Record Information
Version1.0
Creation date2010-04-08 22:12:53 UTC
Update date2019-11-26 03:14:20 UTC
Primary IDFDB017173
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-xyloside
DescriptionCyanidin 3-xyloside 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-xyloside is found, on average, in the highest concentration within a few different foods, such as black chokeberries (Photinia melanocarpa), rubus (blackberry, raspberry), and apples (Malus pumila). Cyanidin 3-xyloside has also been detected, but not quantified in, several different foods, such as common grapes (Vitis vinifera), sunflowers (Helianthus annuus), black elderberries (Sambucus nigra), summer grapes (Vitis aestivalis), and pomes. This could make cyanidin 3-xyloside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cyanidin 3-xyloside.
CAS Number29761-24-8
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP1.45ALOGPS
logP1.06ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area173.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.3 m³·mol⁻¹ChemAxon
Polarizability40.62 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H19O10
IUPAC name3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C20H18O10/c21-7-16-17(26)18(27)20(30-16)29-15-6-10-12(24)4-9(22)5-14(10)28-19(15)8-1-2-11(23)13(25)3-8/h1-6,16-18,20-21,26-27H,7H2,(H3-,22,23,24,25)/p+1/t16-,17+,18-,20-/m1/s1
InChI KeySBBFXSBQYRSIPP-AJYBTWMASA-O
Isomeric SMILES[H][C@]1(CO)O[C@@]([H])(OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C=C2)[C@]([H])(O)[C@@]1([H])O
Average Molecular Weight419.3589
Monoisotopic Molecular Weight419.097821828
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
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Anthocyanidin
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • Pentose monosaccharide
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCyanidin 3-xyloside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9103100000-dc4b089066163937bbb5Spectrum
Predicted GC-MSCyanidin 3-xyloside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01di-6910228000-6f3638e0ac882407d680Spectrum
Predicted GC-MSCyanidin 3-xyloside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-xyloside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090200000-6a8bdbf6e9a21f8aa9992017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0190000000-fd45b61ff1366c4847a42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1890000000-f2fbab6d16b8f592f9002017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0091800000-3f58e4084ab530969d592021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0296400000-324bfcd255eedb7bb7042021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0550-2190000000-919d228ff28211c1f7a02021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID53
DrugBank IDNot Available
HMDB IDHMDB37984
CRC / DFC (Dictionary of Food Compounds) IDODW39-O:KWM96-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00006651
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 ID53
Duplicate IDSNot Available
Old DFC IDSCMQ73-Z:KWM96-Q
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— 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.