Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:12:27 UTC |
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Update date | 2020-09-17 15:36:58 UTC |
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Primary ID | FDB016478 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB 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). |
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CAS Number | 480-10-4 |
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Structure | |
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Synonyms | Synonym | 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 | 3,4',5,7-Tetrahydroxyflavone; 3-O-b-D-Glucopyranoside | db_source |
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Predicted Properties | |
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Chemical Formula | C21H20O11 |
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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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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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Isomeric 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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Average Molecular Weight | 448.3769 |
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Monoisotopic Molecular Weight | 448.100561482 |
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Classification |
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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 | Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 56.25%; H 4.50%; O 39.25% | DFC |
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Melting Point | Mp 178° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]18D +16.9 (c, 0.62 in MeOH) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Astragalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f8i-8914600000-70416132b3766fd636fb | Spectrum | Predicted GC-MS | Astragalin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0f72-4730019000-7036585c066b67f1f0ce | Spectrum | Predicted GC-MS | Astragalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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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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NMR | Not Available |
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External Links |
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ChemSpider ID | 4445311 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C12249 |
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Pubchem Compound ID | 5282102 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 319 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB37429 |
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CRC / DFC (Dictionary of Food Compounds) ID | KRH29-Q:KRH29-Q |
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EAFUS ID | Not Available |
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Dr. Duke ID | ASTRAGALIN|KAEMPFEROL-3-O-GLUCOSIDE|KAEMPFEROL-3-O-BETA-D-GLUCOSIDE|KAEMPFEROL-3-MONOGLUCOSIDE|KAEMPFEROL-3-BETA-D-GLUCOSIDE|KAEMPFEROL-3-0-GLUCOSIDE|3-O-BETA-D-KAEMPFEROL-GLUCOSIDE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00005138 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Astragalin |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Angiotensin converting enzyme inhibitor | 35457 | An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke. | DUKE | Aldose reductase inhibitor | 48550 | An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy. | DUKE | Anti HIV | 22587 | An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression. | DUKE | Anti leukemic | 35610 | An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies. | DUKE | Anti-viral | 22587 | An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19. | DUKE | Choleretic | | An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function. | DUKE | Expectorant | 52217 | An agent that thins and loosens mucus, making it easier to cough up, reducing congestion. It aids in clearing respiratory tract secretions, commonly used to relieve coughs, colds, and bronchitis, promoting easier breathing and soothing irritated airways. | DUKE | Hypotensive | | An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications. | DUKE | Immunostimulant | 50847 | An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
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