Record Information
Version1.0
Creation date2010-04-08 22:07:25 UTC
Update date2015-07-20 22:12:34 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. Cyanidin 3-rutinoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Cyanidin 3-rutinoside is found, on average, in the highest concentration within a few different foods, such as sweet cherries, olives, and black elderberries and in a lower concentration in gooseberries, sour cherries, and rubus (blackberry, raspberry). Cyanidin 3-rutinoside has also been detected, but not quantified in, several different foods, such as summer grapes, asparagus, banana, pomegranates, and cassava. This could make cyanidin 3-rutinoside a potential biomarker for the consumption of these foods.
CAS Number28338-59-2
Structure
Thumb
Synonyms
SynonymSource
Cyanidin 3-O-rhamnosylglucosideChEBI
Cyanidin 3-rhamnoglucosideChEBI
KeracyaninKegg
Cyanidin-3-rutinosideMeSH
AntirrhininHMDB
CeracyaninHMDB
CyaninosideHMDB
Keracyanin, innHMDB
MeralopHMDB
NoctiluxHMDB
NyctaluxHMDB
OleocyaninHMDB
PrunicyaninHMDB
SambucinHMDB
SambucineHMDB
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00pi-7290080000-4e9e17157d81edbbc7b2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00kk-7270009000-a677df67be0186eddbe9JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000x-0090070000-125bca6d3508badde83fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0090080000-6c6a0d2425f4a8ce2dd0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002u-0690200000-d0f495f57a6a08951ae3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0090000000-5d9be53d8851211d98b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000x-0090050000-edf1f099fb6afbd7bdd4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0090000000-3fbc8f30a8f68e2b6b12JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-50fc7a85af67b684d655JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090030000-6c1cc95884382202267aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090020000-af027bb2664bb06e30d3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0211090000-99bd764f2c2a7dca281eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-0711090000-878065c4a8c8fed57e8cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rb-6911010000-4f517c2e03a1ff30becfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-4421090000-61295fb4e486fff583fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ow-5911020000-3e796461f98c10c1e95fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0c04-9520000000-9e3f42b0650d9235dca8JSpectraViewer
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.