Record Information
Version1.0
Creation date2010-04-08 22:05:24 UTC
Update date2020-02-24 19:11:06 UTC
Primary IDFDB002501
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVitexin
DescriptionVitexin 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 .
CAS Number3681-93-4
Structure
Thumb
Synonyms
SynonymSource
8-b-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
8-Glucopyranosyl-4',5,7-trihydroxyflavonedb_source
8-Glucopyranosylapigenindb_source
8-Glucosylapigenindb_source
Apigenin 8-C-glucosidemanual
Orientosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility1.73 g/LALOGPS
logP0.36ALOGPS
logP-0.051ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity106.03 m³·mol⁻¹ChemAxon
Polarizability41.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H20O10
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
InChI IdentifierInChI=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
InChI KeySGEWCQFRYRRZDC-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(C(O)C(O)C1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C=C1
Average Molecular Weight432.3775
Monoisotopic Molecular Weight432.10564686
Classification
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.34%; H 4.66%; O 37.00%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -14.5 (c, 2.79 in Py)DFC
Spectroscopic UV Data336 () (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSVitexin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-003r-2500948000-9602b155e7528f818557Spectrum
Predicted GC-MSVitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-6398600000-32d47907099e4eb77fdeSpectrum
Predicted GC-MSVitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_3_19, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_4_23, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_4_25, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_4_26, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_5_17, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_5_18, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_5_19, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_6_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TBDMS_3_19, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TBDMS_4_23, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TBDMS_4_26, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, "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, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVitexin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0003900000-c85af2e6067513ff7b2a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0003900000-6f12d68683f1af09bc592021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0003900000-23a381746616792b88ef2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0910000000-97e820ce7cc99fd172be2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0194000000-fa8b33fb7f7b3d7808562021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-02ti-1930000000-677e3bacca878af047c72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-1920000000-347dc116011ee01fc9202021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0194000000-adc9deaf16dd2ff408432021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0149500000-8286f532e21c42b6dd422021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03e9-0049400000-3c2074cf667b2392d98a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0049500000-faac86d2153dcec7473a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0194000000-8f3030ecc51bfd13e8ed2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0001900000-958c99e5dd8f93cb7d842016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-4324900000-09b1bdaa3f1336b36f0a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-5194000000-bca39f308b9ddf54a00b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1011900000-a6689e1e349d5b719f2d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-045c-9256700000-24a4b43d1cb46da46b7d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mp-9262000000-72d91a652228e0bd5d482016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000900000-509ee28ef47ce2bd195a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000900000-509ee28ef47ce2bd195a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-0609600000-594b0f20ae3ffca5241a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-96b50b9840c4a64e416b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000900000-9eea965addbce350e5032021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-0925200000-f5f9c91aef959bf58e002021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID262
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCMC90-K:CMC90-K
EAFUS IDNot Available
Dr. Duke IDVITEXIN
BIGG IDNot Available
KNApSAcK IDC00001110
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Angiotensin converting enzyme inhibitor35457 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 inhibitor48550 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-arrhythmic38070 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-bradiquinicAn 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 dermatitic50177 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 histaminic37956 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-inflammatory35472 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-oxidant22586 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-serotoninic48278 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-thyroidAn agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease.DUKE
Aphidifuge25944 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 inhibitor23924 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 preventive35610 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
GoitrogenicA 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
HypotensiveAn 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 inhibitor23924 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 inhibitor50427 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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.