Record Information |
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Version | 1.0 |
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Created at | 2022-09-04 00:40:41 UTC |
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Updated at | 2022-09-04 00:40:41 UTC |
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NP-MRD ID | NP0185306 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s,5s)-2-benzyl-5-(2-methylpropyl)pyrazine-2,3,5,6-tetrol |
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Description | Lepistamide B belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. (2s,5s)-2-benzyl-5-(2-methylpropyl)pyrazine-2,3,5,6-tetrol is found in Lepista sordida. It was first documented in 2022 (PMID: 36057848). Based on a literature review a significant number of articles have been published on Lepistamide B (PMID: 36057827) (PMID: 36057824) (PMID: 36057799) (PMID: 36057792). |
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Structure | CC(C)C[C@@]1(O)N=C(O)[C@@](O)(CC2=CC=CC=C2)N=C1O InChI=1S/C15H20N2O4/c1-10(2)8-14(20)12(18)17-15(21,13(19)16-14)9-11-6-4-3-5-7-11/h3-7,10,20-21H,8-9H2,1-2H3,(H,16,19)(H,17,18)/t14-,15-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C15H20N2O4 |
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Average Mass | 292.3350 Da |
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Monoisotopic Mass | 292.14231 Da |
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IUPAC Name | (2S,5S)-2-benzyl-5-(2-methylpropyl)-2,5-dihydropyrazine-2,3,5,6-tetrol |
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Traditional Name | (2S,5S)-2-benzyl-5-(2-methylpropyl)pyrazine-2,3,5,6-tetrol |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C[C@@]1(O)N=C(O)[C@@](O)(CC2=CC=CC=C2)N=C1O |
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InChI Identifier | InChI=1S/C15H20N2O4/c1-10(2)8-14(20)12(18)17-15(21,13(19)16-14)9-11-6-4-3-5-7-11/h3-7,10,20-21H,8-9H2,1-2H3,(H,16,19)(H,17,18)/t14-,15-/m0/s1 |
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InChI Key | BFFIQSKYESGUSO-GJZGRUSLSA-N |
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Experimental Spectra |
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| Not Available | 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 alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alpha amino acids and derivatives |
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Alternative Parents | |
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Substituents | - Alpha-amino acid or derivatives
- Dioxopiperazine
- 2,5-dioxopiperazine
- Monocyclic benzene moiety
- 1,4-diazinane
- Piperazine
- Benzenoid
- Carboxamide group
- Lactam
- Secondary carboxylic acid amide
- Alkanolamine
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- 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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General References | - Gong X, Shi L, Wu Y, Luo Y, Kwok T: B Vitamin Supplementation Slows Cognitive Decline in Mild Cognitive Impairment Patients with Frontal Lobe Atrophy. J Alzheimers Dis. 2022 Sep 1. pii: JAD220685. doi: 10.3233/JAD-220685. [PubMed:36057827 ]
- Cardoso CP, da Silva Nunes G, da Silva JLF, de Mello Prado R, de Farias Guedes VH, de Bortoli SA, de Souza Junior JP: Silicon and boron on cauliflower induce attractiveness and mortality in Plutella xylostella. Pest Manag Sci. 2022 Dec;78(12):5432-5436. doi: 10.1002/ps.7165. Epub 2022 Sep 20. [PubMed:36057848 ]
- Ohno K, Abdelhamid M, Zhou C, Jung CG, Michikawa M: Bifidobacterium breve MCC1274 Supplementation Increased the Plasma Levels of Metabolites with Potential Anti-Oxidative Activity in APP Knock-In Mice. J Alzheimers Dis. 2022;89(4):1413-1425. doi: 10.3233/JAD-220479. [PubMed:36057824 ]
- Cheung L, Chan K, Heffernan MG, Pakosh M, Hitzig SL, Marzolini S, Kalsi-Ryan S, Musselman KE: The impact of sport participation for individuals with spinal cord injury: A scoping review. NeuroRehabilitation. 2022;51(3):353-395. doi: 10.3233/NRE-220037. [PubMed:36057799 ]
- Petersen H, Kecklund G, Akerstedt T: Disturbed sleep and its attribution to stress and other causes: A population-based survey. Scand J Psychol. 2023 Apr;64(2):99-104. doi: 10.1111/sjop.12867. Epub 2022 Sep 3. [PubMed:36057792 ]
- LOTUS database [Link]
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