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 (633.2857)
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

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)

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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ALB, CNP, EDN1, EGFR, MAPK14, MAPK8, MYLK, STAT1, STAT3
Peripheral membrane protein 1 SORD
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 1 EGFR
Mitochondrion membrane 1 SORD
Nucleus 7 ALB, EGFR, JUN, MAPK14, MAPK8, STAT1, STAT3
cytosol 8 ALB, KCNN4, MAPK14, MAPK8, MYLK, SORD, STAT1, STAT3
dendrite 2 KCNB1, STAT1
mitochondrial membrane 1 SORD
centrosome 1 ALB
nucleoplasm 5 JUN, MAPK14, MAPK8, STAT1, STAT3
RNA polymerase II transcription regulator complex 3 JUN, STAT1, STAT3
Cell membrane 6 EGFR, KCNB1, KCNMA1, KCNN3, KCNN4, TNF
Lipid-anchor 1 CNP
Cleavage furrow 1 MYLK
lamellipodium 1 MYLK
ruffle membrane 2 EGFR, KCNN4
Cell projection, axon 1 KCNB1
Early endosome membrane 1 EGFR
Multi-pass membrane protein 5 KCNA3, KCNB1, KCNMA1, KCNN3, KCNN4
Synapse 4 CNP, KCNB1, MAPK8, MYLK
cell junction 1 EGFR
cell surface 3 EGFR, KCNB1, TNF
glutamatergic synapse 3 EGFR, KCNA3, MAPK14
Golgi apparatus 1 ALB
Golgi membrane 1 EGFR
mitochondrial inner membrane 2 CNP, OTC
neuronal cell body 3 KCNN3, KCNN4, TNF
presynaptic membrane 1 KCNA3
sarcolemma 1 KCNB1
endosome 1 EGFR
plasma membrane 10 EGFR, IFNLR1, KCNA3, KCNB1, KCNMA1, KCNN3, KCNN4, MYLK, STAT3, TNF
Membrane 9 CNP, EGFR, IFNLR1, KCNA3, KCNB1, KCNMA1, KCNN3, KCNN4, SORD
apical plasma membrane 3 EGFR, KCNB1, KCNMA1
axon 4 KCNA3, KCNB1, MAPK8, STAT1
basolateral plasma membrane 1 EGFR
caveola 1 KCNMA1
extracellular exosome 3 ALB, CNP, SORD
endoplasmic reticulum 1 ALB
extracellular space 6 ALB, CNP, EDN1, EGFR, SORD, TNF
perinuclear region of cytoplasm 5 CNP, EGFR, KCNA3, KCNB1, STAT1
mitochondrion 2 MAPK14, OTC
protein-containing complex 3 ALB, EGFR, STAT1
Single-pass type I membrane protein 2 EGFR, IFNLR1
Secreted 2 ALB, EDN1
extracellular region 4 ALB, EDN1, MAPK14, TNF
mitochondrial outer membrane 1 CNP
basal part of cell 1 EDN1
neuronal cell body membrane 1 KCNB1
Mitochondrion matrix 1 OTC
mitochondrial matrix 1 OTC
anchoring junction 1 ALB
transcription regulator complex 2 JUN, STAT3
motile cilium 1 SORD
nuclear membrane 1 EGFR
external side of plasma membrane 1 TNF
actin cytoskeleton 1 MYLK
perikaryon 1 KCNB1
Z disc 1 KCNN3
nucleolus 1 STAT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 KCNN4
postsynaptic membrane 3 KCNA3, KCNB1, KCNMA1
Cell membrane, sarcolemma 1 KCNB1
Cell projection, lamellipodium 1 MYLK
Cell projection, ruffle membrane 1 KCNN4
Membrane raft 3 EGFR, KCNA3, TNF
focal adhesion 1 EGFR
microtubule 1 CNP
intracellular vesicle 1 EGFR
lateral plasma membrane 1 KCNB1
nuclear speck 1 MAPK14
Postsynaptic cell membrane 1 KCNB1
receptor complex 1 EGFR
neuron projection 2 KCNN3, KCNN4
ciliary basal body 1 ALB
chromatin 3 JUN, STAT1, STAT3
phagocytic cup 1 TNF
centriole 1 ALB
spindle pole 2 ALB, MAPK14
nuclear chromosome 1 JUN
blood microparticle 1 ALB
Cell projection, cilium, flagellum 1 SORD
[Isoform 2]: Cell membrane 1 KCNA3
microvillus 1 CNP
Cell projection, dendrite 1 KCNB1
Melanosome 1 CNP
euchromatin 1 JUN
pseudopodium 1 CNP
Cytoplasm, myofibril, sarcomere, Z line 1 KCNN3
stress fiber 1 MYLK
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
voltage-gated potassium channel complex 4 KCNA3, KCNB1, KCNMA1, KCNN4
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 1 ALB
platelet alpha granule lumen 1 ALB
transport vesicle 1 EDN1
calyx of Held 1 KCNA3
clathrin-coated endocytic vesicle membrane 1 EGFR
Cytoplasm, cytoskeleton, stress fiber 1 MYLK
Synapse, synaptosome 1 KCNB1
Lateral cell membrane 1 KCNB1
basal dendrite 1 MAPK8
postsynaptic specialization membrane 1 KCNB1
[Isoform 1]: Cell membrane 1 KCNA3
dendrite membrane 1 KCNB1
cholinergic synapse 1 KCNB1
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
transcription factor AP-1 complex 1 JUN
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
rough endoplasmic reticulum lumen 1 EDN1
Weibel-Palade body 1 EDN1
myelin sheath abaxonal region 1 CNP
myelin sheath adaxonal region 1 CNP
proximal dendrite 1 KCNB1
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
ISGF3 complex 1 STAT1
ciliary transition fiber 1 ALB
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]