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
Synonyms
SynonymSource
Cyanidin 3-O-rhamnosylglucosideChEBI
Cyanidin 3-rhamnoglucosideChEBI
KeracyaninKegg
AntirrhininHMDB
CeracyaninHMDB
CyaninosideHMDB
Keracyanin, innHMDB
MeralopHMDB
NoctiluxHMDB
NyctaluxHMDB
OleocyaninHMDB
PrunicyaninHMDB
SambucinHMDB
SambucineHMDB
Cyanidin 3-rutinosideMeSH
Cyanidin-3-rutinosideMeSH
Cyanidin 3-O-rutinosidemanual
Keracyanin, INNdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP0.66ALOGPS
logP-0.64ChemAxon
logS-2.9ALOGPS
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-0090070000-125bca6d3508badde83fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0090080000-6c6a0d2425f4a8ce2dd0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002u-0690200000-d0f495f57a6a08951ae3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0090000000-5d9be53d8851211d98b9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000x-0090050000-edf1f099fb6afbd7bdd4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0090000000-3fbc8f30a8f68e2b6b12Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-50fc7a85af67b684d655Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090030000-6c1cc95884382202267aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090020000-af027bb2664bb06e30d3Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0030090000-cb5228a5a554147643b0Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000090000-cba1bd53595923c8dc6fSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-735ac235caa69be3d230Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0090000000-14f4866fec6873c2487bSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000090000-fd1c98249ab2ecbed87bSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0070090000-dd1ac5fab438c8b60489Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-2f47b76af7994574f89aSpectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-0090000000-3dfd5d4c6dbc9b0428d4Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-001r-0090000000-91e1340eb79d12ed3d6dSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001r-0090000000-776e76ecfc8c90bd97a9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0211090000-99bd764f2c2a7dca281eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-0711090000-878065c4a8c8fed57e8cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rb-6911010000-4f517c2e03a1ff30becfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-4421090000-61295fb4e486fff583fdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ow-5911020000-3e796461f98c10c1e95fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0c04-9520000000-9e3f42b0650d9235dca8Spectrum
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.