Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:24 UTC |
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Update date | 2020-02-24 19:11:06 UTC |
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Primary ID | FDB002501 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Vitexin |
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Description | Vitexin is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vitexin can be found in a number of food items such as flaxseed, prairie turnip, mung bean, and tree fern, which makes vitexin a potential biomarker for the consumption of these food products. Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves, in the pearl millet (Pennisetum millet), and in Hawthorn . |
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CAS Number | 3681-93-4 |
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Structure | |
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Synonyms | Synonym | Source |
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8-b-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CI | db_source | 8-Glucopyranosyl-4',5,7-trihydroxyflavone | db_source | 8-Glucopyranosylapigenin | db_source | 8-Glucosylapigenin | db_source | Apigenin 8-C-glucoside | manual | Orientoside | db_source |
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Predicted Properties | |
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Chemical Formula | C21H20O10 |
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IUPAC name | 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one |
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InChI Identifier | InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2 |
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InChI Key | SGEWCQFRYRRZDC-UHFFFAOYSA-N |
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Isomeric SMILES | OCC1OC(C(O)C(O)C1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C=C1 |
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Average Molecular Weight | 432.3775 |
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Monoisotopic Molecular Weight | 432.10564686 |
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Classification |
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Description | Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. |
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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 8-C-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-8-c-glycoside
- Hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Phenolic glycoside
- Hexose monosaccharide
- Glycosyl compound
- C-glycosyl compound
- Chromone
- 1-benzopyran
- Benzopyran
- Pyranone
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Pyran
- Monosaccharide
- Monocyclic benzene moiety
- Benzenoid
- Oxane
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Ether
- Dialkyl ether
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Primary alcohol
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- 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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Ontology |
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Disposition | Source: |
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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 58.34%; H 4.66%; O 37.00% | DFC |
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Melting Point | Not Available | |
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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]20D -14.5 (c, 2.79 in Py) | DFC |
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Spectroscopic UV Data | 336 () (MeOH) | DFC |
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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 | Vitexin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-003r-2500948000-9602b155e7528f818557 | Spectrum | Predicted GC-MS | Vitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0089-6398600000-32d47907099e4eb77fde | Spectrum | Predicted GC-MS | Vitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_3_19, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_4_23, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_4_25, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_4_26, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_5_17, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_5_18, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_5_19, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_6_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TBDMS_3_19, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TBDMS_4_23, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TBDMS_4_26, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, "5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one,3TMS,#19" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vitexin, TMS_2_1, 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 - 6V, Positive | splash10-001i-0003900000-c85af2e6067513ff7b2a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-001i-0003900000-6f12d68683f1af09bc59 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-001i-0003900000-23a381746616792b88ef | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-014i-0910000000-97e820ce7cc99fd172be | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-01q9-0194000000-fa8b33fb7f7b3d780856 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-02ti-1930000000-677e3bacca878af047c7 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-014i-1920000000-347dc116011ee01fc920 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-01q9-0194000000-adc9deaf16dd2ff40843 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-01q9-0149500000-8286f532e21c42b6dd42 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-03e9-0049400000-3c2074cf667b2392d98a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-01q9-0049500000-faac86d2153dcec7473a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 6V, Positive | splash10-01q9-0194000000-8f3030ecc51bfd13e8ed | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lr-0001900000-958c99e5dd8f93cb7d84 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-015a-4324900000-09b1bdaa3f1336b36f0a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000t-5194000000-bca39f308b9ddf54a00b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-1011900000-a6689e1e349d5b719f2d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-045c-9256700000-24a4b43d1cb46da46b7d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05mp-9262000000-72d91a652228e0bd5d48 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0000900000-509ee28ef47ce2bd195a | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0000900000-509ee28ef47ce2bd195a | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0159-0609600000-594b0f20ae3ffca5241a | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000900000-96b50b9840c4a64e416b | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0000900000-9eea965addbce350e503 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0bt9-0925200000-f5f9c91aef959bf58e00 | 2021-09-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 262 |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | CMC90-K:CMC90-K |
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EAFUS ID | Not Available |
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Dr. Duke ID | VITEXIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001110 |
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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 | Not Available |
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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-arrhythmic | 38070 | An agent that regulates heart rhythm, correcting irregular heartbeat patterns. Therapeutically, it restores normal cardiac function, commonly used to manage arrhythmias, prevent sudden cardiac death, and treat conditions like atrial fibrillation and ventricular tachycardia. | DUKE | Anti-bradiquinic | | An agent that inhibits bradykinin, reducing inflammation and pain. Therapeutically, it's used to treat conditions like hereditary angioedema, and has potential applications in managing pain, inflammation, and allergic reactions. | DUKE | Anti dermatitic | 50177 | An agent that reduces skin inflammation and irritation, commonly used to treat dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and swelling. | DUKE | Anti histaminic | 37956 | An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis. | DUKE | Anti-inflammatory | 35472 | An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti-serotoninic | 48278 | An agent that blocks the activity of serotonin, a neurotransmitter involved in mood regulation. It reduces serotonin's effects, commonly used in managing schizophrenia, anxiety disorders, and nausea, as well as treating migraine headaches and irritable bowel syndrome. | DUKE | Anti-thyroid | | An agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease. | DUKE | Aphidifuge | 25944 | An agent that repels aphids, used in agriculture to protect plants. Biologically, it disrupts aphid feeding and reproduction. Therapeutically, it has been explored for its potential insecticidal and antiparasitic properties, with possible applications in managing insect-borne diseases and parasitic infections. | DUKE | cAMP-phosphodiesterase inhibitor | 23924 | An agent that blocks the breakdown of cyclic adenosine monophosphate (cAMP), increasing its levels and enhancing cellular signaling. Therapeutically, it is used to treat respiratory diseases such as asthma and chronic obstructive pulmonary disease (COPD), as well as certain cardiovascular conditions. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | Goitrogenic | | A substance that interferes with thyroid hormone production by blocking iodine uptake, leading to increased TSH release and potential goiter formation, with therapeutic applications in managing hyperthyroidism and certain thyroid disorders. | 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 | Thyroid-peroxidase inhibitor | 23924 | An agent that blocks the activity of thyroid peroxidase, an enzyme crucial for thyroid hormone production. It reduces thyroid hormone synthesis, commonly used to treat hyperthyroidism, particularly in conditions like Graves' disease, and to manage thyroid storm. | DUKE | Platelet aggregation inhibitor | 50427 | An agent that prevents platelets from clumping, reducing blood clot formation. It plays a biological role in preventing thrombosis and is therapeutically used to manage cardiovascular diseases, such as myocardial infarction, stroke, and peripheral artery disease. | CHEBI |
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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