CYCLOPIAZONIC ACID (BioDeep_00000005070)
Secondary id: BioDeep_00000265226
PANOMIX_OTCML-2023
代谢物信息卡片
.alpha.-Cyclopiazonic acid
化学式: C20H20N2O3 (336.147385)
中文名称: 青霉青霉的环苯甲酮酸
谱图信息:
最多检出来源 Homo sapiens(blood) 0.67%
分子结构信息
SMILES: CC(=C1C(=O)C2C3C(CC4=C5C3=CNC5=CC=C4)C(N2C1=O)(C)C)O
InChI: InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,23H,7H2,1-3H3/b14-9+/t12-,16+,17+/m1/s1
描述信息
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
D004791 - Enzyme Inhibitors
Cyclopiazonic acid (CPA), a neurotoxic secondary metabolite (SM) made by Aspergillus flavus, is an inhibitor of endoplasmic reticulum calcium ATPase (Ca2+ATPase; SERCA) and a potent inducer of cell death in plants[1].
同义名列表
数据库引用编号
11 个数据库交叉引用编号
- KEGG: C03032
- PubChem: 135398689
- PubChem: 54675761
- Metlin: METLIN44072
- CAS: 18172-33-3
- CAS: 83136-88-3
- PMhub: MS000017761
- ChEBI: CHEBI:17734
- PubChem: 5937
- NIKKAJI: J9.278I
- medchemexpress: HY-N6771
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
- Yu Liang, Hong Liao, Xuanni Chen, Qiwei Wang, Qin Li, Yong Shen, Yuyi Zheng, Xiao-Nian Li, Hucheng Zhu, Dongyan Li, Weiguang Sun, Chunmei Chen, Yonghui Zhang. Pegriseofamines A-E: Five cyclopiazonic acid related indole alkaloids from the fungus Penicillium griseofulvum.
Bioorganic chemistry.
2023 Apr; 136(?):106553. doi:
10.1016/j.bioorg.2023.106553. [PMID: 37119783] - Lingyan Liu, Xueqing Qian, Tao Yang, Dongmei Fang, Zhangyi Qin, Bo Ren, Guoyou Li. Cyclopiazonic Acid and Okaramine Analogues, Including Chlorinated Compounds, from Chrysosporium undulatum YT-1.
Journal of natural products.
2022 11; 85(11):2547-2556. doi:
10.1021/acs.jnatprod.2c00445. [PMID: 36268672] - Xiaoying Ma, Yongli Ye, Jiadi Sun, Jian Ji, Jia-Sheng Wang, Xiulan Sun. Coexposure of Cyclopiazonic Acid with Aflatoxin B1 Involved in Disrupting Amino Acid Metabolism and Redox Homeostasis Causing Synergistic Toxic Effects in Hepatocyte Spheroids.
Journal of agricultural and food chemistry.
2022 Apr; 70(16):5166-5176. doi:
10.1021/acs.jafc.2c01608. [PMID: 35427130] - Yao Xiang, Qi Zeng, Zhi-Mao Mai, Yu-Chan Chen, Xue-Feng Shi, Xia-Yu Chen, Wei-Mao Zhong, Xiao-Yi Wei, Wei-Min Zhang, Si Zhang, Fa-Zuo Wang. Asperorydines N-P, three new cyclopiazonic acid alkaloids from the marine-derived fungus Aspergillus flavus SCSIO F025.
Fitoterapia.
2021 Apr; 150(?):104839. doi:
10.1016/j.fitote.2021.104839. [PMID: 33513431] - Shogo Hamaguchi, Kohei Abe, Momoka Komatsu, Jun Kainuma, Iyuki Namekata, Hikaru Tanaka. Positive Lusitropic Effect of Quercetin on Isolated Ventricular Myocardia from Normal and Streptozotocin-Induced Diabetic Mice.
Biological & pharmaceutical bulletin.
2021; 44(12):1894-1897. doi:
10.1248/bpb.b21-00580. [PMID: 34853274] - Ken Takahashi, Shogo Hayashi, Mari Miyajima, Marei Omori, Jing Wang, Keiko Kaihara, Masatoshi Morimatsu, Chen Wang, Jian Chen, Gentaro Iribe, Keiji Naruse, Masahiro Sokabe. L-type calcium channel modulates mechanosensitivity of the cardiomyocyte cell line H9c2.
Cell calcium.
2019 05; 79(?):68-74. doi:
10.1016/j.ceca.2019.02.008. [PMID: 30836292] - Marine Houdou, Elodie Lebredonchel, Anne Garat, Sandrine Duvet, Dominique Legrand, Valérie Decool, André Klein, Mohamed Ouzzine, Bruno Gasnier, Sven Potelle, François Foulquier. Involvement of thapsigargin- and cyclopiazonic acid-sensitive pumps in the rescue of TMEM165-associated glycosylation defects by Mn2.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2019 02; 33(2):2669-2679. doi:
10.1096/fj.201800387r. [PMID: 30307768] - Pummi Singh, Marc J Orbach, Peter J Cotty. Aspergillus texensis: A Novel Aflatoxin Producer with S Morphology from the United States.
Toxins.
2018 12; 10(12):. doi:
10.3390/toxins10120513. [PMID: 30513994] - Ting Cao, Junhong Ling, Yi Liu, Xiaoqi Chen, Xiaoyue Tian, Dali Meng, Huaqi Pan, Jiangchun Hu, Nan Wang. Characterization and abolishment of the cyclopiazonic acids produced by Aspergillus oryzae HMP-F28.
Bioscience, biotechnology, and biochemistry.
2018 Oct; 82(10):1832-1839. doi:
10.1080/09168451.2018.1490170. [PMID: 29985105] - María Laura Barberini, Lorena Sigaut, Weijie Huang, Silvina Mangano, Silvina Paola Denita Juarez, Eliana Marzol, José Estevez, Mariana Obertello, Lía Pietrasanta, Weihua Tang, Jorge Muschietti. Calcium dynamics in tomato pollen tubes using the Yellow Cameleon 3.6 sensor.
Plant reproduction.
2018 06; 31(2):159-169. doi:
10.1007/s00497-017-0317-y. [PMID: 29236154] - Sui Sheng T Hua, Dan E Parfitt, Siov Bouy L Sarreal, Bertram G Lee, Delilah F Wood. First report of an atypical new Aspergillus parasiticus isolates with nucleotide insertion in aflR gene resembling to A. sojae.
Mycotoxin research.
2018 May; 34(2):151-157. doi:
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Mycologia.
2018 May; 110(3):482-493. doi:
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Applied and environmental microbiology.
2018 03; 84(5):. doi:
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International journal of food microbiology.
2017 Sep; 256(?):36-44. doi:
10.1016/j.ijfoodmicro.2017.05.020. [PMID: 28582664] - Subbaiah C Chalivendra, Catherine DeRobertis, Perng-Kuang Chang, Kenneth E Damann. Cyclopiazonic Acid Is a Pathogenicity Factor for Aspergillus flavus and a Promising Target for Screening Germplasm for Ear Rot Resistance.
Molecular plant-microbe interactions : MPMI.
2017 05; 30(5):361-373. doi:
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Microbial pathogenesis.
2015 Dec; 89(?):18-26. doi:
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American journal of physiology. Cell physiology.
2015 Apr; 308(8):C608-20. doi:
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The Journal of neuroscience : the official journal of the Society for Neuroscience.
2015 Apr; 35(15):5891-903. doi:
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Journal of neurophysiology.
2014 Sep; 112(6):1246-55. doi:
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Biochemical and biophysical research communications.
2014 Feb; 445(1):84-8. doi:
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Molecular pharmaceutics.
2013 Dec; 10(12):4620-8. doi:
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Journal of muscle research and cell motility.
2013 Dec; 34(5-6):379-93. doi:
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The international journal of biochemistry & cell biology.
2013 Aug; 45(8):1758-66. doi:
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Urology.
2013 Jan; 81(1):211.e17-21. doi:
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Cell calcium.
2012 Nov; 52(5):397-404. doi:
10.1016/j.ceca.2012.06.008. [PMID: 22831913] - J F Olivera, Gonzalo Pizarro. A study of store dependent Ca²⁺ influx in frog skeletal muscle.
Journal of muscle research and cell motility.
2012 Jun; 33(2):131-43. doi:
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Mycologia.
2012 May; 104(3):682-97. doi:
10.3852/11-088. [PMID: 22123651] - Francesco Lodola, Umberto Laforenza, Elisa Bonetti, Dmitry Lim, Silvia Dragoni, Cinzia Bottino, Hwei Ling Ong, Germano Guerra, Carlo Ganini, Margherita Massa, Mariangela Manzoni, Indu S Ambudkar, Armando A Genazzani, Vittorio Rosti, Paolo Pedrazzoli, Franco Tanzi, Francesco Moccia, Camillo Porta. Store-operated Ca2+ entry is remodelled and controls in vitro angiogenesis in endothelial progenitor cells isolated from tumoral patients.
PloS one.
2012; 7(9):e42541. doi:
10.1371/journal.pone.0042541. [PMID: 23049731] - H Malekinejad, P Akbari, M Allymehr, R Hobbenaghi, A Rezaie. Cyclopiazonic acid augments the hepatic and renal oxidative stress in broiler chicks.
Human & experimental toxicology.
2011 Aug; 30(8):910-9. doi:
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Bioorganic & medicinal chemistry.
2011 Aug; 19(15):4669-78. doi:
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Journal of neuroscience methods.
2011 May; 198(1):1-7. doi:
10.1016/j.jneumeth.2011.02.009. [PMID: 21345350] - Francisco J Aulestia, Pedro C Redondo, Arancha Rodríguez-García, Juan A Rosado, Ginés M Salido, Maria Teresa Alonso, Javier García-Sancho. Two distinct calcium pools in the endoplasmic reticulum of HEK-293T cells.
The Biochemical journal.
2011 Apr; 435(1):227-35. doi:
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International journal of food microbiology.
2011 Mar; 146(1):38-43. doi:
10.1016/j.ijfoodmicro.2011.01.034. [PMID: 21354643] - Biswarup Ghosh, Yan Li, Stanley A Thayer. Inhibition of the plasma membrane Ca2+ pump by CD44 receptor activation of tyrosine kinases increases the action potential afterhyperpolarization in sensory neurons.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2011 Feb; 31(7):2361-70. doi:
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Molecular plant pathology.
2010 Mar; 11(2):213-26. doi:
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Journal of hypertension.
2010 Mar; 28(3):568-74. doi:
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The Journal of biological chemistry.
2009 Dec; 284(52):36387-36394. doi:
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Annals of botany.
2009 Dec; 104(7):1373-87. doi:
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Mycopathologia.
2009 Oct; 168(4):193-201. doi:
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Gastroenterology.
2009 Sep; 137(3):955-64, 964.e1. doi:
10.1053/j.gastro.2009.03.038. [PMID: 19328800] - Wen-Bo Zhang, Chiu-Yin Kwan. Unrepeatable extracellular Ca2+-dependent contractile effects of cyclopiazonic acid in rat vascular smooth muscle.
European journal of pharmacology.
2009 May; 610(1-3):81-6. doi:
10.1016/j.ejphar.2009.03.030. [PMID: 19292983] - Jyoti C Patel, Paul Witkovsky, Marat V Avshalumov, Margaret E Rice. Mobilization of calcium from intracellular stores facilitates somatodendritic dopamine release.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2009 May; 29(20):6568-79. doi:
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Cardiovascular research.
2009 May; 82(2):324-32. doi:
10.1093/cvr/cvp054. [PMID: 19218288] - S Ponissery Saidu, S D Weeraratne, M Valentine, R Delay, Judith L Van Houten. Role of plasma membrane calcium ATPases in calcium clearance from olfactory sensory neurons.
Chemical senses.
2009 May; 34(4):349-58. doi:
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American journal of physiology. Cell physiology.
2009 Apr; 296(4):C889-99. doi:
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Archives of biochemistry and biophysics.
2009 Jan; 481(2):157-68. doi:
10.1016/j.abb.2008.11.010. [PMID: 19056336] - Gerald Cohen, Jana Raupachova, Thomas Wimmer, Robert Deicher, Walter H Hörl. The uraemic retention solute para-hydroxy-hippuric acid attenuates apoptosis of polymorphonuclear leukocytes from healthy subjects but not from haemodialysis patients.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2008 Aug; 23(8):2512-9. doi:
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Glia.
2008 Jun; 56(8):821-35. doi:
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Phytopathology.
2008 Mar; 98(3):330-6. doi:
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British journal of pharmacology.
2007 Dec; 152(8):1248-59. doi:
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The Journal of pharmacology and experimental therapeutics.
2007 Oct; 323(1):381-90. doi:
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Archives of pharmacal research.
2007 Oct; 30(10):1240-51. doi:
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Endocrinology.
2007 May; 148(5):2496-504. doi:
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Plant physiology.
2007 May; 144(1):503-12. doi:
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Cell calcium.
2007 Mar; 41(3):295-302. doi:
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Plant physiology.
2007 Feb; 143(2):650-60. doi:
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The Journal of physiology.
2007 Jan; 578(Pt 2):481-90. doi:
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Applied microbiology and biotechnology.
2007 Jan; 73(5):1158-68. doi:
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American journal of physiology. Cell physiology.
2006 Dec; 291(6):C1388-94. doi:
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The Plant journal : for cell and molecular biology.
2006 Dec; 48(6):883-94. doi:
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The Journal of physiology.
2006 Aug; 575(Pt 1):69-81. doi:
10.1113/jphysiol.2006.112367. [PMID: 16777939] - Elizabeth A Potter, Gavin Stewart, Craig P Smith. Urea flux across MDCK-mUT-A2 monolayers is acutely sensitive to AVP, cAMP, and [Ca2+]i.
American journal of physiology. Renal physiology.
2006 Jul; 291(1):F122-8. doi:
10.1152/ajprenal.00423.2005. [PMID: 16449356] - Mei-Feng Hsu, Yu-San Chen, Li-Jiau Huang, Lo-Ti Tsao, Sheng-Chu Kuo, Jih-Pyang Wang. GEA3162, a nitric oxide-releasing agent, activates non-store-operated Ca2+ entry and inhibits store-operated Ca2+ entry pathways in neutrophils through thiol oxidation.
European journal of pharmacology.
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