Record Information |
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Version | 1.0 |
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Created at | 2022-09-04 03:19:40 UTC |
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Updated at | 2022-09-04 03:19:40 UTC |
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NP-MRD ID | NP0187231 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2e)-2-{2-[(2r,5r)-2-[(2e)-3-carboxy-3-methylprop-2-en-1-yl]-5-isopropyl-2-methylcyclopentylidene]ethyl}-4-hydroxybut-2-enoic acid |
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Description | Psathyrelloic acid, also known as psathyrelloate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2e)-2-{2-[(2r,5r)-2-[(2e)-3-carboxy-3-methylprop-2-en-1-yl]-5-isopropyl-2-methylcyclopentylidene]ethyl}-4-hydroxybut-2-enoic acid is found in Psathyrella candolleana. It was first documented in 2022 (PMID: 36057848). Based on a literature review a significant number of articles have been published on Psathyrelloic acid (PMID: 36057403) (PMID: 36057425) (PMID: 36057399) (PMID: 36057394) (PMID: 36057827) (PMID: 36057824). |
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Structure | CC(C)[C@H]1CC[C@](C)(C\C=C(/C)C(O)=O)C1=CC\C(=C/CO)C(O)=O InChI=1S/C20H30O5/c1-13(2)16-8-11-20(4,10-7-14(3)18(22)23)17(16)6-5-15(9-12-21)19(24)25/h6-7,9,13,16,21H,5,8,10-12H2,1-4H3,(H,22,23)(H,24,25)/b14-7+,15-9+,17-6?/t16-,20+/m1/s1 |
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Synonyms | Value | Source |
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Psathyrelloate | Generator |
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Chemical Formula | C20H30O5 |
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Average Mass | 350.4550 Da |
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Monoisotopic Mass | 350.20932 Da |
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IUPAC Name | (2E)-2-{2-[(2R,5R)-2-[(2E)-3-carboxy-3-methylprop-2-en-1-yl]-2-methyl-5-(propan-2-yl)cyclopentylidene]ethyl}-4-hydroxybut-2-enoic acid |
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Traditional Name | (2E)-2-{2-[(2R,5R)-2-[(2E)-3-carboxy-3-methylprop-2-en-1-yl]-5-isopropyl-2-methylcyclopentylidene]ethyl}-4-hydroxybut-2-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(C)[C@H]1CC[C@](C)(C\C=C(/C)C(O)=O)C1=CC\C(=C/CO)C(O)=O |
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InChI Identifier | InChI=1S/C20H30O5/c1-13(2)16-8-11-20(4,10-7-14(3)18(22)23)17(16)6-5-15(9-12-21)19(24)25/h6-7,9,13,16,21H,5,8,10-12H2,1-4H3,(H,22,23)(H,24,25)/b14-7+,15-9+,17-6?/t16-,20+/m1/s1 |
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InChI Key | YNSXHFRWBMHNHW-XMZPZSOLSA-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 sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Sesquiterpenoids |
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Direct Parent | Sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Sesquiterpenoid
- Medium-chain hydroxy acid
- Medium-chain fatty acid
- Methyl-branched fatty acid
- Hydroxy fatty acid
- Branched fatty acid
- Fatty acyl
- Fatty acid
- Unsaturated fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic 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 | - Marszalek-Grabska M, Zakrocka I, Budzynska B, Marciniak S, Kaszubska K, Lemieszek MK, Winiarczyk S, Kotlinska JH, Rzeski W, Turski WA: Binge-like mephedrone treatment induces memory impairment concomitant with brain kynurenic acid reduction in mice. Toxicol Appl Pharmacol. 2022 Aug 31;454:116216. doi: 10.1016/j.taap.2022.116216. [PubMed:36057403 ]
- Wang G, Wang F, Pei H, Li M, Bai F, Lei C, Dang R: Genome-wide analysis reveals selection signatures for body size and drought adaptation in Liangzhou donkey. Genomics. 2022 Aug 31;114(6):110476. doi: 10.1016/j.ygeno.2022.110476. [PubMed:36057425 ]
- Wang XY, Lu LJ, Li YM, Xu CF: MicroRNA-376b-3p ameliorates nonalcoholic fatty liver disease by targeting FGFR1 and regulating lipid oxidation in hepatocytes. Life Sci. 2022 Nov 1;308:120925. doi: 10.1016/j.lfs.2022.120925. Epub 2022 Aug 31. [PubMed:36057399 ]
- Chowdhury A, Lewin MR, Carter RW, Casewell NR, Fry BG: Keel venom: Rhabdophis subminiatus (Red-Necked Keelback) venom pathophysiologically affects diverse blood clotting pathways. Toxicon. 2022 Oct 30;218:19-24. doi: 10.1016/j.toxicon.2022.08.017. Epub 2022 Aug 31. [PubMed:36057394 ]
- 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 ]
- Ogawa A, Kojima F, Miyake Y, Yoshimura M, Ishijima N, Iyoda S, Sekine Y, Yamanaka Y, Yamamoto K: Regulation of constant cell elongation and Sfm pili synthesis in Escherichia coli via two active forms of FimZ orphan response regulator. Genes Cells. 2022 Nov;27(11):657-674. doi: 10.1111/gtc.12982. Epub 2022 Sep 18. [PubMed:36057789 ]
- Ben-Azu B, Adebayo OG, Jarikre TA, Oyovwi MO, Edje KE, Omogbiya IA, Eduviere AT, Moke EG, Chijioke BS, Odili OS, Omondiabge OP, Oyovbaire A, Esuku DT, Ozah EO, Japhet K: Taurine, an essential beta-amino acid insulates against ketamine-induced experimental psychosis by enhancement of cholinergic neurotransmission, inhibition of oxidative/nitrergic imbalances, and suppression of COX-2/iNOS immunoreactions in mice. Metab Brain Dis. 2022 Sep 3. pii: 10.1007/s11011-022-01075-5. doi: 10.1007/s11011-022-01075-5. [PubMed:36057735 ]
- Lin H, Xu Y, Zheng Y, Wu D, Ye Z, Xiao J: The association of urinary prostaglandins with uric acid in hyperuricemia patients. BMC Nephrol. 2022 Sep 3;23(1):302. doi: 10.1186/s12882-022-02928-y. [PubMed:36057582 ]
- Teng KT, Aerts M, Jaspers S, Ugarte-Ruiz M, Moreno MA, Saez JL, Collado S, de Frutos C, Dominguez L, Alvarez J: Patterns of antimicrobial resistance in Salmonella isolates from fattening pigs in Spain. BMC Vet Res. 2022 Sep 3;18(1):333. doi: 10.1186/s12917-022-03377-3. [PubMed:36057710 ]
- Feng L, Yang X, Lu X, Kan Y, Wang C, Sun D, Zhang H, Wang W, Yang J: (18)F-FDG PET/CT-based radiomics nomogram could predict bone marrow involvement in pediatric neuroblastoma. Insights Imaging. 2022 Sep 4;13(1):144. doi: 10.1186/s13244-022-01283-8. [PubMed:36057694 ]
- Lee GS, Park B, Hong SH: Stereoretentive cross-coupling of chiral amino acid chlorides and hydrocarbons through mechanistically controlled Ni/Ir photoredox catalysis. Nat Commun. 2022 Sep 3;13(1):5200. doi: 10.1038/s41467-022-32851-7. [PubMed:36057676 ]
- Zhou J, Pang J, Tripathi M, Ho JP, Widjaja AA, Shekeran SG, Cook SA, Suzuki A, Diehl AM, Petretto E, Singh BK, Yen PM: Spermidine-mediated hypusination of translation factor EIF5A improves mitochondrial fatty acid oxidation and prevents non-alcoholic steatohepatitis progression. Nat Commun. 2022 Sep 3;13(1):5202. doi: 10.1038/s41467-022-32788-x. [PubMed:36057633 ]
- Lu XY, Zhang JY, Zhang T, Zhang XQ, Lu J, Miao XF, Chen WB, Jiang JF, Ding D, Du S: Using pre-operative radiomics to predict microvascular invasion of hepatocellular carcinoma based on Gd-EOB-DTPA enhanced MRI. BMC Med Imaging. 2022 Sep 3;22(1):157. doi: 10.1186/s12880-022-00855-w. [PubMed:36057576 ]
- LOTUS database [Link]
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