Microcystin RR (BioDeep_00000002463)

   

Marine Natural Products


代谢物信息卡片


Microcystin RR

化学式: C49H75N13O12 (1037.5658)
中文名称: 微囊藻毒素Microcystin-RR
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C1C(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)NC(C(=O)O)C(C)C(=O)NC(CCCNC(=N)N)C(=O)NC(C=CC(C)=CC(C)C(Cc2ccccc2)OC)C(C)C(=O)NC(C(=O)O)CCC(=O)N1C
InChI: InChI=1S/C49H75N13O12/c1-26(24-27(2)37(74-8)25-32-14-10-9-11-15-32)18-19-33-28(3)40(64)60-36(46(70)71)20-21-38(63)62(7)31(6)43(67)56-30(5)42(66)59-35(17-13-23-55-49(52)53)45(69)61-39(47(72)73)29(4)41(65)58-34(44(68)57-33)16-12-22-54-48(50)51/h9-11,14-15,18-19,24,27-30,33-37,39H,6,12-13,16-17,20-23,25H2,1-5,7-8H3,(H,56,67)(H,57,68)(H,58,65)(H,59,66)(H,60,64)(H,61,69)(H,70,71)(H,72,73)(H4,50,51,54)(H4,52,53,55)/b19-18+,26-24+/t27-,28-,29-,30+,33-,34-,35+,36+,37-,39+/m0/s1

描述信息

A microcystin consisting of D-alanyl, L-arginyl, (3S)-3-methyl-D-beta-aspartyl, L-arginyl, (2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl, D-gamma-glutamyl, and 2,3-didehydro-N-methylalanyl residues joined into a 25-membered macrocycle.
D009676 - Noxae > D002273 - Carcinogens > D052998 - Microcystins
D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3250
CONFIDENCE standard compound; UCHEM_ID 3250; NaToxAq - Natural Toxins and Drinking Water Quality - From Source to Tap (https://natoxaq.ku.dk); EQ cyanopeptide spectra replaced with more comprehensive acquisition.
CONFIDENCE standard compound; UCHEM_ID 3250; NaToxAq - Natural Toxins and Drinking Water Quality - From Source to Tap (https://natoxaq.ku.dk)

同义名列表

4 个代谢物同义名

Microcystin RR; Microcystin-RR; MCRR; Microcystin RR



数据库引用编号

20 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)

2 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 12 ALB, BIRC3, CAT, CD36, CFLAR, GPX1, HIF1A, HPGDS, MTOR, PKM, PRKAA2, VIM
Peripheral membrane protein 1 MTOR
Endoplasmic reticulum membrane 1 MTOR
Nucleus 8 ALB, BIRC3, HIF1A, MTOR, PKM, PRKAA2, THRA, THRB
cytosol 15 ALB, BIRC3, CAT, CFLAR, GPT, GPX1, GSR, HIF1A, HPGDS, MB, MTOR, PKM, PRKAA2, THRA, VIM
dendrite 2 MTOR, PRKAA2
nuclear body 2 HIF1A, THRB
phagocytic vesicle 3 CD36, MTOR, VIM
centrosome 1 ALB
nucleoplasm 7 BIRC3, HIF1A, HPGDS, MTOR, PRKAA2, THRA, THRB
RNA polymerase II transcription regulator complex 3 HIF1A, THRA, THRB
Cell membrane 3 CD36, SLCO1A2, VIM
Cytoplasmic side 1 MTOR
Multi-pass membrane protein 2 CD36, SLCO1A2
Golgi apparatus membrane 1 MTOR
cell surface 1 CD36
Golgi apparatus 3 ALB, CD36, PRKAA2
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
neuronal cell body 1 PRKAA2
Lysosome 1 MTOR
plasma membrane 4 CD36, DIO2, SLCO1A2, VIM
Membrane 6 CAT, CD36, DIO2, MTOR, PRKAA2, SLCO1A2
apical plasma membrane 2 CD36, SLCO1A2
axon 2 PRKAA2, VIM
basolateral plasma membrane 1 SLCO1A2
caveola 1 CD36
extracellular exosome 8 AGT, ALB, CAT, GPT, GSR, MB, PKM, VIM
Lysosome membrane 1 MTOR
endoplasmic reticulum 1 ALB
extracellular space 3 AGT, ALB, CD36
mitochondrion 4 CAT, GPX1, GSR, PKM
protein-containing complex 4 ALB, BIRC3, CAT, HIF1A
intracellular membrane-bounded organelle 2 CAT, HPGDS
Microsome membrane 1 MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 2 AGT, ALB
extracellular region 4 AGT, ALB, CAT, PKM
Mitochondrion outer membrane 1 MTOR
Single-pass membrane protein 1 DIO2
mitochondrial outer membrane 1 MTOR
mitochondrial matrix 3 CAT, GPX1, GSR
anchoring junction 1 ALB
motile cilium 1 HIF1A
external side of plasma membrane 2 CD36, GSR
Extracellular vesicle 1 PKM
axon cytoplasm 1 HIF1A
sarcoplasm 1 MB
vesicle 1 PKM
Apical cell membrane 1 CD36
Membrane raft 1 CD36
Cytoplasm, cytoskeleton 1 VIM
focal adhesion 2 CAT, VIM
Peroxisome 2 CAT, VIM
collagen trimer 1 CD36
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 2 AGT, PKM
intermediate filament 1 VIM
nuclear speck 2 HIF1A, PRKAA2
receptor complex 1 CD36
neuron projection 1 VIM
ciliary basal body 1 ALB
cilium 1 PKM
chromatin 3 HIF1A, THRA, THRB
cell leading edge 1 VIM
cell periphery 1 CD36
cytoskeleton 1 VIM
centriole 1 ALB
brush border membrane 1 CD36
spindle pole 1 ALB
blood microparticle 2 AGT, ALB
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
microtubule organizing center 1 VIM
specific granule membrane 1 CD36
cytoplasmic stress granule 1 PRKAA2
Nucleus speckle 1 HIF1A
euchromatin 1 HIF1A
intermediate filament cytoskeleton 1 VIM
basal plasma membrane 1 SLCO1A2
ficolin-1-rich granule lumen 2 CAT, PKM
secretory granule lumen 2 CAT, PKM
endoplasmic reticulum lumen 1 ALB
nuclear matrix 1 VIM
platelet alpha granule lumen 1 ALB
endocytic vesicle membrane 1 CD36
Nucleus matrix 1 VIM
Basal cell membrane 1 SLCO1A2
CD95 death-inducing signaling complex 1 CFLAR
death-inducing signaling complex 1 CFLAR
ripoptosome 1 CFLAR
Rough endoplasmic reticulum 1 PKM
nucleotide-activated protein kinase complex 1 PRKAA2
Cytoplasmic vesicle, phagosome 1 MTOR
platelet alpha granule membrane 1 CD36
Cytoplasm, sarcoplasm 1 MB
catalase complex 1 CAT
[Isoform Alpha-2]: Cytoplasm 1 THRA
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM
ciliary transition fiber 1 ALB


文献列表

  • H Zaidi, A Amrani, F Sedrati, H Maaref, F Leghrib, M Benamara, H Amara, Zhi Wang, H Nasri. Histological and chemical damage induced by microcystin-LR and microcystin-RR on land snail Helix aspersa tissues after acute exposure. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2021 Jul; 245(?):109031. doi: 10.1016/j.cbpc.2021.109031. [PMID: 33737222]
  • Wanda Czyżewska, Marlena Piontek, Katarzyna Łuszczyńska. The Occurrence of Potential Harmful Cyanobacteria and Cyanotoxins in the Obrzyca River (Poland), a Source of Drinking Water. Toxins. 2020 04; 12(5):. doi: 10.3390/toxins12050284. [PMID: 32354080]
  • Qing Cao, Alan D Steinman, Xiang Wan, Liqiang Xie. Bioaccumulation of microcystin congeners in soil-plant system and human health risk assessment: A field study from Lake Taihu region of China. Environmental pollution (Barking, Essex : 1987). 2018 Sep; 240(?):44-50. doi: 10.1016/j.envpol.2018.04.067. [PMID: 29729568]
  • Łukasz Wejnerowski, Piotr Rzymski, Mikołaj Kokociński, Jussi Meriluoto. The structure and toxicity of winter cyanobacterial bloom in a eutrophic lake of the temperate zone. Ecotoxicology (London, England). 2018 Aug; 27(6):752-760. doi: 10.1007/s10646-018-1957-x. [PMID: 29934736]
  • Wei Li, Jun He, Jun Chen, Ping Xie. Excretion pattern and dynamics of glutathione detoxification of microcystins in Sprague Dawley rat. Chemosphere. 2018 Jan; 191(?):357-364. doi: 10.1016/j.chemosphere.2017.09.083. [PMID: 29049959]
  • Qing Zhong, Feng Sun, Weiguang Wang, Wenqing Xiao, Xiaoni Zhao, Kangding Gu. Water metabolism dysfunction via renin-angiotensin system activation caused by liver damage in mice treated with microcystin-RR. Toxicology letters. 2017 May; 273(?):86-96. doi: 10.1016/j.toxlet.2017.03.019. [PMID: 28330766]
  • Marcelo Gustavo Paulino, Priscila Adriana Rossi, Francine Perri Venturini, Driele Tavares, Naiara Elisabete da Silva Souza, Marise Margareth Sakuragui, Gilberto Moraes, Ana Paula Terezan, João Batista Fernandes, Alessandra Giani, Marisa Narciso Fernandes. Hepatotoxicity and metabolic effects of cellular extract of cyanobacterium Radiocystis fernandoi containing microcystins RR and YR on neotropical fish (Hoplias malabaricus). Chemosphere. 2017 May; 175(?):431-439. doi: 10.1016/j.chemosphere.2017.02.089. [PMID: 28242458]
  • Okechukwu Idumah Okogwu, Ping Xie, Yanyan Zhao, Huihui Fan. Organ-dependent response in antioxidants, myoglobin and neuroglobin in goldfish (Carassius auratus) exposed to MC-RR under varying oxygen level. Chemosphere. 2014 Oct; 112(?):427-34. doi: 10.1016/j.chemosphere.2014.05.011. [PMID: 25048936]
  • Wei Li, Ping Xie, Jun Chen, Jun He, Xiaochun Guo, Dezhao Yu, Liang Chen. Quantitative liquid chromatography-tandem mass spectrometry method for determination of microcystin-RR and its glutathione and cysteine conjugates in fish plasma and bile. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jul; 963(?):113-8. doi: 10.1016/j.jchromb.2014.05.057. [PMID: 24950098]
  • Shruti Pavagadhi, Siria Natera, Ute Roessner, Rajasekhar Balasubramanian. Insights into lipidomic perturbations in zebrafish tissues upon exposure to microcystin-LR and microcystin-RR. Environmental science & technology. 2013 Dec; 47(24):14376-84. doi: 10.1021/es4004125. [PMID: 24152164]
  • Wei Zhang, Gaodao Liang, Laiyan Wu, Xun Tuo, Wenjing Wang, Jun Chen, Ping Xie. Why mammals more susceptible to the hepatotoxic microcystins than fish: evidences from plasma and albumin protein binding through equilibrium dialysis. Ecotoxicology (London, England). 2013 Aug; 22(6):1012-9. doi: 10.1007/s10646-013-1086-5. [PMID: 23700298]
  • Laiyan Wu, Qing Wang, Min Tao, Jun Chen, Zhimei Ma, Ping Xie. Preliminary study of the distribution and accumulation of GSH/Cys metabolites of hepatotoxic microcystins-RR in common carp from a lake with protracted cyanobacterial bloom (Lake Taihu, China). Bulletin of environmental contamination and toxicology. 2013 Mar; 90(3):382-6. doi: 10.1007/s00128-012-0947-6. [PMID: 23272327]
  • Yue Yang, Youngki Park, David A Cassada, Daniel D Snow, Douglas G Rogers, Jiyoung Lee. In vitro and in vivo safety assessment of edible blue-green algae, Nostoc commune var. sphaeroides Kützing and Spirulina plantensis. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Jul; 49(7):1560-4. doi: 10.1016/j.fct.2011.03.052. [PMID: 21473896]
  • Wenmin Huang, Wei Xing, Dunhai Li, Yongding Liu. Morphological and ultrastructural changes in tobacco BY-2 cells exposed to microcystin-RR. Chemosphere. 2009 Aug; 76(7):1006-12. doi: 10.1016/j.chemosphere.2009.03.074. [PMID: 19501874]
  • C Y Yang, W B Wang, D H Li, Y D Liu. Growth and antioxidant system of Escherichia coli in response to microcystin-RR. Bulletin of environmental contamination and toxicology. 2008 Nov; 81(5):427-31. doi: 10.1007/s00128-008-9436-3. [PMID: 18714425]
  • Liyan Yin, Jiaquan Huang, Wei Li, Yongding Liu. Microcystin-RR-induced apoptosis in tobacco BY-2 cells. Toxicon : official journal of the International Society on Toxinology. 2006 Aug; 48(2):204-10. doi: 10.1016/j.toxicon.2006.05.002. [PMID: 16797632]
  • Jimena Cazenave, María de Los Angeles Bistoni, Silvia Fabiana Pesce, Daniel Alberto Wunderlin. Differential detoxification and antioxidant response in diverse organs of Corydoras paleatus experimentally exposed to microcystin-RR. Aquatic toxicology (Amsterdam, Netherlands). 2006 Jan; 76(1):1-12. doi: 10.1016/j.aquatox.2005.08.011. [PMID: 16263184]
  • Liyan Yin, Jiaquan Huang, Wenming Huang, Dunhai Li, Yongding Liu. Responses of antioxidant system in Arabidopsis thaliana suspension cells to the toxicity of microcystin-RR. Toxicon : official journal of the International Society on Toxinology. 2005 Dec; 46(8):859-64. doi: 10.1016/j.toxicon.2004.12.025. [PMID: 16269166]
  • Liyan Yin, Jiaquan Huang, Wenming Huang, Dunhai Li, Gaohong Wang, Yongding Liu. Microcystin-RR-induced accumulation of reactive oxygen species and alteration of antioxidant systems in tobacco BY-2 cells. Toxicon : official journal of the International Society on Toxinology. 2005 Oct; 46(5):507-12. doi: 10.1016/j.toxicon.2005.06.015. [PMID: 16084553]
  • Liqiang Xie, Ping Xie, Longgen Guo, Li Li, Yuichi Miyabara, Ho-Dong Park. Organ distribution and bioaccumulation of microcystins in freshwater fish at different trophic levels from the eutrophic Lake Chaohu, China. Environmental toxicology. 2005 Jun; 20(3):293-300. doi: 10.1002/tox.20120. [PMID: 15892067]
  • Liyan Yin, Jiaquan Huang, Dunhai Li, Yongding Liu. Microcystin-RR uptake and its effects on the growth of submerged macrophyte Vallisneria natans (lour.) hara. Environmental toxicology. 2005 Jun; 20(3):308-13. doi: 10.1002/tox.20122. [PMID: 15892062]
  • Nidhi Gupta, S C Pant, R Vijayaraghavan, P V Lakshmana Rao. Comparative toxicity evaluation of cyanobacterial cyclic peptide toxin microcystin variants (LR, RR, YR) in mice. Toxicology. 2003 Jun; 188(2-3):285-96. doi: 10.1016/s0300-483x(03)00112-4. [PMID: 12767698]
  • Wei Shi, Huigang Zhu, Xiaorong Yan, Zhijun Zhou. [Sub-acute hepatotoxicity of low doses of microcystins]. Huan jing ke xue= Huanjing kexue. 2002 Sep; 23(5):47-51. doi: NULL. [PMID: 12533925]
  • Emiko Ito, Akira Takai, Fumio Kondo, Hiroaki Masui, Susumu Imanishi, Ken-ichi Harada. Comparison of protein phosphatase inhibitory activity and apparent toxicity of microcystins and related compounds. Toxicon : official journal of the International Society on Toxinology. 2002 Jul; 40(7):1017-25. doi: 10.1016/s0041-0101(02)00099-5. [PMID: 12076656]
  • J McElhiney, L A Lawton, C Leifert. Investigations into the inhibitory effects of microcystins on plant growth, and the toxicity of plant tissues following exposure. Toxicon : official journal of the International Society on Toxinology. 2001 Sep; 39(9):1411-20. doi: 10.1016/s0041-0101(01)00100-3. [PMID: 11384731]
  • R Nishiwaki-Matsushima, S Nishiwaki, T Ohta, S Yoshizawa, M Suganuma, K Harada, M F Watanabe, H Fujiki. Structure-function relationships of microcystins, liver tumor promoters, in interaction with protein phosphatase. Japanese journal of cancer research : Gann. 1991 Sep; 82(9):993-6. doi: 10.1111/j.1349-7006.1991.tb01933.x. [PMID: 1657848]
  • K W Cho, R L Malvin. Renin inactivation during in vitro experiments. The American journal of physiology. 1979 May; 236(5):F501-4. doi: 10.1152/ajprenal.1979.236.5.f501. [PMID: 443387]