| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 01:39:47 UTC |
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| Updated at | 2022-04-28 01:39:48 UTC |
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| NP-MRD ID | NP0055680 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Artocarpanone |
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| Description | Artocarpanone belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Artocarpanone is found in Artocarpus integrifolia , Artocarpus champeden Spreng., Artocarpus heterophyllus , Mimosa hostilis and Mimosa tenuiflora. Artocarpanone was first documented in 2016 (PMID: 26834825). Based on a literature review a small amount of articles have been published on artocarpanone (PMID: 35011235) (PMID: 29943393) (PMID: 28512600) (PMID: 26304444). |
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| Structure | COC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=C(O)C=C1O InChI=1S/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)10-3-2-8(17)4-11(10)18/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C16H14O6 |
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| Average Mass | 302.2820 Da |
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| Monoisotopic Mass | 302.07904 Da |
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| IUPAC Name | (2S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one |
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| Traditional Name | (2S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-2,3-dihydro-1-benzopyran-4-one |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=C(O)C=C1O |
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| InChI Identifier | InChI=1S/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)10-3-2-8(17)4-11(10)18/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 |
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| InChI Key | FQGBGNHGEUOZIW-AWEZNQCLSA-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 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Flavonoids |
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| Sub Class | O-methylated flavonoids |
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| Direct Parent | 7-O-methylated flavonoids |
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| Alternative Parents | |
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| Substituents | - 7-methoxyflavonoid-skeleton
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- Flavanone
- Hydroxyflavonoid
- Flavan
- Chromone
- Chromane
- Benzopyran
- 1-benzopyran
- Anisole
- Aryl alkyl ketone
- Phenol ether
- Resorcinol
- Aryl ketone
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- Monocyclic benzene moiety
- Benzenoid
- Vinylogous acid
- Ketone
- Organoheterocyclic compound
- Ether
- Oxacycle
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic 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 | - Dej-Adisai S, Parndaeng K, Wattanapiromsakul C, Hwang JS: Three New Isoprenylated Flavones from Artocarpus chama Stem and Their Bioactivities. Molecules. 2021 Dec 21;27(1):3. doi: 10.3390/molecules27010003. [PubMed:35011235 ]
- Septama AW, Jantan I, Panichayupakaranant P: Flavonoids of Artocarpus heterophyllus Lam. heartwood inhibit the innate immune responses of human phagocytes. J Pharm Pharmacol. 2018 Sep;70(9):1242-1252. doi: 10.1111/jphp.12952. Epub 2018 Jun 25. [PubMed:29943393 ]
- Septama AW, Xiao J, Panichayupakaranant P: A synergistic effect of artocarpanone from Artocarpus heterophyllus L. (Moraceae) on the antibacterial activity of selected antibiotics and cell membrane permeability. J Intercult Ethnopharmacol. 2017 Apr 3;6(2):186-191. doi: 10.5455/jice.20170327073745. eCollection 2017 Apr-Jun. [PubMed:28512600 ]
- Nguyen HX, Nguyen NT, Nguyen MH, Le TH, Van Do TN, Hung TM, Nguyen MT: Tyrosinase inhibitory activity of flavonoids from Artocarpus heterophyllous. Chem Cent J. 2016 Jan 29;10:2. doi: 10.1186/s13065-016-0150-7. eCollection 2016. [PubMed:26834825 ]
- Dong X, Zhu Q, Dai Y, He J, Pan H, Chen J, Zheng ZP: Encapsulation artocarpanone and ascorbic acid in O/W microemulsions: Preparation, characterization, and antibrowning effects in apple juice. Food Chem. 2016 Feb 1;192:1033-40. doi: 10.1016/j.foodchem.2015.07.124. Epub 2015 Jul 28. [PubMed:26304444 ]
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