Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:57:20 UTC |
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Updated at | 2020-12-07 19:07:46 UTC |
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CannabisDB ID | CDB000793 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Astragalin |
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Description | Kaempferol 3-O-beta-D-glucoside also known as astragalin, is a kaempferol O-glucoside in which the glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage. Astragalin has been isolated from many different plants and plant families including members of the Fabaceae, Convolvulaceae, Ebenaceae, Rosaceae and Eucommiaceae families. This compound is well known for its diverse pharmacological applications such as anti-inflammatory, antioxidant, neuroprotective, cardioprotective, antiobesity, antiosteoporotic, anticancer, antiulcer, and antidiabetic properties (PMID: 29853868 ). It appears to carry out these activities by the regulation and modulation of various molecular targets such as transcription factors (NF-κB, TNF-α, and TGF-β1), enzymes (iNOS, COX-2, PGE2, MMP-1, MMP-3, MIP-1α, COX-2, PGE-2, HK2, AChe, SOD, DRP-1, DDH, PLCŒ≥1, and GPX), kinases (JNK, MAPK, Akt, ERK, SAPK, IκBα, PI3K, and PKCβ2), cell adhesion proteins (E-cadherin, vimentin PAR-2, and NCam), apoptotic and antiapoptotic proteins (Beclin-1, Bcl-2, Bax, Bcl-xL, cytochrome c, LC3A/B, caspase-3, caspase-9, procaspase-3, procaspase-8, and IgE), and inflammatory cytokines (SOCS-3, SOCS-5, IL-1β, IL-4, IL-6, IL-8, IL-13, MCP-1, CXCL-1, CXCL-2, and IFN-γ) (PMID: 29853868 ). Astragalin was first identified in cold-pressed cannabis seed oil in 2016. (PMID: 27076277 ). |
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Structure | |
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Synonyms | Value | Source |
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3,4',5,7-Tetrahydroxyflavone-3-glucoside | ChEBI | 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranoside | ChEBI | Astragaline | ChEBI | Kaempferol 3-O-glucoside | ChEBI | Kaempferol-3-O-beta-glucopyranoside | ChEBI | Kaempferol 3-O-beta-D-glucoside | Kegg | 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl b-D-glucopyranoside | Generator | 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl β-D-glucopyranoside | Generator | Kaempferol-3-O-b-glucopyranoside | Generator | Kaempferol-3-O-β-glucopyranoside | Generator | Kaempferol 3-O-b-D-glucoside | Generator | Kaempferol 3-O-β-D-glucoside | Generator | Kaempferol 3-O-beta-D-glucopyranoside | MeSH | Astragalin | ChEBI | 3,4',5,7-Tetrahydroxyflavone | HMDB | 3-O-b-D-Glucopyranoside | HMDB | 3-O-b-D-Glucopyranosyloxy-4',5,7-trihydroxyflavone | HMDB | Asragalin | HMDB | Kaempferol 3-glucoside | HMDB | Kaempferol-3-beta-glucopyranoside | HMDB | Kaempferol-3-beta-monoglucoside | HMDB | Kaempferol-3-D-glucoside | HMDB | Kaempferol-3-glucoside | HMDB | Kaempferol-3-O-glucoside | HMDB | 3-Glucosylkaempferol | PhytoBank | 4',5,7-Trihydroxyflavone 3-beta-D-glucopyranoside | PhytoBank | 4',5,7-Trihydroxyflavone 3-β-D-glucopyranoside | PhytoBank | 4’,5,7-Trihydroxyflavone 3-β-D-glucopyranoside | PhytoBank | Kaemferol 3-O-glucopyranoside | PhytoBank | Kaempferol 3-O-glucopyranoside | PhytoBank | Kaempferol 3-O-β-D-glucopyranoside | PhytoBank | Kaempferol 3-O-beta-glucoside | PhytoBank | Kaempferol 3-O-β-glucoside | PhytoBank | Kaempferol 3-beta-D-glucopyranoside | PhytoBank | Kaempferol 3-β-D-glucopyranoside | PhytoBank | Kaempferol 3-beta-D-glucoside | PhytoBank | Kaempferol 3-β-D-glucoside | PhytoBank | Kaempherol 3-O-beta-D-glucopyranoside | PhytoBank | Kaempherol 3-O-β-D-glucopyranoside | PhytoBank |
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Chemical Formula | C21H20O11 |
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Average Molecular Weight | 448.38 |
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Monoisotopic Molecular Weight | 448.1006 |
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IUPAC Name | 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(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 | astragalin |
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CAS Registry Number | 480-10-4 |
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SMILES | OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21+/m1/s1 |
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InChI Key | JPUKWEQWGBDDQB-QSOFNFLRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-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 | Flavonoid glycosides |
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Direct Parent | Flavonoid-3-O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-3-o-glycoside
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Hexose monosaccharide
- Chromone
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Pyran
- Monocyclic benzene moiety
- Oxane
- Monosaccharide
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Primary alcohol
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 178 °C | 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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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0iki-0930000000-20176d350f94ae4a84ed | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0002-0020900000-182256be3fac5a878f1b | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-001i-0090100000-7bd32a5c1969c5a248ac | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0560-0090000000-1c2e7f81b693e6297183 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-0a6r-0090000000-364026dfdcefd0d2e3a9 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0002-0000900030-4139a6b8a2e916a0ea74 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0002-0000900000-b3cdd88343725a79c5e0 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0002-0000900010-9834ce03ded5a1fe8c48 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0002-0020900000-182256be3fac5a878f1b | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-001i-0090100000-7bd32a5c1969c5a248ac | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-0560-0090000000-1c2e7f81b693e6297183 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-0a6r-0090000000-364026dfdcefd0d2e3a9 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0002-0000900030-4139a6b8a2e916a0ea74 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-052b-0090400000-98b6bb6a62f4d8812fde | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0020900010-4e6aa6edffb0c4b2f832 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a59-0090000000-94e191a13790b3b49952 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-0000900000-1c8fa629cb5881a42933 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-055b-0090200000-269c7f2460a6f35009c8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a7i-0090000000-d43f3a3dfafef985b9ef | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000j-0190800000-d3b297eb0fe481caa10a | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0190000000-1e520254d0769f8f845e | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05n0-3590000000-7f6360b543570fc55716 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000b-1151900000-879fdf0c200d1a8caf5b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1190200000-8b8be60a1a225937d8d8 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-3590000000-22efe60043282fcdf379 | 2016-08-03 | View Spectrum |
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General References | - Riaz A, Rasul A, Hussain G, Zahoor MK, Jabeen F, Subhani Z, Younis T, Ali M, Sarfraz I, Selamoglu Z: Astragalin: A Bioactive Phytochemical with Potential Therapeutic Activities. Adv Pharmacol Sci. 2018 May 2;2018:9794625. doi: 10.1155/2018/9794625. eCollection 2018. [PubMed:29853868 ]
- Smeriglio A, Galati EM, Monforte MT, Lanuzza F, D'Angelo V, Circosta C: Polyphenolic Compounds and Antioxidant Activity of Cold-Pressed Seed Oil from Finola Cultivar of Cannabis sativa L. Phytother Res. 2016 Aug;30(8):1298-307. doi: 10.1002/ptr.5623. Epub 2016 Apr 14. [PubMed:27076277 ]
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