Record Information |
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Version | 2.0 |
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Created at | 2022-04-28 13:49:21 UTC |
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Updated at | 2022-04-28 13:49:21 UTC |
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NP-MRD ID | NP0068557 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (-)-Fumiquinozoline F |
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Description | Fumiquinazoline F belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. (-)-Fumiquinozoline F is found in Aspergillus fumigatus, Penicillium aethiopicum, Penicillium corylophilum and Penicillium thymicola. It was first documented in 2012 (PMID: 22902615). Based on a literature review a significant number of articles have been published on fumiquinazoline F (PMID: 26771621) (PMID: 33332106) (PMID: 27521635) (PMID: 24001842). |
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Structure | C[C@@H]1NC(=O)[C@@H](CC2=CNC3=CC=CC=C23)N2C(=O)C3=CC=CC=C3N=C12 InChI=1S/C21H18N4O2/c1-12-19-24-17-9-5-3-7-15(17)21(27)25(19)18(20(26)23-12)10-13-11-22-16-8-4-2-6-14(13)16/h2-9,11-12,18,22H,10H2,1H3,(H,23,26)/t12-,18+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C21H18N4O2 |
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Average Mass | 358.4010 Da |
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Monoisotopic Mass | 358.14298 Da |
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IUPAC Name | (1S,4R)-4-[(1H-indol-3-yl)methyl]-1-methyl-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione |
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Traditional Name | (1S,4R)-4-(1H-indol-3-ylmethyl)-1-methyl-1H,2H,4H-pyrazino[2,1-b]quinazoline-3,6-dione |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1NC(=O)[C@@H](CC2=CNC3=CC=CC=C23)N2C(=O)C3=CC=CC=C3N=C12 |
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InChI Identifier | InChI=1S/C21H18N4O2/c1-12-19-24-17-9-5-3-7-15(17)21(27)25(19)18(20(26)23-12)10-13-11-22-16-8-4-2-6-14(13)16/h2-9,11-12,18,22H,10H2,1H3,(H,23,26)/t12-,18+/m0/s1 |
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InChI Key | SUVZUTHVKIBYOH-KPZWWZAWSA-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 quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazanaphthalenes |
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Sub Class | Benzodiazines |
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Direct Parent | Quinazolines |
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Alternative Parents | |
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Substituents | - Quinazoline
- 3-alkylindole
- Indole
- Indole or derivatives
- Pyrimidone
- Pyrimidine
- Substituted pyrrole
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Secondary carboxylic acid amide
- Lactam
- Carboxamide group
- Carboxylic acid derivative
- Azacycle
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | - Lan WJ, Fu SJ, Xu MY, Liang WL, Lam CK, Zhong GH, Xu J, Yang DP, Li HJ: Five New Cytotoxic Metabolites from the Marine Fungus Neosartorya pseudofischeri. Mar Drugs. 2016 Jan 13;14(1):18. doi: 10.3390/md14010018. [PubMed:26771621 ]
- Matsushita T, Kishimoto S, Hara K, Hashimoto H, Watanabe K: Structural and Functional Analyses of a Spiro-Carbon-Forming, Highly Promiscuous Epoxidase from Fungal Natural Product Biosynthesis. Biochemistry. 2020 Dec 29;59(51):4787-4792. doi: 10.1021/acs.biochem.0c00896. Epub 2020 Dec 17. [PubMed:33332106 ]
- Nguyen HDT, McMullin DR, Ponomareva E, Riley R, Pomraning KR, Baker SE, Seifert KA: Ochratoxin A production by Penicillium thymicola. Fungal Biol. 2016 Aug;120(8):1041-1049. doi: 10.1016/j.funbio.2016.04.002. Epub 2016 Apr 12. [PubMed:27521635 ]
- Ates E, Godula M, Stroka J, Senyuva H: Screening of plant and fungal metabolites in wheat, maize and animal feed using automated on-line clean-up coupled to high resolution mass spectrometry. Food Chem. 2014 Jan 1;142:276-84. doi: 10.1016/j.foodchem.2013.07.054. Epub 2013 Jul 19. [PubMed:24001842 ]
- Gao X, Haynes SW, Ames BD, Wang P, Vien LP, Walsh CT, Tang Y: Cyclization of fungal nonribosomal peptides by a terminal condensation-like domain. Nat Chem Biol. 2012 Oct;8(10):823-30. doi: 10.1038/nchembio.1047. [PubMed:22902615 ]
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