Record Information |
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Version | 1.0 |
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Created at | 2022-06-29 17:30:30 UTC |
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Updated at | 2022-06-29 17:30:30 UTC |
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NP-MRD ID | NP0138459 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Homopterocarpin |
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Description | Homopterocarpin belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Homopterocarpin is found in Ononis natrix, Ononis viscosa, Platymiscium floribundum and Pterocarpus macrocarpus. It was first documented in 2018 (PMID: 30174522). Based on a literature review a significant number of articles have been published on Homopterocarpin (PMID: 32555159) (PMID: 32495561) (PMID: 35736133) (PMID: 35722767). |
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Structure | COC1=CC2=C(C=C1)[C@@H]1COC3=C(C=CC(OC)=C3)[C@@H]1O2 InChI=1S/C17H16O4/c1-18-10-4-6-13-15(7-10)20-9-14-12-5-3-11(19-2)8-16(12)21-17(13)14/h3-8,14,17H,9H2,1-2H3/t14-,17-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C17H16O4 |
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Average Mass | 284.3110 Da |
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Monoisotopic Mass | 284.10486 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 606-91-7 |
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SMILES | COC1=CC2=C(C=C1)[C@@H]1COC3=C(C=CC(OC)=C3)[C@@H]1O2 |
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InChI Identifier | InChI=1S/C17H16O4/c1-18-10-4-6-13-15(7-10)20-9-14-12-5-3-11(19-2)8-16(12)21-17(13)14/h3-8,14,17H,9H2,1-2H3/t14-,17-/m0/s1 |
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InChI Key | VPGIGLKLCFOWDN-YOEHRIQHSA-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 pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Isoflavonoids |
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Sub Class | Furanoisoflavonoids |
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Direct Parent | Pterocarpans |
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Alternative Parents | |
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Substituents | - Pterocarpan
- Isoflavanol
- Isoflavan
- Chromane
- 1-benzopyran
- Benzopyran
- Coumaran
- Benzofuran
- Anisole
- Alkyl aryl ether
- Benzenoid
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen 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 | - Ciesielski P, Metz P: Asymmetric one-pot transformation of isoflavones to pterocarpans and its application in phytoalexin synthesis. Nat Commun. 2020 Jun 18;11(1):3091. doi: 10.1038/s41467-020-16933-y. [PubMed:32555159 ]
- Zhu MM, Wang H, Mi CN, Mei WL, Gai CJ, Dai HF, Yu M, Wu XQ, Wang H: [A new cytotoxic isoflavane from Dalbergiae Odoriferae Lignum]. Zhongguo Zhong Yao Za Zhi. 2020 May;45(9):2122-2129. doi: 10.19540/j.cnki.cjcmm.20200107.202. [PubMed:32495561 ]
- Chen J, Ge S, Liu Z, Zhang D, Peng W: GC-MS explores health care components in the extract of Pterocarpus Macarocarpus Kurz. Saudi J Biol Sci. 2018 Sep;25(6):1196-1201. doi: 10.1016/j.sjbs.2017.12.013. Epub 2018 Jan 11. [PubMed:30174522 ]
- Kwiecinski JM, Jelani DA, Fuentes EJ, Horswill AR: Therapeutic Inhibition of Staphylococcus aureus ArlRS Two-Component Regulatory System Blocks Virulence. Antimicrob Agents Chemother. 2022 Jul 19;66(7):e0018722. doi: 10.1128/aac.00187-22. Epub 2022 Jun 23. [PubMed:35736133 ]
- Ajaegbu EE, Eboka CJ, Okoye FBC, Proksch P: Cytotoxic effect and antioxidant activity of pterocarpans from Millettia aboensis root. Nat Prod Res. 2023 Mar;37(5):829-834. doi: 10.1080/14786419.2022.2089984. Epub 2022 Jun 18. [PubMed:35722767 ]
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