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Isovitexin (FDB000614)

Record Information
Version1.0
Creation date2010-04-08 22:04:38 UTC
Update date2020-02-24 19:11:06 UTC
Primary IDFDB000614
Secondary Accession Numbers
  • FDB016656
Chemical Information
FooDB NameIsovitexin
DescriptionIsovitexin is a member of the class of compounds known as flavonoid c-glycosides. Flavonoid c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Isovitexin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isovitexin can be found in a number of food items such as common salsify, winged bean, flaxseed, and common buckwheat, which makes isovitexin a potential biomarker for the consumption of these food products. Isovitexin (or homovitexin, saponaretin) is a flavone. the apigenin-6-C-glucoside. It can be found in the passion flower, Cannabis, and the açaí palm .
CAS Number38953-85-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.73 g/LALOGPS
logP0.37ALOGPS
logP-0.051ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.14ChemAxon
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
Polarizability42.47 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)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2
InChI KeyMYXNWGACZJSMBT-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(C(O)C(O)C1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC=C(O)C=C2)C=C1O
Average Molecular Weight432.3775
Monoisotopic Molecular Weight432.10564686
Classification
Description Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent6-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • 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]D +16.2 (EtOH)DFC
Spectroscopic UV Data336 () (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-001i-0000900000-7e8773e6dffdca2e961c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-02u0-0019300000-bf1e8c212114257bd52c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-03e9-0039000000-cb3b3d5ff1fe66f3e8d02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-03e9-0059000000-d7c269cffa08f1db2a332020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-01q9-0296000000-24d27898fce539d6c57f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-01q9-0039300000-e763314082ae66e5e7232020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-001i-0049400000-770c6ade47e7eee594452020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-01q9-0069000000-bc1f50fe4e8cd50527242020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-015a-0960000000-de27f2f6c53ef2b932c92020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-001i-0000900000-189d312716882cab26222020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, negativesplash10-001i-0003900000-0b4998a725ea9d79085d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-03dl-0009100000-7d9cb987c1ddb226ec9c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, negativesplash10-03e9-0059000000-82799a3d9dfe72bc95962020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, negativesplash10-001i-0092000000-6949e8b972ab42b08ab22020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 30V, negativesplash10-03di-0009000000-28d0ea8ae44c76a430bf2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 43V, negativesplash10-03dl-0009000000-d44475245655ad4aedd72020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-001i-0001900000-9499ee7df6f0a43630472020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-001i-0003900000-111bf3302482cdf9765b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-01q9-0007900000-7df52e75f6796aad4abc2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0001900000-befc1cf568ed659e0e532017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-4324900000-e6a94e47ae288eb8a27f2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-4294000000-b3f38a64e6c632a8265e2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1011900000-bdbc26b4ba26fb0d70012017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-045c-9256700000-c131102de0dd7b21a5be2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mp-9362000000-6d40ed50c23c875c82d12017-06-28View 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 ID267
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFD64-C:BFD64-C
EAFUS IDNot Available
Dr. Duke IDSAPONARETIN|APIGENIN-6-C-GLUCOSIDE|ISOVITEXIN
BIGG IDNot Available
KNApSAcK IDC00001059
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
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
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
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.
— 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.