Record Information |
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Version | 1.0 |
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Created at | 2020-12-07 18:25:14 UTC |
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Updated at | 2021-07-15 16:45:26 UTC |
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NP-MRD ID | NP0003070 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Minutellin A |
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Provided By | NPAtlas |
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Description | Minutellin A belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Minutellin A is found in Annulohypoxylon minutellum and Jackrogersella minutella. It was first documented in 2017 (PMID: 28215421). Based on a literature review very few articles have been published on Minutellin A (PMID: 34340252) (PMID: 34337505) (PMID: 34329479) (PMID: 34314179) (PMID: 34369645) (PMID: 34364329). |
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Structure | [H]O[C@]1([H])C([H])([H])C(=O)C(C2=C([H])C3=C([H])C(=O)[C@@]4(OC(=O)C(C(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=C4C3=C([H])O2)C([H])([H])[H])=C(C([H])([H])[H])C1([H])[H] InChI=1S/C27H30O7/c1-4-5-6-7-8-9-19(29)24-25-18-14-33-21(23-15(2)10-17(28)13-20(23)30)11-16(18)12-22(31)27(25,3)34-26(24)32/h11-12,14,17,28H,4-10,13H2,1-3H3/t17-,27-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C27H30O7 |
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Average Mass | 466.5300 Da |
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Monoisotopic Mass | 466.19915 Da |
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IUPAC Name | (6aR)-3-[(4S)-4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl]-6a-methyl-9-octanoyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione |
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Traditional Name | (6aR)-3-[(4S)-4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl]-6a-methyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCC(=O)C1=C2C3=COC(=CC3=CC(=O)[C@]2(C)OC1=O)C1=C(C)C[C@H](O)CC1=O |
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InChI Identifier | InChI=1S/C27H30O7/c1-4-5-6-7-8-9-19(29)24-25-18-14-33-21(23-15(2)10-17(28)13-20(23)30)11-16(18)12-22(31)27(25,3)34-26(24)32/h11-12,14,17,28H,4-10,13H2,1-3H3/t17-,27-/m0/s1 |
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InChI Key | QMIVTDDJTVQZLY-SOKVYYICSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty alcohols |
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Direct Parent | Annonaceous acetogenins |
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Alternative Parents | |
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Substituents | - Annonaceae acetogenin skeleton
- Cyclohexenone
- Alpha-acyloxy ketone
- Pyran
- 2-furanone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Dihydrofuran
- Cyclic ketone
- Secondary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | - Kuhnert E, Surup F, Halecker S, Stadler M: Minutellins A - D, azaphilones from the stromata of Annulohypoxylon minutellum (Xylariaceae). Phytochemistry. 2017 May;137:66-71. doi: 10.1016/j.phytochem.2017.02.014. Epub 2017 Feb 17. [PubMed:28215421 ]
- Liu W, Xue F, Poon MC, Chen L, Jin Z, Zhang L, Yang R: Current status of haemophilia inhibitor management in mainland China: a haemophilia treatment centres survey on treatment preferences and real-world clinical practices. Br J Haematol. 2021 Aug 2. doi: 10.1111/bjh.17677. [PubMed:34340252 ]
- Moller T, Engedal MS, Plum LM, Aasvang EK: Reduced Need for Urinary Bladder Catheterization in the Postanesthesia Care Unit After Implementation of an Evidence-based Protocol: A Prospective Cohort Comparison Study. Eur Urol Open Sci. 2021 Feb 16;26:27-34. doi: 10.1016/j.euros.2021.01.013. eCollection 2021 Apr. [PubMed:34337505 ]
- Bartsch U, Corbin LJ, Hellmich C, Taylor M, Easey KE, Durant C, Marston HM, Timpson NJ, Jones MW: Schizophrenia-associated variation at ZNF804A correlates with altered experience-dependent dynamics of sleep slow waves and spindles in healthy young adults. Sleep. 2021 Jul 30. pii: 6331689. doi: 10.1093/sleep/zsab191. [PubMed:34329479 ]
- Esposito VJ, Liu T, Wang G, Caracciolo A, Vansco MF, Marchetti B, Karsili TNV, Lester MI: Photodissociation Dynamics of CH2OO on Multiple Potential Energy Surfaces: Experiment and Theory. J Phys Chem A. 2021 Aug 5;125(30):6571-6579. doi: 10.1021/acs.jpca.1c03643. Epub 2021 Jul 27. [PubMed:34314179 ]
- Ji K, Alharbi KN, Solana-Madruga E, Moyo GT, Ritter C, Attfield JP: Double double to double perovskite transformations in ternary manganese oxides. Angew Chem Int Ed Engl. 2021 Aug 9. doi: 10.1002/anie.202108586. [PubMed:34369645 ]
- Patanen M, Abid AR, Pratt ST, Kivimaki A, Trofimov AB, Skitnevskaya AD, Grigoricheva EK, Gromov EV, Powis I, Holland DMP: Valence shell photoelectron angular distributions and vibrationally resolved spectra of imidazole: A combined experimental-theoretical study. J Chem Phys. 2021 Aug 7;155(5):054304. doi: 10.1063/5.0058983. [PubMed:34364329 ]
- Branstetter SA, Krebs N, Muscat JE: Household Smoking Restrictions, Time to First Cigarette and Tobacco Dependence. J Smok Cessat. 2021 Apr 15;2021:5517773. doi: 10.1155/2021/5517773. eCollection 2021. [PubMed:34306221 ]
- Yang Q, Wang W, Lin Y, Lin Y, Tang Z, Wang J, Tao J, Tang W, Liu W: Correction: Characterization of a carboxyl methyltransferase in Fusarium graminearum provides insights into the biosynthesis of fusarin A. Org Biomol Chem. 2021 Aug 5;19(30):6718. doi: 10.1039/d1ob90103f. [PubMed:34296733 ]
- Weber TR, da Silva RL, Cossul S, Alves MSL, Lee SVS, Marques JLB: The use of echocardiography in type 1 diabetes. Rev Port Cardiol. 2021 Jul 19. pii: S0870-2551(21)00249-3. doi: 10.1016/j.repc.2020.11.012. [PubMed:34294474 ]
- Liu W, Hou C, Hou M, Xu QQ, Wang H, Gu PP, Sun L, Lv HT, Ding YY: Ultrasonography to detect cardiovascular damage in children with essential hypertension. Cardiovasc Ultrasound. 2021 Jul 21;19(1):26. doi: 10.1186/s12947-021-00257-y. [PubMed:34289865 ]
- Gong FX, Zhan G, Han R, Yang Z, Fu X, Xiao R: De-dimerization of PTB is catalyzed by PDI and is involved in the regulation of p53 translation. Nucleic Acids Res. 2021 Aug 17. pii: 6353810. doi: 10.1093/nar/gkab708. [PubMed:34403458 ]
- Morbach C, Gelbrich G, Tiffe T, Eichner FA, Christa M, Mattern R, Breunig M, Cejka V, Wagner M, Heuschmann PU, Stork S: Prevalence and determinants of the precursor stages of heart failure: results from the population-based STAAB cohort study. Eur J Prev Cardiol. 2021 Aug 9;28(9):924-934. doi: 10.1177/2047487320922636. [PubMed:34402874 ]
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