Vitexin 6''-O-malonyl 2''-O-xyloside (CHEM023943)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:23:10 UTC
Update Date2016-11-09 01:17:48 UTC
Accession NumberCHEM023943
Identification
Common NameVitexin 6''-O-malonyl 2''-O-xyloside
ClassSmall Molecule
DescriptionAn apigenin flavone glycoside, which is found in the passion flower, bamboo leaves and pearl millet
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Apigenin 8-C-glucosideChEBI
8-Glycosyl-apigeninMeSH
8-GlycosylapigeninMeSH
8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-onePhytoBank
8-β-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-onePhytoBank
5,7,4'-Trihydroxyflavone 8-C-beta-D-glucopyranosidePhytoBank
5,7,4'-Trihydroxyflavone 8-C-β-D-glucopyranosidePhytoBank
5,7,4’-Trihydroxyflavone 8-C-β-D-glucopyranosidePhytoBank
8-C-GlucosylapigeninPhytoBank
8-C-beta-D-GlucopyranosylapigeninPhytoBank
8-C-β-D-GlucopyranosylapigeninPhytoBank
Apigenin 8-C-beta-D-glucosidePhytoBank
Apigenin 8-C-β-D-glucosidePhytoBank
Apigenin 8-C-beta-glucopyranosidePhytoBank
Apigenin 8-C-β-glucopyranosidePhytoBank
Apigenin-8-C-beta-D-glucopyranosidePhytoBank
Apigenin-8-C-β-D-glucopyranosidePhytoBank
OrientosidePhytoBank
VitexinaPhytoBank
VitexinePhytoBank
Chemical FormulaC21H20O10
Average Molecular Mass432.378 g/mol
Monoisotopic Mass432.106 g/mol
CAS Registry Number205584-37-8
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Namevitexin
SMILESOC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1
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/t14-,17-,18+,19-,21+/m1/s1
InChI KeySGEWCQFRYRRZDC-VPRICQMDSA-N
Chemical Taxonomy
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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability41.52 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-00lr-0980000000-a7106606775ccbb5f877Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 70V, Negativesplash10-014i-0920000000-ff12e5d6160ba3267209Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0920000000-ff12e5d6160ba3267209Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0920000000-ff12e5d6160ba3267209Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-01q9-0096000000-5352d14a270cef7d0573Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-001i-0190000000-33aab7c5c534e3bd93d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-001i-0189600000-fd0b1e9721d23e12d4c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-001i-0048900000-f581534a320bf875bc5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-02ai-0029400000-1abc6ec4a624fc7ffdbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-03yj-0019400000-f245a00fa402ce62fbebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-001i-0047900000-74b4b570ebb03db5e2d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-03e9-0049000000-d0c10f5af6fd40c34bbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-053r-0490000000-4f55f96dd316c01bf6b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-015a-0019700000-0c79eae7767fc558a318Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-03yj-0029200000-b9b5015bff3ee345cfaeSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-03e9-0049000000-c5394c9b574d28534668Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-01q9-0098000000-6af859afe0807d2c5738Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-01q9-0095000000-70a6a6fd27047ca2c666Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 30V, positivesplash10-014i-0009700000-98479ff8e0b88ae1ab79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0001900000-958c99e5dd8f93cb7d84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-4324900000-09b1bdaa3f1336b36f0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-5194000000-bca39f308b9ddf54a00bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1011900000-a6689e1e349d5b719f2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-045c-9256700000-24a4b43d1cb46da46b7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mp-9262000000-72d91a652228e0bd5d48Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0301980
FooDB IDFDB001706
Phenol Explorer IDNot Available
KNApSAcK IDC00001110
BiGG IDNot Available
BioCyc IDVITEXIN
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVitexin
Chemspider ID4444098
ChEBI ID16954
PubChem Compound ID5280441
Kegg Compound IDC01460
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21809948
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22408451
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22683902
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22941432
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23099258