Record Information |
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Version | 2.0 |
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Created at | 2022-09-05 05:17:57 UTC |
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Updated at | 2022-09-05 05:17:58 UTC |
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NP-MRD ID | NP0208339 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one |
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Description | (+-)-Fukugiside belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Garcinia multiflora and Garcinia xanthochymus. It was first documented in 2016 (PMID: 30508346). Based on a literature review a significant number of articles have been published on (+-)-Fukugiside (PMID: 30052177) (PMID: 29229355) (PMID: 28824646) (PMID: 28163970). |
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Structure | OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2C2C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C36H30O16/c37-12-25-30(45)32(47)33(48)36(52-25)51-24-11-21(44)26-20(43)10-22(14-3-6-17(40)18(41)7-14)49-35(26)28(24)29-31(46)27-19(42)8-16(39)9-23(27)50-34(29)13-1-4-15(38)5-2-13/h1-11,25,29-30,32-34,36-42,44-45,47-48H,12H2/t25-,29?,30-,32+,33-,34?,36-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C36H30O16 |
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Average Mass | 718.6200 Da |
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Monoisotopic Mass | 718.15338 Da |
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IUPAC Name | 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one |
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Traditional Name | 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2C2C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C36H30O16/c37-12-25-30(45)32(47)33(48)36(52-25)51-24-11-21(44)26-20(43)10-22(14-3-6-17(40)18(41)7-14)49-35(26)28(24)29-31(46)27-19(42)8-16(39)9-23(27)50-34(29)13-1-4-15(38)5-2-13/h1-11,25,29-30,32-34,36-42,44-45,47-48H,12H2/t25-,29?,30-,32+,33-,34?,36-/m1/s1 |
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InChI Key | XUDCXSSDAZIAPT-YWYCBELZSA-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 biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. |
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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 | Biflavonoids and polyflavonoids |
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Direct Parent | Biflavonoids and polyflavonoids |
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Alternative Parents | |
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Substituents | - Bi- and polyflavonoid skeleton
- Stilbene glycoside
- Flavonoid-7-o-glycoside
- Flavonoid o-glycoside
- Pyranoisoflavonoid
- Hydroxyflavonoid
- Flavanone
- Isoflavanone
- 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- Hydroxyisoflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Isoflavonoid skeleton
- Isoflavan
- Flavan
- Isoflavonoid
- Phenolic glycoside
- Stilbene
- Hexose monosaccharide
- Chromone
- O-glycosyl compound
- Glycosyl compound
- 1-benzopyran
- Benzopyran
- Chromane
- Aryl ketone
- Aryl alkyl ketone
- Catechol
- Pyranone
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Benzenoid
- Pyran
- Oxane
- Monosaccharide
- Vinylogous acid
- Heteroaromatic compound
- Secondary alcohol
- Ketone
- Ether
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Acetal
- Primary alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- 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 | - Nandu TG, Subramenium GA, Shiburaj S, Viszwapriya D, Iyer PM, Balamurugan K, Rameshkumar KB, Karutha Pandian S: Fukugiside, a biflavonoid from Garcinia travancorica inhibits biofilm formation of Streptococcus pyogenes and its associated virulence factors. J Med Microbiol. 2018 Sep;67(9):1391-1401. doi: 10.1099/jmm.0.000799. Epub 2018 Jul 27. [PubMed:30052177 ]
- Sabogal-Guaqueta AM, Carrillo-Hormaza L, Osorio E, Cardona-Gomez GP: Effects of biflavonoids from Garcinia madruno on a triple transgenic mouse model of Alzheimer's disease. Pharmacol Res. 2018 Mar;129:128-138. doi: 10.1016/j.phrs.2017.12.002. Epub 2017 Dec 8. [PubMed:29229355 ]
- Tabares-Guevara JH, Lara-Guzman OJ, Londono-Londono JA, Sierra JA, Leon-Varela YM, Alvarez-Quintero RM, Osorio EJ, Ramirez-Pineda JR: Natural Biflavonoids Modulate Macrophage-Oxidized LDL Interaction In Vitro and Promote Atheroprotection In Vivo. Front Immunol. 2017 Aug 4;8:923. doi: 10.3389/fimmu.2017.00923. eCollection 2017. [PubMed:28824646 ]
- Inoue T, Kainuma M, Baba K, Oshiro N, Kimura N, Chan EW: Garcinia subelliptica Merr. (Fukugi): A multipurpose coastal tree with promising medicinal properties. J Intercult Ethnopharmacol. 2017 Jan 3;6(1):121-127. doi: 10.5455/jice.20161229060034. eCollection 2017 Jan-Mar. [PubMed:28163970 ]
- Aravind APA, Pandey R, Kumar B, Asha KRT, Rameshkumar KB: Phytochemical Screening of Garcinia travancorica by HPLC-ESI-QTOF Mass Spectrometry and Cytotoxicity Studies of the Major Biflavonoid Fukugiside. Nat Prod Commun. 2016 Dec;11(12):1839-1842. [PubMed:30508346 ]
- LOTUS database [Link]
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