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Showing Compound Vicenin 2 (FDB002630)

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, also known as vicenin II, 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 found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Vicenin 2 has also been detected, but not quantified in, several different foods, such as soy beans (Glycine max), tartary buckwheats (Fagopyrum tataricum), amaranths (Amaranthus), spelts (Triticum spelta), and oriental wheats (Triticum turanicum). This could make vicenin 2 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vicenin 2.
CAS Number23666-13-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Apigenin-6,8-di-C-glycopyranosideMeSH
Vicenin-2MeSH
Vicenin IIMeSH
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-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
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
Predicted GC-MSVicenin 2, "Vicenin 2,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVicenin 2, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-0005290000-9a78bec3e031b476b9832017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-0094770000-4a713c915b058c32b42c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-01ox-0052950000-b3d4ef3891bc5396575c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-0029730000-195463720c0564fc0e412017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-01q9-0049410000-b9e46e9b61fd04b1fd542017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0006-0005190000-c3bc69d503efe086b1042021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-002b-0159000000-73201d25ff9bd498fbbc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0006590000-0b790319282d96c7f1b22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0294000000-c48ccbabbc82b2e704362021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0009810000-02776207343f58da4e292021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0570-0009710000-467ea3b5a1fccdb37cb62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0ue9-0009100000-3c3c2fcb4c91260284672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-002b-0005690000-6661389fc4db228fec6b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0000190000-48ccaded9e493aef60782015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vj-1200390000-d10e5bb5b26e0eefb0f72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0550-1007940000-a8fcd22df6cf3cfc54582015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0000190000-48ccaded9e493aef60782015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vj-1200390000-d10e5bb5b26e0eefb0f72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0550-1007940000-a8fcd22df6cf3cfc54582015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000390000-d59360ecaa9a1208b0d42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fu-3100690000-9b42c7acc566ef75a9f72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7c-7306960000-804c13a60653afea62e12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000390000-d59360ecaa9a1208b0d42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fu-3100690000-9b42c7acc566ef75a9f72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7c-7306960000-804c13a60653afea62e12015-04-25View Spectrum
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 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
Anti-angiogenic48422 An agent that inhibits the formation of new blood vessels, playing a crucial role in cancer treatment by starving tumors of oxygen and nutrients. Therapeutically, it is used to manage cancer, age-related macular degeneration, and other diseases characterized by excessive angiogenesis, reducing tumor growth and slowing disease progression.DUKE
Anti-cancer35610 An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.DUKE
Anti carcinomic35610 An agent that inhibits the growth and proliferation of cancer cells, playing a crucial role in cancer prevention and treatment. Therapeutically, it is used to manage and treat various types of cancer, reducing tumor size and slowing disease progression, with key medical uses in oncology and chemotherapy.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 proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
ApoptoticAn agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.DUKE
Cyclin-B1 inhibitor35222 An agent that blocks the activity of cyclin-B1, a protein involved in cell cycle regulation, reducing cell proliferation. Therapeutically, it has applications in cancer treatment, particularly in inhibiting tumor growth and inducing apoptosis. Key medical uses include managing various types of cancer, such as leukemia and solid tumors.DUKE
Cyclin-D1 inhibitor35222 An agent that blocks the activity of cyclin-D1, a protein involved in cell cycle regulation, reducing cancer cell growth. Therapeutically, it is used to treat various cancers, including breast, lung, and lymphoma, by inhibiting tumor progression and inducing apoptosis.DUKE
Oviposition stimulantAn agent that stimulates egg-laying, particularly in insects, by activating the ovipositor. Its biological role is to induce reproduction, and it has therapeutic applications in pest control and entomology. Key medical uses include managing insect populations and understanding reproductive biology.DUKE
Radioprotective35232 An agent that shields cells from radiation damage, reducing oxidative stress and DNA harm. Its biological role is to mitigate radiation-induced injury, and it has therapeutic applications in cancer treatment, space exploration, and nuclear medicine, with key medical uses including protection of healthy tissues during radiation therapy.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.