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Cyanidin 3-rutinoside (FDB007049)

Record Information
Version1.0
Creation date2010-04-08 22:07:25 UTC
Update date2020-02-24 19:10:47 UTC
Primary IDFDB007049
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-rutinoside
DescriptionCyanidin 3-rutinoside, also known as keracyanin, belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Thus, cyanidin 3-rutinoside is considered to be a flavonoid. Cyanidin 3-rutinoside is found, on average, in the highest concentration within a few different foods, such as blackberries (Rubus), andean blackberries (Rubus glaucus), and sweet cherries (Prunus avium) and in a lower concentration in sour cherries (Prunus cerasus), olives (Olea europaea), and blackcurrants (Ribes nigrum). Cyanidin 3-rutinoside has also been detected, but not quantified in, several different foods, such as lowbush blueberries (Vaccinium angustifolium), highbush blueberries (Vaccinium corymbosum), summer grapes (Vitis aestivalis), wheats (Triticum), and common grapes (Vitis vinifera). This could make cyanidin 3-rutinoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cyanidin 3-rutinoside.
CAS Number28338-59-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP0.66ALOGPS
logP-0.64ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area252.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity147.13 m³·mol⁻¹ChemAxon
Polarizability56.93 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H31O15
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C27H30O15/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31)/p+1/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+/m0/s1
InChI KeyUSNPULRDBDVJAO-FXCAAIILSA-O
Isomeric SMILES[H][C@@]1(C)O[C@@]([H])(OC[C@@]2([H])O[C@@]([H])(OC3=CC4=C(C=C(O)C=C4O)[O+]=C3C3=CC(O)=C(O)C=C3)[C@]([H])(O)[C@@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O
Average Molecular Weight595.526
Monoisotopic Molecular Weight595.166295322
Classification
Description Belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-3-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Anthocyanidin
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCyanidin 3-rutinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00pi-7290080000-4e9e17157d81edbbc7b2Spectrum
Predicted GC-MSCyanidin 3-rutinoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kk-7270009000-a677df67be0186eddbe9Spectrum
Predicted GC-MSCyanidin 3-rutinoside, "Cyanidin 3-rutinoside,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-rutinoside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000x-0090070000-125bca6d3508badde83f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0090080000-6c6a0d2425f4a8ce2dd02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002u-0690200000-d0f495f57a6a08951ae32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0090000000-5d9be53d8851211d98b92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000x-0090050000-edf1f099fb6afbd7bdd42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0090000000-3fbc8f30a8f68e2b6b122017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-50fc7a85af67b684d6552017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090030000-6c1cc95884382202267a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090020000-af027bb2664bb06e30d32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0030090000-cb5228a5a554147643b02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000090000-cba1bd53595923c8dc6f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-735ac235caa69be3d2302021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0090000000-14f4866fec6873c2487b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000090000-fd1c98249ab2ecbed87b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0070090000-dd1ac5fab438c8b604892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-2f47b76af7994574f89a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-0090000000-3dfd5d4c6dbc9b0428d42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-001r-0090000000-91e1340eb79d12ed3d6d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001r-0090000000-776e76ecfc8c90bd97a92021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0211090000-99bd764f2c2a7dca281e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-0711090000-878065c4a8c8fed57e8c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rb-6911010000-4f517c2e03a1ff30becf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-4421090000-61295fb4e486fff583fd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ow-5911020000-3e796461f98c10c1e95f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0c04-9520000000-9e3f42b0650d9235dca82016-08-03View Spectrum
NMRNot Available
ChemSpider ID390288
ChEMBL IDCHEMBL505251
KEGG Compound IDC08620
Pubchem Compound ID441674
Pubchem Substance IDNot Available
ChEBI ID16726
Phenol-Explorer ID56
DrugBank IDNot Available
HMDB IDHMDB31458
CRC / DFC (Dictionary of Food Compounds) IDODW39-O:BFH51-Q
EAFUS IDNot Available
Dr. Duke IDANTIRRHININ|ANTIRHININ|CYANIDIN-3-RHAMNOSYLGLUCOSIDE|CYANIDIN-3-RUTINOSIDE|KERACYANIN|SAMBUCINE
BIGG IDNot Available
KNApSAcK IDC00002376
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCyanidin_3-rutinoside
Phenol-Explorer Metabolite ID10
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
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
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.