Record Information |
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Version | 1.0 |
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Created at | 2021-06-21 00:25:41 UTC |
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Updated at | 2021-06-30 00:18:13 UTC |
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NP-MRD ID | NP0042870 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2S)-3'-formyl-4',5,7-trihydroxyflavanone |
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Provided By | JEOL Database![JEOL Logo](/attributions/jeol_logo.png) |
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Description | (S)-3'-Formyl-4',5,7-trihydroxyflavanone belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. (2S)-3'-formyl-4',5,7-trihydroxyflavanone is found in Feroniella lucida. It was first documented in 2015 (PMID: 26411007). Based on a literature review a significant number of articles have been published on (S)-3'-Formyl-4',5,7-trihydroxyflavanone (PMID: 33011529) (PMID: 30884485) (PMID: 28075580) (PMID: 26721195). |
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Structure | [H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C(C([H])=O)=C(O[H])C([H])=C3[H])C([H])([H])C2=O)=C1[H] InChI=1S/C16H12O6/c17-7-9-3-8(1-2-11(9)19)14-6-13(21)16-12(20)4-10(18)5-15(16)22-14/h1-5,7,14,18-20H,6H2/t14-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C16H12O6 |
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Average Mass | 300.2660 Da |
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Monoisotopic Mass | 300.06339 Da |
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IUPAC Name | 5-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-2-hydroxybenzaldehyde |
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Traditional Name | 5-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-2-hydroxybenzaldehyde |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C(C([H])=O)=C(O[H])C([H])=C3[H])C([H])([H])C2=O)=C1[H] |
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InChI Identifier | InChI=1S/C16H12O6/c17-7-9-3-8(1-2-11(9)19)14-6-13(21)16-12(20)4-10(18)5-15(16)22-14/h1-5,7,14,18-20H,6H2/t14-/m0/s1 |
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InChI Key | DOFLNDASWRCTNW-AWEZNQCLSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| 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, 100 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, chcl3, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, chcl3, 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 | Species Name | Source | Reference |
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Feroniella lucida | JEOL database | - Sriyatep, T., et al. J. Tetrahedron 70, 1458 (2014)
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. |
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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 | Flavans |
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Direct Parent | Flavanones |
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Alternative Parents | |
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Substituents | - 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavanone
- Hydroxyflavonoid
- Chromone
- Benzopyran
- Chromane
- 1-benzopyran
- Hydroxybenzaldehyde
- Aryl ketone
- Benzaldehyde
- Benzoyl
- Aryl alkyl ketone
- Aryl-aldehyde
- Phenol
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organic oxygen compound
- Aldehyde
- Organic oxide
- Organooxygen compound
- Hydrocarbon derivative
- 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 | - Hu Z, Wu Z, Su Q, Li M, Wu S, Meng R, Ding W, Li C: Metabolites with phytopathogenic fungi inhibitory activities from the mangrove endophytic fungus Botryosphaeria ramose. Bioorg Chem. 2020 Nov;104:104300. doi: 10.1016/j.bioorg.2020.104300. Epub 2020 Sep 22. [PubMed:33011529 ]
- Subramanian M, Thotakura B, Chandra Sekaran SP, Jyothi AK, Sundaramurthi I: Naringin (4',5,7-Trihydroxyflavanone 7-Rhamnoglucoside) Attenuates beta-Cell Dysfunction in Diabetic Rats through Upregulation of PDX-1. Cells Tissues Organs. 2018;206(3):133-143. doi: 10.1159/000496506. Epub 2019 Mar 18. [PubMed:30884485 ]
- Muharini R, Diaz A, Ebrahim W, Mandi A, Kurtan T, Rehberg N, Kalscheuer R, Hartmann R, Orfali RS, Lin W, Liu Z, Proksch P: Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits of Amorpha fruticosa. J Nat Prod. 2017 Jan 27;80(1):169-180. doi: 10.1021/acs.jnatprod.6b00809. Epub 2017 Jan 11. [PubMed:28075580 ]
- Aroui S, Aouey B, Chtourou Y, Meunier AC, Fetoui H, Kenani A: Naringin suppresses cell metastasis and the expression of matrix metalloproteinases (MMP-2 and MMP-9) via the inhibition of ERK-P38-JNK signaling pathway in human glioblastoma. Chem Biol Interact. 2016 Jan 25;244:195-203. doi: 10.1016/j.cbi.2015.12.011. Epub 2015 Dec 22. [PubMed:26721195 ]
- 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 ]
- Sriyatep, T., et al. (2014). Sriyatep, T., et al. J. Tetrahedron 70, 1458 (2014). J. Tetrahedron.
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