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Showing Compound Vitexin (FDB002501)

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
MOLSDFPDBSMILESInChI
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 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 3-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0003900000-c85af2e6067513ff7b2aSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0003900000-6f12d68683f1af09bc59Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0003900000-23a381746616792b88efSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0910000000-97e820ce7cc99fd172beSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0194000000-fa8b33fb7f7b3d780856Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-02ti-1930000000-677e3bacca878af047c7Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-1920000000-347dc116011ee01fc920Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0194000000-adc9deaf16dd2ff40843Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0149500000-8286f532e21c42b6dd42Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03e9-0049400000-3c2074cf667b2392d98aSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0049500000-faac86d2153dcec7473aSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01q9-0194000000-8f3030ecc51bfd13e8edSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0001900000-958c99e5dd8f93cb7d84Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-4324900000-09b1bdaa3f1336b36f0aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-5194000000-bca39f308b9ddf54a00bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1011900000-a6689e1e349d5b719f2dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-045c-9256700000-24a4b43d1cb46da46b7dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mp-9262000000-72d91a652228e0bd5d48Spectrum
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 EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bradiquinicDUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti serotoninic48278 DUKE
anti thyroidDUKE
aphidifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
cAMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
goitrogenicDUKE
hypotensiveDUKE
thyroid-peroxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
platelet aggregation inhibitor50427 A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.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.