| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-27 23:57:57 UTC |
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| Updated at | 2022-04-27 23:57:57 UTC |
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| NP-MRD ID | NP0053232 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (E)-6-(3,7-dimethyl-2,6-octadienyl)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one |
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| Description | Macarangin belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position. Thus, macarangin is considered to be a flavonoid. Macarangin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (E)-6-(3,7-dimethyl-2,6-octadienyl)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one is found in Macaranga denticulata , Macaranga vedeliana and Monotes africanus. (E)-6-(3,7-dimethyl-2,6-octadienyl)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one was first documented in 2010 (PMID: 20079813). Based on a literature review a small amount of articles have been published on macarangin (PMID: 26791751) (PMID: 29194388) (PMID: 26662866). |
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| Structure | CC(C)=CCC\C(C)=C\CC1=C(O)C=C2OC(=C(O)C(=O)C2=C1O)C1=CC=C(O)C=C1 InChI=1S/C25H26O6/c1-14(2)5-4-6-15(3)7-12-18-19(27)13-20-21(22(18)28)23(29)24(30)25(31-20)16-8-10-17(26)11-9-16/h5,7-11,13,26-28,30H,4,6,12H2,1-3H3/b15-7+ |
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| Synonyms | | Value | Source |
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| 6-(3,7-Dimethylocta-2,6-dienyl)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one | ChEBI |
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| Chemical Formula | C25H26O6 |
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| Average Mass | 422.4770 Da |
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| Monoisotopic Mass | 422.17294 Da |
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| IUPAC Name | 6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one |
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| Traditional Name | macarangin |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)=CCC\C(C)=C\CC1=C(O)C=C2OC(=C(O)C(=O)C2=C1O)C1=CC=C(O)C=C1 |
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| InChI Identifier | InChI=1S/C25H26O6/c1-14(2)5-4-6-15(3)7-12-18-19(27)13-20-21(22(18)28)23(29)24(30)25(31-20)16-8-10-17(26)11-9-16/h5,7-11,13,26-28,30H,4,6,12H2,1-3H3/b15-7+ |
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| InChI Key | MBIJQAHZUBUPNM-VIZOYTHASA-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 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position. |
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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 | Flavones |
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| Direct Parent | 6-prenylated flavones |
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| Alternative Parents | |
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| Substituents | - 6-prenylated flavone
- 3-hydroxyflavone
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- Hydroxyflavonoid
- 7-hydroxyflavonoid
- Chromone
- Bicyclic monoterpenoid
- Monoterpenoid
- Benzopyran
- 1-benzopyran
- Aromatic monoterpenoid
- Pyranone
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- 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 | - Zhang LB, Lei C, Gao LX, Li JY, Li J, Hou AJ: Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata. Nat Prod Bioprospect. 2016 Feb;6(1):25-30. doi: 10.1007/s13659-015-0082-2. Epub 2016 Jan 20. [PubMed:26791751 ]
- Hasanat A, Chowdhury TA, Kabir MSH, Chowdhury MS, Chy MNU, Barua J, Chakrabarty N, Paul A: Antinociceptive Activity of Macaranga denticulata Muell. Arg. (Family: Euphorbiaceae): In Vivo and In Silico Studies. Medicines (Basel). 2017 Dec 1;4(4). pii: medicines4040088. doi: 10.3390/medicines4040088. [PubMed:29194388 ]
- Omar RM, Igoli J, Gray AI, Ebiloma GU, Clements C, Fearnley J, Ebel RA, Zhang T, De Koning HP, Watson DG: Chemical characterisation of Nigerian red propolis and its biological activity against Trypanosoma Brucei. Phytochem Anal. 2016 Mar-Apr;27(2):107-15. doi: 10.1002/pca.2605. Epub 2015 Dec 11. [PubMed:26662866 ]
- Petrova A, Popova M, Kuzmanova C, Tsvetkova I, Naydenski H, Muli E, Bankova V: New biologically active compounds from Kenyan propolis. Fitoterapia. 2010 Sep;81(6):509-14. doi: 10.1016/j.fitote.2010.01.007. Epub 2010 Jan 15. [PubMed:20079813 ]
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