| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-09 21:27:30 UTC |
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| Updated at | 2022-09-09 21:27:30 UTC |
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| NP-MRD ID | NP0290669 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (2r)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one |
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| Description | 4',5-Dihydroxy-7-methoxyflavanone 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. (2r)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one is found in Artemisia campestris. (2r)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one was first documented in 2005 (PMID: 15797607). Based on a literature review a small amount of articles have been published on 4',5-Dihydroxy-7-methoxyflavanone (PMID: 26411007) (PMID: 25375331). |
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| Structure | COC1=CC(O)=C2C(=O)C[C@@H](OC2=C1)C1=CC=C(O)C=C1 InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C16H14O5 |
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| Average Mass | 286.2830 Da |
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| Monoisotopic Mass | 286.08412 Da |
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| IUPAC Name | (2R)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one |
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| Traditional Name | (2R)-5-hydroxy-2-(4-hydroxyphenyl)-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=C1 |
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| InChI Identifier | InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m1/s1 |
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| InChI Key | DJOJDHGQRNZXQQ-CQSZACIVSA-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 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
- Flavanone
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- Hydroxyflavonoid
- Flavan
- Chromone
- Benzopyran
- Chromane
- 1-benzopyran
- Anisole
- Aryl alkyl ketone
- Aryl ketone
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Vinylogous acid
- Ketone
- Organoheterocyclic compound
- Oxacycle
- Ether
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- 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 | - Ticha LA, Klaasen JA, Green IR, Naidoo S, Baker B, Pietersen RD: Phytochemical and Antimicrobial Screening of Flavanones and Chalcones from Galenia africana and Dicerothamnus rhinocerotis. Nat Prod Commun. 2015 Jul;10(7):1185-90. [PubMed:26411007 ]
- Nobakht M, Grkovic T, Trueman SJ, Wallace HM, Katouli M, Quinn RJ, Brooks PR: Chemical constituents of kino extract from Corymbia torelliana. Molecules. 2014 Nov 4;19(11):17862-71. doi: 10.3390/molecules191117862. [PubMed:25375331 ]
- Lambert JD, Sang S, Dougherty A, Caldwell CG, Meyers RO, Dorr RT, Timmermann BN: Cytotoxic lignans from Larrea tridentata. Phytochemistry. 2005 Apr;66(7):811-5. doi: 10.1016/j.phytochem.2005.02.007. [PubMed:15797607 ]
- LOTUS database [Link]
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