045. [PMID: 29432619]
  • Ge Cheng, Ming-Shun Chen, Lieceng Zhu. 12-Oxo-Phytodienoic Acid Enhances Wheat Resistance to Hessian Fly (Diptera: Cecidomyiidae) Under Heat Stress. Journal of economic entomology. 2018 04; 111(2):917-922. doi: 10.1093/jee/tox374. [PMID: 29420735]
  • Simone Findling, Henrik U Stotz, Maria Zoeller, Markus Krischke, Mark Zander, Christiane Gatz, Susanne Berger, Martin J Mueller. TGA2 signaling in response to reactive electrophile species is not dependent on cysteine modification of TGA2. PloS one. 2018; 13(4):e0195398. doi: 10.1371/journal.pone.0195398. [PMID: 29608605]
  • Takaomi Yaguchi, Tomohisa Kinami, Tetsuya Ishida, Takaomi Yasuhara, Kosaku Takahashi, Hideyuki Matsuura. Induction of plant disease resistance upon treatment with yeast cell wall extract. Bioscience, biotechnology, and biochemistry. 2017 Nov; 81(11):2071-2078. doi: 10.1080/09168451.2017.1379351. [PMID: 28950768]
  • Hoon Cheong, Izailda Barbosa Dos Santos, Wenshan Liu, Heather N Gosse, Sang-Wook Park. Cyclophilin 20-3 is positioned as a regulatory hub between light-dependent redox and 12-oxo-phytodienoic acid signaling. Plant signaling & behavior. 2017 09; 12(9):e1362520. doi: 10.1080/15592324.2017.1362520. [PMID: 28805482]
  • Ernst H Oliw, Mats Hamberg. An allene oxide and 12-oxophytodienoic acid are key intermediates in jasmonic acid biosynthesis by Fusarium oxysporum. Journal of lipid research. 2017 08; 58(8):1670-1680. doi: 10.1194/jlr.m077305. [PMID: 28572515]
  • Ivan D Meza-Canales, Stefan Meldau, Jorge A Zavala, Ian T Baldwin. Herbivore perception decreases photosynthetic carbon assimilation and reduces stomatal conductance by engaging 12-oxo-phytodienoic acid, mitogen-activated protein kinase 4 and cytokinin perception. Plant, cell & environment. 2017 Jul; 40(7):1039-1056. doi: 10.1111/pce.12874. [PMID: 27925291]
  • M Soledade C Pedras, Q Huy To. Defense and signalling metabolites of the crucifer Erucastrum canariense: Synchronized abiotic induction of phytoalexins and galacto-oxylipins. Phytochemistry. 2017 Jul; 139(?):18-24. doi: 10.1016/j.phytochem.2017.03.005. [PMID: 28390240]
  • Putri Pratiwi, Genta Tanaka, Tomohiro Takahashi, Xiaonan Xie, Koichi Yoneyama, Hideyuki Matsuura, Kosaku Takahashi. Identification of Jasmonic Acid and Jasmonoyl-Isoleucine, and Characterization of AOS, AOC, OPR and JAR1 in the Model Lycophyte Selaginella moellendorffii. Plant & cell physiology. 2017 04; 58(4):789-801. doi: 10.1093/pcp/pcx031. [PMID: 28340155]
  • Katrin Janik, Axel Mithöfer, Margot Raffeiner, Hagen Stellmach, Bettina Hause, Katja Schlink. An effector of apple proliferation phytoplasma targets TCP transcription factors-a generalized virulence strategy of phytoplasma?. Molecular plant pathology. 2017 04; 18(3):435-442. doi: 10.1111/mpp.12409. [PMID: 27037957]
  • Ying-Hsuan Sun, Chiu-Yueh Hung, Jie Qiu, Jianjun Chen, Farooqahmed S Kittur, Carla E Oldham, Richard J Henny, Kent O Burkey, Longjiang Fan, Jiahua Xie. Accumulation of high OPDA level correlates with reduced ROS and elevated GSH benefiting white cell survival in variegated leaves. Scientific reports. 2017 03; 7(?):44158. doi: 10.1038/srep44158. [PMID: 28276518]
  • Hirofumi Enomoto, Takuya Sensu, Kei Sato, Futoshi Sato, Thanai Paxton, Emi Yumoto, Koji Miyamoto, Masashi Asahina, Takao Yokota, Hisakazu Yamane. Visualisation of abscisic acid and 12-oxo-phytodienoic acid in immature Phaseolus vulgaris L. seeds using desorption electrospray ionisation-imaging mass spectrometry. Scientific reports. 2017 02; 7(?):42977. doi: 10.1038/srep42977. [PMID: 28211480]
  • Miu Iijima, Hiromichi Kenmoku, Hironobu Takahashi, Jung-Bum Lee, Masao Toyota, Yoshinori Asakawa, Fumiya Kurosaki, Futoshi Taura. Characterization of 12-Oxophytodienoic Acid Reductases from Rose-scented Geranium (Pelargonium graveolens). Natural product communications. 2016 Dec; 11(12):1775-1782. doi: ". [PMID: 30508331]
  • Weifeng Luo, Yohei Nanjo, Setsuko Komatsu, Hideyuki Matsuura, Kosaku Takahashi. Proteomics of Physcomitrella patens protonemata subjected to treatment with 12-oxo-phytodienoic acid. Bioscience, biotechnology, and biochemistry. 2016 Dec; 80(12):2357-2364. doi: 10.1080/09168451.2016.1222268. [PMID: 27558085]
  • Claus Wasternack, Bettina Hause. OPDA-Ile - a new JA-Ile-independent signal?. Plant signaling & behavior. 2016 11; 11(11):e1253646. doi: 10.1080/15592324.2016.1253646. [PMID: 27813689]
  • Claus Wasternack, Miroslav Strnad. Jasmonate signaling in plant stress responses and development - active and inactive compounds. New biotechnology. 2016 Sep; 33(5 Pt B):604-613. doi: 10.1016/j.nbt.2015.11.001. [PMID: 26581489]
  • Anders K Nilsson, Per Fahlberg, Oskar N Johansson, Mats Hamberg, Mats X Andersson, Mats Ellerström. The activity of HYDROPEROXIDE LYASE 1 regulates accumulation of galactolipids containing 12-oxo-phytodienoic acid in Arabidopsis. Journal of experimental botany. 2016 09; 67(17):5133-44. doi: 10.1093/jxb/erw278. [PMID: 27422994]
  • Muluneh Tamiru, Hiroki Takagi, Akira Abe, Takao Yokota, Hiroyuki Kanzaki, Haruko Okamoto, Hiromasa Saitoh, Hideyuki Takahashi, Koki Fujisaki, Kaori Oikawa, Aiko Uemura, Satoshi Natsume, Yusuke Jikumaru, Hideyuki Matsuura, Kenji Umemura, Matthew J Terry, Ryohei Terauchi. A chloroplast-localized protein LESION AND LAMINA BENDING affects defence and growth responses in rice. The New phytologist. 2016 06; 210(4):1282-97. doi: 10.1111/nph.13864. [PMID: 26864209]
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  • Mark Lemos, Yanmei Xiao, Marta Bjornson, Jin-Zheng Wang, Derrick Hicks, Amancio de Souza, Chang-Quan Wang, Panyu Yang, Shisong Ma, Savithramma Dinesh-Kumar, Katayoon Dehesh. The plastidial retrograde signal methyl erythritol cyclopyrophosphate is a regulator of salicylic acid and jasmonic acid crosstalk. Journal of experimental botany. 2016 Mar; 67(5):1557-66. doi: 10.1093/jxb/erv550. [PMID: 26733689]
  • Gilles Curien, Cécile Giustini, Jean-Luc Montillet, Sarah Mas-Y-Mas, David Cobessi, Jean-Luc Ferrer, Michel Matringe, Alexander Grechkin, Norbert Rolland. The chloroplast membrane associated ceQORH putative quinone oxidoreductase reduces long-chain, stress-related oxidized lipids. Phytochemistry. 2016 Feb; 122(?):45-55. doi: 10.1016/j.phytochem.2015.11.015. [PMID: 26678323]
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