| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-30 16:47:44 UTC |
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| Updated at | 2024-11-01 01:39:09 UTC |
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| NP-MRD ID | NP0137285 |
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| Natural Product DOI | https://doi.org/10.57994/2298 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Microcystin-LR |
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| Description | Microcystin-LR belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. These toxins can break down slowly at high temperature (40 C or 104 F ) at either very low (<1) or high (>9) pH. The half-life, the time it takes for one-half of the toxin to degrade, at pH 1 and 40 oC is 3 weeks; at typical ambient conditions half-life is 10 weeks. Microcystin-LR is a very strong basic compound (based on its pKa). Microcystin-LR (MC-LR) is a naturally occurring toxin produced by cyanobacteria. Microcystin-LR is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Microcystins also activate the enzyme phosphorylase b, which plays a very important role in the affairs of the hepatocyte. The molecular target are a group of enzymes called protein phosphatases that play a role in regulating protein interactions and activities. The toxins are also resistant to enzymatic hydrolysis (in guts of animals) by some general proteases, such as pepsin, trypsin, collagenase, and chymotrypsin. Microcystin-LR was first documented in 2024 (PMID: 38311594). The site of action of microcystins is the hepatocyte, the commonest cell type in the liver. |
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| Structure | COC(CC1=CC=CC=C1)C(C)C=C(C)C=CC1NC(=O)C(CCCN=C(N)N)NC(=O)C(C)C(NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(=C)N(C)C(=O)CCC(NC(=O)C1C)C(O)=O)C(O)=O 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) |
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| Synonyms | Not Available |
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| Chemical Formula | C49H74N10O12 |
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| Average Mass | 995.1717 Da |
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| Monoisotopic Mass | 994.54877 Da |
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| IUPAC Name | 15-{3-[(diaminomethylidene)amino]propyl}-18-(6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid |
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| Traditional Name | 15-{3-[(diaminomethylidene)amino]propyl}-18-(6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid |
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| CAS Registry Number | Not Available |
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| SMILES | COC(CC1=CC=CC=C1)C(C)C=C(C)C=CC1NC(=O)C(CCCN=C(N)N)NC(=O)C(C)C(NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(=C)N(C)C(=O)CCC(NC(=O)C1C)C(O)=O)C(O)=O |
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| InChI Identifier | 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) |
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| InChI Key | ZYZCGGRZINLQBL-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| TOCSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental) | jricca2014@fau.edu | Florida Atlantic University | John Ricca | 2024-05-03 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental) | jricca2014@fau.edu | Florida Atlantic University | John Ricca | 2024-05-03 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental) | jricca2014@fau.edu | Florida Atlantic University | John Ricca | 2024-05-03 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Peptidomimetics |
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| Sub Class | Hybrid peptides |
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| Direct Parent | Hybrid peptides |
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| Alternative Parents | |
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| Substituents | - Cyclic hybrid peptide
- Alpha-oligopeptide
- Macrolactam
- Beta amino acid or derivatives
- Alpha-amino acid or derivatives
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Benzenoid
- Tertiary carboxylic acid amide
- Carboxamide group
- Guanidine
- Lactam
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Carboxylic acid
- Dialkyl ether
- Ether
- Azacycle
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Hydrocarbon derivative
- Organopnictogen compound
- Carbonyl group
- Organic oxide
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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