Record Information
Version1.0
Creation date2010-04-08 22:05:27 UTC
Update date2020-02-24 19:10:35 UTC
Primary IDFDB002630
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVicenin 2
DescriptionVicenin 2 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. Vicenin 2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Vicenin 2 is found, on average, in the highest concentration within sweet oranges. Vicenin 2 has also been detected, but not quantified in, several different foods, such as common buckwheats, fenugreeks, teffs, ryes, and spelts. This could make vicenin 2 a potential biomarker for the consumption of these foods.
CAS Number23666-13-9
Structure
Thumb
Synonyms
SynonymSource
5,7,4'-Trihydroxyflavone-6,8-di-C-glucosideHMDB
6,8-Di-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9ciHMDB
6,8-Di-C-glucopyranosylapigeninHMDB
6,8-Di-C-glucosyl-4',5,7-trihydroxyflavoneHMDB
6,8-Di-C-glucosylapigeninHMDB
Apigenin 6,8-di-C-glucosideHMDB
Vicenin-2HMDB
Vicenin-1MeSH
6-C-beta-D-Xylopyranosyl-8-C-beta-D-glucopyranosyl apigeninMeSH
ViceninMeSH
6,8-Di-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility9.88 g/LALOGPS
logP-0.97ALOGPS
logP-2.8ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)5.76ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area267.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity139.15 m³·mol⁻¹ChemAxon
Polarizability57.58 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H30O15
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
InChI IdentifierInChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2
InChI KeyFIAAVMJLAGNUKW-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(C(O)C(O)C1O)C1=C(O)C(C2OC(CO)C(O)C(O)C2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1
Average Molecular Weight594.5181
Monoisotopic Molecular Weight594.15847029
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

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.55%; H 5.09%; O 40.37%DFC
Melting PointMp 233-236° (214-216° dec.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +71 (c, 0.36 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSVicenin 2, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0w59-0000390000-4715bf8584b5737232b4Spectrum
Predicted GC-MSVicenin 2, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0571-2300179000-2bd75622b8a0edf7d54fSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-0005290000-9a78bec3e031b476b983Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-0094770000-4a713c915b058c32b42cSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-01ox-0052950000-b3d4ef3891bc5396575cSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-0029730000-195463720c0564fc0e41Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-01q9-0049410000-b9e46e9b61fd04b1fd54Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0000190000-48ccaded9e493aef6078Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vj-1200390000-d10e5bb5b26e0eefb0f7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0550-1007940000-a8fcd22df6cf3cfc5458Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0000190000-48ccaded9e493aef6078Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vj-1200390000-d10e5bb5b26e0eefb0f7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0550-1007940000-a8fcd22df6cf3cfc5458Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000390000-d59360ecaa9a1208b0d4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fu-3100690000-9b42c7acc566ef75a9f7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7c-7306960000-804c13a60653afea62e1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000390000-d59360ecaa9a1208b0d4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fu-3100690000-9b42c7acc566ef75a9f7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7c-7306960000-804c13a60653afea62e1Spectrum
NMRNot Available
ChemSpider ID2341472
ChEMBL IDNot Available
KEGG Compound IDC10195
Pubchem Compound ID3084407
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID247
DrugBank IDNot Available
HMDB IDHMDB30708
CRC / DFC (Dictionary of Food Compounds) IDCMT14-X:CMT14-X
EAFUS IDNot Available
Dr. Duke IDVICENIN-2|APIGENIN-6,8-DI-C-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00006229
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
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti carcinomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti proliferantDUKE
apoptoticDUKE
cyclin-B1 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
cyclin-D1 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
oviposition stimulantDUKE
radioprotective35232 Any pharmaceutical compound containing a radioisotope.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.