Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C49H74N10O12 |
| Molecular Weight | 995.1717 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CO[C@@H](CC1=CC=CC=C1)[C@@H](C)\C=C(C)\C=C\[C@@H]2NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]2C)C(O)=O)C(O)=O
InChI
InChIKey=ZYZCGGRZINLQBL-GWRQVWKTSA-N
InChI=1S/C49H74N10O12/c1-26(2)23-37-46(66)58-40(48(69)70)30(6)42(62)55-35(17-14-22-52-49(50)51)45(65)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)57-37/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1
| Molecular Formula | C49H74N10O12 |
| Molecular Weight | 995.1717 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 2 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Liver tumor promotion by the cyanobacterial cyclic peptide toxin microcystin-LR. | 1992 |
|
| An investigation of the role of vitamin E in the protection of mice against microcystin toxicity. | 2003 Apr |
|
| Effects of microcystin-LR on patterns of iNOS and cytokine mRNA expression in macrophages in vitro. | 2005 Feb |
|
| A retrospective analysis of toxicogenomics in the safety assessment of drug candidates. | 2007 Aug |
|
| Phosphoprotein analysis for investigation of in vivo relationship between protein phosphatase inhibitory activities and acute hepatotoxicity of microcystin-LR. | 2007 Dec |
|
| Hepatic gene expression changes in mice associated with prolonged sublethal microcystin exposure. | 2007 Jun |
|
| Hepatoprotective efficacy of certain flavonoids against microcystin induced toxicity in mice. | 2007 Oct |
|
| Alteration of proteins expression in apoptotic FL cells induced by MCLR. | 2008 Aug |
|
| Characterization of organic anion transporting polypeptide 1b2-null mice: essential role in hepatic uptake/toxicity of phalloidin and microcystin-LR. | 2008 May |
|
| Oxidative stress induced by microcystin-LR on PLHC-1 fish cell line. | 2009 Dec |
|
| Oatp-associated uptake and toxicity of microcystins in primary murine whole brain cells. | 2009 Jan 15 |
|
| Stimulation effect of microcystin-LR on matrix metalloproteinase-2/-9 expression in mouse liver. | 2010 Dec 15 |
|
| Proteomic analysis of hepatic tissue of zebrafish (Danio rerio) experimentally exposed to chronic microcystin-LR. | 2010 Jan |
|
| The role of organic anion transporting polypeptides (OATPs/SLCOs) in the toxicity of different microcystin congeners in vitro: a comparison of primary human hepatocytes and OATP-transfected HEK293 cells. | 2010 May 15 |
|
| p53 Plays an important role in cell fate determination after exposure to microcystin-LR. | 2010 Sep |
|
| Sulforaphane protects Microcystin-LR-induced toxicity through activation of the Nrf2-mediated defensive response. | 2010 Sep 1 |
|
| Activation of Nrf2 by microcystin-LR provides advantages for liver cancer cell growth. | 2010 Sep 20 |
|
| Transmembrane transport of microcystin to Danio rerio zygotes: insights into the developmental toxicity of environmental contaminants. | 2011 Aug |
|
| Sulforaphane prevents microcystin-LR-induced oxidative damage and apoptosis in BALB/c mice. | 2011 Aug 15 |
|
| Microcystin congener- and concentration-dependent induction of murine neuron apoptosis and neurite degeneration. | 2011 Dec |
|
| Regulation of heat shock protein 27 phosphorylation during microcystin-LR-induced cytoskeletal reorganization in a human liver cell line. | 2011 Dec 15 |
|
| Microcystin-LR induces cytoskeleton system reorganization through hyperphosphorylation of tau and HSP27 via PP2A inhibition and subsequent activation of the p38 MAPK signaling pathway in neuroendocrine (PC12) cells. | 2011 Dec 18 |
|
| Human glutathione transferases catalyzing the conjugation of the hepatoxin microcystin-LR. | 2011 Jun 20 |
|
| Similar uptake profiles of microcystin-LR and -RR in an in vitro human intestinal model. | 2011 Nov 28 |
|
| Toxic effect on tissues and differentially expressed genes in hepatopancreas identified by suppression subtractive hybridization of freshwater pearl mussel (Hyriopsis cumingii) following microcystin-LR challenge. | 2012 Jul |
|
| The toxic effects of microcystin-LR on rat spermatogonia in vitro. | 2012 Jul 7 |
|
| Hyperphosphorylation of intermediate filament proteins is involved in microcystin-LR-induced toxicity in HL7702 cells. | 2012 Oct 17 |
|
| Microcystin-LR induced reactive oxygen species mediate cytoskeletal disruption and apoptosis of hepatocytes in Cyprinus carpio L. | 2013 |
|
| In vivo study on the effects of microcystin-LR on the apoptosis, proliferation and differentiation of rat testicular spermatogenic cells of male rats injected i.p. with toxins. | 2013 |
|
| The interactive effects of cytoskeleton disruption and mitochondria dysfunction lead to reproductive toxicity induced by microcystin-LR. | 2013 |
|
| Detection of statin cytotoxicity is increased in cells expressing the OATP1B1 transporter. | 2013 Jul |
|
| The suppression of hematopoiesis function in Balb/c mice induced by prolonged exposure of microcystin-LR. | 2013 May 23 |
|
| Microcystin-LR exhibits immunomodulatory role in mouse primary hepatocytes through activation of the NF-κB and MAPK signaling pathways. | 2013 Nov |
|
| Microcystin (-LR) induced testicular cell apoptosis via up-regulating apoptosis-related genes in vivo. | 2013 Oct |
|
| Microcystin-LR induces anoikis resistance to the hepatocyte uptake transporter OATP1B3-expressing cell lines. | 2014 Dec 4 |
|
| Molecular cloning of manganese superoxide dismutase gene in the cladoceran Daphnia magna: effects of microcystin, nitrite, and cadmium on gene expression profiles. | 2014 Mar |
|
| Spatial learning and memory impairment and pathological change in rats induced by acute exposure to microcystin-LR. | 2014 Mar |
|
| Microcystin-LR stabilizes c-myc protein by inhibiting protein phosphatase 2A in HEK293 cells. | 2014 May 7 |
|
| Microcystin-LR induces protein phosphatase 2A alteration in a human liver cell line. | 2014 Nov |
|
| Molecular cloning and functional characterization of a rainbow trout liver Oatp. | 2014 Nov 1 |
|
| Neurotoxic action of microcystin-LR is reflected in the transcriptional stress response of Caenorhabditis elegans. | 2014 Nov 5 |
|
| Roles of miRNAs in microcystin-LR-induced Sertoli cell toxicity. | 2015 Aug 15 |
|
| Microcystin-LR induced thyroid dysfunction and metabolic disorders in mice. | 2015 Feb 3 |
|
| Alterations of tau and VASP during microcystin-LR-induced cytoskeletal reorganization in a human liver cell line. | 2015 Jan |
|
| Microcystin-LR Alters the Gene Transcription and Activities of Iodothyronine Deiodinases in the Hepatic Cells of Grass Carp (Ctenopharyngodon Idella). | 2015 Jul |
|
| Hyperphosphorylation of microfilament-associated proteins is involved in microcystin-LR-induced toxicity in HL7702 cells. | 2015 Jul 8 |
|
| Microcystin-LR-caused ROS generation involved in p38 activation and tau hyperphosphorylation in neuroendocrine (PC12) cells. | 2015 Mar |
|
| Okadaic acid is taken-up into the cells mediated by human hepatocytes transporter OATP1B3. | 2015 Sep |
|
| Zebrafish Oatp-mediated transport of microcystin congeners. | 2016 May |
|
| The role of GSH in microcystin-induced apoptosis in rat liver: Involvement of oxidative stress and NF-κB. | 2016 May |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:47:41 GMT 2023
by
admin
on
Sat Dec 16 09:47:41 GMT 2023
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| Record UNII |
EQ8332842Y
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| Record Status |
Validated (UNII)
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| Record Version |
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101043-37-2
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Microcystin-LR
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EQ8332842Y
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| Related Record | Type | Details | ||
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PARENT -> IMPURITY |
Unit: ng/g (LC-MS); Concentrations of microcystins in 36 Spirulina samples collected in China.
ASSAY (HPLC)
Batch Data
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