okadaic acid (BioDeep_00000317276)

   

natural product Marine Natural Products


代谢物信息卡片


(2R)-3-[(2S,6R,8S,11R)-2-[(2R)-4-[(2S,2R,4R,4aS,6R,8aR)-4-hydroxy-2-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5-oxolane]-2-yl]but-3-en-2-yl]-11-hydroxy-4-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-2-hydroxy-2-methylpropanoic acid

化学式: C44H68O13 (804.4659678)
中文名称: 冈田(软海绵)酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C1C(O)C2OC3(CCC(C=CC(C)C4CC(C)=CC5(OC(OC(C)(O)C(=O)O)CCC5O)O4)O3)CCC2CC1C(O)CC(C)C1OC2(CCCCO2)CCC1C
InChI: InChI=1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1

描述信息

D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins
D009676 - Noxae > D002273 - Carcinogens
D049990 - Membrane Transport Modulators
D004791 - Enzyme Inhibitors
D007476 - Ionophores
A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.

同义名列表

3 个代谢物同义名

(2R)-3-[(2S,6R,8S,11R)-2-[(2R)-4-[(2S,2R,4R,4aS,6R,8aR)-4-hydroxy-2-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5-oxolane]-2-yl]but-3-en-2-yl]-11-hydroxy-4-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-2-hydroxy-2-methylpropanoic acid; okadaic acid; Okadaic acid



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)

71 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

  • Bang Wang, Xiaoshu Pan, I-Ting Teng, Xiaowei Li, Firas Kobeissy, Zo-Yu Wu, Jiepei Zhu, Guangzheng Cai, He Yan, Xin Yan, Mingwei Liang, Fahong Yu, Jianrong Lu, Zunyi Yang, Elisa Biondi, William Haskins, Y Charles Cao, Steven A Benner, Weihong Tan, Kevin K Wang. Functional Selection of Tau Oligomerization-Inhibiting Aptamers. Angewandte Chemie (International ed. in English). 2024 Apr; 63(18):e202402007. doi: 10.1002/anie.202402007. [PMID: 38407551]
  • Vignesh Narasimman, Saravanan Ramachandran. Purification, structural characterization, and neuroprotective effect of 3,6-diisobutyl-2,5-piperazinedione from Halomonas pacifica CARE-V15 against okadaic acid-induced neurotoxicity in zebrafish model. Journal of biochemical and molecular toxicology. 2024 Apr; 38(4):e23708. doi: 10.1002/jbt.23708. [PMID: 38597299]
  • Shuang Jiang, Gilwa Borjigin, Jiahui Sun, Qi Li, Qianbo Wang, Yuanqiu Mu, Xuepeng Shi, Qian Li, Xiaotong Wang, Xiaodan Song, Zhibin Wang, Chunjuan Yang. Identification of Uncaria rhynchophylla in the Potential Treatment of Alzheimer's Disease by Integrating Virtual Screening and In Vitro Validation. International journal of molecular sciences. 2023 Oct; 24(20):. doi: 10.3390/ijms242015457. [PMID: 37895137]
  • Lu Huang, Bo Liu, Xiao-Wen Yu, Guang-Qiang Pan, Jia-Yi Xu, Dong Yan, Ya-Li Wang, Qiao-Nan Guo. Rat tight junction proteins are disrupted after subchronic exposure to okadaic acid. Environmental science and pollution research international. 2023 May; 30(22):62201-62212. doi: 10.1007/s11356-023-26471-x. [PMID: 36940028]
  • Jiuming Wang, Ruilong Li, Beibei Liu, Qinzhou Zhang, Xiang Wang, Yaxian Zhu, Yong Zhang. Occurrence and distribution of lipophilic marine algal toxins in the coastal seawater of Southeast China and the South China Sea. Marine pollution bulletin. 2023 Feb; 187(?):114584. doi: 10.1016/j.marpolbul.2023.114584. [PMID: 36642003]
  • Yang Liu, Yang Lu, Yu-Hu Jiao, Da-Wei Li, Hong-Ye Li, Wei-Dong Yang. Multi-omics analysis reveals metabolism of okadaic acid in gut lumen of rat. Archives of toxicology. 2022 03; 96(3):831-843. doi: 10.1007/s00204-021-03219-5. [PMID: 35037095]
  • D Li, W Shi, X Lu, Z Liu, S Zhang, Y Sun, W Shi, X Zhu. A Protective Role of Okadaic Acid in Liver Injury Induced by Amoxicillin. Bulletin of experimental biology and medicine. 2022 Jan; 172(3):328-331. doi: 10.1007/s10517-022-05386-6. [PMID: 35006487]
  • Estela Pires, Fábio de Melo Tarouco, Thiago Pereira Alves, Carlos Eduardo da Rosa, Paulo da Cunha Lana, Luiz Laureno Mafra. Antioxidant responses and okadaic acid accumulation in Laeonereis acuta (Annelida) exposed to the harmful dinoflagellate Prorocentrum cf. lima. Toxicon : official journal of the International Society on Toxinology. 2021 Nov; 203(?):104-114. doi: 10.1016/j.toxicon.2021.10.004. [PMID: 34662628]
  • Han-Wen Luo, Dan-Dan Yin, Zheng Xiao, Lu Wen, Ying-Jun Liao, Cheng-Yuan Tang, Dong Zeng, Heng-Ting Xiao, Ying Li. Anti-renal interstitial fibrosis effect of norcantharidin is exerted through inhibition of PP2Ac-mediated C-terminal phosphorylation of Smad3. Chemical biology & drug design. 2021 02; 97(2):293-304. doi: 10.1111/cbdd.13781. [PMID: 32896083]
  • Yang Gao, Xiao-Qing Wang, Shuai Ma, Yong-Cai Dong, Ya-Zhen Shang. Flavonoids from Stem and Leaf of Scutellaria Baicalensis Georgi Inhibit the Phosphorylation on Multi-sites of Tau Protein Induced by Okadaic Acid and the Regulative Mechanism of Protein Kinases in Rats. Combinatorial chemistry & high throughput screening. 2021; 24(7):1126-1136. doi: 10.2174/1386207323666200901101233. [PMID: 32875975]
  • Jiangbing Qiu, Ying Ji, Yuan Fang, Mingyue Zhao, Shuqin Wang, Qinghui Ai, Aifeng Li. Response of fatty acids and lipid metabolism enzymes during accumulation, depuration and esterification of diarrhetic shellfish toxins in mussels (Mytilus galloprovincialis). Ecotoxicology and environmental safety. 2020 Dec; 206(?):111223. doi: 10.1016/j.ecoenv.2020.111223. [PMID: 32891913]
  • Zeming Zhang, Xinru Yu, Jian Zhao, Xizhi Shi, Aili Sun, Haifeng Jiao, Tingting Xiao, Dexiang Li, Jiong Chen. A fluorescence microplate assay based on molecularly imprinted silica coated quantum dot optosensing materials for the separation and detection of okadaic acid in shellfish. Chemosphere. 2020 May; 246(?):125622. doi: 10.1016/j.chemosphere.2019.125622. [PMID: 31918075]
  • Lili Gu, Jiaqi Lu, Qin Li, Ningzi Wu, Lingxi Zhang, Hongxing Li, Wenmin Xing, Xinyue Zhang. A network-based analysis of key pharmacological pathways of Andrographis paniculata acting on Alzheimer's disease and experimental validation. Journal of ethnopharmacology. 2020 Apr; 251(?):112488. doi: 10.1016/j.jep.2019.112488. [PMID: 31866509]
  • Yingying Wang, Xiuyun Song, Dandan Liu, Yu-Xia Lou, Piao Luo, Tianbi Zhu, Qi Wang, Naihong Chen. IMM-H004 reduced okadaic acid-induced neurotoxicity by inhibiting Tau pathology in vitro and in vivo. Neurotoxicology. 2019 12; 75(?):221-232. doi: 10.1016/j.neuro.2019.09.012. [PMID: 31562916]
  • Declan F Doherty, Sridesh Nath, Justin Poon, Robert F Foronjy, Michael Ohlmeyer, Abdoulaye J Dabo, Matthias Salathe, Mark Birrell, Maria Belvisi, Nathalie Baumlin, Michael D Kim, Sinéad Weldon, Clifford Taggart, Patrick Geraghty. Protein Phosphatase 2A Reduces Cigarette Smoke-induced Cathepsin S and Loss of Lung Function. American journal of respiratory and critical care medicine. 2019 07; 200(1):51-62. doi: 10.1164/rccm.201808-1518oc. [PMID: 30641028]
  • Hu Wang, Fanny Cheung, Anna C Stoll, Patricia Rockwell, Maria E Figueiredo-Pereira. Mitochondrial and calcium perturbations in rat CNS neurons induce calpain-cleavage of Parkin: Phosphatase inhibition stabilizes pSer65Parkin reducing its calpain-cleavage. Biochimica et biophysica acta. Molecular basis of disease. 2019 06; 1865(6):1436-1450. doi: 10.1016/j.bbadis.2019.02.016. [PMID: 30796971]
  • Christopher J Coates, Jenson Lim, Katie Harman, Andrew F Rowley, David J Griffiths, Helena Emery, Will Layton. The insect, Galleria mellonella, is a compatible model for evaluating the toxicology of okadaic acid. Cell biology and toxicology. 2019 06; 35(3):219-232. doi: 10.1007/s10565-018-09448-2. [PMID: 30426330]
  • Seong Hee Lee, Janusz J Zwiazek. Regulation of water transport in Arabidopsis by methyl jasmonate. Plant physiology and biochemistry : PPB. 2019 Jun; 139(?):540-547. doi: 10.1016/j.plaphy.2019.04.023. [PMID: 31029027]
  • Hsin-Hung Lin, Yu-Chi King, Yu-Chi Li, Chih-Ching Lin, Yu-Chi Chen, Jeng-Shane Lin, Shih-Tong Jeng. The p38-like MAP kinase modulated H2O2 accumulation in wounding signaling pathways of sweet potato. Plant science : an international journal of experimental plant biology. 2019 Mar; 280(?):305-313. doi: 10.1016/j.plantsci.2018.12.011. [PMID: 30824008]
  • Yan Tang, JungWoo Yang, Wang Zheng, Jingfeng Tang, Xing-Zhen Chen, Jianzheng Yang, Zuocheng Wang. Polycystin-1 Inhibits Cell Proliferation through Phosphatase PP2A/B56α. BioMed research international. 2019; 2019(?):2582401. doi: 10.1155/2019/2582401. [PMID: 31641668]
  • Yuxiang Pan, Xinwei Wei, Tao Liang, Jie Zhou, Hao Wan, Ning Hu, Ping Wang. A magnetic beads-based portable flow cytometry immunosensor for in-situ detection of marine biotoxin. Biomedical microdevices. 2018 07; 20(3):60. doi: 10.1007/s10544-018-0304-6. [PMID: 30006678]
  • Zhen-Zhen Yuan, You-Rui Suo, Xue-Yan Hao, Shu-Lin Wang, Gang Li, Hong-Lun Wang. Triterpenic Acids from Potentilla parvifolia and Their Protective Effects against Okadaic Acid Induced Neurotoxicity in Differentiated SH-SY5Y Cells. Biological & pharmaceutical bulletin. 2018 Jun; 41(6):885-890. doi: 10.1248/bpb.b17-01010. [PMID: 29618699]
  • Ghada Souid, Nouha Souayed, Zohra Haouas, Khira Maaroufi. Does the phycotoxin Okadaic acid cause oxidative stress damages and histological alterations to seabream (Sparus aurata)?. Toxicon : official journal of the International Society on Toxinology. 2018 Mar; 144(?):55-60. doi: 10.1016/j.toxicon.2018.02.001. [PMID: 29427566]
  • Lorenzo Camoni, Francesca Barbero, Patrizia Aducci, Massimo E Maffei. Spodoptera littoralis oral secretions inhibit the activity of Phaseolus lunatus plasma membrane H+-ATPase. PloS one. 2018; 13(8):e0202142. doi: 10.1371/journal.pone.0202142. [PMID: 30096181]
  • Paula Abal, M Carmen Louzao, Toshiyuki Suzuki, Ryuichi Watanabe, Natalia Vilariño, Cristina Carrera, Ana M Botana, Mercedes R Vieytes, Luis M Botana. Toxic Action Reevaluation of Okadaic Acid, Dinophysistoxin-1 and Dinophysistoxin-2: Toxicity Equivalency Factors Based on the Oral Toxicity Study. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2018; 49(2):743-757. doi: 10.1159/000493039. [PMID: 30176657]
  • Silvia M Nascimento, M Cristina Q Mendes, Mariângela Menezes, Francisco Rodríguez, Catharina Alves-de-Souza, Suema Branco, Pilar Riobó, José Franco, José Marcos C Nunes, Mariusz Huk, Steven Morris, Santiago Fraga. Morphology and phylogeny of Prorocentrum caipirignum sp. nov. (Dinophyceae), a new tropical toxic benthic dinoflagellate. Harmful algae. 2017 12; 70(?):73-89. doi: 10.1016/j.hal.2017.11.001. [PMID: 29169570]
  • Polina A Kameneva, Ekaterina A Krasheninina, Valentina V Slobodskova, Sergey P Kukla, Tatiana Yu Orlova. Accumulation and Tissue Distribution of Dinophysitoxin-1 and Dinophysitoxin-3 in the Mussel Crenomytilus grayanus Feeding on the Benthic Dinoflagellate Prorocentrum foraminosum. Marine drugs. 2017 Oct; 15(10):. doi: 10.3390/md15100330. [PMID: 29064453]
  • Rongzhi Wang, Linmao Zeng, Hang Yang, Yanfang Zhong, Juncheng Wang, Sumei Ling, Abdullah Farhan Saeed, Jun Yuan, Shihua Wang. Detection of okadaic acid (OA) using ELISA and colloidal gold immunoassay based on monoclonal antibody. Journal of hazardous materials. 2017 Oct; 339(?):154-160. doi: 10.1016/j.jhazmat.2017.06.030. [PMID: 28648727]
  • A Reum Yang, Sangbum Lee, Young Du Yoo, Hyung Seop Kim, Eun Ju Jeong, Jung-Rae Rho. Limaol: A Polyketide from the Benthic Marine Dinoflagellate Prorocentrum lima. Journal of natural products. 2017 05; 80(5):1688-1692. doi: 10.1021/acs.jnatprod.7b00127. [PMID: 28383915]
  • Paula Abal, M Carmen Louzao, José Manuel Cifuentes, Natalia Vilariño, Ines Rodriguez, Amparo Alfonso, Mercedes R Vieytes, Luis M Botana. Characterization of the dinophysistoxin-2 acute oral toxicity in mice to define the Toxicity Equivalency Factor. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2017 Apr; 102(?):166-175. doi: 10.1016/j.fct.2017.02.023. [PMID: 28223118]
  • Barbara Juraszek, Katarzyna A Nałęcz. Protein phosphatase PP2A - a novel interacting partner of carnitine transporter OCTN2 (SLC22A5) in rat astrocytes. Journal of neurochemistry. 2016 11; 139(4):537-551. doi: 10.1111/jnc.13777. [PMID: 27537937]
  • Liang Zhao, Yan Xiao, Xiao-Liang Wang, Jinjing Pei, Zhi-Zhong Guan. Original Research: Influence of okadaic acid on hyperphosphorylation of tau and nicotinic acetylcholine receptors in primary neurons. Experimental biology and medicine (Maywood, N.J.). 2016 10; 241(16):1825-33. doi: 10.1177/1535370216650759. [PMID: 27190248]
  • Bo Chen, Jin Li, Haibo Zhu. AMP-activated protein kinase attenuates oxLDL uptake in macrophages through PP2A/NF-κB/LOX-1 pathway. Vascular pharmacology. 2016 10; 85(?):1-10. doi: 10.1016/j.vph.2015.08.012. [PMID: 26297684]
  • Rouba Hage-Sleiman, Asmaa B Hamze, Aimée F El-Hed, Randa Attieh, Lina Kozhaya, Sarah Kabbani, Ghassan Dbaibo. Ceramide inhibits PKCθ by regulating its phosphorylation and translocation to lipid rafts in Jurkat cells. Immunologic research. 2016 08; 64(4):869-86. doi: 10.1007/s12026-016-8787-9. [PMID: 26798039]
  • Ewa Krzywińska, Maria Bucholc, Anna Kulik, Arkadiusz Ciesielski, Małgorzata Lichocka, Janusz Dębski, Agnieszka Ludwików, Michał Dadlez, Pedro L Rodriguez, Grażyna Dobrowolska. Phosphatase ABI1 and okadaic acid-sensitive phosphoprotein phosphatases inhibit salt stress-activated SnRK2.4 kinase. BMC plant biology. 2016 06; 16(1):136. doi: 10.1186/s12870-016-0817-1. [PMID: 27297076]
  • Zita Zendong, Medina Kadiri, Christine Herrenknecht, Elisabeth Nézan, Antonia Mazzeo, Philipp Hess. Algal toxin profiles in Nigerian coastal waters (Gulf of Guinea) using passive sampling and liquid chromatography coupled to mass spectrometry. Toxicon : official journal of the International Society on Toxinology. 2016 May; 114(?):16-27. doi: 10.1016/j.toxicon.2016.02.011. [PMID: 26896635]
  • Yanrong Zhang, Xiaoliang Jiang, Chuan Qin, Santiago Cuevas, Pedro A Jose, Ines Armando. Dopamine D2 receptors' effects on renal inflammation are mediated by regulation of PP2A function. American journal of physiology. Renal physiology. 2016 Jan; 310(2):F128-34. doi: 10.1152/ajprenal.00453.2014. [PMID: 26290374]
  • YanYan Guo, YuanJun Deng, XiaoQing Li, Yong Ning, XuePing Lin, ShuiMing Guo, MeiXue Chen, Min Han. Glutaminolysis Was Induced by TGF-β1 through PP2Ac Regulated Raf-MEK-ERK Signaling in Endothelial Cells. PloS one. 2016; 11(9):e0162658. doi: 10.1371/journal.pone.0162658. [PMID: 27612201]
  • Cui-cui Yang, Xue-xian Kuai, Wen-bin Gao, Jian-chun Yu, Qi Wang, Lin Li, Lan Zhang. Morroniside-Induced PP2A Activation Antagonizes Tau Hyperphosphorylation in a Cellular Model of Neurodegeneration. Journal of Alzheimer's disease : JAD. 2016; 51(1):33-44. doi: 10.3233/jad-150728. [PMID: 26836014]
  • Hao Zhang, Pu Wang, Haoli Hou, Huan Wen, Hong Zhou, Fei Gao, Jinping Wu, Zhengming Qiu, Lijia Li. Histone Modification Is Involved in Okadaic Acid (OA) Induced DNA Damage Response and G2-M Transition Arrest in Maize. PloS one. 2016; 11(5):e0155852. doi: 10.1371/journal.pone.0155852. [PMID: 27196101]
  • Ryoji Matsushima, Hajime Uchida, Satoshi Nagai, Ryuichi Watanabe, Michiya Kamio, Hiroshi Nagai, Masaki Kaneniwa, Toshiyuki Suzuki. Assimilation, Accumulation, and Metabolism of Dinophysistoxins (DTXs) and Pectenotoxins (PTXs) in the Several Tissues of Japanese Scallop Patinopecten yessoensis. Toxins. 2015 Dec; 7(12):5141-54. doi: 10.3390/toxins7124870. [PMID: 26633503]
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