Record Information |
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Version | 1.0 |
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Created at | 2022-04-27 21:58:51 UTC |
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Updated at | 2022-04-27 21:58:51 UTC |
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NP-MRD ID | NP0050606 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Agathisflavone |
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Description | Agathisflavone, also known as 6,8''-biapigenin, 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''. Thus, agathisflavone is considered to be a flavonoid lipid molecule. A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-6 and C-8 of the two chromene rings. Agathisflavone is found in Agathis dammara, Agathis palmerstoni, Araucaria bidwillii , Bauhinia vahlii , Campylospermum flavum, Campylospermum sulcatum, Canarium manii, Garcinia xanthochymus , Juniperus virginiana, Orthopterygium huaucui, Ouratea sulcata, Picea smithiana, Rhus coriaria, Rhus punjabensis, Rhus succedanea , Schinus terebinthifolia and Toxicodendron succedaneum. It was first documented in 1992 (PMID: 1484886). Agathisflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 21106357) (PMID: 21281018) (PMID: 21594945). |
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Structure | OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(=C(O)C=C2O1)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C=C1 InChI=1S/C30H18O10/c31-15-5-1-13(2-6-15)22-11-20(36)26-24(39-22)12-21(37)27(29(26)38)28-18(34)9-17(33)25-19(35)10-23(40-30(25)28)14-3-7-16(32)8-4-14/h1-12,31-34,37-38H |
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Synonyms | Value | Source |
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5,5',7,7'-Tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-(6,8'-bi-4H-1-benzopyran)-4,4'-dione | ChEBI | 6,8''-Biapigenin | ChEBI | 7''-Methyl-agathisflavone | MeSH |
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Chemical Formula | C30H18O10 |
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Average Mass | 538.4640 Da |
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Monoisotopic Mass | 538.09000 Da |
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IUPAC Name | 6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one |
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Traditional Name | agathisflavone |
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CAS Registry Number | Not Available |
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SMILES | OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(=C(O)C=C2O1)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C30H18O10/c31-15-5-1-13(2-6-15)22-11-20(36)26-24(39-22)12-21(37)27(29(26)38)28-18(34)9-17(33)25-19(35)10-23(40-30(25)28)14-3-7-16(32)8-4-14/h1-12,31-34,37-38H |
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InChI Key | BACLASYRJRZXMY-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | 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
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Chromone
- Benzopyran
- 1-benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Organoheterocyclic compound
- Oxacycle
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- 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 | - Anand KK, Gupta VN, Rangari V, Singh B, Chandan BK: Structure and hepatoprotective activity of a biflavonoid from Canarium manii. Planta Med. 1992 Dec;58(6):493-5. doi: 10.1055/s-2006-961533. [PubMed:1484886 ]
- Konan NA, Lincopan N, Diaz IE, de Fatima Jacysyn J, Tiba MM, Amarante Mendes JG, Bacchi EM, Spira B: Cytotoxicity of cashew flavonoids towards malignant cell lines. Exp Toxicol Pathol. 2012 Jul;64(5):435-40. doi: 10.1016/j.etp.2010.10.010. Epub 2010 Nov 23. [PubMed:21106357 ]
- Paulsen BS, Souza CS, Chicaybam L, Bonamino MH, Bahia M, Costa SL, Borges HL, Rehen SK: Agathisflavone enhances retinoic acid-induced neurogenesis and its receptors alpha and beta in pluripotent stem cells. Stem Cells Dev. 2011 Oct;20(10):1711-21. doi: 10.1089/scd.2010.0446. Epub 2011 Mar 18. [PubMed:21281018 ]
- Njock GB, Bartholomeusz TA, Foroozandeh M, Pegnyemb DE, Christen P, Jeannerat D: NASCA-HMBC, a new NMR methodology for the resolution of severely overlapping signals: application to the study of agathisflavone. Phytochem Anal. 2012 Mar-Apr;23(2):126-30. doi: 10.1002/pca.1333. Epub 2011 May 19. [PubMed:21594945 ]
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