penitrem A (BioDeep_00000003924)

Main id: BioDeep_00000171898

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


NCGC00163403-03_C37H44ClNO6_(2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8S,9aR,14bS,14cR,16aS)-12-Chloro-2-isopropenyl-14b,14c,17,17-tetramethyl-10-methylene-3,3a,6,6a,7,8,9,9a,10,11,14,14b,14c,15,16,16a-hexadecahydro-2H,4bH-7,8-(epoxymethano)cyclobuta[5,6]benzo[1,2-e]oxireno[4,4a]chromeno[5,6:6,7]indeno[1,2-b]indole-3,4b,7d(5H)-triol

化学式: C37H44ClNO6 (633.2856993999999)
中文名称: 青霉震颤素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C(C)C1OC2CCC3(C)C4(C)c5[nH]c6cc(Cl)c7c8c6c5C(OC(C)(C)C5CC(C(=C)C7)C85O)C4CCC3(O)C23OC3C1O
InChI: InChI=1S/C37H44ClNO6/c1-15(2)28-27(40)31-37(45-31)23(43-28)9-10-33(6)34(7)18(8-11-35(33,37)41)29-25-24-21(39-30(25)34)14-20(38)17-12-16(3)19-13-22(32(4,5)44-29)36(19,42)26(17)24/h14,18-19,22-23,27-29,31,39-42H,1,3,8-13H2,2,4-7H3/t18-,19+,22+,23-,27-,28+,29-,31+,33+,34+,35-,36+,37-/m0/s1

描述信息

D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins
CONFIDENCE Reference Standard (Level 1)
Penitrem A is an indole diterpene neurotoxic alkaloid produced by Penicillium, acts as a selective BK channel antagonist with antiproliferative and anti-invasive activities against multiple malignancies. Penitrem A increases the spontaneous release of endogenous glutamate, gamma-aminobutyric acid (GABA) and aspartate from cerebrocortical synaptosomes, and induces tremorgenic syndromes in animals[1][2].

同义名列表

3 个代谢物同义名

penitrem A; NCGC00163403-03_C37H44ClNO6_(2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8S,9aR,14bS,14cR,16aS)-12-Chloro-2-isopropenyl-14b,14c,17,17-tetramethyl-10-methylene-3,3a,6,6a,7,8,9,9a,10,11,14,14b,14c,15,16,16a-hexadecahydro-2H,4bH-7,8-(epoxymethano)cyclobuta[5,6]benzo[1,2-e]oxireno[4,4a]chromeno[5,6:6,7]indeno[1,2-b]indole-3,4b,7d(5H)-triol; Penitrem A_120257



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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INOH(0)

PlantCyc(0)

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48 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

  • Silvio Uhlig, Lada Ivanova, Pauline Voorspoels, Christiane Kruse Fæste. In Vitro Toxicokinetics and Phase I Biotransformation of the Mycotoxin Penitrem A in Dogs. Toxins. 2020 05; 12(5):. doi: 10.3390/toxins12050293. [PMID: 32375391]
  • Mia Niklasson, Gianluca Maddalo, Zuzana Sramkova, Ercan Mutlu, Shimei Wee, Petra Sekyrova, Linnéa Schmidt, Nicolas Fritz, Ivar Dehnisch, Gregorios Kyriatzis, Michaela Krafcikova, Brittany B Carson, Jennifer M Feenstra, Voichita D Marinescu, Anna Segerman, Martin Haraldsson, Anna-Lena Gustavsson, Lars G J Hammarström, Annika Jenmalm Jensen, Lene Uhrbom, A F Maarten Altelaar, Sten Linnarsson, Per Uhlén, Lukas Trantirek, C Theresa Vincent, Sven Nelander, Per Øyvind Enger, Michael Andäng. Membrane-Depolarizing Channel Blockers Induce Selective Glioma Cell Death by Impairing Nutrient Transport and Unfolded Protein/Amino Acid Responses. Cancer research. 2017 04; 77(7):1741-1752. doi: 10.1158/0008-5472.can-16-2274. [PMID: 28087597]
  • Amira A Goda, Khayria M Naguib, Magdy M Mohamed, Hassan A Amra, Somaia A Nada, Abdel-Rahman B Abdel-Ghaffar, Chris R Gissendanner, Khalid A El Sayed. Astaxanthin and Docosahexaenoic Acid Reverse the Toxicity of the Maxi-K (BK) Channel Antagonist Mycotoxin Penitrem A. Marine drugs. 2016 Nov; 14(11):. doi: 10.3390/md14110208. [PMID: 27834847]
  • Shu-Shan Gao, Xiao-Ming Li, Katherine Williams, Peter Proksch, Nai-Yun Ji, Bin-Gui Wang. Rhizovarins A-F, Indole-Diterpenes from the Mangrove-Derived Endophytic Fungus Mucor irregularis QEN-189. Journal of natural products. 2016 08; 79(8):2066-74. doi: 10.1021/acs.jnatprod.6b00403. [PMID: 27462726]
  • Shinichi Asano, Ian N Bratz, Zachary C Berwick, Ibra S Fancher, Johnathan D Tune, Gregory M Dick. Penitrem A as a tool for understanding the role of large conductance Ca(2+)/voltage-sensitive K(+) channels in vascular function. The Journal of pharmacology and experimental therapeutics. 2012 Aug; 342(2):453-60. doi: 10.1124/jpet.111.191072. [PMID: 22580348]
  • B Kyle, E Bradley, S Ohya, G P Sergeant, N G McHale, K D Thornbury, M A Hollywood. Contribution of Kv2.1 channels to the delayed rectifier current in freshly dispersed smooth muscle cells from rabbit urethra. American journal of physiology. Cell physiology. 2011 Nov; 301(5):C1186-200. doi: 10.1152/ajpcell.00455.2010. [PMID: 21813710]
  • Asheesh K Tiwary, Birgit Puschner, Robert H Poppenga. Using roquefortine C as a biomarker for penitrem A intoxication. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 2009 Mar; 21(2):237-9. doi: 10.1177/104063870902100210. [PMID: 19286504]
  • Elizabeth R Tor, Birgit Puschner, Michael S Filigenzi, Asheesh K Tiwary, Robert H Poppenga. LC-MS/MS screen for penitrem A and roquefortine C in serum and urine samples. Analytical chemistry. 2006 Jul; 78(13):4624-9. doi: 10.1021/ac0601617. [PMID: 16808474]
  • S J Wadsworth, A Chander. H+-and K+-dependence of Ca2+ uptake in lung lamellar bodies. The Journal of membrane biology. 2000 Mar; 174(1):41-51. doi: 10.1007/s002320001030. [PMID: 10741431]
  • L H Arp, J L Richard. Experimental intoxication of guinea pigs with multiple doses of the mycotoxin, penitrem A. Mycopathologia. 1981 Feb; 73(2):109-13. doi: 10.1007/bf00562600. [PMID: 7219513]
  • A W Hayes, R D Phillips, L C Wallace. Effect of penitrem A on mouse liver composition. Toxicon : official journal of the International Society on Toxinology. 1977; 15(4):293-300. doi: 10.1016/0041-0101(77)90011-3. [PMID: 882992]